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) ![At the Oakland Preserve. Nice Boardwalk plus an animal sanctuary ](https://images.trvl-media.com/place/6360404/d013c781-9bde-4c95-8530-be7e0380ccba.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Gregg Yutko ![](https://images.trvl-media.com/place/6360404/d013c781-9bde-4c95-8530-be7e0380ccba.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 [Jan 17 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=6360404&startDate=2026-01-17&endDate=2026-01-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 18 - Jan 19](https://www.expedia.ca/Hotel-Search?regionId=6360404&startDate=2026-01-18&endDate=2026-01-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=6360404&startDate=2026-01-23&endDate=2026-01-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=6360404&startDate=2026-01-30&endDate=2026-02-01&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) ![Buffet](https://images.trvl-media.com/lodging/2000000/1470000/1460500/1460425/e9850ee8.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) ![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 (4,392 reviews) "Very nice place to stay with family. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anick CA $166 CA $187 total includes taxes & fees Jan 23 - Jan 24 [](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/d9e7d6aa.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) ![Lounge](https://images.trvl-media.com/lodging/6000000/5970000/5963300/5963292/9434d59a.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 (6,064 reviews) "Great place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Peggy CA $185 CA $208 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Orlando-Hotels-Universals-Cabana-Bay-Beach-Resort.h5963292.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) ![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) ![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) ### 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 (5,548 reviews) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephanie CA $102 CA $115 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Orlando-Hotels-Rosen-Inn-At-Pointe-Orlando.h8892.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) ![Reception](https://images.trvl-media.com/lodging/1000000/30000/23200/23110/de6f64bd.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) ![Food and drink](https://images.trvl-media.com/lodging/1000000/30000/23200/23110/90000976.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 9.2/10 Wonderful (4,337 reviews) "Great stay!" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Sylvie CA $160 CA $180 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Orlando-Hotels-Sheraton-Vistana-Resort-Villas.h23110.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/5400/5398/2a0a635b.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) ![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) ### 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 (6,908 reviews) "Great location, clean room, friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joseph CA $143 CA $160 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-At-The-Entrance-To-Universal-Orlando.h5398.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/40900/40865/075cd42b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 restaurants, breakfast, lunch, dinner served; Italian cuisine](https://images.trvl-media.com/lodging/1000000/50000/40900/40865/3d0051dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Royal Suite, 1 King Bed, Pool View](https://images.trvl-media.com/lodging/1000000/50000/40900/40865/034de12f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/40900/40865/w3836h2561x3y0-6cfb6f06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Caribe Royale Orlando [](https://www.expedia.ca/Orlando-Hotels-Caribe-Royale-Orlando.h40865.Hotel-Information) 26 km from Oakland 9.2/10 Wonderful (4,601 reviews) "Beautiful resort " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melanie CA $191 CA $275 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Orlando-Hotels-Caribe-Royale-Orlando.h40865.Hotel-Information) ![Lobby lounge](https://images.trvl-media.com/lodging/49000000/48550000/48542100/48542054/ec5c4036.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/49000000/48550000/48542100/48542054/6be4ba41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/49000000/48550000/48542100/48542054/0c88fbbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/49000000/48550000/48542100/48542054/2d27f9c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aloft Orlando Lake Buena Vista [](https://www.expedia.ca/Orlando-Hotels-Aloft-Orlando-Lake-Buena-Vista.h48542054.Hotel-Information) 22.5 km from Oakland 8.8/10 Excellent (1,943 reviews) "Super nice hotel at a great price." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Terry CA $114 CA $128 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Orlando-Hotels-Aloft-Orlando-Lake-Buena-Vista.h48542054.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) ![Property amenity](https://images.trvl-media.com/lodging/1000000/330000/327400/327322/fee6a1f5.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 (1,869 reviews) "Great hotel." ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Rory CA $158 CA $178 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Orlando-Hotels-Holiday-Inn-Express-Orlando-International-Airport.h327322.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 (2,085 reviews) "Great quick stay for a good value!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pamela CA $145 CA $163 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Orlando-Hotels-Avid-Hotels-Orlando-International-Airport.h39065095.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) ![Combined shower/tub, free toiletries, hair dryer, towels](https://images.trvl-media.com/lodging/2000000/1820000/1813900/1813900/8c29ff94.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 (3,370 reviews) "Very nice clean hotel" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Magdalena CA $79 CA $90 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/Orlando-Hotels-Seasons-Florida-Resort.h1813900.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) ![Breakfast, lunch and dinner served](https://images.trvl-media.com/lodging/1000000/20000/19600/19535/c2c15966.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) ![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) ### 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 (3,645 reviews) "Great location and staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristen CA $97 CA $157 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Orlando-Hotels-Holiday-Inn-Resort-Orlando-Lake-Buena-Vista.h19535.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/24200/24103/49c71b80.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) ### 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 (5,539 reviews) "Staff was reallyh nice and the hotel is awesome. great place to stayh. " ![Singapore](https://a.travel-assets.com/egds/marks/flags/sg.svg) Wei-Kai Victor CA $225 CA $253 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Orlando-Hotels-Drury-Plaza-Hotel-Orlando-Lake-Buena-Vista.h24103.Hotel-Information) ![2 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/34000000/33780000/33770400/33770341/c8859517.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/34000000/33780000/33770400/33770341/8be4b8c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/34000000/33780000/33770400/33770341/d80c5432.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/34000000/33780000/33770400/33770341/742ee36a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Universal's Endless Summer Resort - Dockside Inn and Suites [](https://www.expedia.ca/Orlando-Hotels-Universals-Endless-Summer-Dockside-Inn-Suites.h33770341.Hotel-Information) 19.8 km from Oakland 9.2/10 Wonderful (5,074 reviews) "Excellent resort, clean, friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carolina CA $207 CA $233 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Orlando-Hotels-Universals-Endless-Summer-Dockside-Inn-Suites.h33770341.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/48000000/47050000/47041400/47041344/0c7cf300.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 (3,745 reviews) "Great location and hotel for the price " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rose Marie CA $124 CA $140 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Orlando-Hotels-Tru-By-Hilton-Orlando-Convention-Center-Area.h47041344.Hotel-Information) ![Suite, 2 Queen Beds](https://images.trvl-media.com/lodging/1000000/460000/455400/455359/13049557.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Laptop workspace, blackout drapes, iron/ironing board, cribs/infant beds](https://images.trvl-media.com/lodging/1000000/460000/455400/455359/ed9eb5b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/460000/455400/455359/91158b64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/460000/455400/455359/w3836h2560x4y4-812a7872.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sonesta Essential Orlando Airport [](https://www.expedia.ca/Orlando-Hotels-Sonesta-Essential-Orlando.h455359.Hotel-Information) 29.4 km from Oakland 8.0/10 Very good (390 reviews) "Room was clean and staff was friendly and helpful" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tatiana Francine CA $105 CA $118 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Orlando-Hotels-Sonesta-Essential-Orlando.h455359.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/48000000/47040000/47032500/47032414/19cc3c4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/48000000/47040000/47032500/47032414/6f19544c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/48000000/47040000/47032500/47032414/f16a931e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/48000000/47040000/47032500/47032414/c5c46907.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wyndham Garden Orlando Universal / I Drive [](https://www.expedia.ca/Orlando-Hotels-Wyndham-Garden-Orlando-Universal-I-Drive.h47032414.Hotel-Information) 19.7 km from Oakland 9.4/10 Exceptional (1,944 reviews) "Clean, friendly staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Timothy CA $159 CA $179 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Orlando-Hotels-Wyndham-Garden-Orlando-Universal-I-Drive.h47032414.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/2000000/1760000/1759600/1759572/2ab817e2.