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Vacation Rentals & House Rentals in Key West

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467 house rentals

Conch Haven Old Town 1/1 MONTHLY Rental

Key West apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$76

Spectacular Atlantic Ocean View Condo (MONTHLY)

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Amazing Views And A Great Condo” My wife and I stayed here on our honeymoon and were absolutely 100% pleased with the condo. I have to honestly say it was the nicest condo either of us have stayed in. The view was amazing and the patio was very tranquil. The patio faces south so you don't get blasted with the morning or evening sun making it very comfortable having your morning coffee or evening cocktail while enjoying the view. The owners have put a lot of thought into furnishing and accessorizing the unit. Tess and Mimi were wonderful to work with (Mimi met us at the condo and had great advice on where to eat, what to do...)I have stayed in several condos and this was by far my favorite, if your thinking of staying here you will not be disappointed. I will definitely be back the next time I visit the keys.

Price per night from

$342

Key West Townhouse in stunning 5 Star Resort * Close to Duval Street and beach

Key West townhouse

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$572

Tropical Escape

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 5

“Very comfortable and all around great place to stay.” It was very clean, comfortable and homey. The pool was great and it's very close to Key West and a beach. We really enjoyed our stay. Provided plenty of towels, pool accessories, kitchenware, etc.... No complaints.

Price per night from

$248

Studio Blue

Key West apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$244

Casa Del Sol, a Key West Vacation (Truman Annex)

Key West house

2 bedrooms / 3 bathrooms / sleeps 6

“awesome” the condo was beautiful. very good location. 2 suggestions. the grill did not have gas . the bed that opens up to king. not so much, mattress is 2 different heights and slides if you try to sleep on it. very very uncomfortable.

Responds fast! avg. 2 hours 33 minutes

Price per night from

$231

Top floor, two bedroom,two bath condo with private balcony,close to the Ocean

Key West condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 43 minutes

Price per night from

$315

Key West Beachfront Luxury 2/2 Condo A212 No Hurricane Damage

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Perfect place to experience Key West” This is a lovely condo with a tropical, quiet view. Many extras are included: beach towels, bikes, and kitchen supplies. The pool area was our favorite spot, and we had coffee every morning on the balcony with chairs for all 6 of us. My husband enjoyed watching March Madness on the large T.V. Kathy did a fantastic job with all communications and provided great tourist tips. We would definitely stay here again!

Responds fast! avg. 2 hours 28 minutes

Price per night from

$430

Casa Havana

Key West house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$1,005

Southard Square Hideaway

Key West condo

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$90

Key West Island Vacation

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$539

Sunny View

Key West house

1 bedroom / 2 bathrooms / sleeps 2

Price per night from

$110

Welcome Aboard! Relax, unwind, enjoy the water! in key west

Key West yacht

4 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$321

Coconut Beach

Key West apartment

1 bedroom / 2 bathrooms / sleeps 4

Price per night from

$294

Southard Getaway

Key West apartment

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$215

Real World MTV House Key West

Key West house

10 bedrooms / 6 bathrooms / sleeps 20

“Haha Buffalo, New York” This year while my friends and neighbors froze to death in Buffalo, my extended family and a few friends escaped the cold at the Real World MTV House in Key West. It was cold in Key West as well just 78 degrees, all the locals were complaining.and wore sweaters (haha). Everything was great and we laughed as we watched the weather on the TV at night up north. The 2 houses (main and Racket ball) are absolutely perfect for 20 guests. The property is huge . No complaints, we loved the paddle boards and kayaks, and how easy it was to put in the ocean behind the house and go!! Aric, the caretaker, gave us a few good tips for riding the paddle boards, fishing holes and restaurants. A nice quiet guy!!!

Responds fast! avg. 2 hours 56 minutes

Price per night from

$2,013

Bayview Harbor

Key West apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$200

Seaside Place Key West FL 5 Bedroom House 4 Baths

Key West house

5 bedrooms / 4 bathrooms / sleeps 12

“Paradise in Paradise” Just returned from a marvelous vacation in Key West. While the tan is already starting to fade, the memories of our stay at Seaside Place remain vivid. We absolutely loved this house. It is very charming and offers all the amenities you'll ever need and then some, from a kitchen that Julia Child would not have found wanting, gorgeous, large rooms each with its very own character, spacious communal dining areas and a beautiful large pool with romantic lighting, a soothing waterfall feature and total privacy. The owners' love for providing the best experience is evident in every detail, from the painstaking labeling of all switches and outlets to the folders of carefully compiled information about where to go, and what to do and see. The house is just a block from the quiet end of Duval Street (there is such a thing), yet far enough removed from the Key West bar scene responsible for the prevailing serious shortage of liver donors. We thoroughly enjoyed every minute of our stay and can't wait to return soon. And we can't help but think that if Hemingway had stayed here he might still be alive today

Responds fast! avg. 3 hours 34 minutes

Price per night from

$1,442

Shipyard-1/2 Block Duval Street

Key West townhouse

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$247

Big house

Key West house

5 bedrooms / 5 bathrooms / sleeps 12

“Bachelorette in Key West” I rented this house for my sister-in-law's bachelorette weekend in Key West. The house was spacious, clean, and overall the best place I've ever stayed! It was worth every penny!

