Title: 10 Best Hotels in Oakland, Winter Garden for 2026 | Expedia.ca [Vacation Rentals in Winter Garden](https://expedia.ca/Winter-Garden-Vacation-Rentals.d7898.Travel-Guide-VacationRentals)[Flights to Winter Garden](https://expedia.ca/Cheap-Flights-To-Winter-Garden.d7898.Travel-Guide-Flights)[Things to do in Winter Garden](https://expedia.ca/Things-To-Do-In-Winter-Garden.d7898.Travel-Guide-Activities)[Oakland Car Rentals](https://expedia.ca/Car-Rentals-In-Oakland.d6360404.Car-Rental-Guide)[Oakland Vacations](https://expedia.ca/Oakland.d6360404.Destination-Travel-Guides) ![Panoramic view of Lake Apopka and nature Florida.](https://images.trvl-media.com/place/6360403/5cbd79a8-2e61-4cef-8769-e792f96b305a.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Hotels in Oakland, Winter Garden - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Tonight [Dec 24 - Dec 25](https://www.expedia.ca/Hotel-Search?regionId=6360404&startDate=2025-12-24&endDate=2025-12-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 25 - Dec 26](https://www.expedia.ca/Hotel-Search?regionId=6360404&startDate=2025-12-25&endDate=2025-12-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6360404&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6360404&startDate=2026-01-02&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Recommended Price (low to high) Distance Star rating ## Our top choices for Oakland hotels ![Outdoor banquet area](https://images.trvl-media.com/lodging/2000000/1470000/1460500/1460425/abbcc72a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1470000/1460500/1460425/6214f96f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake](https://images.trvl-media.com/lodging/2000000/1470000/1460500/1460425/eba0fe5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![11 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/2000000/1470000/1460500/1460425/edfdae69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rosen Shingle Creek [](https://www.expedia.ca/Orlando-Hotels-Rosen-Shingle-Creek.h1460425.Hotel-Information) 24.2 km from Oakland 9.4/10 Exceptional (4373) "Great place to stay. Definitely will stay here again.." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Donnell CA $140 CA $158 total includes taxes & fees Jan 23 - Jan 24, 2026 [](https://www.expedia.ca/Orlando-Hotels-Rosen-Shingle-Creek.h1460425.Hotel-Information) ![Poolside Family Suite - Exterior Entry (Includes Early Park Admission*) | View from room](https://images.trvl-media.com/lodging/6000000/5970000/5963300/5963292/4c48bd3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Volcano Bay View 2-Bedroom Suite (Includes Early Park Admission*)](https://images.trvl-media.com/lodging/6000000/5970000/5963300/5963292/74f24d6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/6000000/5970000/5963300/5963292/09c3f299.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Volcano Bay View 2-Bedroom Suite (Includes Early Park Admission*)](https://images.trvl-media.com/lodging/6000000/5970000/5963300/5963292/d9e7d6aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Universal's Cabana Bay Beach Resort [](https://www.expedia.ca/Orlando-Hotels-Universals-Cabana-Bay-Beach-Resort.h5963292.Hotel-Information) 18.5 km from Oakland 9.0/10 Wonderful (5847) "Solid place for a vacation Will be staying again in the future " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jared G CA $182 CA $205 total includes taxes & fees Jan 6 - Jan 7, 2026 [](https://www.expedia.ca/Orlando-Hotels-Universals-Cabana-Bay-Beach-Resort.h5963292.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/2000000/1820000/1813900/1813900/c5ff34ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed](https://images.trvl-media.com/lodging/2000000/1820000/1813900/1813900/462c6852.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1820000/1813900/1813900/1492ecfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/2000000/1820000/1813900/1813900/94d5773b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Seasons Florida Resort [](https://www.expedia.ca/Orlando-Hotels-Seasons-Florida-Resort.h1813900.Hotel-Information) 30.2 km from Oakland 8.8/10 Excellent (3307) "Excellent location and value, very clean and friendly check in" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jason CA $68 CA $78 total includes taxes & fees Jan 19 - Jan 20, 2026 [](https://www.expedia.ca/Orlando-Hotels-Seasons-Florida-Resort.h1813900.Hotel-Information) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/4000/3916/55b45a9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard view](https://images.trvl-media.com/lodging/1000000/10000/4000/3916/ab16f193.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard view](https://images.trvl-media.com/lodging/1000000/10000/4000/3916/627a379d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor wedding](https://images.trvl-media.com/lodging/1000000/10000/4000/3916/f815fe49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wyndham I-Drive Avanti Resort & Conference Center [](https://www.expedia.ca/Orlando-Hotels-Avanti-Palms-Resort-And-Conference-Center.h3916.Hotel-Information) 19.2 km from Oakland 7.4/10 Good (3922) "Excellent room and the beds were very comfortable, also very clean " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daisy CA $85 CA $124 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Orlando-Hotels-Avanti-Palms-Resort-And-Conference-Center.h3916.Hotel-Information) ![Courtyard](https://images.trvl-media.com/lodging/1000000/10000/5400/5398/a43383ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/1000000/10000/5400/5398/446449ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (Parlor) | Living area](https://images.trvl-media.com/lodging/1000000/10000/5400/5398/b3768da5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, iron/ironing board](https://images.trvl-media.com/lodging/1000000/10000/5400/5398/421b240d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton at the Entrance to Universal Orlando [](https://www.expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-At-The-Entrance-To-Universal-Orlando.h5398.Hotel-Information) 19.2 km from Oakland 8.4/10 Very good (6914) "Great hotel great food" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Malika CA $122 CA $138 total includes taxes & fees Jan 15 - Jan 16, 2026 [](https://www.expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-At-The-Entrance-To-Universal-Orlando.h5398.Hotel-Information) ![View from room](https://images.trvl-media.com/lodging/1000000/10000/8900/8892/8068a653.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge, alfresco dining, open daily](https://images.trvl-media.com/lodging/1000000/10000/8900/8892/301f7287.