Title: Oakland Holidays 2026 from £644 | Expedia.co.uk [Hotels in Oakland](https://expedia.co.uk/Oakland-Winter-Garden-Hotels.0-n6360404-0.Travel-Guide-Filter-Hotels)[Flights to Winter Garden](https://expedia.co.uk/Cheap-Flights-To-Winter-Garden.d7898.Travel-Guide-Flights)[Things to do in Winter Garden](https://expedia.co.uk/Things-To-Do-In-Winter-Garden.d7898.Travel-Guide-Activities)[Oakland Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Oakland.d6360404.Car-Hire-Guide) ![](https://images.trvl-media.com/place/6360404/d013c781-9bde-4c95-8530-be7e0380ccba.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Oakland Holidays from £644 ## Book a Hotel + Flight or Car together to unlock savings Photo by Gregg Yutko - ## Plan, book, travel with confidence - ### Better together Save up to £335 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Packages with flights are ATOL protected ### Your Oakland Holiday Organising your next exciting getaway just got simpler with a holiday package to Oakland. Immerse yourself in everything this neighbourhood has to offer while creating precious memories you'll treasure. Your trip to Oakland wouldn't be complete without a visit to top attractions nearby such as [West Orange Trail](https://www.expedia.co.uk/West-Orange-Trail-Winter-Garden.d553248621532653939.Attraction), [Garden Theatre](https://www.expedia.co.uk/Garden-Theatre-Winter-Garden.d553248621532653937.Attraction) and [Winter Garden Heritage Museum](https://www.expedia.co.uk/Winter-Garden-Heritage-Museum-Winter-Garden.d553248621532653938.Attraction). Expedia is here to put your travel plans into action. Book your dream Oakland holiday today. Price found within the past 48 hours. Click for updated prices. ![Westgate Vacation Villas Resort](https://images.trvl-media.com/lodging/1000000/100000/99000/98920/b8afec09_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Westgate Vacation Villas Resort £644 per person 13 Apr - 19 Apr found 1 day ago Return direct flight included London (LHR) to Orlando (MCO) 8/10 Very Good! (1,703 reviews) Paying to enter water park when you are not using the amenities Reviewed on 22 Feb 2026 ![Westgate Palace Hotel / Universal / I-Drive](https://images.trvl-media.com/lodging/1000000/110000/106200/106143/01c960b0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Westgate Palace Hotel / Universal / I-Drive International Drive District Save 100% on your flight £822 per person 2 May - 9 May found 11 hours ago Return direct flight included London (LHR) to Orlando (MCO) 8.8/10 Excellent! (1,085 reviews) Clean room and amenities Reviewed on 23 Feb 2026 ![Westgate Lakes Resort & Spa Universal Studios Area](https://images.trvl-media.com/lodging/1000000/810000/805000/804984/86e77c07_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Westgate Lakes Resort & Spa Universal Studios Area £710 per person 2 May - 9 May found 11 hours ago Return direct flight included London (LHR) to Orlando (MCO) 8.2/10 Very Good! (5,482 reviews) I love everything good Costumer service, everything is clean I will recommended 100% Reviewed on 22 Feb 2026 ![Westgate Town Center Resort](https://images.trvl-media.com/lodging/1000000/430000/426900/426819/410a3d83_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Westgate Town Center Resort £670 per person 2 May - 9 May found 11 hours ago Return direct flight included London (LHR) to Orlando (MCO) 8/10 Very Good! (1,367 reviews) Great service, great amenities, great room. Home away from home. Reviewed on 23 Feb 2026 ![Margaritaville Cottages Orlando with H2O Waterpark by Vstays](https://images.trvl-media.com/lodging/36000000/35110000/35109100/35109061/0a506e54_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Margaritaville Cottages Orlando with H2O Waterpark by Vstays Save 100% on your flight £1,362 per person 6 May - 13 May found 1 day ago Return flight included Edinburgh (EDI) to Orlando (MCO) 9.2/10 Wonderful! (1,001 reviews) Everything was excellent. Beautiful house that was spotless. Reviewed on 22 Feb 2026 ## Top hotels in Oakland ![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 £110 18 Mar - 19 Mar includes taxes & fees [](https://expedia.co.uk/Hotel-Search?startDate=18%2F03%2F2026&endDate=19%2F03%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 Fully refundableReserve now, pay when you stay £174 26 Feb - 27 Feb includes taxes & fees 8/10 Very Good! (9,104 reviews) Clean, beautiful spacious rooms. I had a three bedroom two bath full kitchen laundry facility. Everything weight staff was very nice resort it was beautiful. Reviewed on 23 Feb 2026 [](https://expedia.co.uk/Hotel-Search?startDate=26%2F02%2F2026&endDate=27%2F02%2F2026&selected=4691657&PinnedHotelID=4691657&HadPinnedHotel=true®ionId=6360404) ![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=340&ch=150) ### DoubleTree by Hilton at the Entrance to Universal Orlando 5780 Major Blvd Orlando