Oakland Vacations from $304
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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.
Margaritaville Cottages Orlando with H2O Waterpark by Vstays
Price was $1,132, price is now $579 per person
$579
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
9.2/10 Wonderful! (1,001 reviews)
House could have been a bit cleaner otherwise we enjoyed our stay
Reviewed on Jan 11, 2026
Westgate Towers Resort
Save 100% on your flight
Price was $737, price is now $377 per person
$377
per person
Mar 15 - Mar 20
found 21 hours ago
Roundtrip flight included
San Juan (SJU) to Orlando (MCO)
8.6/10 Excellent! (1,002 reviews)
Fine for a place to sleep, but I wouldn’t stay here again. It feels very dated.
Reviewed on Jan 12, 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! (5,996 reviews)
The mobile check-in counter representative was amazing. Everything about this hotel is remarkable…
Reviewed on Jan 10, 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 15 to Jan 16
$90 total
Jan 15 - Jan 16
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
$218 nightly
The price is $245 total per night from Jan 13 to Jan 14
$245 total
Jan 13 - Jan 14
Total with taxes and fees
8/10 Very Good! (8,949 reviews)
the room was spotless. the grounds were well kept. staff was amazing. the walls were kinda thin. could hear the noise from the other rooms, but overall this was the best place to stay for families and kids.
Reviewed on Jan 11, 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
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
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
- Hotels near Walt Disney World® Resort
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- Hotels near Oakland Nature Preserve
- 5 Star Hotels in Killarney
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- Hotels near Garden Theatre
- Hotels near Winter Garden Art Association
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- Hotel Wedding Venues Hotels in Winter Garden
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- RV Parks in Winter Garden
- Best Western Hotels in Winter Garden
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- Golf Hotels in Winter Garden
- Condo Rentals in Winter Garden
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- Hilton Hotels in Winter Garden
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- Universal Orlando Resort in Winter Garden
- Diamond Resorts in Winter Garden
- Vacation Homes in Winter Garden
- Hotels on the Lake in Winter Garden
- 3 Star Hotels in Winter Garden
- Red Lion Hotels in Winter Garden
- Hotels with smoking rooms in Winter Garden
- 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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- National Car Rental Rental Cars in Winter Garden
- Dollar Rent A Car Rental Cars in Winter Garden
- 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.