Title: 5 Stars Hotels in Oakland, Winter Garden from CA $137 - Find Cheap Oakland Hotels With 5 Stars | Expedia.ca [Oakland Travel Guide](https://expedia.ca/Winter-Garden-Oakland.dx6360404)[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 # 5 Stars Hotels in Oakland, Winter Garden from CA $137 - ![](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 availability on Oakland 5 Star Hotels Tonight [Dec 28 - Dec 29](https://www.expedia.ca/Hotel-Search?regionId=6360404&startDate=2025-12-28&endDate=2025-12-29&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 29 - Dec 30](https://www.expedia.ca/Hotel-Search?regionId=6360404&startDate=2025-12-29&endDate=2025-12-30&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6360404&startDate=2026-01-02&endDate=2026-01-04&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=6360404&startDate=2026-01-09&endDate=2026-01-11&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Oakland 5-star hotels ![Exterior](https://images.trvl-media.com/lodging/3000000/2440000/2432800/2432727/0589fd64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/3000000/2440000/2432800/2432727/9de42c2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/3000000/2440000/2432800/2432727/d76e5658.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, 2 Queen Beds (Holiday Haven)](https://images.trvl-media.com/lodging/3000000/2440000/2432800/2432727/ab1dfef6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waldorf Astoria Orlando - An Official Walt Disney World® Hotel [](https://www.expedia.ca/Orlando-Hotels-Waldorf-Astoria-Orlando.h2432727.Hotel-Information) Orlando 9.2/10 Wonderful (431) "Great stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cheryl CA $533 CA $677 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Orlando-Hotels-Waldorf-Astoria-Orlando.h2432727.Hotel-Information) ![Outdoor pool, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/91000000/90610000/90603800/90603710/9dffefcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/91000000/90610000/90603800/90603710/10675d1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Barron Suite | View from room](https://images.trvl-media.com/lodging/91000000/90610000/90603800/90603710/5c44bf64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sports facility](https://images.trvl-media.com/lodging/91000000/90610000/90603800/90603710/fa18c89f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Conrad Orlando at Evermore [](https://www.expedia.ca/Orlando-Hotels-Conrad-Orlando.h90603710.Hotel-Information) Orlando 9.6/10 Exceptional (349) "Place was freaking amazing!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shaun CA $829 CA $1,000 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Orlando-Hotels-Conrad-Orlando.h90603710.Hotel-Information) ![3 outdoor pools, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/8000000/7380000/7374500/7374428/d1187640.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/8000000/7380000/7374500/7374428/3e74ad68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Grand Suite, 1 King Bed with Sofa bed | Living area](https://images.trvl-media.com/lodging/8000000/7380000/7374500/7374428/b73bddcf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/8000000/7380000/7374500/7374428/60c5847d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort [](https://www.expedia.ca/Orlando-Hotels-Four-Seasons-Resort-Orlando-At-WALT-DISNEY-WORLD-Resort.h7374428.Hotel-Information) Golden Oak 9.6/10 Exceptional (878) "Fantastic hotel, lovely front desk and housekeeping staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tanis CA $1,442 CA $1,700 total includes taxes & fees Jan 19 - Jan 20, 2026 [](https://www.expedia.ca/Orlando-Hotels-Four-Seasons-Resort-Orlando-At-WALT-DISNEY-WORLD-Resort.h7374428.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/1000000/920000/914200/914146/2e35acb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![7 restaurants, dinner served, American cuisine](https://images.trvl-media.com/lodging/1000000/920000/914200/914146/be002023.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Couples treatment rooms, body treatments, hot stone massages](https://images.trvl-media.com/lodging/1000000/920000/914200/914146/952e01ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Food and drink](https://images.trvl-media.com/lodging/1000000/920000/914200/914146/818ce775.