FL Fully refundable £112 22 Mar - 23 Mar includes taxes & fees 8.4/10 Very Good! (6,915 reviews) Great Location. Great Room. Great Amenities. Reviewed on 23 Feb 2026 [](https://expedia.co.uk/Hotel-Search?startDate=22%2F03%2F2026&endDate=23%2F03%2F2026&selected=5398&PinnedHotelID=5398&HadPinnedHotel=true®ionId=6360404) [See all 39,511 properties in Oakland](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=25%2F02%2F2026&endDate=26%2F02%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/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Holidays [](https://expedia.co.uk/lp/theme-holidays/all-inclusive-holidays?rfrr=editorial.All_Inclusive%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Holidays [](https://expedia.co.uk/lp/theme-holidays/beach-holidays?rfrr=editorial.Beach_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/kid-friendly-holidays?rfrr=editorial.Family_Friendly%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Holidays [](https://expedia.co.uk/lp/theme-holidays/golf-holidays?rfrr=editorial.Golf_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Holidays [](https://expedia.co.uk/lp/theme-holidays/luxury-holidays?rfrr=editorial.Luxury_Holidays.click) ![gay friendly holidays](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ+ Holidays [](https://expedia.co.uk/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ+_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Holidays [](https://expedia.co.uk/lp/theme-holidays/romantic-holidays?rfrr=editorial.Romantic_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Holidays [](https://expedia.co.uk/lp/theme-holidays/ski-holidays?rfrr=editorial.Ski_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/22/hero-image-pet-friendly_copy.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Pet Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/pet-friendly-holidays?rfrr=editorial.Pet_Friendly%20Holidays.click) ![Holiday in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.co.uk/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ## Frequently asked questions ### How much does an Oakland travel package cost? ### If I'm not able to travel, can I cancel my Oakland travel package? ### How do I get a cheap travel package to Oakland? ### Does Expedia offer Book Now, Pay Later Oakland holidays? > - Pay monthly holidays: Klarna has convenient monthly payment plans that work for all budgets, so you can escape on that well-earned holiday now. > - Pay in instalments holidays: Into the idea of paying off your holiday in multiple transactions? Consider this Book Now, Pay Later option with Klarna. > - Low deposit holidays: If paying a small percentage of your getaway (rather than the total upfront) makes it easier to click that "book now" button, go for a low deposit holiday payment plan from Klarna. ### Where should I stay in Oakland? ### What are the top hotels in Oakland? ### How far in advance should I book my Oakland holiday? ### What does an Expedia Oakland travel package include? ### What should I know before booking an Oakland travel package? ### Can I choose my airline with an Oakland Expedia travel package? ### Popular places to visit #### Disney's Magnolia Golf Course 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.co.uk/Disneys-Magnolia-Golf-Course-Bay-Lake.d6241695.Attraction) #### Surfari Water Park 5/5(7 reviews) Enjoy the thrill rides with your children 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.co.uk/Surfari-Water-Park-Orlando.d553248635975177890.Attraction) #### Winter Garden Heritage Museum You can browse the exhibits at Winter Garden Heritage Museum, a museum with a story of its own, during your trip to Winter Garden. Stroll along the lakeside in this family-friendly area or visit its top-notch restaurants. [](https://expedia.co.uk/Winter-Garden-Heritage-Museum-Downtown-Winter-Garden.d553248621532653938.Attraction) ### Things to do ![Universal Orlando Resort](https://mediaim.expedia.com/localexpert/326356/5d9c8dfe-d368-4628-b402-718c6edaf918.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Universal Orlando Resort Theme Park Tickets £427 per adult **92%** of travellers recommend [](https://expedia.co.uk/things-to-do/universal-orlando-resort-theme-park-tickets.a326356.activity-details) ![Aquatica Orlando](https://mediaim.expedia.com/localexpert/407892/33b09fce-abbf-446b-bce5-738d4c15128d.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Aquatica Orlando £39 per traveller **84%** of travellers recommend [](https://expedia.co.uk/things-to-do/aquatica-orlando.a407892.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 £9 per adult **90%** of travellers recommend [](https://expedia.co.uk/things-to-do/orlando-7-d-dark-ride-entry-ticket.a45731783.activity-details) [See all activities in Winter Garden](https://expedia.co.uk/things-to-do/search?rid=6360404) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.