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Key West Rentals with Pools

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93 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

$898

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 56 minutes

Match: Swimming pool

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Price per night from

$303

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. 2 hours 46 minutes

Match: Swimming pool

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Price per night from

$469

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 32 minutes

Match: Swimming pool

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Price per night from

$647

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 39 minutes

Match: Swimming pool

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Price per night from

$2,079

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!

Match: Swimming pool

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Price per night from

$308

Island vibe, Downtown Nightlife, Evening sunsets, Beachside afternoons.

Key West apartment

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 58 minutes

Match: Swimming pool

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Price per night from

$344

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

$506

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

$414

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

3 bedrooms / 3 bathrooms / sleeps 7

Match: Swimming pool

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Price per night from

$1,910

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

“Fantastic Stay!” My husband and two sons (21 & 24) stayed in this condo over Christmas. This was our first stay in Key West and we wanted to be close to everything, but yet not right on Duval St. This location was perfect; literally a stones throw away from Duval St. The unit inside was decorated very lovely and had all the amenities one would need. I found the owners were nice to do business with, especially Deb who I mostly communicated with. My family and I enjoyed our stay in Key West immensely, we had so much fun! We met many very friendly people out and about town. We would love to visit again, if we do, we would like to stay in this condo or the Bella Vita, the owner's other condo.

Responds fast! avg. 2 hours 50 minutes

Match: Swimming pool

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Price per night from

$178

Salty Breezes, Exquisite Sunrises & a luxuriously upgraded Condo in Key West.

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 58 minutes

Match: Swimming pool

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Price per night from

$716

One-bedroom suite in the heart of Old Key West

Key West condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 43 minutes

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Price per night from

$326

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Key West apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 58 minutes

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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

Match: Swimming pool

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Price per night from

$336

HISTORIC KEY WEST - Cigar House - Sleeps 4

Key West house

1 bedroom / 1 bathroom / sleeps 4

Match: Swimming pool

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Price per night from

$1,102

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!!!

Match: Swimming pool

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Price per night from

$309

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

Key West condo

2 bedrooms / 1 bathroom / sleeps 4

Match: Swimming pool

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Price per night from

$379

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

Match: Swimming pool

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Price per night from

$336

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. 57 minutes

Match: Swimming pool

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Price per night from

$422

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Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 58 minutes

Match: Swimming pool

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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

Responds fast! avg. 2 hours 58 minutes

Match: Swimming pool

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Price per night from

$682

HISTORIC KEY WEST - Conch House - Sleeps 5

Key West house

2 bedrooms / 1 bathroom / sleeps 5

Match: Swimming pool

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Price per night from

$1,102

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

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 58 minutes

Match: Swimming pool

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Price per night from

$716

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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.

Responds fast! avg. 2 hours 58 minutes

Match: Swimming pool

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Price per night from

$1,145

Amazingly Transformed in 2022 - Luxurious renovation, Fantastic Ocean View.

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 58 minutes

Match: Swimming pool

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Price per night from

$659

** 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!~

Responds fast! avg. 2 hours 58 minutes

Match: Swimming pool

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Price per night from

$446

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

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 58 minutes

Match: Swimming pool

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Price per night from

$498

Crystal blue seas, Island Breezes, Morning Sunrises & Key West Island days.

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 58 minutes

Match: Swimming pool

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Price per night from

$172

Olivia Place

Key West house

4 bedrooms / 4 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$331

Ocean Front Key West Oasis. Island Tones, Charming Historical Downtown area.

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 58 minutes

Match: Swimming pool

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Price per night from

$210

Salty ocean breezes, Island vibe & Downtown Nighlife within 10 minutes.

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 58 minutes

Match: Swimming pool

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Price per night from

$134

A Change in Latitudes - TRUMAN ANNEX

Key West condo

2 bedrooms / 1 bathroom / sleeps 4

Match: Swimming pool

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Price per night from

$166

Salty Sea Breezes, Exquisite Morning Sunrises, Luxurious Condo. Fall Specials

Key West apartment

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 58 minutes

Match: Swimming pool

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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

Match: Swimming pool

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Price per night from

$1,433

Key West Morning reflections, Balmy Ocean Breezes, Downtown family fun. KWF

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 58 minutes

Match: Swimming pool

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Price per night from

$153

SEAPORT SERENITY in Old Town—Beach-Pool-BBQ-Hot Tub

Key West condo

2 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$855

Key West, Private Beach, Fishing Pier, Old Town, Galleon Resort

Key West condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 42 minutes

Match: Swimming pool

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Price per night from

$552

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