Title: Oakland Vacation Packages | Holiday Packages & Trips 2026/2026 from CA $679 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 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 CA $679 per person Feb 8 - Feb 15 found 1 day ago Roundtrip flight included Toronto (YTO) to Orlando (MCO) 8/10 Very Good! (1,703 reviews) Great room very clean and comfortable. Reviewed on Nov 30, 2025 ![Residence Inn by Marriott Daytona Beach Oceanfront](https://images.trvl-media.com/lodging/1000000/30000/21400/21379/ea96e4af_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Residence Inn by Marriott Daytona Beach Oceanfront CA $1,215 per person Feb 26 - Mar 3 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Orlando (MCO) 8.6/10 Excellent! (1,002 reviews) The outside of the building could use some tlc but inside was clean and updated. Staff was attentive, polite, & helpful. Breakfast was surprisingly better than I anticipated with hot options outside of the traditional continental options. Furniture around pool was pressure washed every morning and plentiful. There are no seating options for the beach however we would definitely stay here again. Reviewed on Nov 30, 2025 ![The Shores Resort & Spa](https://images.trvl-media.com/lodging/1000000/20000/15800/15752/b7ce5af2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Shores Resort & Spa CA $723 per person Jan 21 - Jan 26 found 5 hours ago Roundtrip non-stop flight included Ottawa (YOW) to Orlando (MCO) 9/10 Wonderful! (1,696 reviews) Clean room. Exceptional service from all the staff each day. Amazing amenities. And gorgeous views. Reviewed on Dec 14, 2025 ![Florida Hotel & Conference Center in the Florida Mall](https://images.trvl-media.com/lodging/1000000/20000/17800/17739/3ccef447_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Florida Hotel & Conference Center in the Florida Mall CA $690 per person Feb 19 - Feb 24 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Orlando (MCO) 9.2/10 Wonderful! (2,333 reviews) Fantastic room, excellent dining options, free parking, helpful staff, excellent pools Reviewed on Dec 16, 2025 ![Boardwalk Inn and Suites](https://images.trvl-media.com/lodging/2000000/1060000/1059000/1058935/a139708f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Boardwalk Inn and Suites Davis CA $1,019 per person Feb 26 - Mar 3 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Orlando (MCO) 8.4/10 Very Good! (1,591 reviews) Room was clean staff very kind.Was upset that hotel not having a lot of guests and yet put me on the third floor with the closest elevator to me out of service Reviewed on Dec 16, 2025 ## Oakland Hotel Deals ![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 Fully refundableReserve now, pay when you stay CA $100 CA $151 total Jan 3 - Jan 4, 2026 includes taxes & fees 7.4/10 Good! (6,261 reviews) Clean room. Friendly staff Reviewed on Dec 17, 2025 [](https://expedia.ca/Hotel-Search?startDate=03%2F01%2F2026&endDate=04%2F01%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 Fully refundableReserve now, pay when you stay CA $183 CA $206 total Jan 6 - Jan 7, 2026 includes taxes & fees 8.8/10 Excellent! (5,744 reviews) Excelentes servicio with the room staff; a very good environment with good entertainment. Reviewed on Dec 14, 2025 [](https://expedia.ca/Hotel-Search?startDate=06%2F01%2F2026&endDate=07%2F01%2F2026&selected=5963292&PinnedHotelID=5963292&HadPinnedHotel=true®ionId=6360404) ![Wyndham I-Drive Avanti Resort & Conference Center](https://images.trvl-media.com/lodging/1000000/10000/4000/3916/55b45a9e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Wyndham I-Drive Avanti Resort & Conference Center 6515 International Drive Orlando FL Fully refundableReserve now, pay when you stay CA $86 CA $124 total Dec 22 - Dec 23 includes taxes & fees 7.2/10 Good! (3,925 reviews) Everything Reviewed on Dec 16, 2025 [](https://expedia.ca/Hotel-Search?startDate=22%2F12%2F2025&endDate=23%2F12%2F2025&selected=3916&PinnedHotelID=3916&HadPinnedHotel=true®ionId=6360404) [See all 39,770 properties in Oakland](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=20%2F12%2F2025&endDate=21%2F12%2F2025®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 walkable area. [](https://expedia.ca/Flamingo-Crossings-Town-Center-Bay-Lake.d863361053793378304.Vacation-Attraction) #### Surfari Water Park 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 ![Aquatica Orlando](https://mediaim.expedia.com/localexpert/407892/33b09fce-abbf-446b-bce5-738d4c15128d.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Aquatica Orlando CA $73 per traveller **84%** of travellers recommend [](https://expedia.ca/things-to-do/aquatica-orlando.a407892.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 CA $38 per traveller **88%** of travellers recommend [](https://expedia.ca/things-to-do/wonderworks-all-access-after-dark.a887154.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 CA $17 per adult **90%** of travellers recommend [](https://expedia.ca/things-to-do/orlando-7-d-dark-ride-entry-ticket.a45731783.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.