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) ![](https://images.trvl-media.com/place/6360403/5cbd79a8-2e61-4cef-8769-e792f96b305a.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 [Feb 5 - Feb 6](https://www.expedia.ca/Hotel-Search?regionId=6360404&startDate=2026-02-05&endDate=2026-02-06&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 6 - Feb 7](https://www.expedia.ca/Hotel-Search?regionId=6360404&startDate=2026-02-06&endDate=2026-02-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=6360404&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=6360404&startDate=2026-02-13&endDate=2026-02-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Recommended Price (low to high) Distance Star rating ## Our top choices for Oakland hotels ![Reception](https://images.trvl-media.com/lodging/101000000/100840000/100837800/100837786/81e6b4c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/101000000/100840000/100837800/100837786/6e9ade0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/101000000/100840000/100837800/100837786/e1b28117.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sauna](https://images.trvl-media.com/lodging/101000000/100840000/100837800/100837786/9705bd68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kompose Boutique Resort at Theme Parks [](https://www.expedia.ca/Orlando-Hotels-Kompose-Boutique-Resort-At-Theme-Parks.h100837786.Hotel-Information) 24.9 km from Oakland 9.4/10 Exceptional (2,611 reviews) "amazing place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) caleb CA $85 CA $151 total includes taxes & fees Feb 6 - Feb 7 [](https://www.expedia.ca/Orlando-Hotels-Kompose-Boutique-Resort-At-Theme-Parks.h100837786.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) ![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) ![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) ![5 restaurants, breakfast, lunch, dinner served; Italian cuisine](https://images.trvl-media.com/lodging/1000000/50000/40900/40865/ed3e2ef0.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 (4,690 reviews) "Great resort " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Samuel CA $171 CA $251 total includes taxes & fees Feb 7 - Feb 8 [](https://www.expedia.ca/Orlando-Hotels-Caribe-Royale-Orlando.h40865.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) ![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) ![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) ![Property amenity](https://images.trvl-media.com/lodging/1000000/460000/455400/455359/w3836h2560x4y4-13f194ee.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 (503 reviews) "great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ibrahim CA $119 CA $134 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Orlando-Hotels-Sonesta-Essential-Orlando.h455359.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) ![Restaurant](https://images.trvl-media.com/lodging/32000000/31950000/31941500/31941472/32572eec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/32000000/31950000/31941500/31941472/ac9ae7dd.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) ### 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 (1,507 reviews) "Great place to stay and great amenities" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Darshan CA $165 CA $186 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Orlando-Hotels-Hyatt-House-Orlando-International-Drive.h31941472.Hotel-Information) ![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) ![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) ![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) ### Rosen Shingle Creek [](https://www.expedia.ca/Orlando-Hotels-Rosen-Shingle-Creek.h1460425.Hotel-Information) 24.2 km from Oakland 9.4/10 Exceptional (4,465 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 Mar 6 - Mar 7 [](https://www.expedia.ca/Orlando-Hotels-Rosen-Shingle-Creek.h1460425.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/5400/5398/2a0a635b.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 (6,910 reviews) "Very nice hotel" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) XIAOLAN CA $158 CA $178 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-At-The-Entrance-To-Universal-Orlando.h5398.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) ![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) ![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) ![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) ### 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 (3,710 reviews) "Very nice staff ,clean rooms" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Luis CA $97 CA $155 total includes taxes & fees Mar 4 - Mar 5 [](https://www.expedia.ca/Orlando-Hotels-Holiday-Inn-Resort-Orlando-Lake-Buena-Vista.h19535.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/30000/24000/23965/698d5998.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/24000/23965/b2867366.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/1000000/30000/24000/23965/w5616h3741x0y0-9981df3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/24000/23965/15ac33c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Place Orlando/Lake Buena Vista [](https://www.expedia.ca/Orlando-Hotels-Hyatt-Place-OrlandoLake-Buena-Vista.h23965.Hotel-Information) 22.6 km from Oakland 8.4/10 Very good (1,479 reviews) "Nice hotel, fast check-in love it" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Yuberka CA $149 CA $168 total includes taxes & fees Feb 10 - Feb 11 [](https://www.expedia.ca/Orlando-Hotels-Hyatt-Place-OrlandoLake-Buena-Vista.h23965.Hotel-Information) ![4 outdoor pools, open 7:00 AM to 11:00 PM, cabanas (surcharge)](https://images.trvl-media.com/lodging/1000000/860000/853600/853519/w4000h2662x0y0-7b7256af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/860000/853600/853519/718c25b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/1000000/860000/853600/853519/48c854e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/860000/853600/853519/bb132b7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Marriott's Grande Vista [](https://www.expedia.ca/Orlando-Hotels-Marriotts-Grande-Vista.h853519.Hotel-Information) 24.8 km from Oakland 9.0/10 Wonderful (3,857 reviews) "Great stay" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Lina CA $174 CA $196 total includes taxes & fees Feb 25 - Feb 26 [](https://www.expedia.ca/Orlando-Hotels-Marriotts-Grande-Vista.h853519.