Oakland Vacations from $341
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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 Lakes Resort & Spa Universal Studios Area
Save 100% on your flight
per person
Sep 7 - Sep 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.2/10 Very Good! (5,097 reviews)
I took my two kids for a getaway weekend trip before school starts and we had the best time! My building was at a perfect spot. I was close to the pool area and the water park. I loved that everything was walkable. My kids and I really enjoyed the shops and the Waterpark was so fun! The wave pool was great, along with the water slides and lazy river.. overall, it was a great trip and our room was very nice as well. I definitely recommend.
Reviewed on Jul 28, 2025
Westgate Vacation Villas Resort
Save 100% on your flight
per person
Aug 29 - Sep 5
found 23 hours ago
Roundtrip flight included
New York (NYC) to Orlando (MCO)
7.8/10 Good! (1,649 reviews)
I liked everything about the property; however I did not get a balcony as it stated in my confirmation email and upon booking. I also did not like that the times available for the waterpark did not meet me needs at all, and it was closed as well as the pool whenever i wanted to go. I had a relative that stayed at the Westgate in Orlando, and their pool was open until 11pm and I enjoyed her balcony as I did not get one.
Reviewed on Jul 22, 2025
Ocean Sands Beach Boutique Inn - 1 Acre Private Beach
Vilano Beach
Save 100% on your flight
per person
Oct 19 - Oct 25
found 15 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.6/10 Excellent! (543 reviews)
Breakfast was great and view was stunning... decor was unique
Reviewed on Jul 20, 2025
Where to stay in Oakland
Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
Vista del Lago
While Vista del Lago isn't home to many top sights, Orange Lake Golf and Island H2O Live! are some notable places to visit nearby.
Oakland Hotel Deals
DoubleTree by Hilton at the Entrance to Universal Orlando
5780 Major Blvd, Orlando, FL
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $114 total per night from Aug 14 to Aug 15
$114 total
Aug 14 - Aug 15
Total includes taxes and fees
8.2/10 Very Good! (6,492 reviews)
"Kid friendly"
Reviewed on Jul 25, 2025
Marriott's Grande Vista
5925 Avenida Vista, Orlando, FL
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $98 total per night from Aug 18 to Aug 19
$98 total
Aug 18 - Aug 19
Total includes taxes and fees
8.8/10 Excellent! (2,705 reviews)
"All was great"
Reviewed on Jul 28, 2025
Kompose Boutique Resort at Theme Parks
7491 W Irlo Bronson Memorial Hwy, Kissimmee, FL
Fully refundableReserve now, pay when you stay
$90 nightly
The price is $102 total per night from Aug 26 to Aug 27
$102 total
Aug 26 - Aug 27
Total includes taxes and fees
9.4/10 Exceptional! (792 reviews)
"Nice hotel great service"
Reviewed on Jul 25, 2025
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 family-friendly area.
Orange County National Golf Club
4.5/5(25 reviews)
Enjoy a round of golf in Winter Garden at Orange County National Golf Club. Amble around this family-friendly area's lakeside or experience its entertainment choices.
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.
Things to do
Universal Orlando Resort Express Passes
$245
per traveler
86% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
$27
per adult
90% of travellers recommend
Explore a world of travel with Expedia
Explore a world of travel with Expedia
- Orlando Hotels
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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
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- 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
- Hertz Rental Cars in Winter Garden
- Avis Rental Cars in Winter Garden
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- Dollar Rental Cars in Winter Garden
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.