Deals on vacations and trips to Key West Historic District

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Key West Historic District flight + hotel vacation packages

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

Creekside Inn

2.5 out of 5
Price was $2,165, price is now $1,018 per person
$1,018
per person
Jun 3 - Jun 10
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.
Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Price was $4,324, price is now $1,986 per person
$1,986
per person
May 14 - May 17
found 1 day 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.
The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was $12,699, price is now $6,195 per person
$6,195
per person
May 14 - May 17
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.
EAST Miami Residences

EAST Miami Residences

5 out of 5
Brickell
Save 100% on your flight
Price was $3,356, price is now $1,934 per person
$1,934
per person
May 13 - May 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This luxury hotel features 2 restaurants, 4 outdoor pools, and a 24-hour gym. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi. Enjoy the a rooftop terrace and conveniences like a 24-hour front desk and concierge services.
Villas At Hawks Cay Resort

Villas At Hawks Cay Resort

4 out of 5
Save 100% on your flight
Price was $3,405, price is now $1,977 per person
$1,977
per person
May 13 - May 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This luxury resort 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. Bring the family and enjoy the children's club, children's pool, and arcade/game room.

Top Key West Historic District hotels deals

Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

4 out of 5
1500 Reynolds Street Key West FL
Free Cancellation
Reserve now, pay when you stay
$559 nightly
The price is $629 total per night
$629 total
Mar 22 - Mar 23
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
Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
1 Duval St Key West FL
Free Cancellation
Reserve now, pay when you stay
$612 nightly
The price is $688 total per night
$688 total
Apr 12 - Apr 13
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
Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

4 out of 5
245 Front Street Key West FL
Free Cancellation
Reserve now, pay when you stay
$534 nightly
The price is $601 total per night
$601 total
Apr 12 - Apr 13
Total with taxes and fees
A marina, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Enjoy the outdoor pool and visit the 3 bars/lounges and poolside bar for drinks.
The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton

4 out of 5
1435 Simonton Street Key West FL
Free Cancellation
Reserve now, pay when you stay
$507 nightly
The price is $571 total per night
$571 total
Mar 22 - Mar 23
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
NYAH Key West - Adults Only

NYAH Key West - Adults Only

3 out of 5
420 Margaret Street Key West FL
Free Cancellation
Reserve now, pay when you stay
$315 nightly
The price is $355 total per night
$355 total
Mar 26 - Mar 27
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
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
725 Truman Avenue Key West FL
Free Cancellation
Reserve now, pay when you stay
$464 nightly
The price is $522 total per night
$522 total
Apr 13 - Apr 14
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
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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 featuring signage

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.

Duval Street
Mallory Square which includes a sunset and a bay or harbor as well as a large group of people

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.

Mallory Square
Ernest Hemingway Home and Museum featuring heritage elements and a house

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.

Ernest Hemingway Home and Museum

Frequently asked questions

How much are vacation packages to Key West Historic District?
$1,018 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.

Photos of local treasures

Browse Key West Historic District vacation photos for more inspiration

Audubon House and Tropical Gardens featuring a house
Audubon House and Tropical Gardens featuring a house
Saint Mary Star of the Sea which includes a church or cathedral
Ernest Hemingway Home and Museum featuring interior views and a house
Custom House Museum featuring heritage architecture

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