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Ritz-Carlton Orlando, Grande Lakes [](https://www.expedia.ca/Orlando-Hotels-The-Ritz-Carlton-Orlando.h914146.Hotel-Information) Orlando 9.2/10 Wonderful (1001) "Great service, clean rooms, large property with many amenities . Fabulous food at highball & harvest. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) SAUL CA $812 CA $998 total includes taxes & fees Jan 18 - Jan 19, 2026 [](https://www.expedia.ca/Orlando-Hotels-The-Ritz-Carlton-Orlando.h914146.Hotel-Information) ![Outdoor pool, open 9:00 AM to 6:00 PM, free cabanas, pool umbrellas](https://images.trvl-media.com/lodging/71000000/70110000/70100300/70100240/b0dc020b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Frette Italian sheets, premium bedding, down comforters](https://images.trvl-media.com/lodging/71000000/70110000/70100300/70100240/cc2288f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/71000000/70110000/70100300/70100240/3ab1a639.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/71000000/70110000/70100300/70100240/7affaeb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ette hotel [](https://www.expedia.ca/Orlando-Hotels-Ette-Hotel.h70100240.Hotel-Information) Kissimmee 9.8/10 Exceptional (383) "Great spa!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Claudette CA $369 CA $419 total includes taxes & fees Jan 6 - Jan 7, 2026 [](https://www.expedia.ca/Orlando-Hotels-Ette-Hotel.h70100240.Hotel-Information) ![Outdoor pool, a heated pool, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/16000000/15200000/15190600/15190527/97f0e69c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Elite House, 6 Bedrooms, Private Pool (Westside) | Living area](https://images.trvl-media.com/lodging/16000000/15200000/15190600/15190527/27999263.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury House, 5 Bedrooms, Private Pool (Westside)](https://images.trvl-media.com/lodging/16000000/15200000/15190600/15190527/dd0febbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/16000000/15200000/15190600/15190527/e97da1e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Encore Resort and Water Park at Reunion by Rentyl [](https://www.expedia.ca/Orlando-Hotels-Encore-Resort-At-Reunion.h15190527.Hotel-Information) Kissimmee 8.4/10 Very good (1007) "The home rental was wonderful. The staff and amenities were great! My family and I have stayed at Encore Resort several times. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Felicia CA $340 CA $976 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Orlando-Hotels-Encore-Resort-At-Reunion.h15190527.Hotel-Information) ![3 outdoor pools](https://images.trvl-media.com/lodging/1000000/880000/871900/871864/bee84a5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Boating](https://images.trvl-media.com/lodging/1000000/880000/871900/871864/0667637b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/880000/871900/871864/2da8378b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Water View. Hearing accessible - visual alarms and notifications. 2 queen beds, 1 daybed.](https://images.trvl-media.com/lodging/1000000/880000/871900/871864/61547462.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Disney's Beach Club Resort [](https://www.expedia.ca/Orlando-Hotels-Disneys-Beach-Club-Resort.h871864.Hotel-Information) Bay Lake 9.0/10 Wonderful (697) "Very nice place to stay in Disney World resort place for vacation which has shuttle buses for every where and walking distance to EPCOT. Wonderful experience there!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Yong Hoon [](https://www.expedia.ca/Orlando-Hotels-Disneys-Beach-Club-Resort.h871864.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/51000000/50700000/50698800/50698715/501d2e5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake](https://images.trvl-media.com/lodging/51000000/50700000/50698800/50698715/efebbeb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 2 Bedrooms | Living room](https://images.trvl-media.com/lodging/51000000/50700000/50698800/50698715/37c2a9ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 2 Bedrooms | Balcony](https://images.trvl-media.com/lodging/51000000/50700000/50698800/50698715/e31e29cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gorgeous Two Bedroom Apt Close to Disney 306 4721 @Storey Lake Resort [](https://www.expedia.ca/Orlando-Hotels-306-Storey-Lake-Resort.h50698715.Hotel-Information) Kissimmee 8.4/10 Very good (10) "The complex was nice and very nice clean rooms, the water park was nice and huge. Definitely would visit again " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Vernon [](https://www.expedia.ca/Orlando-Hotels-306-Storey-Lake-Resort.h50698715.