Key West Historic District Vacation Packages 2026 from $332

Key West Historic District flight + hotel vacation packages

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

President Hotel

South Beach

Save 100% on your flight

$332

per person

Feb 25 - Feb 28

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This hotel features an outdoor pool and a bar/lounge. Guests will appreciate free perks like full breakfast and WiFi in public areas. Valet parking, a terrace, and a garden are also offered.

Bay Breeze Premium Apartments By Eskape Collection

$527

per person

Feb 22 - Feb 28

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This aparthotel features an outdoor pool and a rooftop terrace. WiFi in public areas is free. Self parking, a garden, and luggage storage are also offered.

Hawks Cay Resort

$1,033

per person

Feb 22 - Feb 28

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This luxury hotel features a private beach, a full-service spa, and a marina. Spend a day at the beach snorkeling, or relax with sun loungers and beach umbrellas. There's fun for all ages with a children's club and a children's pool, and families will appreciate the picnic area.

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$12,898

per person

Jan 19 - Jan 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This condo resort features 2 restaurants, 3 outdoor pools, and a gym. There's fun for all ages with a children's club and a children's pool, and babysitting is an added bonus. Enjoy the a rooftop terrace and perks like free WiFi.

Pelican Hotel

South Beach

$349

per person

Feb 1 - Feb 4

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

A restaurant and a bar/lounge are featured at this hotel. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. Valet parking, a business center, and limo/town car service are also offered.

Top Key West Historic District hotels deals

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Free Cancellation

$262 nightly

$295 total

Dec 16 - Dec 17

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 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

$382 nightly

$430 total

Dec 15 - Dec 16

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

Free Cancellation

Reserve now, pay when you stay

$274 nightly

$308 total

Dec 14 - Dec 15

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

Pier House Resort & Spa

1 Duval St Key West FL

Free Cancellation

Reserve now, pay when you stay

$377 nightly

$424 total

Dec 14 - Dec 15

Total with taxes and fees

This smoke-free resort features a private beach, a full-service spa, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling on business? Take advantage of the 2 conference rooms, business center, and express check-in.

On private beach

Pool

The Reach Key West, Curio Collection by Hilton

1435 Simonton Street Key West FL

$299 nightly

$337 total

Dec 15 - Dec 16

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

Amsterdam's Curry Mansion Inn

511 Caroline St Key West FL

$286 nightly

$322 total

Dec 17 - Dec 18

Total with taxes and fees

An area shuttle is featured at this guesthouse, along with an outdoor pool and a terrace. WiFi in public areas is free. A business center, a garden, and a snack bar/deli are also on offer.

Pool

Pet friendly

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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

Duval Street

4.5/5(3,475 reviews)

With a visit to Duval Street, a favorite shopping spot in Key West, you can search for that perfect souvenir. Wander the seaside or discover the area's beautiful sunsets.

Mallory Square

4.5/5(3,096 reviews)

Arrive at this square at day’s end to find street performers, food carts and one of the most beautiful sunsets in the United States.

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.

Frequently asked questions

How much are vacation packages to Key West Historic District?

$332 is all you need to spend for a fantastic break in Key West Historic District. Bundle your flights and hotel into a Travelocity package and watch how the savings start to add up. With these kinds of prices, you'll want to start packing your suitcase now!

Where can I get the best vacation package deals for Key West Historic District?

Walking away with a great package deal to Key West Historic District is a breeze with Travelocity. With as many as 400 air carriers and 1,000,000 properties all over the globe, you'll have loads of choice when it comes to your hotels and flights.

Why should I purchase my Key West Historic District vacation bundle via Travelocity?

By booking your hotel, flights, activities and car rental all in one place, you'll save time and money. 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 are you waiting for? Book that dream vacation today and start packing!

Can I save on my Key West Historic District car rental if I combine it with my hotel or flight?

You certainly can — and booking one of our Key West Historic District vacation packages is the easiest way to do this. Bundle any combination of a hotel, flight, car and tour and land great discounts. The more you book, the more you save. There are loads of exciting sights in and around Key West Historic District that are worth a road trip, including Zoo Miami (110 mi from Key West Historic District). Nothing beats exploring amazing places like this with the freedom of your own rental car.

What is the best time of year to go to Key West Historic District?

January, March and July are the most popular months to visit, while September, October and December are typically quieter. If you have a limited budget, you'd be better off visiting in . is usually the priciest time of the year to stop by.

What is there to do in Key West Historic District?

Pull out your travel plan and pencil in Ernest Hemingway Home and Museum and Audubon House and Tropical Gardens. They're two of the most well-known attractions in Key West Historic District.