Key West Historic District Vacation Packages 2026 from $382

Name: Southwinds Motel
Price range: $196 total

Key West Historic District flight + hotel vacation packages

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

Cavalier Hotel South Beach

South Beach

Save 100% on your flight

$382

per person

Aug 19 - Aug 23

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. Valet parking, a terrace, and express check-out are also offered.

Casablanca Miami Beach

North Beach

$2,130

per person

Sep 10 - Sep 14

found 17 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

An outdoor pool, valet parking, and laundry facilities are featured at this aparthotel. A grocery/convenience store, a communal living room, and express check-out are also on offer.

MirabileCondoDwntown MIA Brickell w PRKG

Downtown Miami

Save 100% on your flight

$970

per person

Jul 19 - Jul 23

found 1 day ago

Roundtrip flight included

Dallas (DAL) to Miami (MIA)

This apartment features a restaurant, an indoor pool, and a bar/lounge. WiFi in public areas is free. Self parking and a coffee shop are also offered on site.

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$7,233

per person

Aug 19 - Aug 23

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

This aparthotel 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.

Bay Breeze Premium Apartments By Eskape Collection

Save 100% on your flight

$396

per person

Sep 10 - Sep 14

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.

Top Key West Historic District hotels deals

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Free Cancellation

Reserve now, pay when you stay

$266 nightly

$299 total

Jun 29 - Jun 30

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

Pool

Spa

Casa Marina Key West, Curio Collection by Hilton

1500 Reynolds Street Key West FL

Free Cancellation

Reserve now, pay when you stay

$317 nightly

$356 total

Jun 29 - Jun 30

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

Hyatt Centric Key West Resort and Spa

601 Front St Key West FL

Free Cancellation

Reserve now, pay when you stay

$261 nightly

$294 total

Jun 21 - Jun 22

Total with taxes and fees

This smoke-free resort features a full-service spa, a marina, and a restaurant. Enjoy the outdoor pool and perks like free WiFi. Enjoy the 24-hour gym 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

$333 nightly

$374 total

Jun 29 - Jun 30

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.

The Reach Key West, Curio Collection by Hilton

1435 Simonton Street Key West FL

Free Cancellation

Reserve now, pay when you stay

$243 nightly

$274 total

Jun 28 - Jun 29

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.

Southwinds Motel

1321 Simonton Street Key West FL

$175 nightly

$196 total

Jun 22 - Jun 23

Total with taxes and fees

This hotel features 2 outdoor pools and a bar/lounge. Enjoy the free continental breakfast each morning. Self parking, a picnic area, and luggage storage are also offered.

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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(3,520 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(3,147 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(1,744 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?

$382 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.