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/10000/8900/8892/f7c213fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/10000/8900/8892/b06b206b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rosen Inn at Pointe Orlando [](https://www.expedia.ca/Orlando-Hotels-Rosen-Inn-At-Pointe-Orlando.h8892.Hotel-Information) 20.7 km from Oakland 8.6/10 Excellent (5431) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephanie CA $113 CA $128 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Orlando-Hotels-Rosen-Inn-At-Pointe-Orlando.h8892.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/40600/40513/b94616ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/40600/40513/daabd874.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast and dinner served, American cuisine](https://images.trvl-media.com/lodging/1000000/50000/40600/40513/7e8c0576.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily full breakfast for a fee](https://images.trvl-media.com/lodging/1000000/50000/40600/40513/48efc8c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ramada by Wyndham Kissimmee Gateway [](https://www.expedia.ca/Orlando-Hotels-Ramada-By-Wyndham-Kissimmee-Gateway.h40513.Hotel-Information) 25.2 km from Oakland 8.0/10 Very good (3913) "Phenomenal hotel for the price point as well as the children. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Destiny CA $69 CA $106 total includes taxes & fees Jan 7 - Jan 8, 2026 [](https://www.expedia.ca/Orlando-Hotels-Ramada-By-Wyndham-Kissimmee-Gateway.h40513.Hotel-Information) ![View from room](https://images.trvl-media.com/lodging/1000000/10000/1300/1264/2a9be677.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception hall](https://images.trvl-media.com/lodging/1000000/10000/1300/1264/d4034270.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/1300/1264/4f5f3b5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Buffet](https://images.trvl-media.com/lodging/1000000/10000/1300/1264/6086e66b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rosen Inn Lake Buena Vista [](https://www.expedia.ca/Orlando-Hotels-Rosen-Inn-Lake-Buena-Vista.h1264.Hotel-Information) 22.9 km from Oakland 8.6/10 Excellent (5639) "Great property to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deepankar CA $96 CA $109 total includes taxes & fees Jan 9 - Jan 10, 2026 [](https://www.expedia.ca/Orlando-Hotels-Rosen-Inn-Lake-Buena-Vista.h1264.Hotel-Information) ![6 outdoor pools, free cabanas, pool umbrellas](https://images.trvl-media.com/lodging/1000000/30000/23200/23110/91c45539.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Mini-golf](https://images.trvl-media.com/lodging/1000000/30000/23200/23110/45c63d74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/30000/23200/23110/de6f64bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/1000000/30000/23200/23110/b1f61811.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando [](https://www.expedia.ca/Orlando-Hotels-Sheraton-Vistana-Resort-Villas.h23110.Hotel-Information) 24.3 km from Oakland 9.4/10 Exceptional (4166) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shawna CA $152 CA $171 total includes taxes & fees Jan 21 - Jan 22, 2026 [](https://www.expedia.ca/Orlando-Hotels-Sheraton-Vistana-Resort-Villas.h23110.Hotel-Information) ![Business centre](https://images.trvl-media.com/lodging/1000000/20000/16000/15927/5cf8836a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio, 1 King Bed](https://images.trvl-media.com/lodging/1000000/20000/16000/15927/a489bc76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/16000/15927/faa812b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/20000/16000/15927/2ba89a06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spark by Hilton Orlando near Universal [](https://www.expedia.ca/Orlando-Hotels-Spark-By-Hilton-Orlando-Near-Universal.h15927.Hotel-Information) 18.9 km from Oakland 9.0/10 Wonderful (472) "The rooms and breakfast were lovely" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MacKenzie Rose CA $121 CA $137 total includes taxes & fees Jan 13 - Jan 14, 2026 [](https://www.expedia.ca/Orlando-Hotels-Spark-By-Hilton-Orlando-Near-Universal.h15927.Hotel-Information) ![In-room safe, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/20000/14800/14701/de0795f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/14800/14701/07b4d960.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/14800/14701/f253be82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/1000000/20000/14800/14701/9a6d0287.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Palazzo Lakeside Hotel [](https://www.expedia.ca/Orlando-Hotels-Palazzo-Lakeside.h14701.Hotel-Information) 28.9 km from Oakland 8.2/10 Very good (5136) "Beautiful place to stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mohammad CA $66 CA $122 total includes taxes & fees Jan 7 - Jan 8, 2026 [](https://www.expedia.ca/Orlando-Hotels-Palazzo-Lakeside.h14701.Hotel-Information) ![Outdoor wedding area](https://images.trvl-media.com/lodging/2000000/1760000/1759600/1759572/w3541h1754x2y0-2f9e02a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine, pool views ](https://images.trvl-media.com/lodging/2000000/1760000/1759600/1759572/d2867ff8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine, pool views ](https://images.trvl-media.com/lodging/2000000/1760000/1759600/1759572/2ab817e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception hall](https://images.trvl-media.com/lodging/2000000/1760000/1759600/1759572/564d65cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Meliá Orlando Celebration [](https://www.expedia.ca/Orlando-Hotels-Melia-Orlando-Celebration.h1759572.Hotel-Information) 26.5 km from Oakland 8.6/10 Excellent (1575) "was a very nice stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Taylor Elaine CA $127 CA $194 total includes taxes & fees Jan 7 - Jan 8, 2026 [](https://www.expedia.ca/Orlando-Hotels-Melia-Orlando-Celebration.h1759572.Hotel-Information) ![Outdoor pool, a heated pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/19600/19535/0f12768a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/20000/19600/19535/882d3cc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool views, serves lunch, dinner, and happy hour](https://images.trvl-media.com/lodging/1000000/20000/19600/19535/c939bf2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/19600/19535/87d53b31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Resort Orlando - Lake Buena Vista by IHG [](https://www.expedia.ca/Orlando-Hotels-Holiday-Inn-Resort-Orlando-Lake-Buena-Vista.h19535.Hotel-Information) 24 km from Oakland 8.4/10 Very good (3580) "Great place to stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nathaniel CA $90 CA $148 total includes taxes & fees Jan 25 - Jan 26, 2026 [](https://www.expedia.ca/Orlando-Hotels-Holiday-Inn-Resort-Orlando-Lake-Buena-Vista.h19535.