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) ![Lounge](https://images.trvl-media.com/lodging/6000000/5970000/5963300/5963292/9434d59a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/6000000/5970000/5963300/5963292/09c3f299.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 (6,261 reviews) "Great spot for families." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lyndon CA $186 CA $209 total includes taxes & fees Feb 10 - Feb 11 [](https://www.expedia.ca/Orlando-Hotels-Universals-Cabana-Bay-Beach-Resort.h5963292.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) ![2 outdoor pools, open 8:00 AM to 11:00 PM, cabanas (surcharge)](https://images.trvl-media.com/lodging/1000000/60000/52900/52821/ee39e243.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, cabanas (surcharge)](https://images.trvl-media.com/lodging/1000000/60000/52900/52821/9c8d7a65.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) 24.6 km from Oakland 8.4/10 Very good (1,277 reviews) "Clean room, good price and staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacob CA $91 CA $131 total includes taxes & fees Feb 25 - Feb 26 [](https://www.expedia.ca/Orlando-Hotels-Holiday-Inn-Resort-Kissimmee-By-The-Parks-By-IHG.h52821.Hotel-Information) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/62000000/61350000/61340900/61340843/2b752fc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/62000000/61350000/61340900/61340843/92f137bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/62000000/61350000/61340900/61340843/d5a68d29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, open 8:00 AM to 11:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/62000000/61350000/61340900/61340843/dd1719a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center [](https://www.expedia.ca/Orlando-Hotels-Fairfield-Inn-Suites-By-Marriott-Orlando-Flamingo-CrossingWestern-Entrance.h61340843.Hotel-Information) 19.3 km from Oakland 9.4/10 Exceptional (4,499 reviews) "Amazing room and great breakfasts for the price " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christian CA $158 CA $178 total includes taxes & fees Mar 3 - Mar 4 [](https://www.expedia.ca/Orlando-Hotels-Fairfield-Inn-Suites-By-Marriott-Orlando-Flamingo-CrossingWestern-Entrance.h61340843.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/49000000/48550000/48542100/48542054/0c88fbbb.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/49000000/48550000/48542100/48542054/59b49068.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 (1,962 reviews) "Super nice hotel at a great price." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Terry CA $123 CA $138 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Orlando-Hotels-Aloft-Orlando-Lake-Buena-Vista.h48542054.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/59000000/58080000/58072600/58072517/08ef9167.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![42-inch flat-screen TV with satellite channels, TV](https://images.trvl-media.com/lodging/59000000/58080000/58072600/58072517/c91cd6b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, open 9:00 AM to 10:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/59000000/58080000/58072600/58072517/w3837h2557x0y0-c7800382.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/59000000/58080000/58072600/58072517/ccd30aed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home2 Suites by Hilton Orlando at Flamingo Crossings [](https://www.expedia.ca/Orlando-Hotels-Home2-Suites-By-Hilton-Orlando-Flamingo-Crossings.h58072517.Hotel-Information) 19.2 km from Oakland 9.2/10 Wonderful (5,240 reviews) "great place to stay nearest to all location ." ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) VIMAL CA $146 CA $164 total includes taxes & fees Mar 3 - Mar 4 [](https://www.expedia.ca/Orlando-Hotels-Home2-Suites-By-Hilton-Orlando-Flamingo-Crossings.h58072517.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) ![Gazebo](https://images.trvl-media.com/lodging/1000000/50000/40600/40513/43e4c8a8.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 (3,890 reviews) "Comfy clean beds and easy check in and out. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard CA $50 CA $84 total includes taxes & fees Feb 11 - Feb 12 [](https://www.expedia.ca/Orlando-Hotels-Ramada-By-Wyndham-Kissimmee-Gateway.h40513.Hotel-Information) ![View from room](https://images.trvl-media.com/lodging/1000000/10000/8900/8892/8068a653.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/1000000/10000/8900/8892/36e35fbc.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) ![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 (5,676 reviews) "Great place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kamasha CA $105 CA $119 total includes taxes & fees Feb 11 - Feb 12 [](https://www.expedia.ca/Orlando-Hotels-Rosen-Inn-At-Pointe-Orlando.h8892.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) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1820000/1813900/1813900/1492ecfb.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) ![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 (3,411 reviews) "Great stay for the price" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $79 CA $90 total includes taxes & fees Feb 23 - Feb 24 [](https://www.expedia.ca/Orlando-Hotels-Seasons-Florida-Resort.h1813900.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/24200/24103/49c71b80.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 (5,591 reviews) "Great hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gary CA $231 CA $260 total includes taxes & fees Feb 10 - Feb 11 [](https://www.expedia.ca/Orlando-Hotels-Drury-Plaza-Hotel-Orlando-Lake-Buena-Vista.h24103.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) ![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) ![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) ![Mini-golf](https://images.trvl-media.com/lodging/1000000/30000/23200/23110/45c63d74.