Deals on vacations and trips to Oakland

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Oakland flight + hotel vacation packages

Prices and availability subject to change. Additional terms may apply.
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Save 100% on your flight
per person
May 30 - Jun 3
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This hotel features an outdoor pool, a gym, and a restaurant. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and a picnic area are also on offer.
Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
Florida Center
per person
May 24 - May 31
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This resort features an outdoor pool, a gym, and a restaurant. Bring the family and enjoy the children's pool, free theme park shuttle, and kid-friendly dining. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi.
Westgate Blue Tree Resort in Lake Buena Vista

Westgate Blue Tree Resort in Lake Buena Vista

3.5 out of 5
Save 100% on your flight
per person
Jun 10 - Jun 17
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This hotel features an outdoor pool and a gym. There's fun for all ages with mini golf and a children's pool, and barbecue grills are available on site. Enjoy the spa tub and perks like free self parking.
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight
per person
Jun 6 - Jun 9
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This smoke-free hotel features a full-service spa, a water park, and a marina. There's fun for all ages with a lazy river and a children's club, and barbecue grills are available on site. Enjoy the 7 outdoor pools and get free valet parking.
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

3 out of 5
Florida Center
Save 100% on your flight
per person
May 24 - May 31
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This aparthotel features an outdoor pool and a rooftop terrace. Enjoy the spa tub and free perks like on-the-go breakfast and free self parking. A business center, free WiFi in public areas, and a terrace are also on offer.

Top Oakland hotel deals

DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

4 out of 5
5780 Major Blvd, Orlando, FL
Free Cancellation
Reserve now, pay when you stay
The price is $93 per night
$93
per night
May 13 - May 14
This hotel features 2 restaurants, an outdoor pool, and a 24-hour gym. There's fun for all ages with a children's pool and an arcade/game room, and families will appreciate the onsite laundry facilities. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue, Winter Garden, FL
The price is $202 per night
$202
per night
May 12 - May 13
Free water park access, 3 restaurants, and 3 outdoor pools are all featured at this resort. Bring the family and enjoy the lazy river, children's club, and mini golf. Relax with a drink at one of the 2 poolside bars and get perks like free WiFi.
Holiday Inn Resort Orlando Suites - Waterpark, an IHG Hotel

Holiday Inn Resort Orlando Suites - Waterpark, an IHG Hotel

3.5 out of 5
14500 Continental Gateway, Orlando, FL
Free Cancellation
The price is $84 per night
$84
per night
Apr 28 - Apr 29
A water park, 2 outdoor pools, and 2 spa tubs are all featured at this smoke-free hotel. There's fun for all ages with mini golf and a waterslide, and families will appreciate the onsite laundry facilities. Enjoy the gym and perks like free WiFi.
Hot Tub
Pet friendly
Universal's Endless Summer Resort - Dockside Inn and Suites

Universal's Endless Summer Resort - Dockside Inn and Suites

3 out of 5
7125 Universal Boulevard, Orlando, FL
Free Cancellation
Reserve now, pay when you stay
The price is $144 per night
$144
per night
Apr 25 - Apr 26
This smoke-free hotel features 2 outdoor pools, a gym, and a restaurant. There's fun for all ages with a children's pool and an arcade/game room, and families will appreciate the onsite laundry facilities. Relax with a drink at one of the 3 bars/lounges and get perks like free WiFi.
Breakfast available
Pool
Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

3.5 out of 5
6550 Adventure Way, Orlando, FL
Free Cancellation
Reserve now, pay when you stay
The price is $201 per night
$201
per night
Apr 25 - Apr 26
This smoke-free hotel features 2 restaurants, 2 outdoor pools, and 2 spa tubs. There's fun for all ages with a lazy river and a bowling alley, and families will appreciate the onsite laundry facilities. Unwind with a drink at one of the 2 poolside bars and enjoy freebies like WiFi in public areas and a theme park shuttle.
Lake Buena Vista Resort Village & Spa

Lake Buena Vista Resort Village & Spa

4 out of 5
8113 Resort Village Drive, Orlando, FL
Get rates
A full-service spa, 3 restaurants, and 2 outdoor pools are all featured at this condo resort. Enjoy the 3 spa tubs and perks like free self parking and a free theme park shuttle. 2 coffee shops/cafes, 2 bars/lounges, and a poolside bar offer an array of options for drinks and a bit to eat.
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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.

Popular places to visit

Image for Flamingo Crossings Town Center

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.

Flamingo Crossings Town Center
Image for Disney's Palm Golf Course

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 Palm Golf Course
Image for Orange County National Golf Club

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.

Orange County National Golf Club

Frequently asked questions

How much are vacation packages to Oakland?
Starting from as little as $232, hotel and flight packages are a superb way to make your travel budget stretch further. Watch out Oakland — here you come!
Where can I get the best vacation package deals for Oakland?
There are awesome Oakland package deals to score with Travelocity. Did you know we partner with as many as 400 airlines and 1,000,000 properties all over the world? Keep this in mind the next time you’re ready to cross another place off your bucket list.
Why should I book my Oakland vacation bundle with Travelocity?
The three S’s — savings, support and a stress-free booking — are just the tip of the iceberg. Enjoy a fulfilling travel experience knowing you have access to 24/7 customer support. With the Travelocity Price Match Guarantee, you know you’re getting the best deal available.
Can I save on my Oakland car rental if I book it with my hotel or flight?
Sure can — combine your hotel, car and flight into an Oakland vacation package and you’ll save plenty. With so many places to explore in and around Oakland, that set of wheels will come in handy. Once you’re in the driver’s seat, turn up the stereo and head toward Daytona International Speedway, a must-see attraction approximately 55 mi from Oakland.
What is the best time of year to go to Oakland?
You can sidestep the crowds and save a tidy sum in April, May and December, the quietest period for tourism. High season months of January, February and March are of course busier (and more expensive), but there’ll be more going on around Oakland. Lock in a hotel in and you’ll see your budget go further. Room rates are usually higher in .
Which airport is best for Oakland?
Orlando Intl. Airport (MCO), located around 20 mi southeast of inner Oakland, is most likely where you’ll land. Your other choices are Orlando Sanford Intl. Airport (SFB) (30 mi away from central Oakland) and Daytona Beach Intl. Airport (DAB) (55 mi away from central Oakland).
Where should I stay when visiting Oakland?
If you’re after a place to lay your head, check out the The Oak View Place. It’s the top pick for many visitors.