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/40000000/39070000/39065100/39065095/c574100e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/40000000/39070000/39065100/39065095/cc14cd88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/40000000/39070000/39065100/39065095/91d93c2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/40000000/39070000/39065100/39065095/88896d87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### avid hotel Orlando International Airport by IHG [](https://www.expedia.ca/Orlando-Hotels-Avid-Hotels-Orlando-International-Airport.h39065095.Hotel-Information) 31.5 km from Oakland 9.2/10 Wonderful (2028) "Easy check in, great people service, clean room, great location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tiffany CA $146 CA $165 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Orlando-Hotels-Avid-Hotels-Orlando-International-Airport.h39065095.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/24200/24103/6af5b762.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/24200/24103/027db371.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/24200/24103/d852690a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/24200/24103/5bd5bdc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Drury Plaza Hotel Orlando - Disney Springs Area [](https://www.expedia.ca/Orlando-Hotels-Drury-Plaza-Hotel-Orlando-Lake-Buena-Vista.h24103.Hotel-Information) 23.1 km from Oakland 9.8/10 Exceptional (5442) "Great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kiran CA $221 CA $248 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Orlando-Hotels-Drury-Plaza-Hotel-Orlando-Lake-Buena-Vista.h24103.Hotel-Information) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/48000000/47050000/47041400/47041344/0f250490.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/48000000/47050000/47041400/47041344/0c7cf300.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/48000000/47050000/47041400/47041344/a0e5b1e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/48000000/47050000/47041400/47041344/753a80d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tru By Hilton Orlando Convention Center Area, FL [](https://www.expedia.ca/Orlando-Hotels-Tru-By-Hilton-Orlando-Convention-Center-Area.h47041344.Hotel-Information) 22 km from Oakland 9.0/10 Wonderful (3705) "Friendly staff, great service, clean rooms, enjoyed the stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Katherine CA $122 CA $138 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Orlando-Hotels-Tru-By-Hilton-Orlando-Convention-Center-Area.h47041344.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/61000000/60520000/60517400/60517339/a3e034f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/61000000/60520000/60517400/60517339/bcc37d1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/61000000/60520000/60517400/60517339/e1d8ed2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Accessible, Non Smoking](https://images.trvl-media.com/lodging/61000000/60520000/60517400/60517339/56cb6aec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cambria Hotel Orlando Airport [](https://www.expedia.ca/Orlando-Hotels-Cambria-Hotel-Orlando-Airport.h60517339.Hotel-Information) 31.4 km from Oakland 8.8/10 Excellent (1942) "Clean room and pleasant staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mariama Velinique CA $123 CA $138 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Orlando-Hotels-Cambria-Hotel-Orlando-Airport.h60517339.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/330000/327400/327322/dcc2b70c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/330000/327400/327322/91f01ca9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/330000/327400/327322/b063e7a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/1000000/330000/327400/327322/dffbfa04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Orlando International Airport by IHG [](https://www.expedia.ca/Orlando-Hotels-Holiday-Inn-Express-Orlando-International-Airport.h327322.Hotel-Information) 31.3 km from Oakland 9.0/10 Wonderful (1883) " Nice hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shalanda CA $150 CA $169 total includes taxes & fees Jan 6 - Jan 7, 2026 [](https://www.expedia.ca/Orlando-Hotels-Holiday-Inn-Express-Orlando-International-Airport.h327322.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/52900/52821/48f5f27b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/52900/52821/044c9db1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 outdoor pools, open 8:00 AM to 11:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/60000/52900/52821/9c8d7a65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool views, open daily](https://images.trvl-media.com/lodging/1000000/60000/52900/52821/3522d101.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Resort Kissimmee by the Parks by IHG [](https://www.expedia.ca/Orlando-Hotels-Holiday-Inn-Resort-Kissimmee-By-The-Parks-By-IHG.h52821.Hotel-Information) 24.7 km from Oakland 8.4/10 Very good (1089) "Great hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steven CA $97 CA $137 total includes taxes & fees Jan 7 - Jan 8, 2026 [](https://www.expedia.ca/Orlando-Hotels-Holiday-Inn-Resort-Kissimmee-By-The-Parks-By-IHG.h52821.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/32000000/31950000/31941500/31941472/05cb2d91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/32000000/31950000/31941500/31941472/fab2d3be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/32000000/31950000/31941500/31941472/32572eec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom (2 Queenbed & 1 Sofabed)](https://images.trvl-media.com/lodging/32000000/31950000/31941500/31941472/5cf2d29a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt House Orlando International Drive [](https://www.expedia.ca/Orlando-Hotels-Hyatt-House-Orlando-International-Drive.h31941472.Hotel-Information) 20.6 km from Oakland 9.4/10 Exceptional (1389) "Good location, good breakfast " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrea CA $161 CA $182 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Orlando-Hotels-Hyatt-House-Orlando-International-Drive.h31941472.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2026-01-08&endDate=2026-01-09®ionId=6360404&adults=2&sort=RECOMMENDED&openPlayBack=true) ## Where to stay in Oakland Find the best Oakland areas and neighborhoods for the activities you enjoy most. - Horizon West - Vista del Lago - Downtown Winter Garden - Killarney ![](https://mediaim.expedia.com/destination/1/37b5977531ce6620ae360dd863ce8f7c.