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.
Days Inn by Wyndham St Augustine/Historic Downtown
Uptown
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Stay at this hotel in St. Augustine. Enjoy free WiFi, a free area shuttle, and parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Castillo de San Marcos National Monument and St. George Street are located nearby.
The Kenwood Inn
St. Augustine Historic District
Save 100% on your flight
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Stay at this 3.5-star B&B in St. Augustine. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions St. Augustine Beach and St. George Street are located nearby.
Casa Monica Resort & Spa, Autograph Collection
St. Augustine Historic District
Save 100% on your flight
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Stay at this 4-star luxury hotel in St. Augustine. Enjoy a full-service spa, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions St. Augustine Beach and St. George Street are located nearby.
Hilton Garden Inn Jacksonville Ponte Vedra Sawgrass
Palm Valley
per person
Oct 5 - Oct 9
found 10 hours ago
Roundtrip flight included
Philadelphia (PHL) to Orlando (MCO)
Stay at this 3-star business-friendly hotel in Ponte Vedra Beach. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions TPC Sawgrass and Jacksonville Beach Pier are located nearby.
Old City House Inn and Restaurant
St. Augustine Historic District
Save 100% on your flight
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Stay at this 3.5-star historic B&B in St. Augustine. Enjoy free breakfast, free WiFi, and room service. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions St. Augustine Beach and St. George Street are located nearby.
St George Inn
St. Augustine Historic District
Save 100% on your flight
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Stay at this 3.5-star hotel in St. Augustine. Enjoy free breakfast, free WiFi, and room service. Our guests praise the helpful staff in our reviews. Popular attractions St. Augustine Beach and Castillo de San Marcos National Monument are located nearby.
Top Hotel Deals
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 ...
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. ...
Kompose Boutique Resort at Theme Parks
7491 W Irlo Bronson Memorial Hwy, Kissimmee, FL
24.93 km from Oakland
Stay at this 4-star business-friendly resort in Kissimmee. Enjoy free breakfast, free WiFi, and 2 hot tubs. Popular attractions Disney's Animal Kingdom® Theme ...
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 ...
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 ...
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 ...
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 Four Corners. Enjoy 6 outdoor pools, 3 restaurants, and 2 hot tubs. Our guests praise the pool and the helpful ...
DoubleTree by Hilton Hotel Orlando Downtown
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
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
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
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
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 ...
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.
Sat, Sep 6 - Wed, Sep 10
PHL
Philadelphia Intl.
MCO
Orlando Intl.
$87 Roundtrip, found 4 hours ago
$87
Roundtrip
found 4 hours ago
Thu, Sep 11 - Sun, Sep 14
DTW
Detroit Metropolitan Wayne County
MCO
Orlando Intl.
$104 Roundtrip, found 6 days ago
$104
Roundtrip
found 6 days ago
Fri, Sep 5 - Sun, Sep 7
SWF
Stewart Intl.
MCO
Orlando Intl.
$125 Roundtrip, found 5 days ago
$125
Roundtrip
found 5 days ago
Sat, Nov 1 - Wed, Nov 5
EWR
Newark Liberty Intl. Airport
MCO
Orlando Intl.
$137 Roundtrip, found 4 days ago
$137
Roundtrip
found 4 days ago
Sun, Sep 14 - Fri, Sep 26
JFK
John F. Kennedy Intl.
MCO
Orlando Intl.
$139 Roundtrip, found 6 days ago
$139
Roundtrip
found 6 days ago
Best points of interest in Winter Garden
- Walt Disney World® Resort Vacations
- Universal Studios Florida Vacations
- Universal Orlando Resort Vacations
- Disney SpringsTM 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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