Title: Visit Oakland: 2026 Oakland, Winter Garden Travel Guide | Expedia.com [Hotels in Oakland](https://expedia.com/Oakland-Winter-Garden-Hotels.0-n6360404-0.Travel-Guide-Filter-Hotels)[Flights to Winter Garden](https://expedia.com/Cheap-Flights-To-Winter-Garden.d7898.Travel-Guide-Flights)[Things to do in Winter Garden](https://expedia.com/Things-To-Do-In-Winter-Garden.d7898.Travel-Guide-Activities)[Car Rentals in Oakland](https://expedia.com/Car-Rentals-In-Oakland.d6360404.Car-Rental-Guide)[Oakland Vacations](https://expedia.com/Oakland.d6360404.Destination-Travel-Guides) # Oakland, FL ## Winter Garden ![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=1040&h=580&q=mediumHigh) ![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=1040&h=580&q=mediumHigh) ![Panoramic view of Lake Apopka and nature Florida.](https://images.trvl-media.com/place/6360403/5cbd79a8-2e61-4cef-8769-e792f96b305a.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ## Visit Oakland Things to do Hotels Where to stay [Winter Garden Travel Guide](https://expedia.com/Winter-Garden.dx7898) --- ### Popular places to visit #### Flamingo Crossings Town Center You can do some window-shopping at Flamingo Crossings Town Center during your visit to Winter Garden. Discover the top-notch restaurants and entertainment choices in this family-friendly area. [](https://expedia.com/Flamingo-Crossings-Town-Center-Bay-Lake.d863361053793378304.Vacation-Attraction) #### Disney's Magnolia Golf Course 4/5(6 reviews) Enjoy a round of golf in Winter Garden at Disney's Magnolia Golf Course. Discover the top-notch restaurants and entertainment choices in this family-friendly area. [](https://expedia.com/Disneys-Magnolia-Golf-Course-Bay-Lake.d6241695.Vacation-Attraction) #### Disney's Palm Golf Course 5/5(1 review) Enjoy a round of golf in Winter Garden at Disney's Palm Golf Course. Discover the top-notch restaurants and entertainment choices in this family-friendly area. [](https://expedia.com/Disneys-Palm-Golf-Course-Bay-Lake.d6069339.Vacation-Attraction) #### Orange County National Golf Club 4.5/5(25 reviews) Enjoy a round of golf in Winter Garden at Orange County National Golf Club. Amble around this family-friendly area's lakeside or experience its entertainment choices. [](https://expedia.com/Orange-County-National-Golf-Club-Horizon-West.d6239843.Vacation-Attraction) #### AdventHealth Winter Garden Though AdventHealth Winter Garden might be what brings you to town, perhaps you'll have a chance to explore more of Winter Garden while you are here. [](https://expedia.com/AdventHealth-Winter-Garden-Winter-Garden.d624551183952064512.Vacation-Attraction) #### Surfari Water Park 4.5/5(374 reviews) Enjoy a fun-filled day at Surfari Water Park as part of your trip to Four Corners. Make time for the shops and golf courses in this family-friendly area. [](https://expedia.com/Surfari-Water-Park-Orlando.d553248635975177890.Vacation-Attraction) ### Things to do ![LEGOLAND® Florida Tickets](https://mediaim.expedia.com/localexpert/181157/60ed688e-5b2f-40df-80f4-7ffb770fb5fd.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### LEGOLAND® Florida Tickets $71 per traveler **86%** of travellers recommend [](https://expedia.com/things-to-do/legoland-florida-tickets.a181157.activity-details) ![Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options](https://mediaim.expedia.com/localexpert/454609/83845a17-35d9-41e3-b805-6e10dd19a62d.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options $27 per adult **92%** of travellers recommend [](https://expedia.com/things-to-do/icon-park-sea-life-aquarium.a454609.activity-details) ![Universal Orlando Resort Express Passes](https://mediaim.expedia.com/localexpert/4777911/745cf81c-4793-481e-a99e-c05d90bfee90.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Universal Orlando Resort Express Passes $192 per traveler **82%** of travellers recommend [](https://expedia.com/things-to-do/universal-orlando-resort-express-passes.a4777911.activity-details) ![Orlando: 7-D Dark Ride Entry Ticket](https://mediaim.expedia.com/localexpert/45731783/f633bb03-18af-4994-be9e-adff20b9b1e4.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Orlando: 7-D Dark Ride Entry Ticket $12 per adult **90%** of travellers recommend [](https://expedia.com/things-to-do/orlando-7-d-dark-ride-entry-ticket.a45731783.activity-details) ![Titanic : The Artifact Exhibition Ticket in Orlando](https://mediaim.expedia.com/localexpert/690897/d494fb93-b772-4417-8014-8c58df17e106.