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [](https://www.expedia.ca/Hotel-Search?pwaOverlay=map®ionId=977491569791938560) ![Horizon West map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:gtrlDr%7ChqNis%40oFg_%40%7B_%40iY%7CXoc%40xC%7B%5CwEosEn%40a%40o%7EEdW_SiLqPTojApiAf%40%7CVoXnjAmBgAqt%40%60z%40spAlpAlShy%40kYhy%40szCnOaJbk%40mBMxdK%5CvkApDdkDwp%40pIqaA%60h%40&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=n3TSCtO6nPipKEzIk53t6RYKq48=) ### Horizon West While visiting Horizon West, you might make a stop by sights like Walt Disney World® Resort and Orange County National Golf Club. [See properties](https://www.expedia.ca/Hotel-Search?regionId=977491569791938560) [](https://www.expedia.ca/Hotel-Search?pwaOverlay=map®ionId=553248635976471720) ![Vista del Lago map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:qsalDbkhqNuTMSum%40bMBb%40%7BIaFkIAmHnSCG%7CB_AjAb%40fBtMlGnGw%40pBpGdNIDsCzMDKd%5Ew%7C%40RA%7CX&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=playiTafgON9EE4xbK3rnHR1y1U=) ### Vista del Lago While Vista del Lago isn't home to many top sights, Orange Lake Golf and Flamingo Crossings Town Center are some notable places to visit nearby. [See properties](https://www.expedia.ca/Hotel-Search?regionId=553248635976471720) [](https://www.expedia.ca/Hotel-Search?pwaOverlay=map®ionId=944538218785796096) ![Downtown Winter Garden map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:eximDn%7C%7EpNsMUGcP%7DIIGme%40fBOhV%5DArn%40MjI&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=1VUib_Z3T3Au8u27r8QEdv-WKNs=) ### Downtown Winter Garden While visiting Downtown Winter Garden, you might make a stop by sights like West Orange Trail and Central Florida Railroad Museum. [See properties](https://www.expedia.ca/Hotel-Search?regionId=944538218785796096) [](https://www.expedia.ca/Hotel-Search?pwaOverlay=map®ionId=6360403) ![Killarney map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:keimDj%60mqNij%40saB%7EHu%7B%40rcBkG%7EFat%40hb%40kDhz%40z%60BuCv%7B%40sSfZuu%40zE%7DxAj%60%40&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=QMWxfWyixWBofYiTIYo5XkD4OX8=) ### Killarney If you're looking for some top things to see and do in Killarney and surrounding area, you can visit Bella Collina Golf Club and West Orange Trail. [See properties](https://www.expedia.ca/Hotel-Search?regionId=6360403) ## Top Oakland Hotel Reviews ![DoubleTree by Hilton Hotel Orlando at SeaWorld](https://images.trvl-media.com/lodging/1000000/20000/18900/18874/69019073_y.jpg) ### DoubleTree by Hilton Hotel Orlando at SeaWorld 10/10 Excellent "good" [](https://expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-Hotel-Orlando-At-SeaWorld.h18874.Hotel-Information) ![The Grove Resort & Water Park Orlando](https://images.trvl-media.com/lodging/5000000/4700000/4691700/4691657/c5a7d392_y.jpg) ### The Grove Resort & Water Park Orlando 10/10 Excellent "Everything was great about my expectations " [](https://expedia.ca/Orlando-Hotels-The-Grove-Resort-Water-Park-Orlando.h4691657.Hotel-Information) ![Avanti International Resort](https://images.trvl-media.com/lodging/1000000/10000/3900/3832/b0f81967_y.jpg) ### Avanti International Resort 10/10 Excellent "yes" [](https://expedia.ca/Orlando-Hotels-Avanti-International-Resort.h3832.Hotel-Information) ![Embassy Suites by Hilton Orlando International Dr Conv Ctr](https://images.trvl-media.com/lodging/1000000/10000/7000/6905/c015e5a9_y.jpg) ### Embassy Suites by Hilton Orlando International Dr Conv Ctr 10/10 Excellent "The room was great and the pool and hot tub are awesome as well. The staff is friendly and very helpful and informative. I will stay there again when we go back." [](https://expedia.ca/Orlando-Hotels-Embassy-Suites-By-Hilton-Orlando-International-Dr-Conv-Ctr.h6905.Hotel-Information) ![Caribe Royale Orlando](https://images.trvl-media.com/lodging/1000000/50000/40900/40865/033f2fa5_y.jpg) ### Caribe Royale Orlando 10/10 Excellent "Yes" [](https://expedia.ca/Orlando-Hotels-Caribe-Royale-Orlando.h40865.Hotel-Information) ![Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando](https://images.trvl-media.com/lodging/1000000/30000/23200/23110/ade3b60d_y.jpg) ### Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando 10/10 Excellent "Perfect" [](https://expedia.ca/Orlando-Hotels-Sheraton-Vistana-Resort-Villas.h23110.Hotel-Information) ![Walt Disney World Dolphin](https://images.trvl-media.com/lodging/1000000/20000/12800/12710/a6b6c49c_y.jpg) ### Walt Disney World Dolphin 10/10 Excellent "Convenience to Epcot and Hollywood Studios will bring me back. " [](https://expedia.ca/Orlando-Hotels-Walt-Disney-World-Dolphin.h12710.Hotel-Information) ![Waldorf Astoria Orlando - An Official Walt Disney World® Hotel](https://images.trvl-media.com/lodging/3000000/2440000/2432800/2432727/0589fd64_y.jpg) ### Waldorf Astoria Orlando - An Official Walt Disney World® Hotel 10/10 Excellent "Great stay " [](https://expedia.ca/Orlando-Hotels-Waldorf-Astoria-Orlando.h2432727.Hotel-Information) ![Lake Buena Vista Resort Village & Spa](https://images.trvl-media.com/lodging/2000000/1360000/1350900/1350864/16b6b8e7_y.jpg) ### Lake Buena Vista Resort Village & Spa 10/10 Excellent "We enjoyed our stay here. We had a 3 bwdroom suite for a very reasonable price. The rooms are a bit dated but everything was very clean. The staff was helpful and kind. It was also easy to get to everything. " [](https://expedia.ca/Orlando-Hotels-Lake-Buena-Vista-Resort-Village-Spa.h1350864.Hotel-Information) ## Find out more about Oakland ### Top reasons to visit Oakland - **Family-Friendly Activities:** Oakland offers a variety of engaging activities perfect for families, ensuring fun for all ages. - **Beautiful Outdoor Spaces:** Explore scenic locations like Oak Island, Oak Groves, and Oak Lake Beach, ideal for relaxation and recreation. - **Water Sports & Wellness:** Enjoy a mix of thrilling water sports and calming wellness centres, catering to both adventure and relaxation seekers. - **Diverse Accommodations:** Choose from family-friendly resorts and pet-friendly hotels that provide excellent amenities for a comfortable stay. - **Rich Local Culture:** Experience the inviting vibe of friendly communities and cultural excursions that highlight Oakland's natural beauty. ### Find great hotels near Oakland Experience a delightful stay in Oakland, Winter Garden, Florida, where a variety of accommodations await you. Whether you're seeking a family-friendly resort, a pet-friendly hotel, or a business-themed getaway, you'll find ideal options like the Oakland Resort, Oakwood Resort, and Oak Island Resort. Enjoy the serene atmosphere and excellent amenities that cater to every traveller's needs for an unforgettable vacation. - **[Universal's Cabana Bay Beach Resort: ](https://www.expedia.ca/Orlando-Hotels-Universals-Cabana-Bay-Beach-Resort.h5963292.Hotel-Information)** Embrace a nostalgic family vacation at Universal's Cabana Bay Beach Resort, where the vibrant retro theme sets the tone for a fun-filled getaway. Located 19.3km from Oakland, this 3.5-star hotel is perfect for families seeking adventure and entertainment. The property boasts a plethora of amenities designed for children, including a free arcade game room and complimentary cribs, ensuring a memorable