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Key West Rentals with Pools

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158 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

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Price per night from

$572

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 26 minutes

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Price per night from

$342

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 35 minutes

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Price per night from

$485

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 22 minutes

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Price per night from

$69

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 35 minutes

Match: Swimming pool

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Price per night from

$2,192

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

$1,947

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 48 minutes

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Price per night from

$319

Downtown Key West Oasis, Tropical Paradise Steps from Duval & Ft Zach

Key West apartment

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$295

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

$514

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

$428

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

3 bedrooms / 3 bathrooms / sleeps 7

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Price per night from

$1,946

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 52 minutes

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Price per night from

$263

Luxurious Renovation with sweeping ocean views. A true Paradise

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$602

One-bedroom suite in the heart of Old Key West

Key West condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 10 minutes

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Price per night from

$217

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Key West apartment

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$476

Comfy Family Home in a Gorgeous Gated Community

Key West townhouse

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 33 minutes

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Price per night from

$342

HISTORIC KEY WEST - Cigar House - Sleeps 4

Key West house

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$915

Tee by the Sea - Luxury 2/2 1/2 with huge pool, parking and 7 Bikes FREE

Key West apartment

2 bedrooms / 3 bathrooms / sleeps 6

“Absolutely Perfect!!!” I chose this place to rent because it looked nice and it was affordable. I knew going in that it was not located on the Key West island, which was fine considering the condo came with bikes you could ride onto the island...What I experienced during my stay here is nothing short of Perfect!!! The entire condo was clean and spacious, everything inside the condo worked, the beds and all furniture were clean and comfortable, plenty of towels and linens, the showers, water presure and plumbing were excellent, the pool was clean, relaxing and private, the nights were quiet for sleeping and the gated community within the condo were friendly and fun. The bikes were the best part...10-15 minutes and you were on Duval Street, or the Southernmost Point, or Fort Zachery beach with no hassles what so ever, and I got some good exercise!!! I will definately stay here again!!!

Responds fast! avg. 3 hours 52 minutes

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Price per night from

$314

KEY WEST and 3 Bikes or Walk Everywhere! 2 Porches, Pool, Parking & WIFI

Key West condo

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 11 minutes

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Price per night from

$392

Sunrise at Seaside Condo 2 Bedroom

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 5

“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.

Responds fast! avg. 3 hours 28 minutes

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Price per night from

$314

Henry's Piece Of Paradise On The Ocean In Key West

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 5

“nice place” Accommodations were nice Good view Henry was great to work with

Responds fast! avg. 2 hours 4 minutes

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Price per night from

$428

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Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$533

Anchor Drop in Key West modern elegance, luxury finishes. Bike to Old Town

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$567

Sunrise At Seaside Condo 2 bedroom 2 bath

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 5

“Exactly what we needed.” Owner responded in timely manner and was pleasant and answered all questions. The unit was easy to find and close to the airport. We worried about airport traffic noise interfering with sleep, but never heard them inside the condo. Condo was clean and had washer and dryer inside the unit. It was amazing to be able to do laundry when I wanted. Pool was clean, heated, and refreshing. Loved having private covered parking. It kept the car nice and cool when you got in. We'll definitely visit again in the future!

Responds fast! avg. 3 hours 28 minutes

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Price per night from

$342

HISTORIC KEY WEST - Conch House - Sleeps 5

Key West house

2 bedrooms / 1 bathroom / sleeps 5

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Price per night from

$912

Tastefully renovated Key West Oasis views of the Sunrise and Smathers Beach

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$602

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Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Outstanding!” 1800 altantic was the perfect place to stay for our "friends" reunion. Our condo was clean and well equipped. The place was extremely safe and secure.

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Price per night from

$687

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Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$544

** Steps from Duval 1 Bedroom Townhouse in great complex Hidden secret **

Key West house

1 bedroom / 1 bathroom / sleeps 4

“The perfect place to stay in Key West” This property is just 1 block off Duval -- but closer to the quiet, quaint side. I was so impressed with the accomodations -- fully equipped! We could have stayed there a month! The grounds are beautiful, lush, tropical and quiet. Staff was super friendly -- it is also very private with a large locking wrought iron gate keeping the units apart from the street -- we loved everything about it! We will stay here again on our next visit for sure!~

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Price per night from

$304

Spacious Key West Condo on the Ocean with upgraded master suite. Paradise Key

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$498

* Winter in Paradise Available Jan 1st - April 1st 2021 - Discounts *

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$172

Olivia Place

Key West house

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 2 hours 30 minutes

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Price per night from

$343

Ocean Front Key West Oasis. Tropical paradise awaits

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$192

* Beautifully renovated Condo on the Ocean Available Feb & March 20201 *

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$144

A Change in Latitudes - TRUMAN ANNEX

Key West condo

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$172

Keys to Paradise luxury at its finest on the on the ocean front.

Key West apartment

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$344

HISTORIC KEY WEST - Turtle House - Sleeps 6

Key West house

2 bedrooms / 1 bathroom / sleeps 6

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Price per night from

$1,144

*Key West Morning Reflections Paradise Awaits April - Sep 2022*

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$153

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