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Titanic : The Artifact Exhibition Ticket in Orlando $34 per adult **96%** of travellers recommend [](https://expedia.com/things-to-do/titanic-the-artifact-exhibition-ticket-in-orlando.a690897.activity-details) ![WonderWorks All Access After Dark](https://mediaim.expedia.com/localexpert/887154/1fe1a6bb-2a2b-4a72-8592-dab72ffd3861.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### WonderWorks All Access After Dark $28 per traveler **88%** of travellers recommend [](https://expedia.com/things-to-do/wonderworks-all-access-after-dark.a887154.activity-details) [See all activities in Winter Garden](https://expedia.com/Things-To-Do-In-Winter-Garden.d7898.Travel-Guide-Activities) --- ## Oakland Hotel Deals ![The Grove Resort & Water Park Orlando](https://images.trvl-media.com/lodging/5000000/4700000/4691700/4691657/c5a7d392_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Grove Resort & Water Park Orlando 14501 Grove Resort Avenue Winter Garden FL $229 nightly $257 total Apr 12 - Apr 13 Total with taxes and fees Book a stay at this family-friendly resort in Four Corners. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff ... 8/10 Very Good! (9,179 reviews) The pool was shut down elevator was working door wasn’t working in hallway Reviewed on Mar 11, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F12%2F2026&endDate=4%2F13%2F2026&selected=4691657&PinnedHotelID=4691657&HadPinnedHotel=true®ionId=6360404) ![Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando](https://images.trvl-media.com/lodging/1000000/30000/23200/23110/91c45539_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando 8800 Vistana Centre Dr Orlando FL Fully refundableReserve now, pay when you stay $147 nightly $166 total Apr 10 - Apr 11 Total with taxes and fees Book a stay at this family-friendly condo in Orlando. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff in ... 9.2/10 Wonderful! (4,840 reviews) Spacious rooms and proximity to the pool. Only issue is villa is hard to find when it's in the dark. I'll consider coming again. Reviewed on Mar 11, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F10%2F2026&endDate=4%2F11%2F2026&selected=23110&PinnedHotelID=23110&HadPinnedHotel=true®ionId=6360404) ![Rosen Inn at Pointe Orlando](https://images.trvl-media.com/lodging/1000000/10000/8900/8892/8068a653_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Rosen Inn at Pointe Orlando 9000 International Drive Orlando FL $84 nightly $95 total Mar 29 - Mar 30 Total with taxes and fees Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 3 outdoor pools, and 2 coffee shops/cafes. Our guests praise the pool and the helpful ... 8.6/10 Excellent! (5,984 reviews) Nice overall. A little dated but was ok for our stay. Staff at check in was great. Staff cleaning rooms and helping in the buildings were oblivious to guests. Would walk in front if guests to get on and off the elevator, blacking the walkways with carts. Carts were being used in elevators for guests, ... Reviewed on Mar 11, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F29%2F2026&endDate=3%2F30%2F2026&selected=8892&PinnedHotelID=8892&HadPinnedHotel=true®ionId=6360404) ![Universal's Cabana Bay Beach Resort](https://images.trvl-media.com/lodging/6000000/5970000/5963300/5963292/4c48bd3d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Universal's Cabana Bay Beach Resort 6550 Adventure Way Orlando FL $133 nightly $150 total Apr 9 - Apr 10 Total with taxes and fees Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in ... 9/10 Wonderful! (6,459 reviews) Love this hotel love the pool. Great family resort. Reviewed on Mar 12, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F9%2F2026&endDate=4%2F10%2F2026&selected=5963292&PinnedHotelID=5963292&HadPinnedHotel=true®ionId=6360404) ![Westgate Lakes Resort & Spa Universal Studios Area](https://images.trvl-media.com/lodging/1000000/810000/805000/804984/ffaf091a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Westgate Lakes Resort & Spa Universal Studios Area 9500 Turkey Lake Rd Orlando FL $143 nightly $161 total Apr 12 - Apr 13 Total with taxes and fees Book a stay at this spa hotel in Orlando. Enjoy free parking, 7 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ... 8.4/10 Very Good! (5,974 reviews) We had a wonderful time! Reviewed on Mar 11, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F12%2F2026&endDate=4%2F13%2F2026&selected=804984&PinnedHotelID=804984&HadPinnedHotel=true®ionId=6360404) ![Kompose Boutique Resort at Theme Parks](https://images.trvl-media.com/lodging/101000000/100840000/100837800/100837786/81e6b4c7_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Kompose Boutique Resort at Theme Parks 7491 W Irlo Bronson Memorial Hwy Kissimmee FL $130 nightly $148 total Mar 31 - Apr 1 Total with taxes and fees Stay at this resort in Kissimmee. Enjoy free breakfast, free WiFi, and 2 hot tubs. