Vacation Rentals & House Rentals in Key West

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181 house rentals

Houseboat Trawler MV Coconuts: Once in a Lifetime Vacation With Pool Access

Key West house

3 bedrooms / 2 bathrooms / sleeps 8

“Nice alternatif for hotel” We were on the boat with only 2 people, so plenty of place ! We liked the marina and the boat very well. Something completely different than an hotelroom ... We had perfect weather so we used the different terraces on the boat depending on the wind and sun. The only point what could be better is the quality of the bedding (sheets, blankets, towels...) For this price you expect some better quality. Anyway, when we wil go back to the us I certainly will search for something similar to stay on

Match: Shared outdoor pool (unheated)

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Price per night from

$258

Southard Square Hideaway

Key West condo

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$147

Southard Getaway

Key West apartment

2 bedrooms / 1 bathroom / sleeps 5

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Price per night from

$200

President's Walk

Key West house

2 bedrooms / 1 bathroom / sleeps 4

Match: Shared outdoor pool (unheated)

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Price per night from

$195

Bayview Harbor

Key West apartment

2 bedrooms / 1 bathroom / sleeps 5

Match: Shared outdoor pool (unheated)

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Price per night from

$160

Artist Garden

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

“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!!!

Match: Shared outdoor pool (unheated)

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Price per night from

$285

William's Loft

Key West cottage

2 bedrooms / 1 bathroom / sleeps 3

Match: Shared outdoor pool (unheated)

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Price per night from

$87

Newton's Nest

Key West apartment

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$106

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..

Match: Shared outdoor pool (unheated)

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Price per night from

$240

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

Key West apartment

2 bedrooms / 1 bathroom / sleeps 4

Match: Shared outdoor pool (unheated)

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Price per night from

$367

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.

Match: Shared outdoor pool (unheated)

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Price per night from

$265

Finn Key

Key West apartment

2 bedrooms / 1 bathroom / sleeps 4

“Loved Finn Key” Condo and furnishings were very nice and clean. Loved the patio and proximity to the pool! Location was extremely central- easy access to Duval, Mallory Square & Fort Zach Beach. Great being able to walk to almost anything we wanted to do. Only complaint was the noise level in condo- walls and ceiling are thin & we heard everything upstairs, especially in the morning! But that is not the fault of the owners or rental company- bring a noisemaker to sleep at night! We would definitely stay here again, great time!

Match: Shared outdoor pool (unheated)

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Price per night from

$180

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!

Match: Shared outdoor pool (unheated)

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Price per night from

$80

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

3 bedrooms / 2 bathrooms / sleeps 7

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Price per night from

$1,259

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Key West apartment

2 bedrooms / 2 bathrooms / sleeps 4

Match: Shared outdoor pool (unheated)

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Price per night from

$515

** Totally Renovated Ocean View Condo Great Prices **

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

Match: Shared outdoor pool (unheated)

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Price per night from

$602

City Cay

Key West apartment

1 bedroom / 1 bathroom / sleeps 2

Match: Shared outdoor pool (unheated)

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Price per night from

$160

A Barefoot Retreat

Key West apartment

2 bedrooms / 1 bathroom / sleeps 4

“Fantastic Vacation” Great property. Exactly as described. Fully stocked kitchen. Perfect for my husband and I. We were looking to just relax between Christmas and New Years. We would have given the property 5 stars but the parking is a little wonky. Pretty far walk from the parking lot to the unit with groceries. Nice cross breeze with the front balcony and back deck door open. Sun on the back deck was great. Even had a visitor passing through as I sat on the deck reading a book. (See pic) Quiet but close to Duval's action and eateries. Will absolutely book Barefoot Retreat again.

Match: Shared outdoor pool (unheated)

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Price per night from

$180

Boat House

Key West house

1 bedroom / 2 bathrooms / sleeps 2

Match: Shared outdoor pool (unheated)

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Price per night from

$93

One-bedroom suite in the heart of Old Key West

Key West condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 4 minutes

Match: Shared outdoor pool (unheated)

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Price per night from

$218

Crowner's Jewel

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

“First visit to Key West” Took our family to Key West for the first time and we had a wonderful time. Rental was in great location and good condition. My family will visit again.

Match: Shared outdoor pool (unheated)

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Price per night from

$220

Key West Charming

Key West apartment

2 bedrooms / 1 bathroom / sleeps 4

“Key West the beautiful” Our stay at the Key West was indeed charming, home was absolutely beautiful as seen on the pics, very comfy, clean and all the amenities were included, all we had to do was shop for food, lol. This was our first time in Key West and I must say my family and I would def go back and when we do we will def stay here. Home was close to everything, we did not need our car for anything, pool was very nice and clean, the surrounding area around was simply beautiful, loved it, Thank you so much for such beauty. Sincerely Maria King and family

Match: Shared outdoor pool (unheated)

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Price per night from

$160

Tranquility

Key West cottage

1 bedroom / 1 bathroom / sleeps 4

“Hidden Conch Treasure” This perfect conch rental provided everything my family needed for a wonderful family vacation. Abundant sunshine was included with this historic treasure nestled in a small community. The pool was an added delightful treat. I recommend this hidden treasure.