Price per night from

$700

Oceanfront 2 Bedroom 2 Bath Condo Key West Florida

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Perfect location and great value!” From the moment we arrived, this condo was everything we wanted without breaking the bank. We spent days looking for a place in Key West for Christmas week. What was available was crazy expensive, so to be honest when we found this place for the price we were slightly apprehensive. It is close to everything, the check-in and check-out were easy, the people who live in the complex were very friendly and welcoming and always willing to offer advice on where to go and what to do. Everything worked and was clean and we could not have asked for a better vacation. Can't wait to go back!

Responds fast! avg. 2 hours 59 minutes

Price per night from

$321

William's Loft

Key West cottage

2 bedrooms / 1 bathroom / sleeps 3

Price per night from

$87

Artist Garden

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

“Beautiful House, sometimes loud” We stayed at the artist's Garden for one week. There were 4 adults and an 11 month old. The house is gorgeous, lots of interesting art. Some of it we had to move out of reach of our 11 month old, but that was easy enough. The only downside to this house is that it's located across the street from the post office. It wouldn't be bad except the bedroom windows face the post office. Some mornings the postal trucks banged around starting at 4:52 am! I finally had to put on a white noise app every night to drown them and the roosters out. (The roosters is a Key West issue, not this houses's ;-) ) .. It was in a great location, easy to access all the restaurants, Duval Street and Mallory square. The pool is very close and well maintained. We definitely would consider staying here again, but if a different house in Truman annex were available not close to the post office, we'd probably choose that first. We would definitely go through at Home in Key West, though! They were wonderful and helpful. They also recommended using The Hip Tourist for renting baby equipment and it was perfect!!!

Price per night from

$285

First Breath

Key West house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$100

"Little Paradise" Historic Seaport Old Town Key West

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 42 minutes

Price per night from

$504

Duval Breeze

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

“Warm and inviting condo” The condo is very cozy and inviting. I would definitely go back. Everything you need is right there (even a starter kit) in the condo. Duval street is heaven and parking is safe. We walked to everywhere (restaurant, groceries, shopping). What a great place to stay..

Price per night from

$240

Isle Of View II

Key West boathouse

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 35 minutes

Price per night from

$289

Key West Found

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

“Great rental” This is a great location. Walked to everything including snorkeling every day at Zachery beach. Stayed for a week without a car or bikes. Townhouse is extremely clean, maintained and well furnished. Need to add a few more dishes (i.e. bowls). Décor was nice but a few minor changes would make it great. Love the shaded porch. All in all a great rental. Truman annex very secure and quiet.

Price per night from

$255

Emma's Escape

Key West apartment

2 bedrooms / 1 bathroom / sleeps 4

“Little Oasis Exceeded Our Expectations” My boyfriend and I stayed at Emma's Escape from 6/22-7/22. It was everything we hoped it would be and more. It truly was an escape. The condo is beautifully decorated and the grounds are very well maintained. We were instantly comfortable from the second we walked in. The backyard is truly a private little oasis. The pool is simply perfect and tranquil. The sun hits the yard most of the day and chilling in the pool with a mojoito is beyond relaxing. We had such an amazing time here! We are already planning our next trip back. The location of Emma's Escape is great as well. It's about 4 blocks off Duval near Willie T's, less than a mile to Captin Tonys or Mallory Square, and its about a 20 minute walk to the historic seaport. We spent a lot of time at the Green Parrot, which is one of our fave KW bars and is only a few blocks from Emma's Escape. We walked and rode our Conch Cruisers everywhere the month we were in KW. We truly miss being there and pieces of our hearts will always be in Key West! Thanks so much Lida, Libby, and everyone from at Home in Key West realtors for helping us to have a place we can think of as home on your special little island!

Price per night from

$80

Newton's Nest

Key West apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$75

** Fantastic Spring& Summer Stay Downtown walk everywhere **

Key West apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$369

Tiki Too Townhouse, 2 blocks from Duval,Pool, Bikes

Key West townhouse

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 3 hours 33 minutes

Price per night from

$360

Lighthouse Villa

Key West house

3 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$193

Key West Gulf front Home with private dock and pool.

Key West house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$327

Truman Annex-Steps to Famous Duval Street

Key West townhouse

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$441

Belle Marie

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$335

Linger Longer

Key West house

2 bedrooms / 1 bathroom / sleeps 5

“Clean and well provisioned” Townhouse was centrally located, clean, and all basic household goods (paper towels, laundry detergent etc.) were there to meet our needs for the week. I would definitely recommend this unit.

Price per night from

$200

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

3 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 3 hours 36 minutes

Price per night from

$1,286

Viewing 38 of 467
rentals in Key West

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About Key West

Located closer to Cuba than to Miami lies the island of Key West. Since its founding in the early 1800s, the island's year-round balmy, subtropical climate and unique "anything goes" flavor have made it an ideal visitor destination.