stay for your little ones. Guests appreciate the family-oriented atmosphere and the resort's close proximity to Universal Studios, making it an ideal choice for thrill-seekers. - **[The Grove Resort & Water Park Orlando: ](https://www.expedia.ca/Orlando-Hotels-The-Grove-Resort-Water-Park-Orlando.h4691657.Hotel-Information)** Experience an exhilarating nature-themed vacation at The Grove Resort & Water Park Orlando, situated 20.9km from Oakland. This 4-star resort offers a splendid array of adventure sports and recreational activities, including onsite surfing, fishing, and swimming, allowing guests to immerse themselves in Florida's natural beauty. With a complimentary water park, children's games, and a dedicated kids' pool, this resort is perfect for families seeking both relaxation and excitement. Guests rave about the diversity of activities available, ensuring that every member of the family has a fantastic time. - **[DoubleTree by Hilton at the Entrance to Universal Orlando: ](https://www.expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-At-The-Entrance-To-Universal-Orlando.h5398.Hotel-Information)** Combining comfort and business facilities, the DoubleTree by Hilton at the Entrance to Universal Orlando is a welcoming 4-star hotel located 19.3km from Oakland. This hotel is perfect for families and business travellers alike, offering accessible meeting rooms and a fully-equipped business centre. Known for its LGBTQIA-friendly environment, the property also caters to children with amenities such as a pool for kids and an arcade game room. Guests appreciate the convenient location and exceptional service, making it a top choice for both leisure and work-related stays. ### Where to stay near Oakland Oakland, Florida, is a delightful destination perfect for family-friendly adventures and outdoor escapades. Nestled near beautiful lakes, it offers stunning views and a relaxing atmosphere ideal for weekend getaways. Explore the friendly local communities and indulge in excursions that highlight the area's natural beauty. With its inviting vibe and a variety of entertainment options, Oakland promises an unforgettable experience for travellers seeking both adventure and tranquility. - **[Killarney: ](https://www.expedia.ca/Killarney-Winter-Garden-Hotels.0-n6360403-0.Travel-Guide-Filter-Hotels)** Located a short 1.3km from Oakland, Killarney is a peaceful neighborhood that attracts visitors seeking outdoor activities and family-friendly experiences. With a peak in traveler arrivals during March, July, and December, the area offers numerous recreational opportunities including golf courses and resorts. The proximity to local landmarks such as a theme park and a picturesque lake adds to its charm, making it an ideal spot for those who enjoy a blend of sports and nature. - **[Winter Garden: ](https://www.expedia.ca/Winter-Garden-Hotels.d7898.Travel-Guide-Hotels)** As a city that encompasses Oakland, Winter Garden boasts a vibrant atmosphere perfect for families and those looking for themed entertainment. Peak visitor seasons occur in January to February and September, with a variety of shopping areas and malls available for exploration. Notable attractions include a nearby theme park and film studio, providing an exciting backdrop for your vacation. Whether you're in the mood for business or leisure, Winter Garden has something to offer everyone. - **[Reavills Corner: ](https://www.expedia.ca/Reavills-Corner-Hotels.d6188540.Travel-Guide-Hotels)** Situated 4.8km from Oakland, Reavills Corner is a quaint village that offers a unique blend of outdoor activities and entertainment options for families. With traveler numbers peaking in March, July, and December, visitors can enjoy local resorts, shopping areas, and educational activities. The village is conveniently located near stunning beaches and theme parks, making it a perfect destination for a fun-filled day with loved ones. The welcoming community atmosphere adds to the charm of this hidden gem. ### Things to do near Oakland Oakland, Florida, offers a delightful mix of family-friendly activities and outdoor adventures. Visitors can explore nearby resorts, enjoy shopping at local malls, and partake in various recreational programs. For those seeking relaxation with a hint of excitement, water sports and wellness centres provide the perfect balance. Whether you’re looking to unwind or engage in fun activities, Oakland has something for everyone. **Shopping** [Flamingo Crossings Town Center](https://www.expedia.ca/Flamingo-Crossings-Town-Center-Hotels.0-l863361053793378304-0.Travel-Guide-Filter-Hotels), 19.3km from Oakland, offers a lively atmosphere with diverse shopping options. [Clermont Regal Shopping Center](https://www.expedia.ca/Clermont-Regal-Shopping-Center-Hotels.0-l553248621563219994-0.Travel-Guide-Filter-Hotels), 9.7km away, is perfect for family outings. [Westgate Square Shopping Center](https://www.expedia.ca/Westgate-Square-Shopping-Center-Hotels.0-l553248621563220175-0.Travel-Guide-Filter-Hotels), located 17.7km from Oakland, combines entertainment and shopping for a fun day out. **Recreation** At [Camping World Stadium](https://www.expedia.ca/Camping-World-Stadium-Hotels.0-l502139-0.Travel-Guide-Filter-Hotels), immerse yourself in the vibrant sports atmosphere and enjoy exciting events. [Disney's Palm Golf Course](https://www.expedia.ca/Disneys-Palm-Golf-Course-Hotels.0-l6069339-0.Travel-Guide-Filter-Hotels) offers a scenic outdoor experience for golf enthusiasts, while [Windermere Country Club](https://www.expedia.ca/Windermere-Country-Club-Hotels.0-l6189616-0.Travel-Guide-Filter-Hotels) provides a luxurious retreat with upscale amenities for relaxation and leisure. **Adventure** [Universal’s Volcano Bay](https://www.expedia.ca/Universals-Volcano-Bay-Hotels.0-l553248633507645899-0.Travel-Guide-Filter-Hotels), 19.3km from Oakland, offers thrilling water rides and fun for the whole family amidst a tropical setting. For a scenic hike, explore the [West Orange Trail](https://www.expedia.ca/West-Orange-Trail-Hotels.0-l553248621532653939-0.Travel-Guide-Filter-Hotels), located 4.8km away, where you can enjoy picturesque views and outdoor adventures. Experience water sports at [Watertoyz of Clermont](https://www.expedia.ca/Watertoyz-Of-Clermont-Hotels.0-l553248621532653925-0.Travel-Guide-Filter-Hotels), 12.9km from Oakland, perfect for those seeking excitement on the water. **Nightlife** In Oakland, [The Orlando Eye at ICON Park](https://www.expedia.ca/The-Orlando-Eye-At-ICON-Park-Hotels.0-l553248621565183042-0.Travel-Guide-Filter-Hotels) offers stunning views on a ferris wheel, perfect for an adventurous night. For arcade fun, head to [Carter Family Bowl](https://www.expedia.ca/Carter-Family-Bowl-Hotels.0-l553248621532653935-0.Travel-Guide-Filter-Hotels), while the [Garden