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Key West Rentals with Pools

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355 house rentals in Key West with pools

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.

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Price per night from

$334

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. 1 hour 21 minutes

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Price per night from

$232

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

Key West townhouse

2 bedrooms / 3 bathrooms / sleeps 6

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$572

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 29 minutes

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$430

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

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$165

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. 1 hour 47 minutes

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$346

Key West Florida Beachfront Condo

Key West condo

2 bedrooms / 2 bathrooms / sleeps 6

“Better than the photos” Condo is perfectly located at the beach. Well designed for easy living both inside and out. Great advise on where to visit and eat thanks

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$403

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.

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Price per night from

$249

Southard Square Hideaway

Key West condo

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$120

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

Key West yacht

4 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$288

Coconut Beach

Key West apartment

1 bedroom / 2 bathrooms / sleeps 4

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$264

President's Walk

Key West house

2 bedrooms / 1 bathroom / sleeps 4

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$195

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!!!

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Price per night from

$285

Bayview Harbor

Key West apartment

2 bedrooms / 1 bathroom / sleeps 5

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$160

Big house

Key West house

5 bedrooms / 5 bathrooms / sleeps 10

“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!

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$700

Real World MTV House Key West

Key West house

10 bedrooms / 6 bathrooms / sleeps 22

“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. 3 hours 10 minutes

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Price per night from

$1,919

Southard Getaway

Key West apartment

2 bedrooms / 1 bathroom / sleeps 5

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Price per night from

$195

Isle Of View II

Key West boathouse

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 26 minutes

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Price per night from

$228

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.

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$255

William's Loft

Key West cottage

2 bedrooms / 1 bathroom / sleeps 3

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$87

Sunshine Key West

Key West house

2 bedrooms / 3 bathrooms / sleeps 5

“Perfect Home for Key West” This place has all the amenities you need! It was our first time renting a home and it couldn't have been more perfect! Quiet neighborhood, but not too far from the action of Duval.

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Price per night from

$107

First Breath

Key West house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$107

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 0 minutes

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Price per night from

$323

Newton's Nest

Key West apartment

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$106

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 27 minutes

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Price per night from

$1,260

Key West Gulf front Home with private dock and pool.

Key West house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$330

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

3 bedrooms / 2 bathrooms / sleeps 7

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Price per night from

$1,272

City Cay

Key West apartment

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$155

The Banyan Resort at Key West

Key West apartment

2 bedrooms / 1 bathroom / sleeps 6

“Wonderful week at The Banyan Resort!!” My husband and I recently stayed in a 2 bedroom/1Bath unit at The Banyan Resort and we were extremely pleased with everything!! Everyone we encountered from the front desk, housekeeping, grounds personnel and other guests were warm and welcoming! The unit was very spacious and comfortable and you can"t beat the location. It's within walking distance of all attractions and Fort Zachary Taylor State Park. The owner was very responsive to all of my questions and a pleasure to work with and we look forward to being repeat guests at The Banyan Resort.

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Price per night from

$265

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!

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Price per night from

$80

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!

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Price per night from

$180

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

Key West townhouse

2 bedrooms / 1 bathroom / sleeps 6

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Price per night from

$360

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..

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Price per night from

$240

Lighthouse Villa

Key West house

3 bedrooms / 4 bathrooms / sleeps 8

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Price per night from

$193

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

Key West apartment

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$263

Coconut Cottage

Key West house

1 bedroom / 2 bathrooms / sleeps 2

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$77

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Key West apartment

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$373

** Totally Renovated Ocean View Condo Great Prices **

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$602

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