Oakland Vacation Packages for 2025

Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*

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Oakland Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Save 100% on your flight
per person
Sep 21 - Sep 27
found 19 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this hotel in Kissimmee. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Old Town and Disney Springs™ are located nearby.

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
per person
Sep 21 - Sep 27
found 19 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this 4-star family-friendly resort in Orlando. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Universal’s Volcano Bay and The Orlando Eye at ICON Park are located nearby.

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
per person
Sep 21 - Sep 27
found 19 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this 4-star spa hotel in Orlando. Enjoy free parking, 7 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions The Orlando Eye at ICON Park and Aquatica are located nearby.

Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Save 100% on your flight
per person
Sep 21 - Sep 27
found 19 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Book a stay at this business-friendly hotel in Kissimmee. Enjoy free WiFi, free parking, and laundry facilities. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Old Town and Disney Springs™ are located nearby.

Vacation Village at Parkway

Vacation Village at Parkway

3 out of 5
Save 100% on your flight
per person
Sep 21 - Sep 27
found 19 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this 3-star family-friendly condo in Kissimmee. Enjoy free WiFi, 7 outdoor pools, and 7 hot tubs. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Old Town and Disney's Hollywood Studios® are located nearby.

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

4 out of 5
Save 100% on your flight
per person
Sep 15 - Sep 19
found 3 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Stay at this 4-star hotel in Kissimmee. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and Disney's Hollywood Studios® are located nearby.

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Top Hotel Deals

Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando

3 out of 5
9000 International Drive, Orlando, FL
20.71 km from Oakland
Stay at this 3-star family-friendly hotel in Orlando. Enjoy free WiFi, 3 outdoor pools, and 2 coffee shops/cafes. Our guests praise the pool and the helpful ...
Marriott's Grande Vista

Marriott's Grande Vista

4 out of 5
5925 Avenida Vista, Orlando, FL
24.82 km from Oakland
Stay at this 4-star spa hotel in Orlando. Enjoy free WiFi, 4 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. ...
Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

4 out of 5
7491 W Irlo Bronson Memorial Hwy, Kissimmee, FL
24.93 km from Oakland
Stay at this 4-star resort in Kissimmee. Enjoy free WiFi, 2 hot tubs, and breakfast (surcharge). Popular attractions Disney's Animal Kingdom® Theme Park and ...
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
19.18 km from Oakland
Stay at this 4-star family-friendly hotel in Orlando. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the pool and the helpful staff in ...
Holiday Inn Resort Orlando Suites - Waterpark by IHG

Holiday Inn Resort Orlando Suites - Waterpark by IHG

3.5 out of 5
14500 Continental Gateway, Orlando, FL
25.06 km from Oakland
Stay at this 3.5-star family-friendly hotel in Orlando. Enjoy 2 outdoor pools, 5 restaurants, and 2 hot tubs. Our guests praise the clean rooms and the family ...
Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings

3 out of 5
341 Flagler Ave, Winter Garden, FL
19.25 km from Oakland
Stay at this 3-star business-friendly hotel in Winter Garden. Enjoy free breakfast, a free theme park shuttle, and a 24-hour fitness center. Our guests praise ...
Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

3.5 out of 5
6550 Adventure Way, Orlando, FL
18.52 km from Oakland
Stay at this 3.5-star family-friendly hotel in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue, Winter Garden, FL
21.72 km from Oakland
Stay at this 4-star family-friendly resort in Four Corners. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff ...
DoubleTree by Hilton Hotel Orlando Downtown

DoubleTree by Hilton Hotel Orlando Downtown

4 out of 5
60 South Ivanhoe Boulevard, Orlando, FL
24.83 km from Oakland
Book a stay at this business-friendly hotel in Orlando. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and ...
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

4 out of 5
8800 Vistana Centre Dr, Orlando, FL
24.26 km from Oakland
Stay at this 4-star eco-certified hotel in Orlando. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff in ...
DoubleTree by Hilton Hotel Orlando at SeaWorld

DoubleTree by Hilton Hotel Orlando at SeaWorld

4 out of 5
10100 International Drive, Orlando, FL
22.77 km from Oakland
Stay at this 4-star family-friendly resort in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the breakfast and the pool in our ...
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

2.5 out of 5
631 FLAGLER AVE, Winter Garden, FL
19.33 km from Oakland
Book a stay at this business-friendly hotel in Winter Garden. Enjoy free breakfast, free WiFi, and a free theme park shuttle. Our guests praise the breakfast ...
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

4 out of 5
12401 International Dr, Orlando, FL
24.06 km from Oakland
Stay at this 4-star eco-certified hotel in Orlando. Enjoy free WiFi, 5 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in ...
CoCo Key Hotel and Water Resort 

CoCo Key Hotel and Water Resort 

3.5 out of 5
7400 International Dr, Orlando, FL
19.39 km from Oakland
Stay at this 3.5-star family-friendly hotel in Orlando. Enjoy 3 outdoor pools, 4 restaurants, and 2 poolside bars. Our guests praise the pool and the helpful ...
Hyatt House Orlando International Drive

Hyatt House Orlando International Drive

4 out of 5
5374 INTERNATIONAL DRIVE, Orlando, FL
20.58 km from Oakland
Stay at this 4-star business-friendly hotel in Orlando. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Orlando International Premium ...
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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.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Sat, Sep 6 - Wed, Sep 10
PHL
Philadelphia Intl.
MCO
Orlando Intl.
$87 Roundtrip, found 1 day ago
$87
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sat, Sep 6 from Philadelphia Intl. to Orlando Intl., returning Wed, Sep 10, priced at $87 found 1 day ago
Breeze Airways
Wed, Oct 15 - Wed, Oct 22
PSM
Portsmouth Intl.
MCO
Orlando Intl.
$102 Roundtrip, found 1 day ago
$102
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Oct 15 from Portsmouth Intl. to Orlando Intl., returning Wed, Oct 22, priced at $102 found 1 day ago
Frontier Airlines
Sat, Sep 6 - Sat, Sep 13
JFK
John F. Kennedy Intl.
MCO
Orlando Intl.
$106 Roundtrip, found 6 days ago
$106
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Sep 6 from John F. Kennedy Intl. to Orlando Intl., returning Sat, Sep 13, priced at $106 found 6 days ago
JetBlue Airways
Mon, Sep 15 - Tue, Sep 23
JFK
John F. Kennedy Intl.
MCO
Orlando Intl.
$139 Roundtrip, found 5 hours ago
$139
Roundtrip
found 5 hours ago
Select JetBlue Airways flight, departing Mon, Sep 15 from John F. Kennedy Intl. to Orlando Intl., returning Tue, Sep 23, priced at $139 found 5 hours ago
Delta
Mon, Aug 25 - Fri, Sep 5
LGA
LaGuardia
MCO
Orlando Intl.
$143 Roundtrip, found 1 day ago
$143
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Aug 25 from LaGuardia to Orlando Intl., returning Fri, Sep 5, priced at $143 found 1 day ago