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 walkable area. [](https://expedia.com/Flamingo-Crossings-Town-Center-Bay-Lake.d863361053793378304.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) #### 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) #### 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) #### 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) #### 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) ### 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 $58 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 $149 per traveler **84%** of travellers recommend [](https://expedia.com/things-to-do/universal-orlando-resort-express-passes.a4777911.activity-details) ![Kissimmee: Old Town Ferris Wheel, Attractions, and Dinner](https://mediaim.expedia.com/localexpert/48183005/9bfbaf91-f2ed-40fc-9743-ee0ffb292c90.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Kissimmee: Old Town Ferris Wheel, Attractions, and Dinner $15 per adult **80%** of travellers recommend [](https://expedia.com/things-to-do/kissimmee-old-town-ferris-wheel.a48183005.activity-details) ![Orlando: 7-D Dark Ride Entry Ticket](https://mediaim.expedia.com/localexpert/45731783/ca757de2-59d9-443c-848e-c370b56bdaed.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) ![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 ![Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando](https://images.trvl-media.com/lodging/1000000/30000/23200/23110/ade3b60d_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 $131 nightly $148 total Mar 15 - Mar 16 Total with taxes and fees Book a stay at this family-friendly hotel 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! (4,569 reviews) Beautiful property, clean and well maintained rooms, very nice staff. Reviewed on Feb 11, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F15%2F2026&endDate=3%2F16%2F2026&selected=23110&PinnedHotelID=23110&HadPinnedHotel=true®ionId=6360404) ![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 $218 nightly $245 total Feb 22 - Feb 23 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! (9,056 reviews) Very clean, friendly staff Reviewed on Feb 11, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F22%2F2026&endDate=2%2F23%2F2026&selected=4691657&PinnedHotelID=4691657&HadPinnedHotel=true®ionId=6360404) ![DoubleTree by Hilton Hotel Orlando at SeaWorld](https://images.trvl-media.com/lodging/1000000/20000/18900/18874/69019073_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### DoubleTree by Hilton Hotel Orlando at SeaWorld 10100 International Drive Orlando FL $117 nightly $131 total Mar 8 - Mar 9 Total with taxes and fees Book a stay at this family-friendly resort in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the breakfast and the pool in our ... 7.4/10 Good! (6,538 reviews) good enough Reviewed on Feb 8, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F8%2F2026&endDate=3%2F9%2F2026&selected=18874&PinnedHotelID=18874&HadPinnedHotel=true®ionId=6360404) ![Universal's Cabana Bay Beach Resort](https://images.trvl-media.com/lodging/6000000/5970000/5963300/5963292/63940f45_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Universal's Cabana Bay Beach Resort 6550 Adventure Way Orlando FL $133 nightly $150 total Mar 13 - Mar 14 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 ... 8.8/10 Excellent! (6,319 reviews) Room was always clean, everyone was super nice and helpful, the furniture in room maybe need to me replaced the couch was ripped up but other than that it was perfect Reviewed on Feb 11, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F13%2F2026&endDate=3%2F14%2F2026&selected=5963292&PinnedHotelID=5963292&HadPinnedHotel=true®ionId=6360404) ![Orlando International Drive North Hotel](https://images.trvl-media.com/lodging/1000000/50000/41500/41493/d062739a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Orlando International Drive North Hotel 5859 American Way Orlando FL $79 nightly $89 total Feb 23 - Feb 24 Total with taxes and fees Book a stay at this business-friendly hotel in Orlando. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ... 7.2/10 Good! (2,825 reviews) awesome continental breakfast Reviewed on Feb 11, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F23%2F2026&endDate=2%2F24%2F2026&selected=41493&PinnedHotelID=41493&HadPinnedHotel=true®ionId=6360404) ![Marriott's Grande Vista](https://images.trvl-media.com/lodging/1000000/860000/853600/853519/77708f65_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Marriott's Grande Vista 5925 Avenida Vista Orlando FL $135 nightly $152 total Feb 22 - Feb 23 Total with taxes and fees Book a stay at this spa hotel in Orlando. Enjoy free WiFi, 4 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. ... 9/10 Wonderful! (3,886 reviews) The main front desk is knowledgeable and helpful. Shuttle staff were professional and willing to help w bags. Room was clean. I had everything I needed to cook a number of items. Reviewed on Feb 11, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F22%2F2026&endDate=2%2F23%2F2026&selected=853519&PinnedHotelID=853519&HadPinnedHotel=true®ionId=6360404) [See all 39,430 properties in Oakland](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=2%2F14%2F2026&endDate=2%2F15%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=2026-02-13&endDate=2026-02-14)[Feb 13 - Feb 14](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6360404&startDate=2026-02-13&endDate=2026-02-14) [Tomorrow night ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6360404&startDate=2026-02-14&endDate=2026-02-15)[Feb 14 - Feb 15](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6360404&startDate=2026-02-14&endDate=2026-02-15) [This weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6360404&startDate=2%2F13%2F2026&endDate=2%2F15%2F2026)[Feb 13 - Feb 15](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6360404&startDate=2%2F13%2F2026&endDate=2%2F15%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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