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/39000000/38820000/38814300/38814230/48f41cfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier Villa, Multiple Bedrooms | Living area](https://images.trvl-media.com/lodging/39000000/38820000/38814300/38814230/39c2ad6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier Villa, Multiple Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/39000000/38820000/38814300/38814230/9031cd18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier Villa, Multiple Bedrooms | Terrace/patio](https://images.trvl-media.com/lodging/39000000/38820000/38814300/38814230/b683aa14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Bear's Den Resort Orlando [](https://www.expedia.ca/Orlando-Hotels-The-Bears-Den-At-Reunion.h38814230.Hotel-Information) Reunion 8.0/10 Very good (22) "Great place , I recommend it to everyone." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacqueline [](https://www.expedia.ca/Orlando-Hotels-The-Bears-Den-At-Reunion.h38814230.Hotel-Information) ![Water park](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852277/5137ee9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852277/982258fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exclusive Apartment | Terrace/patio](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852277/061ee8cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exclusive Apartment | Private kitchen](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852277/eb0d33b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gorgeous 2Bd Apto Close to Disney @ Storey Lake 404 3191 [](https://www.expedia.ca/Orlando-Hotels-Gorgeous-2Bd-Apto-Close-To-Disney-Storey-Lake-404-3191.h95852277.Hotel-Information) Kissimmee 10/10 Exceptional (4) "Parking was easy." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maria Belen [](https://www.expedia.ca/Orlando-Hotels-Gorgeous-2Bd-Apto-Close-To-Disney-Storey-Lake-404-3191.h95852277.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/78000000/77970000/77964100/77964063/c95b3e81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/78000000/77970000/77964100/77964063/4d8782e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Apartment, 2 Bedrooms | Living area](https://images.trvl-media.com/lodging/78000000/77970000/77964100/77964063/c2384133.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Apartment, 2 Bedrooms | In-room dining](https://images.trvl-media.com/lodging/78000000/77970000/77964100/77964063/e3a76a86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stunning 2 Bd Condo Close to Disney 304 3191 [](https://www.expedia.ca/Orlando-Hotels-304-3191-Storey-Lake-Resort-2Bd-7G.h77964063.Hotel-Information) Kissimmee 6.6/10 (4) "The Place Awesome it was a family trip we had great time my 2 kids love the Pool, the Lazy river. they love the hold place. places are not far from Condo. Great communication they always was checking if we needed anything it was great. Thank You " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gema [](https://www.expedia.ca/Orlando-Hotels-304-3191-Storey-Lake-Resort-2Bd-7G.h77964063.Hotel-Information) ![2 outdoor pools, free cabanas, pool umbrellas](https://images.trvl-media.com/lodging/85000000/84150000/84149300/84149201/3c13b724.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo | Private kitchen](https://images.trvl-media.com/lodging/85000000/84150000/84149300/84149201/e1bdf2b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo | Terrace/patio](https://images.trvl-media.com/lodging/85000000/84150000/84149300/84149201/71fb362d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 outdoor pools, free cabanas, pool umbrellas](https://images.trvl-media.com/lodging/85000000/84150000/84149300/84149201/a1b00489.