Old Town Key West Vacation Packages 2026 from $1,049

Old Town Key West flight + hotel vacation packages

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

Hyatt Vacation Club at Windward Pointe, Key West

Save 100% on your flight

$1,049

per person

Jun 8 - Jun 13

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

This hotel features an outdoor pool, a hot tub, and a restaurant. Guests will appreciate free perks like free self parking and WiFi in public areas. A snack bar/deli, concierge services, and barbecue grills are also on offer.

Southernmost House - Adult Exclusive

Old Town Key West

Save 100% on your flight

$1,129

per person

Jun 8 - Jun 13

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Guests will appreciate free perks like continental breakfast and WiFi in public areas. Self parking, a terrace, and a picnic area are also offered.

The Key West Hotel

Key West Historic District

Save 100% on your flight

$1,408

per person

Jun 8 - Jun 13

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

An outdoor pool is featured at this guesthouse, along with free WiFi in public areas and a garden. Luggage storage and concierge services are also provided.

Hyatt Vacation Club at Sunset Harbor, Key West

Old Town Key West

Save 100% on your flight

$1,178

per person

Jun 8 - Jun 13

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

An outdoor pool, self parking, and concierge services are featured at this hotel. WiFi in public areas is free.

Hyatt Vacation Club at Beach House, Key West

Save 100% on your flight

$1,138

per person

Jun 8 - Jun 13

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

This hotel features an outdoor pool and a hot tub. Relax with a drink at the bar/lounge and enjoy perks like free WiFi. Self parking, concierge services, and barbecue grills are also on offer.

Top Old Town Key West hotels deals

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Free Cancellation

$283 nightly

$319 total

May 25 - May 26

Total with taxes and fees

This hotel features a full-service spa, 3 outdoor pools, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling on business? Take advantage of the 2 conference rooms, along with dry cleaning/laundry services.

Pool

Spa

Casa Marina Key West, Curio Collection by Hilton

1500 Reynolds Street Key West FL

Free Cancellation

Reserve now, pay when you stay

$327 nightly

$368 total

May 25 - May 26

Total with taxes and fees

A private beach, a full-service spa, and 2 outdoor pools are all featured at this smoke-free resort. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. Enjoy the gym and perks like free WiFi.

On private beach

Pool

Opal Key Resort & Marina, Key West

245 Front Street Key West FL

Free Cancellation

Reserve now, pay when you stay

$294 nightly

$331 total

May 25 - May 26

Total with taxes and fees

A marina, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Enjoy the outdoor pool and visit the 3 bars/lounges and poolside bar for drinks.

Pool

Hot Tub

The Southernmost Inn - Adults Only

525 United Street Key West FL

Free Cancellation

Reserve now, pay when you stay

$239 nightly

$269 total

May 10 - May 11

Total with taxes and fees

This hotel's 2 outdoor pools and hot tub are among the featured amenities. Enjoy the free continental breakfast each morning. Self parking, a coffee shop, and a terrace are also offered.

Pool

Hot Tub

The Reach Key West, Curio Collection by Hilton

1435 Simonton Street Key West FL

Free Cancellation

Reserve now, pay when you stay

$280 nightly

$315 total

May 25 - May 26

Total with taxes and fees

This resort features a private beach, a full-service spa, and a restaurant. Traveling on business? Take advantage of the express check-out, laundry service, and valet parking. Enjoy the outdoor pool and unwind at the bar/lounge and poolside bar.

On private beach

Pool

Southwinds Motel

1321 Simonton Street Key West FL

$194 nightly

$218 total

Jun 1 - Jun 2

Total with taxes and fees

This hotel features 2 outdoor pools and a bar/lounge. Enjoy the free continental breakfast each morning. Self parking, a picnic area, and luggage storage are also offered.

Pool

Breakfast included

Don't see what you're looking for?

See all available properties in Old Town Key West

View all properties

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.

Popular places to visit

Southernmost Point

4.5/5(3,246 reviews)

Snap a memorable photograph from the edge of North America at this monumental landmark.

Ernest Hemingway Home and Museum

4.5/5(1,744 reviews)

Meet six-toed cats and watch as the life of one America’s great writers unfolds before your eyes at his former home.

South Beach

4/5(999 reviews)

Head to the southernmost beach of the continental United States to relax and swim in the waters where famous writer Tennessee Williams once took his daily swim.

Frequently asked questions

How much are vacation packages to Old Town Key West?

With vacation packages available from as low as $1,049, it's not necessary to blow out the credit card for your visit to Old Town Key West. Travelocity can help. Bundle hotels, flights and experiences into a package and land excellent discounts. The more you book, the more you save.

Where can I get the best vacation package deals for Old Town Key West?

With around 400 air carriers and 1,000,000 hotels across the world, it's hard to top Travelocity. Take advantage of our impressive range and pick up the best package deal to Old Town Key West. Isn't it great when trip planning is that easy?

Why should I purchase my Old Town Key West vacation package with Travelocity?

By booking your hotel, flights, activities and car rental altogether, you'll save big bucks as well as precious time. We offer round-the-clock customer support, and you'll know that you'll always be getting the best deal possible with our Price Match Guarantee. So, what's stopping you? Book your dream getaway today and get packing!

Can I save money on my Old Town Key West car rental if I combine it with my hotel or flight?

Combining your bookings into an Old Town Key West vacation package will save you a tidy sum. Combine a car and flight; a flight, car and hotel; or a hotel and car. There's no better way to explore the greater Old Town Key West region than with your own rental car. You can also add experiences and activities to your Travelocity package.

What is there to do in Old Town Key West?

While wandering about Old Town Key West, be sure to drop by South Beach and Simonton Beach. This neighborhood will keep you on your toes.