Oakland Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Oakland Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Seasons Florida Resort
Save 100% on your flight
Price was $500, price is now $302 per person
$302
per person
Jul 27 - Jul 31
found 2 hours ago
Roundtrip flight included
Hartford (BDL) 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 Disney Springs™ and ESPN Wide World of Sports Complex are located nearby.
Westgate Lakes Resort & Spa Universal Studios Area
Save 100% on your flight
Price was $702, price is now $403 per person
$403
per person
Jul 27 - Jul 31
found 2 hours ago
Roundtrip flight included
Hartford (BDL) to Orlando (MCO)
Book a stay at this 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 Orange County Convention Center and Aquatica are located nearby.
The Delaney Hotel
South Orange
Save 100% on your flight
Price was $1,211, price is now $722 per person
$722
per person
Aug 27 - Sep 3
found 14 hours ago
Roundtrip flight included
New York (LGA) to Orlando (MCO)
Book a stay at this business-friendly hotel in Orlando. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the restaurant and the bar in our reviews. Popular attractions Kia Center and Orlando International Premium Outlets are located nearby.
Florida Hotel & Conference Center in the Florida Mall
Save 100% on your flight
Price was $965, price is now $581 per person
$581
per person
Aug 25 - Aug 30
found 16 hours ago
Roundtrip flight included
Philadelphia (PHL) to Orlando (MCO)
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Universal Epic Universe and Orlando International Premium Outlets are located nearby.
Margaritaville Cottages Orlando by Vstays with H2O Waterpark
Save 100% on your flight
Price was $1,366, price is now $837 per person
$837
per person
Jul 27 - Jul 31
found 2 hours ago
Roundtrip flight included
Hartford (BDL) to Orlando (MCO)
Stay at this 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.
AC Hotel by Marriott Orlando Downtown
Downtown Orlando
Save 100% on your flight
Price was $1,034, price is now $654 per person
$654
per person
Aug 27 - Sep 3
found 1 hour ago
Roundtrip flight included
New York (LGA) to Orlando (MCO)
Stay at this hotel in Orlando. Enjoy breakfast (surcharge), a fitness center, and valet parking (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Kia Center and Orlando International Premium Outlets are located nearby.
Top Hotel Deals
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
8800 Vistana Centre Dr Orlando FL
24.26 km from Oakland
Book a stay at this family-friendly aparthotel in Orlando. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff ...
DoubleTree by Hilton at the Entrance to Universal Orlando
5780 Major Blvd Orlando FL
19.18 km from Oakland
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the pool and the helpful staff in ...
The Grove Resort & Water Park Orlando
14501 Grove Resort Avenue Winter Garden FL
21.59 km from Oakland
Book a stay at this family-friendly resort in Four Corners. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff ...
Universal's Cabana Bay Beach Resort
6550 Adventure Way Orlando FL
18.52 km from Oakland
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in ...
Walt Disney World Dolphin
1500 Epcot Resort Blvd Lake Buena Vista FL
22 km from Oakland
Book a stay at this beach hotel in Lake Buena Vista. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the restaurant ...
Avanti International Resort
8738 International Dr Orlando FL
20.38 km from Oakland
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the pool and the helpful ...
Westgate Lakes Resort & Spa Universal Studios Area
9500 Turkey Lake Rd Orlando FL
20.86 km from Oakland
Book a stay at this 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 ...
Kompose Boutique Resort at Theme Parks
7491 W Irlo Bronson Memorial Hwy Kissimmee FL
24.93 km from Oakland
Stay at this resort in Kissimmee. Enjoy free breakfast, free WiFi, and 2 hot tubs. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World ...
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando
12401 International Dr Orlando FL
24.06 km from Oakland
Book a stay at this family-friendly aparthotel in Orlando. Enjoy free WiFi, 5 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
631 FLAGLER AVE Winter Garden FL
19.29 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 ...
Universal's Endless Summer Resort - Dockside Inn and Suites
7125 Universal Boulevard Orlando FL
19.76 km from Oakland
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 2 outdoor pools, and 3 bars/lounges. Our guests praise the pool and the restaurant in ...
Marriott's Grande Vista
5925 Avenida Vista Orlando FL
24.82 km from Oakland
Book a stay at this spa aparthotel in Orlando. Enjoy free WiFi, 4 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in ...
Waldorf Astoria Orlando - An Official Walt Disney World® Hotel
14200 Bonnet Creek Resort Lane Orlando FL
24.36 km from Oakland
Book a stay at this luxury resort in Orlando. Enjoy 2 outdoor pools, a full-service spa, and 6 restaurants. Our guests praise the helpful staff in our reviews. ...
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.
Tue, Sep 1 - Sat, Sep 12
LGA
LaGuardia
MCO
Orlando Intl.
$96 Roundtrip, just found
$96
Roundtrip
just found
Sat, Jan 9 - Sat, Jan 23
PSM
Portsmouth Intl.
MCO
Orlando Intl.
$147 Roundtrip, found 3 days ago
$147
Roundtrip
found 3 days ago
Tue, Sep 1 - Sat, Sep 12
LGA
LaGuardia
MCO
Orlando Intl.
$177 Roundtrip, just found
$177
Roundtrip
just found
Tue, Sep 1 - Wed, Sep 9
EWR
Newark Liberty Intl. Airport
MCO
Orlando Intl.
$177 Roundtrip, found 7 hours ago
$177
Roundtrip
found 7 hours ago
Tue, Sep 1 - Sat, Sep 12
LGA
LaGuardia
MCO
Orlando Intl.
$177 Roundtrip, just found
$177
Roundtrip
just found