Key West Vacation Rentals & House Rentals - 84 Rentals Available

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1 / 21

Key West Condo
2 BR / 2 BA / Sleeps 5 2 5 7 night min stay
Condo / 2 Bedrooms / Sleeps 5
2 bedrooms 2 bathrooms Sleeps 5
High Speed Internet • Dishwasher • Microwave
"We stayed at Touch of paradise at teh end of Oct and into Nov. Perfert location. I have stayed in Truman Annex many times and Touch of Paradise was a wounderful Unit. Location is everything in Kw because you walk alot and this unit is close to everything...."
- Lynn Stewart Krieger, New Bloomfield Pa
(2) Excellent (2 reviews)
1 / 3

Key West Guesthouse
2 BR / 2 BA / Sleeps 4 2 4 7 night min stay
Guesthouse / 2 Bedrooms / Sleeps 4
2 bedrooms 2 bathrooms Sleeps 4
High Speed Internet • Dishwasher • Microwave
"We rented the Conch House for our honeymoon and it was perfect! We loved the secluded feeling and the private beach. Carol was wonderful to work with and had fresh eggs and champagne waiting for us in our fridge. She picked fresh veggies for us to..."
- Kristi Koenig Martin-Smith, Fort Worth
(3) Excellent (3 reviews)
1 / 23

Key West Apartment
2 BR / 2 BA / Sleeps 6 2 6 Min stay varies
Apartment / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
1 / 28

Key West Villa
6 BR / 7 BA / Sleeps 16 6 16 Min stay varies
Villa / 6 Bedrooms / Sleeps 16
6 bedrooms 7 bathrooms Sleeps 16
High Speed Internet • Dishwasher • Microwave
"This house is great for large groups. We had such a fun time having a reunion here. Close to everything, and staff was attentive and friendly."
- Sean Johnson, Chicago
(3) Excellent (3 reviews)
1 / 21

Key West Home
4 BR / 4 BA / Sleeps 8 4 8 7 night min stay
Home / 4 Bedrooms / Sleeps 8
4 bedrooms 4 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
"Rooms were clean, block off duval, few block to boardwalk and front street. Fabulous location. Reasonable rates. Ask for additional keys prior to arriving if needed, only received 2 keys for 4 rooms. Minor issues with plumbing. we were able to fix..."
- Jody Vincent, LeClaire, Iowa
(8) Excellent (8 reviews)
1 / 42

Key West Condo
2 BR / 2.5 BA / Sleeps 6 2 6 Min stay varies
Condo / 2 Bedrooms / Sleeps 6
2 bedrooms 2.5 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"Our condo was AMAZING! So clean and had all the comforts of home! Their was a detailed binder of places to eat and what to do in the area! Our vacation was perfect because of all the extra touches and information we were provided!"
- Winnie Lucht, Wisconsin
(5) Excellent (5 reviews)
1 / 15

Key West Home
3 BR / 2.5 BA / Sleeps 6 3 6 30 night min stay
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 2.5 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"I have stayed at the Brass Palm Villa several times and I would never stay anywhere else on the island. It is decorated beautifully and exceptionally well maintained. There are many places to relax inside and outside the home. I especially enjoy the outside..."
- Lynne Martino, New Jersey
(2) Excellent (2 reviews)
1 / 55

Key West Villa
5 BR / 5.5 BA / Sleeps 12 5 12 Min stay varies
Villa / 5 Bedrooms / Sleeps 12
5 bedrooms 5.5 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
"I rented this house for my sister- in- law's bachelorette weekend. The house was spacious, clean, and overall one of the best houses we've stayed in."
- Raevin Poli, Lake Worth, FL
(4) Excellent (4 reviews)
1 / 36

Key West Condo
2 BR / 2 BA / Sleeps 6 2 6 2 night min stay
Condo / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"This is a great place. It was a little small for two senior couples, but it was very comfortable and quiet. Just what we wanted for a two night stay."
- Ronald Kurz, Cincinnati, Ohio
(57) Excellent (57 reviews)
1 / 24

