Key West Historic District Vacation Packages 2026 from $495

Key West Historic District flight + hotel vacation packages

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

Casablanca Miami Beach

North Beach

$495

per person

Apr 8 - Apr 14

found 8 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.

Miami Downtown Condos

Downtown Miami

$967

per person

Mar 26 - Mar 29

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This smoke-free condo includes 2 restaurants, an outdoor pool, and a 24-hour gym. Business travelers can take advantage of the business center. A poolside bar, a 24-hour front desk, and a coffee shop are also provided.

Creekside Inn

$836

per person

Mar 27 - Apr 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This smoke-free motel's marina and 2 outdoor pools are some of the highlights. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area and barbecue grills are also provided.

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$6,341

per person

Mar 23 - Mar 27

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.

Solé Miami, A Noble House Resort

Ocean Four

$518

per person

Mar 29 - Apr 2

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. 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 and an off-leash area. Enjoy the 24-hour gym and unwind at the beach bar and poolside bar.

Top Key West Historic District hotels deals

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Free Cancellation

$530 nightly

$596 total

Jan 26 - Jan 27

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

Pier House Resort & Spa

1 Duval St Key West FL

$519 nightly

$584 total

Jan 27 - Jan 28

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

La Concha Key West, Autograph Collection

430 Duval St Key West FL

$399 nightly

$449 total

Jan 25 - Jan 26

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.

Pool

Pet friendly

Winslow's Bungalows - Key West Historic Inns

725 Truman Avenue Key West FL

Free Cancellation

Reserve now, pay when you stay

$505 nightly

$568 total

Jan 26 - Jan 27

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

NYAH Key West - Adults Only

420 Margaret Street Key West FL

Free Cancellation

Reserve now, pay when you stay

$252 nightly

$284 total

Jan 22 - Jan 23

Total with taxes and fees

This guesthouse's 3 outdoor pools and a rooftop terrace are among the featured amenities. Enjoy the hot tub and free continental breakfast each morning. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.

Pool

Hot Tub

Duval House

815 Duval St Key West FL

$361 nightly

$403 total

Jan 27 - Jan 28

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

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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?

$495 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.