Theatre](https://www.expedia.ca/Garden-Theatre-Hotels.0-l553248621532653937-0.Travel-Guide-Filter-Hotels) provides a cultural experience with its romantic and family-friendly shows, all within a short distance. \*Distances are measured in a straight line; actual driving distances may vary depending on the route. ### Booking tips and Expedia advantages for Oakland For a budget-friendly trip to Oakland, consider visiting during the cheaper months of August, September, or November. Book your hotel about a month in advance to snag the best deals, especially on Tuesdays, the least expensive day to stay. Use Expedia’s search tool to filter options by budget and sort by price for special offers. Don't forget to explore free activities and combine your hotel, flights, and activities for additional savings. Lastly, keep an eye out for last-minute deals to maximize your budget while enjoying your stay in Oakland. - **The most and least expensive months on average to stay in a hotel:** The cheapest months to stay around Oakland are August to September and November, where the prices are slightly lower. This is in comparison to March to April and December, where prices are slightly higher. - **The best time to book a hotel:** The cheapest time to book a hotel around Oakland is usually 1 month out from when you are planning to stay, though if you're late to the party, have a look at Expedia's last minute deals - the green banner below the hotel's price indicates a discounted rate. - **The most and least expensive days on average to stay in a hotel:** The least expensive day to stay around Oakland is Tuesday. The most expensive day to stay around Oakland is Saturday. - **Find cheap hotels on Expedia:** Utilize Expedia’s search tool to refine your options based on your budget, desired location, and preferred type of accommodation. To discover the most affordable prices and special offers, sort the price filter from lowest to highest. - **Consider bundling your trip:** You can save money by combining your hotel stay in Oakland with your flights and activities through an Expedia package. ### Find the best attractions near Oakland Oakland, Winter Garden, Florida, offers a delightful vacation for families and outdoor enthusiasts. With attractions like theme parks, golf courses, and arts centres, there's something for everyone. Explore scenic spots such as Oak Island, Oak Groves, and Oak Lake Beach, along with historic seaside resorts. Whether seeking entertainment or cultural experiences, Oakland is the perfect destination for a memorable getaway. - **[Walt Disney World® Resort: ](https://www.expedia.ca/Walt-Disney-World-Resort-Hotels.0-l6034120-0.Travel-Guide-Filter-Hotels)** Experience the magic of this iconic theme park, located 16.1km from Oakland. With enchanting rides, beloved characters, and spectacular shows, it’s a family-friendly destination that promises fun for all ages. - **[Orange County Convention Center: ](https://www.expedia.ca/Orange-County-Convention-Center-Hotels.0-l6034972-0.Travel-Guide-Filter-Hotels)** Situated 20.9km away, this arts centre is a hub of culture and creativity. Enjoy a variety of art exhibitions, performances, and events that showcase local and international talent in a vibrant atmosphere. - **[Universal CityWalk: ](https://www.expedia.ca/Universal-CityWalk-Hotels.0-l6154318-0.Travel-Guide-Filter-Hotels)** Just 19.3km from Oakland, this bustling tourist precinct offers outdoor entertainment, dining, and shopping. Enjoy lively nightlife and family-friendly activities, making it a perfect spot to unwind after a day of exploration. ### Best time to go to Oakland The best time to visit Oakland can depend on the weather and when visitor numbers rise and fall. The hottest average temperature around Oakland falls in August, when visitor numbers are slightly low and weather is mostly sunny with moderate rain. The coolest average temperature around Oakland falls in January, visitor numbers are slightly high and weather is mostly sunny with light rain. | **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | ---------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------- | ------------------------------------------------------------------------------------------------------------- | | January | 59.9°F (15.5°C) | Light Rain | Mostly Sunny | Slightly High | Average | | February | 63.9°F (17.7°C) | Light Rain | Mostly Sunny | Slightly High | Average | | March | 67.3°F (19.6°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High | | April | 72.5°F (22.5°C) | Light Rain | Mostly Sunny | Average | Slightly High | | May | 77.2°F (25.1°C) | Light Rain | Mostly Sunny | Average | Average | | June | 81.0°F (27.2°C) | Moderate Rain | Mostly Sunny | Average | Average | | July | 82.4°F (28.0°C) | Moderate Rain | Mostly Sunny | Average | Average | | August | 82.6°F (28.1°C) | Moderate Rain | Mostly Sunny | Slightly Low | Slightly Low | | September | 80.2°F (26.8°C) | Moderate Rain | Mostly Sunny | Average | Slightly Low | | October | 74.8°F (23.8°C) | Light Rain | Mostly Sunny | Slightly Low | Average | | November | 67.8°F (19.9°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low | | December | 63.7°F (17.6°C) | Light Rain | Mostly Sunny | Average | Slightly High | ### The nearest major airports for your trip to Oakland When visiting Oakland, Winter Garden, Florida, the major airports to consider are Orlando International Airport ([MCO](https://www.expedia.ca/Orlando-Intl-Airport-Hotels.0-aMCO-0.Travel-Guide-Filter-Hotels)) and Kissimmee Gateway Airport ([ISM](https://www.expedia.ca/Kissimmee-Gateway-Airport-Hotels.0-aISM-0.Travel-Guide-Filter-Hotels)). MCO is situated 35.4km from Oakland, with nearby hotels like [The Ritz-Carlton Orlando](https://www.expedia.ca/Orlando-Hotels-The-Ritz-Carlton-Orlando.h914146.Hotel-Information), Grande Lakes and [Hyatt Regency Orlando](https://www.expedia.ca/Orlando-Hotels-Hyatt-Regency-Orlando.h9574.Hotel-Information) offering shuttle services. Alternatively, ISM is also 35.4km away, featuring luxury hotels such as Waldorf Astoria Orlando and [Conrad Orlando at Evermore](https://www.expedia.ca/Orlando-Hotels-Conrad-Orlando.h90603710.Hotel-Information), which provide convenient transportation options to the airport. For those travelling from Daytona Beach, Daytona Beach International Airport ([DAB](https://www.expedia.ca/Daytona-Beach-Intl-Airport-Hotels.0-aDAB-0.Travel-Guide-Filter-Hotels)) is located 90.1km from Oakland, with several hotels close by, including the [Hilton Daytona Beach Oceanfront Resort](https://www.expedia.ca/Daytona-Beach-Hotels-Hilton-Daytona-Beach-Oceanfront-Resort.h5244.Hotel-Information). ## Frequently asked questions ### What are the best family hotels in Oakland? ### What are the most romantic hotels in Oakland for couples? ### Can I cancel my hotel reservation on Expedia? ### How can I save on a Oakland hotel booking with Expedia? ### How much is the nightly rate at a Oakland hotel? