Key West Historic District Vacation Packages 2026/2026 from $533

Key West Historic District flight + hotel vacation packages

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

Le Particulier Miami

Mid Beach

$533

per person

Feb 11 - Feb 15

found 2 days ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This hotel features a restaurant, free WiFi in public areas, and a snack bar/deli. Luggage storage is provided and the front desk is staffed around-the-clock.

Iberostar Waves Berkeley Shore

South Beach

$794

per person

Feb 23 - Feb 28

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the gym and perks like free WiFi. There's a rooftop terrace on site, and a 24-hour front desk and a terrace are also provided.

Iberostar Waves Miami Beach

South Beach

$602

per person

Feb 5 - Feb 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

A restaurant and an outdoor pool are featured at this hotel. WiFi in public areas is free. A coffee shop, a garden, and dry cleaning are also on offer.

Hawks Cay Resort

$1,343

per person

Jan 24 - Jan 31

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.

Bay Breeze Premium Apartments By Eskape Collection

$729

per person

Feb 11 - Feb 15

found 2 days 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.

Top Key West Historic District hotels deals

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Free Cancellation

$280 nightly

$315 total

Dec 17 - Dec 18

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.

Winslow's Bungalows - Key West Historic Inns

725 Truman Avenue Key West FL

Free Cancellation

Reserve now, pay when you stay

$284 nightly

$320 total

Dec 17 - Dec 18

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.

Casa Marina Key West, Curio Collection by Hilton

1500 Reynolds Street Key West FL

Free Cancellation

Reserve now, pay when you stay

$299 nightly

$336 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.

The Reach Key West, Curio Collection by Hilton

1435 Simonton Street Key West FL

Free Cancellation

Reserve now, pay when you stay

$239 nightly

$269 total

Dec 14 - Dec 15

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.

Pier House Resort & Spa

1 Duval St Key West FL

Free Cancellation

Reserve now, pay when you stay

$407 nightly

$458 total

Dec 7 - Dec 8

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.

La Concha Key West, Autograph Collection

430 Duval St Key West FL

Free Cancellation

Reserve now, pay when you stay

$259 nightly

$291 total

Dec 14 - Dec 15

Total with taxes and fees

This smoke-free hotel includes 3 restaurants, an outdoor pool, and a 24-hour gym. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. There's a poolside bar on site, and a 24-hour front desk and concierge services are also provided.

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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

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

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

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?

$533 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.