Oakland Vacations from $250
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Your Oakland Vacation
Experience all the wonderful things this neighborhood has to offer with a tailor-made Oakland vacation package. However you see yourself spending your time here, you'll find countless opportunities for fun, adventure and relaxation. When it's time to get out and explore, you'll find a lot of big-name attractions nearby including West Orange Trail, Resurrection Catholic Church and Oakland Nature Preserve. Visit one or all during your trip to Oakland. No matter what your ideal Oakland vacation looks like, you can make it a reality with Expedia.
The Latest Oakland Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Westgate Vacation Villas Resort
Save 100% on your flight
Price was $719, price is now $327 per person
$327
per person
Mar 16 - Mar 21
found 12 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8/10 Very Good! (1,703 reviews)
We had a wonderful stay here. We came for my birthday and spent two nights, and everything exceeded our expectations. The price was great, and when we arrived, the team upgraded us to a very nice room. It looked recently remodeled, was extremely clean, and felt fresh and comfortable.
Our family was very happy, and the hotel was kind enough to let us check out an hour later so we could pack up without rushing. Everyone we interacted with was friendly and helpful.
Overall, an excellent experience — we would definitely stay here again.
Reviewed on Jan 4, 2026
Westgate Towers Resort
Save 100% on your flight
Price was $522, price is now $253 per person
$253
per person
Mar 28 - Mar 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.6/10 Excellent! (1,002 reviews)
Could not regulate air conditioning but the room was very clean and staff was very friendly and helpful!
Reviewed on Jan 9, 2026
Oakland Hotel Deals
Universal's Cabana Bay Beach Resort
6550 Adventure Way Orlando FL
Fully refundableReserve now, pay when you stay
$133 nightly
The price is $150 total per night from Jan 13 to Jan 14
$150 total
Jan 13 - Jan 14
Total with taxes and fees
8.8/10 Excellent! (5,957 reviews)
This is the place to stay if you have children! Game room, bowling, heated pools - plenty of entertainment. The food was not the best and over priced and served like a cafeteria. But other than that, great location and great place to stay.
Reviewed on Jan 8, 2026
Wyndham I-Drive Avanti Resort & Conference Center
6515 International Drive Orlando FL
Fully refundableReserve now, pay when you stay
$80 nightly
The price is $90 total per night from Jan 13 to Jan 14
$90 total
Jan 13 - Jan 14
Total with taxes and fees
7.2/10 Good! (4,065 reviews)
everything
Reviewed on Jan 6, 2026
The Grove Resort & Water Park Orlando
14501 Grove Resort Avenue Winter Garden FL
Fully refundableReserve now, pay when you stay
$217 nightly
The price is $244 total per night from Jan 26 to Jan 27
$244 total
Jan 26 - Jan 27
Total with taxes and fees
8/10 Very Good! (8,949 reviews)
Good
Reviewed on Jan 6, 2026
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.
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.
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.
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.
Things to do
Universal Orlando Resort Express Passes
$160
per traveler
86% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
$27
per adult
92% of travellers recommend
Explore a world of travel with Expedia
- Orlando Hotels
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- Universal Orlando Resort in Winter Garden
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- Car rental Orlando Airport (MCO)
- Car rentals near Orlando
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- Enterprise Rental Cars in Winter Garden
- Car rentals near Resurrection Catholic Church
- Car rentals near Winter Garden Art Association
- Budget Rental Cars in Winter Garden
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- Avis Rental Cars in Winter Garden
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- Dollar Rental Cars in Winter Garden
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- Luxury Car Rentals in Winter Garden
- National Car Rental Rental Cars in Winter Garden
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- Rent A Wreck Rental Cars in Winter Garden
- Sixt Rental Cars in Winter Garden
- Priceless Car Rental Rental Cars in Winter Garden
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.