Key West Condo
2 BR / 2 BA / Sleeps 6 2 6 Min stay varies
Condo / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"we can"t say enough about the condo or Pam. She takes good care of her rental. Always clean and comfortable.The balcony overlooks the pool area which is well maintained. Pam is always available to answer any questions you might have. We stay the months..."
- Vicki Kuhns, ragersville,ohio
(56) Excellent (56 reviews)
1 / 21

Key West Townhouse
2 BR / 2 BA / Sleeps 4 2 4 Min stay varies
Townhouse / 2 Bedrooms / Sleeps 4
2 bedrooms 2 bathrooms Sleeps 4
High Speed Internet • Dishwasher • Microwave
"Our first trip to key west. We took our 2 teenage daughters. This house had everything needed for a home away from home. The pool was refreshing after a long hot day. Very quiet secluded area, yet Close to everything. Highly recommended. House was very..."
- Michelle Good, Pennsylvania
(2) Excellent (2 reviews)
1 / 20

Key West Condo
2 BR / 2 BA / Sleeps 6 2 6 1 night min stay
Condo / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"Excellent location walking distance to Smather's beach. Gorgeous view of the ocean and perfect location. Full 2 bedrooms and 2 baths as well as a full kitchen and living room. Very clean and modern. Rain Forest pathway to the pool and grilling areas. ..."
- Stephanie Montgomery Johnson, Orlando, FL
(6) Excellent (6 reviews)
1 / 17

Key West Townhouse
2 BR / 2.5 BA / Sleeps 6 2 6 7 night min stay
Townhouse / 2 Bedrooms / Sleeps 6
2 bedrooms 2.5 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"We thoroughly enjoyed our first trip to the keys. The house was perfect for us and the Truman Annex is beautiful. Everything is just a short bike ride away. Location is great. If you don't get bikes and choose to walk the beach is a little to far for ..."
- crystal steedley, Dacula, Ga USA
(15) Excellent (15 reviews)
1 / 21

Key West Cottage
1 BR / 1.5 BA / Sleeps 4 1 4 Min stay varies
Cottage / 1 Bedroom / Sleeps 4
1 bedrooms 1.5 bathrooms Sleeps 4
High Speed Internet • Dishwasher • Microwave
"The home was clean and in a great location. Bars are close by and there is a cute grocery store down the street. Parking is limited to only one space so make sure you only have one car when you visit."
- Idania Reyes, Miami Beach, FLUSA
(3) Excellent (3 reviews)
1 / 28

Key West Townhouse
2 BR / 2.5 BA / Sleeps 6 2 6 Min stay varies
Townhouse / 2 Bedrooms / Sleeps 6
2 bedrooms 2.5 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"The property was located very close everything we wanted. Didn't really need the golf cart we rented for the week. The townhouse was clean, spacious and comfortable. (although there were a lot of tiny ants , especially in the kitchen) We will ..."
- Annette Brand, Texas
(8) Excellent (8 reviews)
1 / 10

Key West Villa
1 BR / 1 BA / Sleeps 2 1 2 7 night min stay
Villa / 1 Bedroom / Sleeps 2
1 bedrooms 1 bathroom Sleeps 2
High Speed Internet • Dishwasher • Microwave
"I have leased this property and another in Marathon. BOTH are just amazing in every way. Mary and Gabby do everything in their power to make it all perfect... I am returning this winter and have already pre booked for 2017..."
- Darin Boyles, Michigan
(2) Excellent (2 reviews)
1 / 23

Key West Home
3 BR / 2 BA / Sleeps 6 3 6 30 night min stay
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"This house is immaculately kept and one of the few houses on a canal in KW. Beautiful interior and plenty of room in the bedrooms. The pool overlooks the canal and has an absolutely beautiful view! If you want a house that makes you feel like you're ..."
- Travis Haddock, Memphis
(1) Excellent (1 review)
1 / 21