Match: Shared outdoor pool (unheated)

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Price per night from

$190

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.

Match: Shared outdoor pool (unheated)

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Price per night from

$195

Sundown Refuge

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 5

“Great Place!” You could have lived in this condo!!! It had everything you could want and more for cooking/entertaining! Folding chairs for Mallory Square, beach towels for the pool, games, paper/pencils! They only bummer was the master bed. The side closest to the sliding doors was squeeky...every time I would move, I was making sounds!! Other that that, a FABULOUS place that I would love to stay at again!!!

Match: Shared outdoor pool (unheated)

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Price per night from

$264

A Place In Paradise

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

“Excellent Location” Our condo was extremely well prepared for our week long vacation, great decorations and included everything one needs for a week....washer/dryer, ironing board, etc. The location of this condo could not be better ....a couple of blocks away from all of the down town restaurants and close to the beautiful waters that only the "Keys" have to offer and fantastic sunsets. Highly recommend.

Match: Shared outdoor pool (unheated)

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Price per night from

$245

Duval On The Square

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

“A really good place to stay” Duval Square is a very good location. Crowd noise is not a problem. However the parrots from the New York restaurant below can get annoying. The inside of the apartment is nicely done. The balcony's overlooking the square are nice but are in need of painting. Service from the rental company was excellent. They respond quickly to requests. Bringing the baggage up to the apartment is easier when you use a shopping cart and the elevator. If a cart is not in the garage take the elevator up to the 2nd floor. They are usually left by the elevator. The worst problem is the parking at the check in site. It is extremely tight and it is a damaged fender waiting to happen. The service once inside is very good.

Match: Shared outdoor pool (unheated)

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Price per night from

$100

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Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

Match: Shared outdoor pool (unheated)

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Price per night from

$572

Leeward Isle Key West Retreat

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

“A little piece of paradise” This house is just beautiful and come equipped with everything you need for a wonderful vacation. The development is small a quiet and feels like an oasis. It is steps from all the action on Duval Street and in walking distance of most things in Key West. Perfect house in a perfect location.

Match: Shared outdoor pool (unheated)

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Price per night from

$250

Ibis

Key West house

1 bedroom / 1 bathroom / sleeps 2

Match: Shared outdoor pool (unheated)

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Price per night from

$75

LA DOLCE VITA, OLD TOWN KEY WEST!! STEPS TO DUVAL!! SLEEPS 2-4, 3 BLKS TO BEACH

Key West apartment

1 bedroom / 1 bathroom / sleeps 4

“Wonderful Experience” Beautiful decor! Perfect location - just off the beaten path but out of the hustle and bustle. Convenient to everything we wanted to do! I whole heartedly recommend this condo for a couple. Also would work nicely for three people. Might be a bit tight for four adults, but it was perfect for my husband and me.

Responds fast! avg. 2 hours 44 minutes

Match: Shared outdoor pool (unheated)

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Price per night from

$250

Atlantic Paradise

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

Match: Shared outdoor pool (unheated)

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Price per night from

$210

Breezy Bungalow

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

Match: Shared outdoor pool (unheated)

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Price per night from

$200

The Prive

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

“What a wonderful place to forget the long cold winter and renew” The house was beautiful . The neighborhood was quiet and peaceful. It was everything we had hoped it would be. Everything you could possibly need in a house was there. The house was spotless, bright and airy. The back yard was beautiful! If you need a place to relax and rejuvenate this is it! I can't wait to rent it again!

Match: Shared outdoor pool (unheated)

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Price per night from

$325

Osprey

Key West studio

Studio / 1 bathroom / sleeps 2

“Perfect location for the "Food" end of Duval!” A perfect sized studio bungalow! Very comfortable, with a fully equipped kitchenette, full bathroom, living room area and comfy queen bed. Everything we needed was provided. Towels, sheets, pillows, blow dryer, on site washer and dryer, etc. The pool was great. Located in a small complex, it was nice to meet other travelers. There's a small store at the end of the block. The entry way has books available to read while lounging at the pool. Walking distance to many restaurants like Seven Fish, McConnell's Pub, Blue Heaven, Santiago's Bodega, etc. Close to Ft. Taylor State Beach, Higgs and Smather's Beaches, too. Not far from Hemingway's House, the USCG Cutter Ingham and Key West Eco-Discovery Center. So much else close by! We were able to walk everywhere. Though we rented bikes for part of our visit available right on Duval, making it much easier to get to around Key West faster.

Match: Shared outdoor pool (unheated)

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Price per night from

$145

Emma's Secret

Key West apartment

2 bedrooms / 1 bathroom / sleeps 4

“Good location for Duval Street” Emmas Secret is a very nice 2 bedroom unit in Old Town just a short walk to Duval Street. Very convenient location if flying into KW no car is needed. The unit is updated and the pool area in the back yard is fantastic. Only problem is loungers by the pool - need more than 1. Will definitely look at this unit on my next visit.

Match: Shared outdoor pool (unheated)

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Price per night from

$80

Shrimp Party

Key West townhouse

2 bedrooms / 2 bathrooms / sleeps 4

Match: Shared outdoor pool (unheated)

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Price per night from

$100

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Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

Match: Shared outdoor pool (unheated)

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Price per night from

$573

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