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 $762, price is now $441 per person
$441
per person
Mar 7 - Mar 14
found 1 day 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 Old Town and Disney Springs™ are located nearby.
Palazzo Lakeside Hotel
Price was $1,345, price is now $480 per person
$480
per person
Apr 13 - Apr 18
found 20 hours ago
Roundtrip flight included
Hartford (BDL) 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 Blue Tree Resort in Lake Buena Vista
Save 100% on your flight
Price was $1,150, price is now $670 per person
$670
per person
Mar 6 - Mar 10
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Orlando (MCO)
Book a stay at this family-friendly hotel in Orlando. Enjoy free parking, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Disney Springs™ and Epcot® are located nearby.
Margaritaville Cottages Orlando with H2O Waterpark by Vstays
Save 100% on your flight
Price was $2,178, price is now $1,295 per person
$1,295
per person
Mar 7 - Mar 14
found 1 day 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.
Destiny Palms Hotel Maingate West
Save 100% on your flight
Price was $871, price is now $548 per person
$548
per person
Mar 7 - Mar 14
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Orlando (MCO)
Stay at this hotel in Kissimmee. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and Disney's Hollywood Studios® are located nearby.
CoCo Key Hotel and Water Resort
International Drive District
Save 100% on your flight
Price was $740, price is now $467 per person
$467
per person
Mar 7 - Mar 14
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Orlando (MCO)
Book a stay at this family-friendly hotel in Orlando. Enjoy 3 outdoor pools, 4 restaurants, and 2 poolside bars. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Universal’s Islands of Adventure and Universal Orlando Resort 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 hotel in Orlando. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff in ...
Rosen Inn at Pointe Orlando
9000 International Drive Orlando FL
20.67 km from Oakland
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 3 outdoor pools, and 2 coffee shops/cafes. Our guests praise the pool and the helpful ...
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 ...
DoubleTree by Hilton Hotel Orlando at SeaWorld
10100 International Drive Orlando FL
22.77 km from Oakland
Book a stay at this family-friendly resort in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the breakfast and the pool in our ...
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 ...
Orlando International Drive North Hotel
5859 American Way Orlando FL
19.62 km from Oakland
Book a stay at this business-friendly hotel in Orlando. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
Wyndham I-Drive Avanti Resort & Conference Center
6515 International Drive Orlando FL
19.17 km from Oakland
Book a stay at this business-friendly hotel in Orlando. Enjoy free WiFi, free parking, and private pools. Our guests praise the pool and the clean rooms in our ...
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 ...
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 ...
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 ...
Lake Buena Vista Resort Village & Spa
8113 Resort Village Drive Orlando FL
26.7 km from Oakland
Book a stay at this spa condo in Orlando. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
Vacation Village Orlando, Celebration
2975 Arabian Nights Blvd Kissimmee FL
26.32 km from Oakland
Book a stay at this 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 ...
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 ...
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, Mar 3 - Sat, Mar 7
ORD
O'Hare Intl.
MCO
Orlando Intl.
$56 Roundtrip, found 2 days ago
$56
Roundtrip
found 2 days ago
Tue, Mar 3 - Wed, Mar 11
EWR
Newark Liberty Intl. Airport
MCO
Orlando Intl.
$72 Roundtrip, found 19 hours ago
$72
Roundtrip
found 19 hours ago
Wed, Mar 4 - Tue, Mar 10
EWR
Newark Liberty Intl. Airport
MCO
Orlando Intl.
$104 Roundtrip, found 2 days ago
$104
Roundtrip
found 2 days ago
Sun, Mar 1 - Fri, Mar 6
LGA
LaGuardia
MCO
Orlando Intl.
$117 Roundtrip, found 4 days ago
$117
Roundtrip
found 4 days ago
Wed, Mar 18 - Thu, Apr 2
JFK
John F. Kennedy Intl.
MCO
Orlando Intl.
$117 Roundtrip, found 3 days ago
$117
Roundtrip
found 3 days ago