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World ... 9.4/10 Exceptional! (3,053 reviews) The property was great and the breakfast was very good. Our room was never cleaned (at all) over a five day stay. I had to ask for a cleaning and it did not happen despite several trips to the front desk to ask as well as to get fresh towels as needed. I was told a manager would reach out to me by ... Reviewed on Mar 11, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F31%2F2026&endDate=4%2F1%2F2026&selected=100837786&PinnedHotelID=100837786&HadPinnedHotel=true®ionId=6360404) [See all 39,358 properties in Oakland](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=3%2F13%2F2026&endDate=3%2F14%2F2026®ionId=6360404) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=DX-NH_SPRING_PROMO_6360404) ## Check Oakland hotel availability [Tonight ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6360404&startDate=2026-03-12&endDate=2026-03-13)[Mar 12 - Mar 13](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6360404&startDate=2026-03-12&endDate=2026-03-13) [Tomorrow night ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6360404&startDate=2026-03-13&endDate=2026-03-14)[Mar 13 - Mar 14](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6360404&startDate=2026-03-13&endDate=2026-03-14) [This weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6360404&startDate=3%2F13%2F2026&endDate=3%2F15%2F2026)[Mar 13 - Mar 15](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6360404&startDate=3%2F13%2F2026&endDate=3%2F15%2F2026) [Next weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6360404&startDate=3%2F20%2F2026&endDate=3%2F22%2F2026)[Mar 20 - Mar 22](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6360404&startDate=3%2F20%2F2026&endDate=3%2F22%2F2026) --- ### Other neighborhoods around Oakland ![Panoramic view of Lake Apopka and nature Florida.](https://images.trvl-media.com/place/6360403/5cbd79a8-2e61-4cef-8769-e792f96b305a.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### 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. [](https://expedia.com/Winter-Garden-Killarney.dx6360403) ![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=350&h=192&q=medium) ### Downtown Winter Garden While visiting Downtown Winter Garden, you might make a stop by sights like West Orange Trail and Central Florida Railroad Museum. [](https://expedia.com/Winter-Garden-Downtown-Winter-Garden.dx944538218785796096) [See our Where To Stay guide](https://expedia.com/Winter-Garden.dx7898.Where-To-Stay?rfrr=TG.LP.Dest.Neigh.Neighborhoods) --- --- - [Stays](?pwaLob=wizard-hotel-pwa-v2) - [Packages](?pwaLob=wizard-package-pwa) - [Flights](?pwaLob=wizard-flight-pwa) - [Things to do](?pwaLob=wizard-lx-pwa) - [Cruises](?pwaLob=wizard-cruise-pwa) - [Cars](?pwaLob=wizard-car-pwa) # Oakland, FL ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - Other - [Orlando Hotels ](https://www.expedia.com/Orlando-Hotels.d178294.Travel-Guide-Hotels) - [Hotels near Walt Disney World® Resort ](https://www.expedia.com/Walt-Disney-World-Resort-Hotels.0-l6034120-0.Travel-Guide-Filter-Hotels) - [Hotels near Universal Studios Florida ](https://www.expedia.com/Universal-Studios-Florida-Hotels.0-l6049239-0.Travel-Guide-Filter-Hotels) - [Hotels near Oakland Nature Preserve ](https://www.expedia.com/Oakland-Nature-Preserve-Hotels.0-l553248621532653932-0.Travel-Guide-Filter-Hotels) - 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[Villas in Winter Garden ](https://www.expedia.com/Winter-Garden-Villas.d7898-aaVillas.Travel-Guide-Accommodation) - [Hotels with a Lazy River in Winter Garden ](https://www.expedia.com/Winter-Garden-Hotels-Hotels-With-A-Lazy-River.0-0-d7898-tHotelswithaLazyRiver.Travel-Guide-Filter-Hotels) - [Historic Hotels in Winter Garden ](https://www.expedia.com/Winter-Garden-Hotels-Historic-Hotel.0-0-d7898-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Winter Garden ](https://www.expedia.com/Winter-Garden-Hotels-Luxury-Hotel.0-0-d7898-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Red Roof Inn Hotels in Winter Garden ](https://www.expedia.com/Winter-Garden-Hotels-Red-Roof-Inn.0-0-d7898--bRedRoofInn.Travel-Guide-Filter-Hotels) - [Hotels with Suites in Winter Garden ](https://www.expedia.com/Winter-Garden-Hotels-Hotel-Suites.0-0-d7898-tHotelSuites.Travel-Guide-Filter-Hotels) - [Hotels with Restaurants in Winter Garden ](https://www.expedia.com/Winter-Garden-Hotels-Hotels-With-Restaurants.0-0-d7898-tHotelswithRestaurants.Travel-Guide-Filter-Hotels) - 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