Over the years, the island has been seasoned by the rich American and Cuban culture of the 1800s, sweetened by the unabashed romantic appeal of its natural beauty, and energized by the world-renowned artistic talents of Ernest Hemingway, Tennessee Williams, Elizabeth Bishop, Robert Frost and Jimmy Buffett among others.

Residents and visitors to the island actively participate in sightseeing, touring museums, outdoor and maritime activities, and shopping by day. Later, they become part of the sunset celebration held each evening at Mallory Square, when tightrope walkers, jugglers and animal acts strive to top a more captivating performer - the fiery sun settling into the Gulf of Mexico.

The cobblestone streets of Old Town are shaded by beautiful banyan trees and lined with colorful, picturesque homes that reflect the architecture of past eras. Whether exploring these quieter streets or rocking to the vibrant beat of renowned Duval Street, visitors can savor an abundance of restaurants offering breakfast, lunch and dinner, most incorporating the Keys' fresh indigenous seafood.

Surrounding Key West are waters ranging from pastel teals to jewel-toned blues. They are home to one of the world's largest coral reefs and a bounty of shipwrecks, which make for exotic diving and snorkeling. Both novice and skilled anglers can challenge themselves to fish the Atlantic Ocean or Gulf of Mexico, targeting game fish like tarpon and marlin.

At night, the isolated island's sky is filled with stars that create a backdrop for entertainment options including jazz clubs, piano bars, drag shows and saloons. In addition, area playhouses feature Broadway-quality performances.

The tiny island has more than a dozen historic museums showing that the city's roots go deeper than picturesque palm trees and enchanting sunsets. One of the most popular is the Ernest Hemingway Home and Museum, which was the legendary author's home during the 1930s and is still home to his famous lineage of six-toed cats. The Mel Fisher Maritime Museum houses the richest single collection of 17th-century maritime and shipwreck antiquities in the Western Hemisphere, including the treasure of the Spanish galleon Nuestra Señora de Atocha.

Though the city is pedestrian friendly, there are two trolleys visitors can take as a method of transportation and for a tour highlighting the city's landmarks, restaurants, bars and historic sites.

Key West can be reached by flying into Miami International Airport and driving from the mainland down the magnificent Overseas Highway - featuring 42 bridges over open water and designated an All-American Road under the National Scenic Byways program - or by ferry from points on Florida's west coast.

The island is also accessible via Key West International Airport, which is serviced by American Eagle, Delta/Express Jet, United/Silver Air, US Airways and others.

Information provided by: The Monroe County Tourist Development Council

Top Destination reviews

Tranquility
Great Stay!

My family of four stayed at your cozy cottage for our friends Celebration of Life for 7 days. It was the perfect place for us. Enough room to spread out and everything we needed at our fingertips. We enjoyed sitting on the back deck watching the iguanas and letting the nice breeze and warm sunshine hit our pale, VA faces. Thanks for sharing your home. We will definitely recommend “TRANQUILITY”!see more
Sunrise Suite Key West 2 Bed Rooms 2 Full Baths
Full kitchen, extra towels including for the pool, extra blankets if needed.

Ed's apartment was fully stocked with all you need, including pool/beach towels & extra blankets and pillows. Washer and Drier worked well and he supplies you with detergent. Supermarkets near by. Balcony with table and 4 chairs with 2 extra chairs in closet which was great as we were 6. Apartment has 2 full bathrooms! Only complaint was from one of my children who said the double bed she shared with her sister was uncomfortable. Other child slept fine. Thank you Ed - your apartment worked perfect for us.see more
Sunrise at Seaside Condo 2 Bedroom
Key West Adventure

We were two couples on our first visit to explore the keys. The condo was nice for four people. Not fancy but adequate. Could use a little updating to make it nicer. Located quite aways from Duval atreet and the action. Uber costs about $20 one way to get downtown. Too far to walk. The pool was amazing. No complaints.see more
Casa Del Sol, a Key West Vacation (Truman Annex)
Casa Del Sol

We absolutely loved this place! We were two short blocks away from Duval street, close to everything we needed. The place was very clean and well stocked. The owners were very friendly and helpful. I would highly recommend this place and we look forward to coming back! … see more
HISTORIC KEY WEST - Main House - Sleeps 8
Excellent location, old Key West ambience

The Bahama Gardens main house was clean and comfortable and very well located in old Key West, 2 blocks from Duval St. We especially loved the private pool and jacuzzi. There were a lot of roosters around that gave us several concerts a day, but we loved it! Would stay again. … see more
2 bedroom Condo Presented Key West Style
Relaxing, Quiet Comfortable and Convenient!

We had such a great time! If you are coming to enjoy Key West but need comfortable, quiet location to reside, this is it. Everything we needed was in order, clean and ready for use in the unit. Pam, the owner, even sent a list of information containing activities to enjoy and places to see. We spent a few quiet mornings eating breakfast in the comfort of our own balcony overlooking the pool. And yes, it was convenient to everything. We could be in the heart of downtown in a few short minutes or the beach in an even shorter time. Her place is the perfect retreat to relax and enjoy. My wife and I will be back really soon!see more

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