Oakland Vacation Packages for 2025
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Photo by Gregg Yutko
Oakland Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Seasons Florida Resort
Save 100% on your flight
per person
Jun 18 - Jun 23
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) 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.
Westgate Palace Hotel / Universal / I-Drive
Florida Center
per person
Jun 18 - Jun 23
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) 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 Town Center Resort
Save 100% on your flight
per person
Jun 18 - Jun 23
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Orlando (MCO)
Stay at this 4-star family-friendly resort in Kissimmee. Enjoy free WiFi, free parking, and 14 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World of Sports are located nearby.
Westgate Vacation Villas Resort
Save 100% on your flight
per person
Jun 18 - Jun 23
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Orlando (MCO)
Stay at this 4-star family-friendly resort in Kissimmee. Enjoy free parking, 14 outdoor pools, and 4 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World of Sports are located nearby.
Westgate Towers Resort
Save 100% on your flight
per person
Jun 18 - Jun 23
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Orlando (MCO)
Stay at this 3.5-star family-friendly hotel in Kissimmee. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World of Sports are located nearby.
Westgate Lakes Resort & Spa Universal Studios Area
Save 100% on your flight
per person
Jun 18 - Jun 23
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) 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 Wheel at ICON Park™ and Aquatica are located nearby.
Top Hotel Deals
DoubleTree by Hilton at the Entrance to Universal Orlando
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 ...
DoubleTree by Hilton Hotel Orlando at SeaWorld
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 ...
Rosen Inn at Pointe Orlando
9000 International Drive, Orlando, FL
20.71 km from Oakland
Stay at this 3-star family-friendly hotel in Orlando. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the pool and the helpful staff in ...
Holiday Inn Resort Orlando Suites - Waterpark by IHG
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 ...
Universal's Cabana Bay Beach Resort
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
14501 Grove Resort Avenue, Winter Garden, FL
21.72 km from Oakland
Stay at this 4-star family-friendly resort in Winter Garden. Enjoy free WiFi, 5 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful ...
Caribe Royale Orlando
8101 World Center Dr, Orlando, FL
25.96 km from Oakland
Book a stay at this luxury hotel in Orlando. Enjoy 3 outdoor pools, a full-service spa, and 4 restaurants. Our guests praise the pool and the restaurant in our ...
Westgate Lakes Resort & Spa Universal Studios Area
9500 Turkey Lake Rd, Orlando, FL
20.86 km from Oakland
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 ...
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
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 ...
Hyatt Regency Orlando
9801 International Dr, Orlando, FL
21.39 km from Oakland
Stay at this 4.5-star luxury hotel in Orlando. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in ...
Hilton Vacation Club Grande Villas Orlando
12118 Turtle Cay Circle, Orlando, FL
22.29 km from Oakland
Stay at this 3.5-star family-friendly hotel in Orlando. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the bar in our reviews. ...
Sheraton Orlando Lake Buena Vista Resort
12205 S Apopka Vineland Rd, Orlando, FL
22.49 km from Oakland
Book a stay at this spa hotel in Orlando. Enjoy 2 outdoor pools, a full-service spa, and 2 hot tubs. Our guests praise the pool and the bar in our reviews. Popular ...
Home2 Suites by Hilton Orlando at Flamingo Crossings
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 ...
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.
Wed, Jun 4 - Wed, Jun 11
DTW
Detroit Metropolitan Wayne County
MCO
Orlando Intl.
$80 Roundtrip, found 5 days ago
$80
Roundtrip
found 5 days ago
Tue, May 6 - Wed, May 14
JFK
John F. Kennedy Intl.
MCO
Orlando Intl.
$82 Roundtrip, found 5 days ago
$82
Roundtrip
found 5 days ago
Sat, May 10 - Sat, May 17
ORD
O'Hare Intl.
MCO
Orlando Intl.
$89 Roundtrip, found 5 days ago
$89
Roundtrip
found 5 days ago
Sun, Jun 8 - Tue, Jun 10
PHL
Philadelphia Intl.
MCO
Orlando Intl.
$90 Roundtrip, found 3 days ago
$90
Roundtrip
found 3 days ago
Best points of interest in Winter Garden
- Walt Disney World® Resort Vacations
- Universal Studios Florida Vacations
- Disney SpringsTM Vacations
- Universal Orlando Resort Vacations
- Magic Kingdom® Park Vacations
- Orange County Convention Center Vacations
- Disney's Animal Kingdom® Theme Park Vacations
- Epcot® Vacations
- Disney's Hollywood Studios® Vacations
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