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxurious 2 Bd Close to Disney @ Storey Lake 204 3131 [](https://www.expedia.ca/Orlando-Hotels-204-3131-Storey-Lake-Resort-2Bd-7G-106454.h84149201.Hotel-Information) Kissimmee 10/10 Exceptional (4) "It was a clean and nice " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Danielle [](https://www.expedia.ca/Orlando-Hotels-204-3131-Storey-Lake-Resort-2Bd-7G-106454.h84149201.Hotel-Information) ![Townhome, 4 Bedrooms | Private pool](https://images.trvl-media.com/lodging/51000000/50700000/50699000/50698993/940c608b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Townhome, 4 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/51000000/50700000/50699000/50698993/e5237c4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Townhome, 4 Bedrooms | In-room dining](https://images.trvl-media.com/lodging/51000000/50700000/50699000/50698993/e0fdae0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Townhome, 4 Bedrooms | Living area](https://images.trvl-media.com/lodging/51000000/50700000/50699000/50698993/57355d06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gorgeous 4 Bedroom w/ Pool Close to Disney 4836 [](https://www.expedia.ca/Orlando-Hotels-4836-Storey-Lake-Resort-77279-77290.h50698993.Hotel-Information) Kissimmee 9.2/10 Wonderful (13) "Clean, loved the pool" ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Stuart [](https://www.expedia.ca/Orlando-Hotels-4836-Storey-Lake-Resort-77279-77290.h50698993.Hotel-Information) ![Water park](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852285/66383de6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Water park](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852285/3e6b6ce2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852285/b410ba4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exclusive House | Children's theme room](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852285/0bebd815.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gorgeous 4Bd with Pool @ Storey Lake Resort 4475 [](https://www.expedia.ca/Orlando-Hotels-Gorgeous-4Bd-With-Pool-At-Storey-Lake-Resort-4475.h95852285.Hotel-Information) Kissimmee 7.6/10 Good (5) "First off the house was not clean. It was only clean where a vacuum can fit. Behind all toilets was dirty, every shower had hair from previous guests. We have a three year old so we were in a rush to leave to get on our cruise and left behind our iPad. We wrote and apparently a cleaner took over two days to get to the house to only come back and say there was no iPad. Security didn’t even ask for ID. The back gate is open to let anyone just enter. Would never stay here again. Didn’t feel clean... ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Shawnte [](https://www.expedia.ca/Orlando-Hotels-Gorgeous-4Bd-With-Pool-At-Storey-Lake-Resort-4475.h95852285.Hotel-Information) ![Water park](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852274/da283eae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Golf view](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852274/1fafff68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852274/304dd1fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852274/f6e99720.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family Friendly 2 Bd Close to Disney @ Champions Gate 8899 [](https://www.expedia.ca/Orlando-Hotels-Family-Friendly-2-Bd-Close-To-Disney-Champions-Gate-8899.h95852274.Hotel-Information) Davenport 8.6/10 Excellent (8) "They kept in contact the whole time we stayed with them. They responded to any questions promptly." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tiffany [](https://www.expedia.ca/Orlando-Hotels-Family-Friendly-2-Bd-Close-To-Disney-Champions-Gate-8899.h95852274.Hotel-Information) ![Water park](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852300/cb2dc650.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Resort view](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852300/a7d356dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exclusive House | Living room](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852300/db2ebe45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Laundry](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852300/283123bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Splendid 5Bd Close to Disney at Storey Lake 4251 [](https://www.expedia.ca/Orlando-Hotels-Splendid-5Bd-Close-To-Disney-At-Storey-Lake-4251.h95852300.Hotel-Information) Kissimmee 9.2/10 Wonderful (12) "Home was great super clean and very cozy and comfortable. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ubeiman [](https://www.expedia.ca/Orlando-Hotels-Splendid-5Bd-Close-To-Disney-At-Storey-Lake-4251.h95852300.Hotel-Information) ![Water park](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852296/141d1de5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exclusive House](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852296/525cf145.