Old Town Key West Vacation Packages 2025/2026 from $643

Old Town Key West flight + hotel vacation packages

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

Hyatt Vacation Club at Beach House, Key West

Save 100% on your flight

per person

Sep 12 - Sep 16

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 self parking and free WiFi. A safe deposit box and concierge services are also provided.

Hyatt Vacation Club at Windward Pointe, Key West

Save 100% on your flight

per person

Oct 10 - Oct 14

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.

Almond Tree Inn Hotel - Adults Only

Old Town Key West

Save 100% on your flight

per person

Oct 10 - Oct 14

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

This hotel features a bar/lounge, a poolside bar, and an outdoor pool. Business travelers can take advantage of the free WiFi in public areas. Enjoy the hot tub and free continental breakfast each morning.

Orchid Key Inn - Adults Only

Old Town Key West

Save 100% on your flight

per person

Oct 10 - Oct 14

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

This hotel features a bar/lounge, a poolside bar, and an outdoor pool. Enjoy the hot tub and free perks like continental breakfast and WiFi in public areas. Self parking, a garden, and dry cleaning are also offered.

Southernmost Beach Resort and Guesthouses

Old Town Key West

Save 100% on your flight

per person

Oct 10 - Oct 14

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

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 for business? Take advantage of the 24-hour business center, laundry service, and conference space.

Top Old Town Key West hotels deals

Southernmost Beach Resort and Guesthouses

1319 Duval Street, Key West, FL

Free Cancellation

$244 nightly

$275 total

Aug 25 - Aug 26

Total includes 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 for business? Take advantage of the 24-hour business center, laundry service, and conference space.

Pool

Spa

Casa Marina Key West, Curio Collection by Hilton

1500 Reynolds Street, Key West, FL

Free Cancellation

Reserve now, pay when you stay

$258 nightly

$290 total

Aug 13 - Aug 14

Total includes 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

The Reach Key West, Curio Collection by Hilton

1435 Simonton Street, Key West, FL

Free Cancellation

Reserve now, pay when you stay

$295 nightly

$332 total

Aug 3 - Aug 4

Total includes 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

The Southernmost Inn - Adults Only

525 United Street, Key West, FL

Free Cancellation

Reserve now, pay when you stay

$139 nightly

$156 total

Aug 21 - Aug 22

Total includes 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

Southwinds Motel

1321 Simonton Street, Key West, FL

$139 nightly

$157 total

Aug 19 - Aug 20

Total includes taxes and fees

This hotel features 2 outdoor pools and a bar/lounge. Enjoy the free continental breakfast each morning. A picnic area, luggage storage, and laundry facilities are also on offer.

Pool

Breakfast included

Winslow's Bungalows - Key West Historic Inns

725 Truman Avenue, Key West, FL

Free Cancellation

Reserve now, pay when you stay

$259 nightly

$291 total

Jul 28 - Jul 29

Total includes taxes and fees

This smoke-free hotel features 3 outdoor pools, a bar/lounge, and a poolside bar. Guests will appreciate free perks like continental breakfast and WiFi in public areas. Self parking, a garden, and luggage storage are also offered.

Pool

Breakfast included

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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

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

South Beach

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.

Ernest Hemingway Home and Museum

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

Frequently asked questions

How much are vacation packages to Old Town Key West?

With vacation packages available from as low as $643, 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.