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 (4,508 reviews) "Room was very nice, staff helpful and great location for travelers. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nancy CA $157 CA $177 total includes taxes & fees Feb 25 - Feb 26 [](https://www.expedia.ca/Orlando-Hotels-Sheraton-Vistana-Resort-Villas.h23110.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) ![In-room safe, desk, laptop workspace, iron/ironing board](https://images.trvl-media.com/lodging/34000000/33780000/33770400/33770341/b33a5f59.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) ### 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 (5,086 reviews) "Enjoyable stay, good value, lots of buses to parks. Would stay again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicholas CA $156 CA $175 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/Orlando-Hotels-Universals-Endless-Summer-Dockside-Inn-Suites.h33770341.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=2026-02-19&endDate=2026-02-20®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://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) ![Orange sunset over distant hills on Lake Apopka near Orlando, Florida.](https://images.trvl-media.com/place/553248635976471720/1fc7b96c-c215-4476-8213-e925a1aa892e.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [](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) ![Love this tiny town, just 20 minutes from Walt Disney World. Inside #PlantStreetMarket you’ll find multiple vendors including local food, honey, coffee and desserts, and #crookedcanbrewing #wintergarden #lifeatexpedia ](https://images.trvl-media.com/place/7898/3b52e4d7-c036-43a0-acdb-0ec758a9700c.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) Photo by Shannon Maya ![March 25, 2023, Winter Garden, FL: The West Orange bicycle trail through Winter Garden, Florida](https://images.trvl-media.com/place/944538218785796096/91cceb08-bb0f-4c59-80cf-9c6369c42839.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![Great coffee shop alert! Axum Coffee in historic Winter Garden not only serves up delicious coffee roasts, flavored lattes, loose leaf teas, but also donates all of its profits to an orphanage in Axum, Ethiopia! A coffee experience that is socially conscious in word and deed.](https://images.trvl-media.com/place/7898/009b6bc5-b7ec-48a0-a990-35b53cd918b0.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) Photo by JoyFilledWander ![A great collection of organic & local products for your kitchen, bath & home. The cafe in the back is delightful, with smoothies, juices, wraps & salads all prepared fresh with as many local & organic ingredients as possible. Stop in and try the La Fiesta wrap, and grab some locally roasted coffee beans on your way out! ](https://images.trvl-media.com/place/7898/cb95c63e-1643-4fd5-9c7d-53d86c64c4a4.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) Photo by JoyFilledWander ![The Crooked Can at the Plant St market in Winter Garden, Fl](https://images.trvl-media.com/place/7898/101b44bd-bc20-4438-abce-90a5ff458dae.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) Photo by Nancy [](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) ![Panoramic view of Lake Apopka and nature Florida.](https://images.trvl-media.com/place/6360403/5cbd79a8-2e61-4cef-8769-e792f96b305a.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [](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 ![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 "Great staff. Angel was excellent" [](https://expedia.ca/Orlando-Hotels-Universals-Endless-Summer-Dockside-Inn-Suites.h33770341.Hotel-Information) ![Avanti International Resort](https://images.trvl-media.com/lodging/1000000/10000/3900/3832/b0f81967_y.jpg) ### Avanti International Resort 10/10 Excellent "Very good value. Great location. " [](https://expedia.ca/Orlando-Hotels-Avanti-International-Resort.h3832.Hotel-Information) ![Universal's Cabana Bay Beach Resort](https://images.trvl-media.com/lodging/6000000/5970000/5963300/5963292/63940f45_y.jpg) ### Universal's Cabana Bay Beach Resort 10/10 Excellent "Clear. Customer service. Transportation convenience " [](https://expedia.ca/Orlando-Hotels-Universals-Cabana-Bay-Beach-Resort.h5963292.Hotel-Information) ![Wyndham I-Drive Avanti Resort & Conference Center](https://images.trvl-media.com/lodging/1000000/10000/4000/3916/55b45a9e_y.jpg) ### Wyndham I-Drive Avanti Resort & Conference Center 10/10 Excellent "Staff was very good " [](https://expedia.ca/Orlando-Hotels-Avanti-Palms-Resort-And-Conference-Center.h3916.Hotel-Information) ![Rosen Inn at Pointe Orlando](https://images.trvl-media.com/lodging/1000000/10000/8900/8892/8068a653_y.jpg) ### Rosen Inn at Pointe Orlando 10/10 Excellent "The room was spotless" [](https://expedia.ca/Orlando-Hotels-Rosen-Inn-At-Pointe-Orlando.h8892.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 "Great cookies handed out during check in " [](https://expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-Hotel-Orlando-At-SeaWorld.h18874.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 "The condo was clean. The staff was friendly. The beds were comfortable and the coffee bar was great. Thank you so much." [](https://expedia.ca/Orlando-Hotels-Sheraton-Vistana-Resort-Villas.h23110.Hotel-Information) ![Marriott's Grande Vista](https://images.trvl-media.com/lodging/1000000/860000/853600/853519/77708f65_y.jpg) ### Marriott's Grande Vista 10/10 Excellent "Very quick and early check in, allowed late check out, clean rooms, gorgeous landscape " [](https://expedia.ca/Orlando-Hotels-Marriotts-Grande-Vista.h853519.Hotel-Information) ![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 "Staff were super friendly, especially the man at the front desk! Room was clean, no smell. Highly recommend. " [](https://expedia.ca/Orlando-Hotels-Orlando-International-Drive-North-Hotel.h41493.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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