Title: Oakland Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $676 Expedia.ca [Hotels in Oakland](https://expedia.ca/Oakland-Winter-Garden-Hotels.0-n6360404-0.Travel-Guide-Filter-Hotels)[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) ![](https://images.trvl-media.com/place/6360404/d013c781-9bde-4c95-8530-be7e0380ccba.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Oakland Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings Photo by Gregg Yutko - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 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 Plan, book, and manage your trip all in one place ## Top Holiday Package Deals in Oakland Price found within the past 48 hours. Click for updated prices. ![Westgate Towers Resort](https://images.trvl-media.com/lodging/1000000/180000/170900/170878/0a149867_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Westgate Towers Resort CA $676 per person May 19 - May 26 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Orlando (MCO) 8.6/10 Excellent! (1,008 reviews) Overall a great experience. Recommend Reviewed on Mar 9, 2026 ![Westgate Town Center Resort](https://images.trvl-media.com/lodging/1000000/430000/426900/426819/62319b88_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Westgate Town Center Resort CA $706 per person May 20 - May 27 found 1 day ago Roundtrip non-stop flight included Halifax (YHZ) to Orlando (MCO) 8/10 Very Good! (1,489 reviews) My family was there for 5 days for spring break the resort was nice and centrally located to everything we enjoyed our trip Reviewed on Mar 11, 2026 ![Westgate Lakes Resort & Spa Universal Studios Area](https://images.trvl-media.com/lodging/1000000/810000/805000/804984/ffaf091a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Westgate Lakes Resort & Spa Universal Studios Area CA $946 per person Apr 18 - Apr 25 found 1 day ago Roundtrip non-stop flight included Halifax (YHZ) to Orlando (MCO) 8.4/10 Very Good! (5,891 reviews) The furniture was very uncomfortable. The couches sank in andhrd to sit on Reviewed on Mar 10, 2026 ![Westgate Blue Tree Resort in Lake Buena Vista](https://images.trvl-media.com/lodging/1000000/200000/191000/190971/b8eca031_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Westgate Blue Tree Resort in Lake Buena Vista CA $818 per person May 19 - May 26 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Orlando (MCO) 8.6/10 Excellent! (1,003 reviews) Clean room, well manicured outside common areas. Reviewed on Mar 10, 2026 ## 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 CA $251 CA $358 total Mar 12 - Mar 13 includes taxes & fees 8/10 Very Good! (9,172 reviews) Room was nice, but simple. Could be updated. Tv in living room did not work. Pool area was convenient but pool chairs were a reserved status charge to sit close to pool even though the pool was empty. Found this ridiculous considering it was not peak season nor crowded. Bar staff was too into their ... Reviewed on Mar 10, 2026 [](https://expedia.ca/Hotel-Search?startDate=12%2F03%2F2026&endDate=13%2F03%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 CA $200 CA $225 total Apr 10 - Apr 11 includes taxes & fees 9.2/10 Wonderful! (4,832 reviews) Very nice hotel for families, the pools were wonderful and great amenities. Reviewed on Mar 10, 2026 [](https://expedia.ca/Hotel-Search?startDate=10%2F04%2F2026&endDate=11%2F04%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 CA $105 CA $119 total Mar 15 - Mar 16 includes taxes & fees 8.6/10 Excellent! (5,974 reviews) Clean rooms friendly staff easy check in. Reviewed on Mar 10, 2026 [](https://expedia.ca/Hotel-Search?startDate=15%2F03%2F2026&endDate=16%2F03%2F2026&selected=8892&PinnedHotelID=8892&HadPinnedHotel=true®ionId=6360404) [See all 39,281 properties in Oakland](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=12%2F03%2F2026&endDate=13%2F03%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 Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.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 Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.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 Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.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 Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.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 Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.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 Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## Frequently asked questions ### How much does an Oakland vacation package cost? ### How do I get a cheap travel package to Oakland? ### Where should I stay in Oakland? ### What are the top hotels in Oakland? ### How far in advance should I book my Oakland vacation? ### 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 vacation package? ### If I'm not able to travel, can I cancel my Oakland vacation package? ### Discover the most popular places to visit in Oakland #### 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.ca/Flamingo-Crossings-Town-Center-Bay-Lake.d863361053793378304.Vacation-Attraction) #### Surfari Water Park 4.5/5(50 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.ca/Surfari-Water-Park-Orlando.d553248635975177890.Vacation-Attraction) #### Central Florida Railroad Museum You can study the exhibits at Central Florida Railroad Museum, a museum with a story of its own, during your travels to Winter Garden. Amble around this family-friendly area's lakeside, or seek out the adventure tours. [](https://expedia.ca/Central-Florida-Railroad-Museum-Downtown-Winter-Garden.d553248621561885339.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 CA $86 per traveller **86%** of travellers recommend [](https://expedia.ca/things-to-do/legoland-florida-tickets.a181157.activity-details) ![Universal Orlando Resort Theme Park Tickets](https://mediaim.expedia.com/localexpert/449578/292355e4-a5b6-4251-bddb-ccea0177846f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Universal Orlando Resort Theme Park Tickets (US & Canada) CA $237 per adult **86%** of travellers recommend [](https://expedia.ca/things-to-do/universal-orlando-resort-theme-park-tickets-us-canada.a449578.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 CA $37 per adult **92%** of travellers recommend [](https://expedia.ca/things-to-do/icon-park-sea-life-aquarium.a454609.activity-details) [See all activities in Winter Garden](https://expedia.ca/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.