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Key West Rentals with Pools

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167 house rentals in Key West with pools

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

Key West townhouse

2 bedrooms / 3 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$573

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

$270

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 3 minutes

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Price per night from

$245

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 14 minutes

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Price per night from

$432

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 55 minutes

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Price per night from

$488

Southard Square Hideaway

Key West condo

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$89

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

$323

Southard Getaway

Key West apartment

2 bedrooms / 1 bathroom / sleeps 5

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Price per night from

$213

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 47 minutes

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Price per night from

$1,989

Bayview Harbor

Key West apartment

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$198

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

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Price per night from

$1,724

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!

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Price per night from

$693

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. 3 hours 34 minutes

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Price per night from

$321

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!!!

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Price per night from

$282

First Breath

Key West house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$99

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

$238

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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Price per night from

$258

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

Newton's Nest

Key West apartment

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$75

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

Key West apartment

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$287

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

$518

Lighthouse Villa

Key West house

3 bedrooms / 4 bathrooms / sleeps 8

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Price per night from

$191

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

$324

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.

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Price per night from

$198

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

3 bedrooms / 2 bathrooms / sleeps 7

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Price per night from

$1,264

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

$198

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.

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Price per night from

$198

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.

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Price per night from

$230

Key West Oasis - Private Pool, Separate Cottage - Great for Couples & Families

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

“Fabulous luxury home in Fabulous Key West” Beautiful, private, historic 2 BR/2 bath home, lovely heated pool, outdoor dining & living areas in addition to most attractive indoor spaces. Wonderful Old Town neighborhood. Can walk, cycle, & Lyft everywhere (including great restaurants)--no car needed. 2nd BR is in the guest house beyond the pool--fabulous outdoor shower completes the "only-in-Key West" ambiance. The owner, Kim, is super responsive.

Responds fast! avg. 1 hour 38 minutes

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Price per night from

$640

** Totally Renovated Ocean View Condo Great Prices **

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$544

Conch Republic Retreat

Key West cottage

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$106

Ibis

Key West house

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$75

City Cay

Key West apartment

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$174

Coconut Cottage

Key West house

1 bedroom / 2 bathrooms / sleeps 2

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Price per night from

$77

tropical Casita

Key West house

1 bedroom / 2 bathrooms / sleeps 2

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Price per night from

$106

Boat House

Key West house

1 bedroom / 2 bathrooms / sleeps 2

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Price per night from

$92

One-bedroom suite in the heart of Old Key West

Key West condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 22 minutes

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Price per night from

$214

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Key West apartment

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$395

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