Oakland Vacations
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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.
Price found within the past 48 hours. Click for updated prices.
- Westgate Town Center Resort
Aug 4 - Aug 11Westgate Town Center Resort + Flight
Kissimmee7 nights8.2/10 - Very Good (1,750 reviews)"Es super increíble me encantó"Reviewed May 31, 2026Roundtrip • Boston (BOS) - Orlando (MCO)BOS - MCO • Nonstop MCO - BOS • Nonstop - Westgate Palace Hotel / Universal / I-Drive
Aug 4 - Aug 11Westgate Palace Hotel / Universal / I-Drive + Flight
International Drive District7 nights8.8/10 - Excellent (1,260 reviews)"Our stay was very pleasant, staff very polite! Great price!"Reviewed June 1, 2026Roundtrip • Boston (BOS) - Orlando (MCO)BOS - MCO • Nonstop MCO - BOS • Nonstop$1,467$599found 1 day agoper traveler - Westgate Vacation Villas Resort
Aug 1 - Aug 8Westgate Vacation Villas Resort + Flight
Kissimmee7 nights8.2/10 - Very Good (1,954 reviews)"Very clean ,home away ftom home excellent Service"Reviewed June 1, 2026Roundtrip • Boston (BOS) - Orlando (MCO)BOS - MCO • Nonstop MCO - BOS • Nonstop - Westgate Cocoa Beach Resort
Aug 18 - Aug 24Westgate Cocoa Beach Resort + Flight
Cocoa Beach6 nights8.6/10 - Excellent (550 reviews)"Esta bien Accesible a todas las amenidades, incluyendo el área de la playa,Solo que es un poco caro el precio por noche, por lo demás todo muy bien."Reviewed May 25, 2026Roundtrip • New York (EWR) - Orlando (MCO)EWR - MCO • Nonstop MCO - EWR • Nonstop - Boardwalk Inn and Suites
Jul 17 - Jul 28Boardwalk Inn and Suites + Flight
Davis11 nights8.4/10 - Very Good (1,849 reviews)"We enjoyed our two-night stay overall. The room itself was nice, though the hardwood floors needed to be cleaned better before we checked in. A good sweeping and mopping from housekeeping would have done the trick. On the plus side, parking is included in the hotel rate—a huge perk compared to nearby beach hotels charging $30+—even if the lot layout is a bit unusual, they make it work for the guests. The location is walkable to the pier, local shops, and dining. We would consider staying here..."Reviewed June 1, 2026Roundtrip • Boston (BOS) - Orlando (MCO)BOS - MCO • Nonstop MCO - BOS • Nonstop
Oakland Hotel Deals
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
8800 Vistana Centre Dr Orlando FL
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $161 total per night from Jun 22 to Jun 23
$161 total
Jun 22 - Jun 23
Total with taxes and fees
9.2/10 Wonderful! (5,649 reviews)
"Great location on the beach."
Reviewed on Jun 1, 2026
DoubleTree by Hilton at the Entrance to Universal Orlando
5780 Major Blvd Orlando FL
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $101 total per night from Jun 14 to Jun 15
$101 total
Jun 14 - Jun 15
Total with taxes and fees
8.6/10 Excellent! (6,943 reviews)
"Great visit"
Reviewed on Jun 1, 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 Jun 7 to Jun 8
$245 total
Jun 7 - Jun 8
Total with taxes and fees
8/10 Very Good! (10,044 reviews)
"Change my room the next day. Down grade my room And still charge the same . Ask for things the come with the room never never received them. Too much walking."
Reviewed on Jun 1, 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 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.
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
Walt Disney World® Resort Disney After Hours
$191
per adult
100% 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
- Hotels near Universal Studios Florida
- Hotels near Oakland Nature Preserve
- 5 Star Hotels in Killarney
- Marriott Hotels & Resorts in Killarney
- Hotels near Killarney
- Winter Garden Hotels
- Hotels near Resurrection Catholic Church
- Hotels near Garden Theatre
- Hotels near Winter Garden Art Association
- Apartments in Winter Garden
- Hotels near Central Florida Railroad Museum
- Resorts in Winter Garden
- B&B in Winter Garden
- Cheap Hotels in Winter Garden
- Walt Disney World Resort in Winter Garden
- Extended Stay America Hotels in Winter Garden
- Pet-Friendly Hotels in Winter Garden
- Waterpark Hotels in Winter Garden
- Extended Stay Hotels in Winter Garden
- Marriott Hotels & Resorts in Winter Garden
- Hotel Wedding Venues Hotels in Winter Garden
- Wyndham Hotels in Winter Garden
- Resorts & Hotels with Spas in Winter Garden
- 5 Star Hotels in Winter Garden
- Villas in Winter Garden
- Hotels with a Lazy River in Winter Garden
- Historic Hotels in Winter Garden
- Luxury Hotels in Winter Garden
- Red Roof Inn Hotels in Winter Garden
- Hotels with Suites in Winter Garden
- Hotels with Restaurants in Winter Garden
- Hotels with Hot Tubs in Winter Garden
- Hotels with Childcare in Winter Garden
- Romantic Hotels in Winter Garden
- Cottages in Winter Garden
- Hotels with Connecting Rooms in Winter Garden
- Hotels with Kitchenettes in Winter Garden
- 4 Star Hotels in Winter Garden
- Family Hotels in Winter Garden
- Hotels with a Gym in Winter Garden
- Aparthotels in Winter Garden
- Hotels with a Pool in Winter Garden
- Motels in Winter Garden
- Hotels with Free Breakfast in Winter Garden
- Rv Parks in Winter Garden
- Best Western Hotels in Winter Garden
- Hotels with Bars in Winter Garden
- La Quinta Inn & Suites Hotels in Winter Garden
- Golf Hotels in Winter Garden
- Condo Rentals in Winter Garden
- Westgate Resorts in Winter Garden
- Cabin Rentals in Winter Garden
- Hilton Hotels in Winter Garden
- Hotels with Balconies in Winter Garden
- 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
- Car rentals near Winter Garden
- 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
- Van Car Rentals in Winter Garden
- Dollar Rental Cars in Winter Garden
- Alamo Rent A Car Rental Cars in Winter Garden
- Luxury Car Rentals in Winter Garden
- 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.