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Water park](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852296/80c2a3f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852296/2cc41b15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Marvelous 4Bd with Pool at Storey Lake Resort 2601 [](https://www.expedia.ca/Orlando-Hotels-Marvelous-4Bd-With-Pool-At-Storey-Lake-Resort-2601.h95852296.Hotel-Information) Kissimmee 10/10 Exceptional (3) [](https://www.expedia.ca/Orlando-Hotels-Marvelous-4Bd-With-Pool-At-Storey-Lake-Resort-2601.h95852296.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/51000000/50700000/50698700/50698655/92507b02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Townhome, 5 Bedrooms | Living area](https://images.trvl-media.com/lodging/51000000/50700000/50698700/50698655/d3b71173.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/51000000/50700000/50698700/50698655/3844c54e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Staircase](https://images.trvl-media.com/lodging/51000000/50700000/50698700/50698655/9a6168f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family Friendly 5 Bedrooms Home Close to Disney 4849 [](https://www.expedia.ca/Orlando-Hotels-4849-Storey-Lake-Resort-Orlando-4148444285.h50698655.Hotel-Information) Kissimmee 8.8/10 Excellent (3) "Everything was well clean and very easy access" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Raquel [](https://www.expedia.ca/Orlando-Hotels-4849-Storey-Lake-Resort-Orlando-4148444285.h50698655.Hotel-Information) ![Indoor pool, outdoor pool, sun loungers, lifeguards on site](https://images.trvl-media.com/lodging/51000000/50700000/50698700/50698689/3b952e94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/51000000/50700000/50698700/50698689/e7c03cd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 5 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/51000000/50700000/50698700/50698689/ebc12056.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 5 Bedrooms | Living room](https://images.trvl-media.com/lodging/51000000/50700000/50698700/50698689/ea264f85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 5 Bedroom Single Family @ Storey Lake Resort Close to Disney 4759 [](https://www.expedia.ca/Orlando-Hotels-4759-Storey-Lake-Resort-53594-53726.h50698689.Hotel-Information) Kissimmee 10/10 Exceptional (2) "Me encantó la propiedad, la comunicación que tuvieron conmigo en todo momento y el precio! Super recomendada!!! " ![Mexico](https://a.travel-assets.com/egds/marks/flags/mx.svg) Patricia [](https://www.expedia.ca/Orlando-Hotels-4759-Storey-Lake-Resort-53594-53726.h50698689.Hotel-Information) ![Exclusive House | Private pool](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852295/85d652c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exclusive House | Private kitchen](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852295/df671427.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852295/9cabd925.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exclusive House | Private pool](https://images.trvl-media.com/lodging/96000000/95860000/95852300/95852295/fa701cc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Marvelous 5Bd w/ Pool Close to Disney @ Storey Lake 2629 [](https://www.expedia.ca/Orlando-Hotels-Marvelous-5Bd-W-Pool-Close-To-Disney-Storey-Lake-2629.h95852295.Hotel-Information) Kissimmee 8.8/10 Excellent (3) "Nice " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Janismarie [](https://www.expedia.ca/Orlando-Hotels-Marvelous-5Bd-W-Pool-Close-To-Disney-Storey-Lake-2629.h95852295.Hotel-Information) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Oakland-Winter-Garden-Hotels.s50-n6360404-0.Travel-Guide-Filter-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Oakland-Winter-Garden-Hotels.s50-n6360404-0.Travel-Guide-Filter-Hotels) ## Explore similar 4-star hotels Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Oakland. ![DoubleTree by Hilton at the Entrance to Universal Orlando](https://images.trvl-media.com/lodging/1000000/10000/5400/5398/4997b5df_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### DoubleTree by Hilton at the Entrance to Universal Orlando 5780 Major Blvd Orlando FL CA $122 CA $137 total Jan 15 - Jan 16, 2026 includes taxes & fees 8.4/10 Very Good! (6,878 reviews) [](https://expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-At-The-Entrance-To-Universal-Orlando.h5398.Hotel-Information) ![Hyatt Regency Orlando](https://images.trvl-media.com/lodging/1000000/10000/9600/9574/1bb0a2ac_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hyatt