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) ![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) ### Meliá Orlando Celebration [](https://www.expedia.ca/Orlando-Hotels-Melia-Orlando-Celebration.h1759572.Hotel-Information) 26.5 km from Oakland 8.6/10 Excellent (1,576 reviews) "Very nice property, clean, with a lot of amenities, we will be back for sure!!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Licet CA $129 CA $197 total includes taxes & fees Feb 2 - Feb 3 [](https://www.expedia.ca/Orlando-Hotels-Melia-Orlando-Celebration.h1759572.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/1000000/10000/4000/3916/627a379d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/4000/3916/eda24b1d.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) ### 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 (4,038 reviews) "I enjoyed my stay and plan to be back soon" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paula CA $93 CA $133 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Orlando-Hotels-Avanti-Palms-Resort-And-Conference-Center.h3916.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/14800/14701/f253be82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/20000/14800/14701/7162505a.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 (5,160 reviews) "Great breakfast Clean rooms Close to all attractions Gated hotel for privacy Beautiful lake and park for the kids " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leslie CA $69 CA $125 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Orlando-Hotels-Palazzo-Lakeside.h14701.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) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/1300/1264/8d8806c0.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 (5,627 reviews) "Great property to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deepankar CA $104 CA $118 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Orlando-Hotels-Rosen-Inn-Lake-Buena-Vista.h1264.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=2026-01-31&endDate=2026-02-01®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 Island H2O Live! 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 ![Orlando International Drive North Hotel](https://images.trvl-media.com/lodging/1000000/50000/41500/41493/d062739a_y.jpg) ### Orlando International Drive North Hotel 10/10 Excellent "Clean room and very nice outdoor space for groups or just anyone to relax and hang out. A cheap and quick uber ride to the universal parks. Breakfast is what you would expect for the price- get there early to avoid the lines " [](https://expedia.ca/Orlando-Hotels-Orlando-International-Drive-North-Hotel.h41493.Hotel-Information) ![Westgate Lakes Resort & Spa Universal Studios Area](https://images.trvl-media.com/lodging/1000000/810000/805000/804984/86e77c07_y.jpg) ### Westgate Lakes Resort & Spa Universal Studios Area 10/10 Excellent "Room spotless, staff were amazing and very helpful. " [](https://expedia.ca/Orlando-Hotels-Westgate-Lakes-Resort-Spa-Universal-Studios-Area.h804984.Hotel-Information) ![Spark by Hilton Orlando near Universal](https://images.trvl-media.com/lodging/1000000/20000/16000/15927/5cf8836a_y.jpg) ### Spark by Hilton Orlando near Universal 10/10 Excellent "The stay at Spark by Hilton Orlando near Universal was delightful. Upon entry into the hotel, I was warmly greeted by staff and was met with a tranquil environment. The room had an enchanting atmosphere, making my stay incredible." [](https://expedia.ca/Orlando-Hotels-Spark-By-Hilton-Orlando-Near-Universal.h15927.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 "Loved our stay- rooms are clean and amazing space" [](https://expedia.ca/Orlando-Hotels-The-Grove-Resort-Water-Park-Orlando.h4691657.Hotel-Information) ![Kompose Boutique Resort at Theme Parks](https://images.trvl-media.com/lodging/101000000/100840000/100837800/100837786/3cf09a4a_y.jpg) ### Kompose Boutique Resort at Theme Parks 10/10 Excellent "Amazingly clean hotel and room. Very nice front desk agent. Excellent breakfast! Definitely plan on returning." [](https://expedia.ca/Orlando-Hotels-Kompose-Boutique-Resort-At-Theme-Parks.h100837786.Hotel-Information) ![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) ![DoubleTree by Hilton at the Entrance to Universal Orlando](https://images.trvl-media.com/lodging/1000000/10000/5400/5398/4997b5df_y.jpg) ### DoubleTree by Hilton at the Entrance to Universal Orlando 10/10 Excellent "Everything was amazing- the room, the staff the overall experience " [](https://expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-At-The-Entrance-To-Universal-Orlando.h5398.Hotel-Information) ![Walt Disney World Swan](https://images.trvl-media.com/lodging/1000000/10000/9800/9711/a789d7e5_y.jpg) ### Walt Disney World Swan 10/10 Excellent "Total package! Clean, inviting hotel. Friendly staff. Great food options. Perfect location. Easy, quick check in! " [](https://expedia.ca/Orlando-Hotels-Walt-Disney-World-Swan.h9711.Hotel-Information) ![Universal's Endless Summer Resort - Dockside Inn and Suites](https://images.trvl-media.com/lodging/34000000/33780000/33770400/33770341/c8859517_y.jpg) ### Universal's Endless Summer Resort - Dockside Inn and Suites 10/10 Excellent "Breakfast was not free." [](https://expedia.ca/Orlando-Hotels-Universals-Endless-Summer-Dockside-Inn-Suites.h33770341.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) - 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