Key West Home
3 BR / 4 BA / Sleeps 8 3 8 7 night min stay
Home / 3 Bedrooms / Sleeps 8
3 bedrooms 4 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
"Howard was great to work with. The house was very nicely furnished. The pool area is small but this is key west. The location was great. Overall very good experience."
- Pat Schaeff, Ohio
(1) Excellent (1 review)
1 / 18

Key West Cottage
4 BR / 3 BA / Sleeps 8 4 8 Min stay varies
Cottage / 4 Bedrooms / Sleeps 8
4 bedrooms 3 bathrooms Sleeps 8
High Speed Internet • Microwave • Air Conditioning
"The visit to Harbor Wall Hideaways was perfect. Me and 3 other guys arrived late and that was no issue for the landlord. The pool was nice to have in between the beaches, bars, and restaurants. The house is located near everything you could want to ..."
- Jon Clifton, Ohio
(12) Excellent (12 reviews)
1 / 29

Key West Townhouse
3 BR / 3 BA / Sleeps 6 3 6 3 night min stay
Townhouse / 3 Bedrooms / Sleeps 6
3 bedrooms 3 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"The place was very nize, cozy, clean and comfortable, felt very much at home would definitely come back again and rent the same place"
- luis torres, Tampa
(2) Excellent (2 reviews)
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About Key West

A laid-back city in the Florida Keys, Key West should be on every traveler's vacation list. With equal parts nature, history, and nightlife, this Florida destination has a little something for everyone.


A Short History of Key West

At the very end of the Florida Keys, this four-square-mile island was first settled by Spanish explorers led by Ponce de León. The remote location was sparsely populated until it was claimed by the United States in the early 19th century. By the turn of the 20th century, Key West was actually the largest and most moneyed city in Florida, thanks to its quick development, naval base, and cigar industry. The locale began to develop its reputation as a tourist hotspot around that time, and this southernmost U.S. city still holds that identity today.


What Key West Does Best

This small island is packed with attractions and activities. Surrounded by the Gulf of Mexico, Key West offers visitors ample natural beauty and great swimming beaches. History buffs love the island’s maritime history and legends of its famous residents, while partygoers can’t get enough of Duval Street, the center of Key West’s nightlife scene.


Natural Beauty

Key West isn’t known for its beaches, but Fort Zachary Taylor Historic State Park is a great place to swim, snorkel, and catch the sunset. Explore the waters around Key West by sailboat, kayak, or sunset cruise to get a closer look at the sparkling gulf. For a unique adventure, head 70 miles offshore to Dry Tortugas National Park. Explore Fort Jefferson, the coral reefs, and the island’s impressive variety of wildlife and tropical plants.
 

Historical Markers

To get a quick look at everything Key West has to offer, hop on the Conch Tour Train. You’ll get an earful of the area’s past, along with a little local trivia. When you’re ready to dig in, make the Ernest Hemingway Home & Museum your first stop. Here you can learn more about the famous writer’s life and see where he penned some of his best selling novels.

Don't miss a tour of the Harry S. Truman Little White House, a command center during World War I and II as well as the winter home of President Harry S. Truman. Today the house is both a museum and a political retreat, and it’s well worth a visit.
 

Vibrant Nightlife

No trip to Key West is complete without a night out on the town, and options range from family-friendly to wildly theatrical. Take the family to Mallory Square, where you’ll find local performers, plenty of fried food, and gorgeous sunset views. For some grownup fun, take in a performance at Key West’s Fringe Theater, the Red Barn Theatre, or the Waterfront Playhouse. Finish the night off with a drink at the Green Parrot, Key West’s oldest bar, or Sloppy Joe’s, one of Hemingway’s favorite hangouts.

Whether you prefer culture or the outdoors, Key West has plenty to offer in a relaxed, welcoming atmosphere. One night here isn’t enough, so book a vacation home and stay awhile on this island destination.