Old Town Key West Vacation Packages 2026 from $1,072

Old Town Key West flight + hotel vacation packages

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

Oceans Edge Key West Resort, Hotel & Marina

$1,072

per person

Mar 21 - Mar 24

found 2 days ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

A marina, 6 outdoor pools, and a 24-hour gym are all featured at this smoke-free hotel. Business travelers can take advantage of the free WiFi in public areas. The restaurant provides options for dining, while the bar/lounge and poolside bar are great spots to unwind.

The Key West Hotel

Key West Historic District

Save 100% on your flight

$2,149

per person

Apr 30 - May 5

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.

Lighthouse Hotel - Key West Historic Inns

Old Town Key West

Save 100% on your flight

$1,569

per person

Apr 30 - May 5

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

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

The Reach Key West, Curio Collection by Hilton

Old Town Key West

Save 100% on your flight

$1,307

per person

Apr 30 - May 5

found 2 days ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

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.

Southernmost Beach Resort and Guesthouses

Old Town Key West

Save 100% on your flight

$1,448

per person

Apr 30 - May 5

found 2 days 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 on business? Take advantage of the 2 conference rooms, along with dry cleaning/laundry services.

Top Old Town Key West hotels deals

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Free Cancellation

$530 nightly

$596 total

Feb 8 - Feb 9

Total with taxes and fees

Pool

Spa

Casa Marina Key West, Curio Collection by Hilton

1500 Reynolds Street Key West FL

Free Cancellation

Reserve now, pay when you stay

$456 nightly

$513 total

Feb 5 - Feb 6

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

Winslow's Bungalows - Key West Historic Inns

725 Truman Avenue Key West FL

$644 nightly

$725 total

Feb 5 - Feb 6

Total with 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

Duval House

815 Duval St Key West FL

$331 nightly

$369 total

Feb 5 - Feb 6

Total with taxes and fees

This bed & breakfast features a terrace, concierge services, and self parking. A garden, a picnic area, and express check-in are also on offer.

Air conditioning

Parking available

The Reach Key West, Curio Collection by Hilton

1435 Simonton Street Key West FL

Free Cancellation

Reserve now, pay when you stay

$634 nightly

$713 total

Feb 5 - Feb 6

Total with taxes and fees

On private beach

Pool

The Southernmost Inn - Adults Only

525 United Street Key West FL

Free Cancellation

Reserve now, pay when you stay

$493 nightly

$554 total

Feb 11 - Feb 12

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

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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

Redondo Beach showing a marina and boating

Southernmost Point

4.5/5(3,182 reviews)

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

Ernest Hemingway Home and Museum

4.5/5(1,707 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(980 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 $1,072, 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.