Regency Orlando 9801 International Dr Orlando FL CA $184 CA $282 total Jan 2 - Jan 3, 2026 includes taxes & fees 9.2/10 Wonderful! (1,880 reviews) [](https://expedia.ca/Orlando-Hotels-Hyatt-Regency-Orlando.h9574.Hotel-Information) ![Walt Disney World Dolphin](https://images.trvl-media.com/lodging/1000000/20000/12800/12710/a6b6c49c_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Walt Disney World Dolphin 1500 Epcot Resort Blvd Lake Buena Vista FL CA $277 CA $380 total Jan 3 - Jan 4, 2026 includes taxes & fees 8.8/10 Excellent! (3,988 reviews) [](https://expedia.ca/Orlando-Hotels-Walt-Disney-World-Dolphin.h12710.Hotel-Information) Still don't see what you're looking for? [See all properties in Oakland.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=29%2F12%2F2025&endDate=30%2F12%2F2025®ionId=6360404&star=50) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=29%2F12%2F2025&endDate=30%2F12%2F2025®ionId=6360404&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=29%2F12%2F2025&endDate=30%2F12%2F2025®ionId=6360404&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=29%2F12%2F2025&endDate=30%2F12%2F2025®ionId=6360404&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=29%2F12%2F2025&endDate=30%2F12%2F2025®ionId=6360404&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=29%2F12%2F2025&endDate=30%2F12%2F2025®ionId=6360404&star=50&star=50&amenities=WATER_PARK) 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. ## Top Oakland Hotel Reviews ## Find out more about Oakland ## Five Star Hotels in Oakland There's nothing wrong with enjoying the finer things in life. Indulge yourself on your next leisure time. After all, this is one of the Top 10 locations in Expedia's portfolio. You'll join the multitudes of vacationers who have made Oakland so fashionable in the last year. We should also mention, the hotels in this area receive outstanding marks for guest services, so you know you'll be looked after during your getaway. You deserve the great vacation you're dreaming about. Book one of Expedia's luxurious 5-star hotels in Oakland and get ready to be pampered like never before. #### Get a Great Deal on 5-Star Hotels in Oakland Don't be afraid to live the high life while you're on vacation, along with pristine rooms. Excellent customer care, spacious rooms, and fabulous spa offerings are all on offer. We have a huge number of hotels in the region, and all of them offer outstanding amenities. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to kick back after your daily adventures. What kind of amenities will make your stay a wonderful one? A concierge to help you plan every detail of your day? A Swedish massage to help your cares fall away? Fluffy down pillows, piping hot coffees, and even space for your family pet in some cases...these hotels have it all. Want to see for yourself? Then explore the 31,943 reviews various guests have left on Expedia and get to know these places. Can't wait to get outside? We've got you covered. You'll find lots of attractions to see in a sprawling city like this one, like visiting art galleries and taking in live performances. Say hi to the locals—they're sure to have advice on what kind of excitement you can find in town. #### Make Your Escape to Oakland The results are in, and Oakland 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. This is a great time to find 5-star hotel deals in Oakland! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Oakland today and settle down in the lap of luxury tomorrow. ## Frequently asked questions ### How much does it cost to stay in a 5-star hotel in Oakland? > - Search for the lowest price per night from CA $137 ### What makes a hotel 5 stars in Oakland? ### Are there any 5-star all-inclusive resorts in Oakland? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [1 Star Hotels in Carver Shores ](https://www.expedia.ca/1Star-Carver-Shores-Orlando-Hotels.s10-n553248635976478799-0.Travel-Guide-Filter-Hotels) - [1 Star Hotels in Disney's Boardwalk ](https://www.expedia.ca/1Star-Disneys-Boardwalk-Hotels.s10-0-d6069355.Travel-Guide-Filter-Hotels) - [1 Star Hotels in Orlando ](https://www.expedia.ca/1Star-Orlando-Hotels.s10-0-d178294.Travel-Guide-Filter-Hotels) - [1 Star Hotels in Southwest Orlando ](https://www.expedia.ca/1Star-Southwest-Orlando-Hotels.s10-0-d553248635976470816.Travel-Guide-Filter-Hotels) - 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