Old Town Key West Vacation Packages 2026 from $1,268

Old Town Key West flight + hotel vacation packages

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

The Palms Hotel

Old Town Key West

Save 100% on your flight

$1,268

per person

Dec 5 - Dec 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

This guesthouse features a bar/lounge, a poolside bar, and an outdoor pool. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A garden, a picnic area, and a computer station are also on offer.

The Key West Hotel

Key West Historic District

Save 100% on your flight

$2,774

per person

Dec 5 - Dec 12

found 1 day ago

Roundtrip 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.

Almond Tree Inn Hotel - Adults Only

Old Town Key West

Save 100% on your flight

$1,861

per person

Dec 5 - Dec 12

found 1 day ago

Roundtrip 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

$1,727

per person

Dec 5 - Dec 12

found 1 day ago

Roundtrip 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 continental breakfast each morning. Self parking, a garden, and dry cleaning are also offered.

Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

Old Town Key West

Save 100% on your flight

$5,907

per person

Dec 29 - Jan 4

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

An outdoor pool is featured at this cottage, along with free WiFi in public areas.

Stay near popular Old Town Key West attractions

Southernmost Point

8.8/10 (17,214 reviews)

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

See properties

Frequently asked questions

How much are vacation packages to Old Town Key West?

With vacation packages available from as low as $1,268, 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.