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.
Seasons Florida Resort
Save 100% on your flight
Price was $435, price is now $259 per person
$259
per person
Nov 10 - Nov 14
found 1 day 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.
Westgate Palace Hotel / Universal / I-Drive
International Drive District
Price was $1,362, price is now $559 per person
$559
per person
Oct 30 - Nov 6
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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
Price was $930, price is now $432 per person
$432
per person
Oct 30 - Nov 6
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.
Westgate Vacation Villas Resort
Save 100% on your flight
Price was $795, price is now $387 per person
$387
per person
Oct 18 - Oct 25
found 14 hours ago
Roundtrip flight included
Philadelphia (PHL) to Orlando (MCO)
Stay at this 4-star family-friendly resort in Kissimmee. Enjoy free parking, 14 outdoor pools, and 2 restaurants. 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.
Vacation Village at Parkway
Save 100% on your flight
Price was $706, price is now $429 per person
$429
per person
Oct 18 - Oct 25
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
International Drive District
Save 100% on your flight
Price was $527, price is now $325 per person
$325
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this 3-star hotel in Orlando. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms and the overall value in our reviews. Popular attractions Universal’s Volcano Bay and Universal’s Islands of Adventure are located nearby.
Top Hotel Deals
Marriott's Grande Vista
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. ...
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 ...
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 ...
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando
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 ...
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, 3 outdoor pools, and 2 coffee shops/cafes. Our guests praise the pool and the helpful ...
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 ...
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
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 ...
Walt Disney World Swan
1200 Epcot Resort Blvd, Lake Buena Vista, FL
22.43 km from Oakland
Stay at this 4-star beach resort in Lake Buena Vista. Enjoy free WiFi, a private beach, and 3 hot tubs. Our guests praise the pool and the helpful staff in our ...
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 ...
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 Four Corners. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff ...
Walt Disney World Dolphin
1500 Epcot Resort Blvd, Lake Buena Vista, FL
21.99 km from Oakland
Stay at this 4-star 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 ...
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 ...
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 ...
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, Oct 7 - Wed, Oct 8
PHL
Philadelphia Intl.
MCO
Orlando Intl.
$77 Roundtrip, found 4 days ago
$77
Roundtrip
found 4 days ago
Wed, Oct 8 - Sat, Oct 11
EWR
Newark Liberty Intl. Airport
MCO
Orlando Intl.
$87 Roundtrip, found 2 days ago
$87
Roundtrip
found 2 days ago
Wed, Oct 15 - Wed, Oct 22
PSM
Portsmouth Intl.
MCO
Orlando Intl.
$122 Roundtrip, found 4 days ago
$122
Roundtrip
found 4 days ago
Thu, Oct 2 - Fri, Oct 3
EWR
Newark Liberty Intl. Airport
MCO
Orlando Intl.
$127 Roundtrip, found 2 days ago
$127
Roundtrip
found 2 days ago
Mon, Nov 3 - Fri, Nov 14
JFK
John F. Kennedy Intl.
MCO
Orlando Intl.
$127 Roundtrip, found 1 day ago
$127
Roundtrip
found 1 day ago