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Stock Island Rentals with Pools

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170 Houses in Stock Island with pools

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Stock Island condo

2 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$134

NEW! Charming 'Boho Breeze' Retreat w/ Pool Access

Stock Island townhouse

3 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 24 minutes

Match: Swimming pool

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Price per night from

$142

Coconut Mallory #411, Key West Convenience + Resort Amenities, Pools, Hot Tub an

Stock Island condo

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$174

* Caribbean Conch Key West Condo offers delightful extras *

Stock Island condo

2 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$498

Ocean Hideaway Key West Retreat Private Nature preserve and Ocean views await

Stock Island condo

2 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$390

Tropical Oasis in Key West with magical Key West Charm throughout

Stock Island condo

2 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$630

*Spring Discounts Stay on the Ocean Last minute Specials Book & Save *

Stock Island condo

2 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$413

Tumi's Time Out - Monthly rental in Windward Park gated compound, shared pool

Stock Island townhouse

2 bedrooms / 2 bathrooms / sleeps 4

Match: Swimming pool

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Price per night from

$184

Coral Palm 3 bedroom, 3 bathroom townhome at Coral Hammock, Pet Friendly!

Stock Island townhouse

3 bedrooms / 3 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$130

Serenity A Romantic Cottage in Bahama Village w/ a Shared pool

Stock Island cottage

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$148

Wind Swept by AT HOME IN KEY WEST

Stock Island townhouse

2 bedrooms / 1 bathroom / sleeps 6

Match: Swimming pool

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Price per night from

$119

A Little Slice of Paradise by AT HOME IN KEY WEST

Stock Island townhouse

2 bedrooms / 1 bathroom / sleeps 5

Match: Swimming pool

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Price per night from

$112

Coral Breeze by AT HOME IN KEY WEST

Stock Island townhouse

2 bedrooms / 1 bathroom / sleeps 4

Match: Swimming pool

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Price per night from

$119

Bye Bye Birdie - Spacious 3 bedroom Golf Club Living

Stock Island townhouse

3 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$148

Bogey's Retreat by AT HOME IN KEY WEST

Stock Island townhouse

2 bedrooms / 1 bathroom / sleeps 4

Match: Swimming pool

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Price per night from

$112

Coral Villa by AT HOME IN KEY WEST

Stock Island townhouse

3 bedrooms / 3 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$130

CORAL GARDEN Family friendly, work from home, 2 bedroom townhome in Paradise

Stock Island townhouse

2 bedrooms / 2 bathrooms / sleeps 4

Match: Swimming pool

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Price per night from

$119

SPA OASIS - Unique home overlooking Key West Golf Course By At Home in Key We

Stock Island house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$148

Cottage by the Pool By At Home in Key West

Stock Island townhouse

2 bedrooms / 1 bathroom / sleeps 4

Match: Swimming pool

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Price per night from

$112

Entire House with Deep Water Dock & Heated Pool - 4 Min. to KW - Pets OK

Stock Island house

4 bedrooms / 3 bathrooms / sleeps 11

Match: Swimming pool

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Price per night from

$896

Great rentals within 20 miles that match your search

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

$315

Harbor Walk Hideaways

Key West b&b

4 bedrooms / 3 bathrooms / sleeps 8

“Location, Location, Location” We were a group of 8 and rented the entire compound! The place was in an amazing location that was easily accessible to everything. We had everything we needed onsite and if we had any questions, Phyllis was always just a phone call away. The music and talking at night from the cigar lounge was a bit loud, but nothing we couldn't tolerate. The only suggestion I'd make is to buy an ionizer for the first two units to help with the cigar smell....again, nothing intolerable, but could make a world of difference. Can't wait to come back for another visit! THANK YOU!

Match: Swimming pool

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Price per night from

$1,300

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. 3 hours 4 minutes

Match: Swimming pool

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Price per night from

$229

Ocean View Estate with Private Pool 15 minutes from Key West

Key West house

4 bedrooms / 2 bathrooms / sleeps 10

“Absolutely Perfect for Our Family of 11” We couldn't have asked for a better place for our family. Everyone had a comfortable bed, we had everything we needed for cooking, and there was plenty for everyone to do. If we needed something, we could find it easily, or we called Cynthia---her help and knowledge is priceless! Kris stopped in twice to check on us, and we found him delightful. He knows so much history about the area! There is a large pool and a large play area with anything and everything you can imagine to play with, Since we had very young children with us, we were very happy with the lack of ocean access, as well as the locking gates to the pool area and the outside stairs. When we come back to the Keys, we will definitely stay at the White Ibis Inn!

Responds fast! avg. 3 hours 47 minutes

Match: Swimming pool

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Price per night from

$544

2 Bedroom, 2 Bath Condo with private balcony and Close to the Ocean

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

“We'll be back...” We found this condo to be very clean and comfortable. We enjoyed sitting at the pool as well. Paul, the caretaker, was very pleasant and most accommodating. We shared the condo with another couple for our two night stay. It was wonderful to have our privacy (2 BR/2 baths) but still be able to share the kitchen/living room area with our friends. We had a rental car so found the location easy for shopping, dining, sightseeing on other keys and, of course, Duval Street.

Responds fast! avg. 1 hour 44 minutes

Match: Swimming pool

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Price per night from

$458

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

Match: Swimming pool

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Price per night from

$257

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 58 minutes

Match: Swimming pool

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Price per night from

$320

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 29 minutes

Match: Swimming pool

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Price per night from

$367

Artist Cottage in Truman Annex

Key West apartment

2 bedrooms / 1 bathroom / sleeps 4

“Key West, Spring 2012” In a word,our stay with you was ”wonderful”. We have been to Key West on several occasions and have loved every visit. Staying in Truman annexe was even more special. We all felt like we were at home with everything we needed. You must feel blessed to live in that part of the world. We will be looking for a job for our 19 year old son,Tom. He wants to come and work over in Key West. We have just arrived home and everything seems grey, and much colder than Key West. Depending on finances( the pound-dollar rate is not too good just now) we hope to come back soon. We will definitely be giving you a call.I would recommend your accommodation and company to future holiday makers. Love and blessings John,Jayne,Jack and Tom

Match: Swimming pool

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Price per night from

$379

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

$2,199

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

Match: Swimming pool

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Price per night from

$1,947

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

$1,144

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

$915

HISTORIC KEY WEST - Main House - Sleeps 8

Key West house

4 bedrooms / 2 bathrooms / sleeps 8

“February visit to Key West” Our family stayed at the Main House for 4 nights and loved it. The location was fabulous! Loved the houses and gardens!!! The owner was very nice and considerate of us. If we get back that is where we would want to be!!

Match: Swimming pool

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Price per night from

$1,831

Sunrise Suite Key West 2 Bed Rooms 2 Full Baths

Key West condo

2 bedrooms / 2 bathrooms / sleeps 6

“Great condo” Great condo - nicely decorated and most well stocked kitchen ever. Everything was so neat and clean and there was an abundance of supples. Would highly recommend

Responds fast! avg. 2 hours 34 minutes

Match: Swimming pool

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Price per night from

$297

6 bedroom Duval Street Compound - Pool, Hot Tub, 2 parking spots - A++ Location

Key West villa

6 bedrooms / 7 bathrooms / sleeps 16

Match: Swimming pool

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Price per night from

$2,004

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

Key West townhouse

2 bedrooms / 1 bathroom / sleeps 6

Match: Swimming pool

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Price per night from

$516

Seaside Condo 2 pools. sunny, quiet, near Old Town

Key West condo

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 47 minutes

Match: Swimming pool

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Price per night from

$100

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