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [Bay Hill Hotels ](https://www.expedia.ca/Bay-Hill-Orlando-Hotels.0-n553248635975849893-0.Travel-Guide-Filter-Hotels) - [Hotels near Bella Collina Golf Club ](https://www.expedia.ca/Bella-Collina-Golf-Club-Hotels.0-l6238991-0.Travel-Guide-Filter-Hotels) - [Hotels near Central Florida Railroad Museum ](https://www.expedia.ca/Central-Florida-Railroad-Museum-Hotels.0-l553248621561885339-0.Travel-Guide-Filter-Hotels) - [Clarcona Hotels ](https://www.expedia.ca/Clarcona-Apopka-Hotels.0-n89774-0.Travel-Guide-Filter-Hotels) - [Clermont Hotels ](https://www.expedia.ca/Clermont-Hotels.d7484.Travel-Guide-Hotels) - [Ferndale Hotels ](https://www.expedia.ca/Ferndale-Hotels.d6360401.Travel-Guide-Hotels) - [Hotels near Forest Lake Golf Club ](https://www.expedia.ca/Forest-Lake-Golf-Club-Hotels.0-l553248621532654264-0.Travel-Guide-Filter-Hotels) - [Gotha Hotels ](https://www.expedia.ca/Gotha-Hotels.d109623.Travel-Guide-Hotels) - [Hotels near Hancock Park ](https://www.expedia.ca/Hancock-Park-Hotels.0-l553248621563219991-0.Travel-Guide-Filter-Hotels) - [Hotels near Isleworth Golf and Country Club ](https://www.expedia.ca/Isleworth-Golf-And-Country-Club-Hotels.0-l6091123-0.Travel-Guide-Filter-Hotels) - [All Inclusive Resorts and in Killarney ](https://www.expedia.ca/Killarney-Winter-Garden-Hotels-All-Inclusive-Hotel.0-n6360403-0-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Killarney ](https://www.expedia.ca/Killarney-Winter-Garden-Hotels-Boutique-Hotel.0-n6360403-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Killarney ](https://www.expedia.ca/Killarney-Winter-Garden-Hotels-Cheap-Hotels.0-n6360403-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Killarney ](https://www.expedia.ca/Killarney-Winter-Garden-Hotels-Couples-Resorts-Hotels.0-n6360403-0-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Family Hotels in Killarney ](https://www.expedia.ca/Killarney-Winter-Garden-Hotels-Family-Hotel.0-n6360403-0-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Golf Hotels in Killarney ](https://www.expedia.ca/Killarney-Winter-Garden-Hotels-Golf-Hotel.0-n6360403-0-tGolfHotel.Travel-Guide-Filter-Hotels) - [Historic Hotels in Killarney ](https://www.expedia.ca/Killarney-Winter-Garden-Hotels-Historic-Hotel.0-n6360403-0-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Killarney ](https://www.expedia.ca/Killarney-Winter-Garden-Hotels-Hotel-With-Pool.0-n6360403-0-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Hotels with Hot Tubs in Killarney ](https://www.expedia.ca/Killarney-Winter-Garden-Hotels-Hotels-With-Hot-Tubs.0-n6360403-0-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels) - [Hotels with an Indoor Pool in Killarney ](https://www.expedia.ca/Killarney-Winter-Garden-Hotels-Hotels-With-Indoor-Pool.0-n6360403-0-tHotelswithIndoorPool.Travel-Guide-Filter-Hotels) - [Hotels with Kitchenettes in Killarney ](https://www.expedia.ca/Killarney-Winter-Garden-Hotels-Hotels-With-Kitchenettes.0-n6360403-0-tHotelswithKitchenettes.Travel-Guide-Filter-Hotels) - [Lake Hotels in Killarney ](https://www.expedia.ca/Killarney-Winter-Garden-Hotels-Lake-Hotels.0-n6360403-0-tLakeHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Killarney ](https://www.expedia.ca/Killarney-Winter-Garden-Hotels-Luxury-Hotel.0-n6360403-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Marriott Hotels & Resorts in Killarney ](https://www.expedia.ca/Killarney-Winter-Garden-Hotels-Marriott-Hotels-Resorts.0-n6360403-0--bMarriottHotelsResorts.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Killarney ](https://www.expedia.ca/Killarney-Winter-Garden-Hotels-Pet-Friendly-Hotel.0-n6360403-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Killarney ](https://www.expedia.ca/Killarney-Winter-Garden-Hotels-Romantic-Hotel.0-n6360403-0-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Killarney ](https://www.expedia.ca/Killarney-Winter-Garden-Hotels-Spa-Hotel.0-n6360403-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [Hotel Wedding Venues Hotels in Killarney ](https://www.expedia.ca/Killarney-Winter-Garden-Hotels-Wedding-Hotels.0-n6360403-0-tWeddingHotels.Travel-Guide-Filter-Hotels) - [Killarney Hotels ](https://www.expedia.ca/Killarney-Winter-Garden-Hotels.0-n6360403-0.Travel-Guide-Filter-Hotels) - [Hotels near Lake Butler ](https://www.expedia.ca/Lake-Butler-Hotels.0-l6361045-0.Travel-Guide-Filter-Hotels) - [Hotels near Lake Louisa State Park ](https://www.expedia.ca/Lake-Louisa-State-Park-Hotels.0-l553248622634281986-0.Travel-Guide-Filter-Hotels) - [Hotels near Legends Golf & Country Club ](https://www.expedia.ca/Legends-Golf-Country-Club-Hotels.0-l553248621532653928-0.Travel-Guide-Filter-Hotels) - [Hotels near Magic Kingdom® Park ](https://www.expedia.ca/Magic-Kingdom-Park-Hotels.0-l6123797-0.Travel-Guide-Filter-Hotels) - [Minneola Hotels ](https://www.expedia.ca/Minneola-Hotels.d6360399.Travel-Guide-Hotels) - [Guest Houses in Montverde ](https://www.expedia.ca/Montverde-Guest-Houses.d6241597-aaGuestHouses.Travel-Guide-Accommodation) - [Beach Hotel Hotels in Montverde ](https://www.expedia.ca/Montverde-Hotels-Beach-Hotel.0-0-d6241597-tBeachHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Montverde ](https://www.expedia.ca/Montverde-Hotels-Cheap-Hotels.0-0-d6241597-tCheapHotels.Travel-Guide-Filter-Hotels) - [Golf Hotels in Montverde ](https://www.expedia.ca/Montverde-Hotels-Golf-Hotel.0-0-d6241597-tGolfHotel.Travel-Guide-Filter-Hotels) - [Green Hotels in Montverde ](https://www.expedia.ca/Montverde-Hotels-Green-Sustainable.0-0-d6241597-tGreenSustainable.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Montverde ](https://www.expedia.ca/Montverde-Hotels-Luxury-Hotel.0-0-d6241597-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Montverde Hotels ](https://www.expedia.ca/Montverde-Hotels.d6241597.Travel-Guide-Hotels) - [Inns in Montverde ](https://www.expedia.ca/Montverde-Inns.d6241597-aaInns.Travel-Guide-Accommodation) - [Resorts in Montverde ](https://www.expedia.ca/Montverde-Resort-Hotels.d6241597-aaResortHotels.Travel-Guide-Accommodation) - [Hotels near National Training Center ](https://www.expedia.ca/National-Training-Center-Hotels.0-l6129706-0.Travel-Guide-Filter-Hotels) - [Ocoee Hotels ](https://www.expedia.ca/Ocoee-Hotels.d9239.Travel-Guide-Hotels) - [Hotels near Orange County National Golf Club ](https://www.expedia.ca/Orange-County-National-Golf-Club-Hotels.0-l6239843-0.Travel-Guide-Filter-Hotels) - [Orlando Hotels ](https://www.expedia.ca/Orlando-Hotels.d178294.Travel-Guide-Hotels) - [Paradise Heights Hotels ](https://www.expedia.ca/Paradise-Heights-Hotels.d553248635975850788.Travel-Guide-Hotels) - [Hotels near Southlake Hospital ](https://www.expedia.ca/Southlake-Hospital-Hotels.0-l6238910-0.Travel-Guide-Filter-Hotels) - [Hotels near Tibet Butler Preserve ](https://www.expedia.ca/Tibet-Butler-Preserve-Hotels.0-l6239675-0.Travel-Guide-Filter-Hotels) - [Hotels near Universal Studios Florida ](https://www.expedia.ca/Universal-Studios-Florida-Hotels.0-l6049239-0.Travel-Guide-Filter-Hotels) - [Vacation Village Hotels ](https://www.expedia.ca/Vacation-Village-Clermont-Hotels.0-n553248635976472555-0.Travel-Guide-Filter-Hotels) - [Hotels near Walt Disney World® Resort ](https://www.expedia.ca/Walt-Disney-World-Resort-Hotels.0-l6034120-0.Travel-Guide-Filter-Hotels) - [Hotels near West Orange Trail ](https://www.expedia.ca/West-Orange-Trail-Hotels.0-l553248621532653939-0.Travel-Guide-Filter-Hotels) - [Windermere Hotels ](https://www.expedia.ca/Windermere-Hotels.d6085091.Travel-Guide-Hotels) - [Farmstay in Winter Garden ](https://www.expedia.ca/Winter-Garden-Agritourism.d7898-aaAgritourism.Travel-Guide-Accommodation) - [Aparthotels in Winter Garden ](https://www.expedia.ca/Winter-Garden-Apart-Hotels.d7898-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Winter Garden ](https://www.expedia.ca/Winter-Garden-Bed-And-Breakfast.d7898-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Winter Garden ](https://www.expedia.ca/Winter-Garden-Chalets.d7898-aaChalets.Travel-Guide-Accommodation) - [Guest Houses in Winter Garden ](https://www.expedia.ca/Winter-Garden-Guest-Houses.d7898-aaGuestHouses.Travel-Guide-Accommodation) - [Holiday Park Resorts in Winter Garden ](https://www.expedia.ca/Winter-Garden-Holiday-Parks.d7898-aaHolidayParks.Travel-Guide-Accommodation) - [Beach Hotel Hotels in Winter Garden ](https://www.expedia.ca/Winter-Garden-Hotels-Beach-Hotel.0-0-d7898-tBeachHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Winter Garden ](https://www.expedia.ca/Winter-Garden-Hotels-Boutique-Hotel.0-0-d7898-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Winter Garden ](https://www.expedia.ca/Winter-Garden-Hotels-Cheap-Hotels.0-0-d7898-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Winter Garden ](https://www.expedia.ca/Winter-Garden-Hotels-Couples-Resorts-Hotels.0-0-d7898-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Family Hotels in Winter Garden ](https://www.expedia.ca/Winter-Garden-Hotels-Family-Hotel.0-0-d7898-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Golf Hotels in Winter Garden ](https://www.expedia.ca/Winter-Garden-Hotels-Golf-Hotel.0-0-d7898-tGolfHotel.Travel-Guide-Filter-Hotels) - [Hotels with Early Check-in in Winter Garden ](https://www.expedia.ca/Winter-Garden-Hotels-Hotel-With-Early-Check-In.0-0-d7898-thotelwithearlycheckin.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Winter Garden ](https://www.expedia.ca/Winter-Garden-Hotels-Hotel-With-Pool.0-0-d7898-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Hotels with a Lazy River in Winter Garden ](https://www.expedia.ca/Winter-Garden-Hotels-Hotels-With-A-Lazy-River.0-0-d7898-tHotelswithaLazyRiver.Travel-Guide-Filter-Hotels) - [Hotels with Balconies in Winter Garden ](https://www.expedia.ca/Winter-Garden-Hotels-Hotels-With-Balconies.0-0-d7898-tHotelswithBalconies.Travel-Guide-Filter-Hotels) - [Hotels with Free Breakfast in Winter Garden ](https://www.expedia.ca/Winter-Garden-Hotels-Hotels-With-Free-Breakfast.0-0-d7898-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels) - [Hotels with an Indoor Pool in Winter Garden ](https://www.expedia.ca/Winter-Garden-Hotels-Hotels-With-Indoor-Pool.0-0-d7898-tHotelswithIndoorPool.Travel-Guide-Filter-Hotels) - [Hotels with Kitchenettes in Winter Garden ](https://www.expedia.ca/Winter-Garden-Hotels-Hotels-With-Kitchenettes.0-0-d7898-tHotelswithKitchenettes.Travel-Guide-Filter-Hotels) - [Lake Hotels in Winter Garden ](https://www.expedia.ca/Winter-Garden-Hotels-Lake-Hotels.0-0-d7898-tLakeHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Winter Garden ](https://www.expedia.ca/Winter-Garden-Hotels-Luxury-Hotel.0-0-d7898-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Winter Garden ](https://www.expedia.ca/Winter-Garden-Hotels-Pet-Friendly-Hotel.0-0-d7898-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Winter Garden ](https://www.expedia.ca/Winter-Garden-Hotels-Spa-Hotel.0-0-d7898-tSpaHotel.Travel-Guide-Filter-Hotels) - [Waterpark Hotels in Winter Garden ](https://www.expedia.ca/Winter-Garden-Hotels-Waterpark-Hotels.0-0-d7898-tWaterparkHotels.Travel-Guide-Filter-Hotels) - [Winter Garden Hotels ](https://www.expedia.ca/Winter-Garden-Hotels.d7898.Travel-Guide-Hotels) - [Inns in Winter Garden ](https://www.expedia.ca/Winter-Garden-Inns.d7898-aaInns.Travel-Guide-Accommodation) - [Lodges in Winter Garden ](https://www.expedia.ca/Winter-Garden-Lodges.d7898-aaLodges.Travel-Guide-Accommodation) - [Motels in Winter Garden ](https://www.expedia.ca/Winter-Garden-Motels.d7898-aaMotels.Travel-Guide-Accommodation) - [Rv Parks in Winter Garden ](https://www.expedia.ca/Winter-Garden-RV-Parks.d7898-aaRVParks.Travel-Guide-Accommodation) - [Resorts in Winter Garden ](https://www.expedia.ca/Winter-Garden-Resort-Hotels.d7898-aaResortHotels.Travel-Guide-Accommodation) - [Townhomes in Winter Garden ](https://www.expedia.ca/Winter-Garden-Townhomes.d7898-aaTownhomes.Travel-Guide-Accommodation) - [Flights to Montverde ](https://www.expedia.ca/Cheap-Flights-To-Montverde.d6241597.Travel-Guide-Flights) - [Flights to Orlando ](https://www.expedia.ca/Cheap-Flights-To-Orlando.d178294.Travel-Guide-Flights) - [Flights to Winter Garden ](https://www.expedia.ca/Cheap-Flights-To-Winter-Garden.d7898.Travel-Guide-Flights) - [Flights from Winter Garden ](https://www.expedia.ca/lp/flights/7898/flights-from-winter-garden) - [Flights from Toronto (YYZ) to Orlando (MCO) ](https://www.expedia.ca/lp/flights/yyz/mco/toronto-to-orlando) - [Bella Collina Golf Club ](https://www.expedia.ca/Bella-Collina-Golf-Club-Montverde.d6238991.Vacation-Attraction) - [Walt Disney World® Resort ](https://www.expedia.ca/Walt-Disney-World-Resort-Orlando.d6034120.Vacation-Attraction) - [Winter Garden Vacations ](https://www.expedia.ca/Winter-Garden.d7898.Destination-Travel-Guides) - [Visit Winter Garden ](https://www.expedia.ca/Winter-Garden.dx7898) - [Rental cars Orlando Intl. airport ](https://www.expedia.ca/Car-Rentals-In-Orlando-Intl.d5194573.Car-Rental-Guide) - [Car rentals near Orlando ](https://www.expedia.ca/Car-Rentals-In-Orlando.d178294.Car-Rental-Guide) - [Car rental Winter Garden ](https://www.expedia.ca/Car-Rentals-In-Winter-Garden.d7898.Car-Rental-Guide) - [Winter Garden Vacation Rentals ](https://www.expedia.ca/Winter-Garden-Vacation-Rentals.d7898.Travel-Guide-VacationRentals) - [Things to do in Winter Garden ](https://www.expedia.ca/Things-To-Do-In-Winter-Garden.d7898.Travel-Guide-Activities) - [Book Hotels in Oakland on Expedia.com ](https://www.expedia.com/Oakland-Winter-Garden-Hotels.0-n6360404-0.Travel-Guide-Filter-Hotels)