Callahan Vacations from $431

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Your Callahan Vacation

Our Callahan vacation packages are a fast and convenient way to plan and book your next retreat. Get to know the essence of this unique neighborhood without the bother of having to organize everything yourself. When it's time to explore the sights, you'll find loads of big-name attractions nearby including Camping World Stadium, Dubsdread Golf Course and Bob Carr Performing Arts Centre. Tick off one, two or all during your trip to Callahan. Don't just think about it — make it a reality! Book your perfect Callahan vacation with Expedia and get to where you're going your way.

The Latest Callahan Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
Save 100% on your flight
Price was $854, price is now $431 per person
$431
per person
Jun 6 - Jun 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.6/10 Excellent! (1,007 reviews)
Everything was great

Reviewed on May 4, 2026

Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
Price was $930, price is now $461 per person
$461
per person
Jun 6 - Jun 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.2/10 Very Good! (1,661 reviews)
That resort was amazing. The only thing missing was a breakfast restaurant because the Mexican restaurant that opened to serve breakfast wasn't very good and didn't offer many good options.

Reviewed on May 7, 2026

Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Save 100% on your flight
Price was $879, price is now $443 per person
$443
per person
Jun 6 - Jun 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.2/10 Very Good! (1,854 reviews)
Todo estuvo bien, tuve inconveniente con los huéspedes continuos a mi habitación pero me resolvieron rápido. Otro asunto que ocurrio en la estadia fue que a traves de Expedia se compró una estadia de una habitacion en particular y cuando llegamos nos indicaron que no habia disponibilidad, ofrecieron un upgrade pero no se ajustaba a la necesidad del momento. Se exigió por lo que se pagó pero aún así se tuvo que pagar adicional para poder tener habitacion con 2 camas, fueron los unicos inconvenientes.

Reviewed on May 4, 2026

Harbor Island Beach Club by Villatel

Harbor Island Beach Club by Villatel

2 out of 5
Price was $2,652, price is now $1,436 per person
$1,436
per person
Jun 11 - Jun 16
found 1 day ago
Roundtrip flight included
New York (NYC) to Orlando (MCO)
9/10 Wonderful! (4 reviews)
This property is great for large groups. The community is relaxed and comfortable. It’s easy walking distance and access to Melbourne beach. Very nice.

Reviewed on Mar 9, 2025

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight
Price was $1,344, price is now $737 per person
$737
per person
Jul 13 - Jul 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.4/10 Very Good! (6,277 reviews)
The amenities were more than you could ask for very clean property and clean rooms. Staff was super friendly and helpful

Reviewed on May 6, 2026

Where to stay in Callahan

Find the best Callahan areas and neighborhoods for the activities you enjoy most. Learn more about Callahan
International Drive District

International Drive District

Adventure activities, iconic attractions, shopping and world-class dining destinations make this famous street one of Orlando’s most popular tourist attractions.

Find hotels in International Drive District

Callahan Hotel Deals

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

4 out of 5
8800 Vistana Centre Dr Orlando FL
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $134 total per night from Jun 1 to Jun 2
$134 total
Jun 1 - Jun 2
Total with taxes and fees
9.2/10 Wonderful! (5,388 reviews)
Nice property offering many amenities.

Reviewed on May 6, 2026

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

3.5 out of 5
6550 Adventure Way Orlando FL
Fully refundableReserve now, pay when you stay
$150 nightly
The price is $169 total per night from May 10 to May 11
$169 total
May 10 - May 11
Total with taxes and fees
Universal's Cabana Bay Beach Resort
DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

4 out of 5
5780 Major Blvd Orlando FL
Fully refundable
$98 nightly
The price is $110 total per night from May 31 to Jun 1
$110 total
May 31 - Jun 1
Total with taxes and fees
8.4/10 Very Good! (6,913 reviews)
Great location close to everything. The pool its very specious and deep and the restaurant wasn’t bad. But the 34 per night parking with half the lot being empty…. Its awful.

Reviewed on May 7, 2026

DoubleTree by Hilton at the Entrance to Universal Orlando
See all 19,619 properties in Callahan
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Callahan

Bob Carr Performing Arts Centre

Bob Carr Performing Arts Centre

Enjoy an outing to Bob Carr Performing Arts Centre during your stay in Orlando. Discover the area's shops, or seek out its golf courses.

Bob Carr Performing Arts Centre
Walt Disney World® Resort

Walt Disney World® Resort

4.5/5(2,451 reviews)

Walt Disney World® Resort is part of Orlando. It makes up part of bustling metropolis that is home to 240,000 inhabitants. Walt Disney World® Resort is approximately 15 miles (24 kilometers) from Orlando’s city center. If you are flying in, Walt Disney World® Resort is approximately 15 miles (24 kilometers) from Orlando International Airport.

Walt Disney World® Resort
Universal Studios Florida

Universal Studios Florida

4.5/5(9,415 reviews)

Thrill rides based on your favorite movies create this internationally acclaimed theme park.

Universal Studios Florida

Things to do

Walt Disney World® Resort Disney After Hours

Walt Disney World® Resort Disney After Hours

$191
per adult
100% of travellers recommend
Walt Disney World® Resort Disney After Hours
LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

$39
per traveler
86% of travellers recommend
LEGOLAND® Florida Tickets
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

$27
per adult
92% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
See all activities in Orlando
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.