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Key West Rentals with Pools

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Key West Rentals with Pools

280 vacation rentals

1/2 Block to Duval, World of its own -Nassau Suite

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Our wedding family stayed here awesome” Fabulous. Clean roomy pool fantastic. Short walk to schooners Wharf Both inside and outside area were excellent

Price per night from

$277

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Steps to Duval, Old Town Charm -Grand Bahama Suite

Key West apartment

3 bedrooms / 2 bathrooms / sleeps 8

“Can't wait to return” We loved staying at the Grand Bahama suite. It was spacious, clean and centrally located just a street from all the action. We loved the courtyard and pool. I was a little concerned about parking but it worked out fine for us.

Price per night from

$327

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1BR Restored Conch House w/ Pool & Deck

Key West house

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$89

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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 tranqu

Price per night from

$134

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Best Location, 1/2 Block to Duval, Bimini Suite

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 5

“Perfect!” This was the perfect size suite for 4 adults, with a little pool oasis right off our doorstep, in the center of it all without the noise of Duval. Loved every second of my stay!

Price per night from

$259

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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 27 minutes

Price per night from

$228

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Center of It All - Paradise Island Suite

Key West apartment

2 bedrooms / 1 bathroom / sleeps 6

“Great location in the heart of Old Town Key West, just a block off Duval..” We stayed in the Paradise Suite. Great front porch to hang out on, pool in back with pergola for lounging. Place was set up perfect, pool towels hanging by the door, bathroom

Price per night from

$248

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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.

Price per night from

$219

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Key West Condo close to the Ocean

Key West condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 48 minutes

Price per night from

$260

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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 b

Price per night from

$208

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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

Price per night from

$300

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Shelleys Rooftop Hideaway

Key West apartment

2 bedrooms / 3 bathrooms / sleeps 4

“great place to stay” Close to every thing in Key West Walking distance to all of down town stores and bar my personal favorite

Price per night from

$290

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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 cha

Responds fast! avg. 2 hours 6 minutes

Price per night from

$348

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The Water's Edge

Key West house

3 bedrooms / 4 bathrooms / sleeps 8

“Perfect for a Memorable Key West Experience!” My family and I absolutely loved staying in this beautiful Key West home. Located in Truman Annex (a quiet, private community in Old Town Key West), the location is perfect for whatever you wish to do duri

Price per night from

$837

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A Touch Of Havana In Key West

Key West condo

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 36 minutes

Price per night from

$307

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President's Walk

Key West house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$195

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Hidden Treasure

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$78

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Villa Deja vu Key West ~ Weekly Rental

Key West house

4 bedrooms / 3 bathrooms / sleeps 10

“Great stay over the 4th of July” The Villa Deja Vu was the perfect place for our group of 10. We were on vacation in Key West for a 30th birthday celebration and had a great experience. The house was wonderful, more than we could have imagined. The pi

Price per night from

$850

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

Key West yacht

4 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$396

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Bayview Harbor

Key West apartment

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$180

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Quilted Giraffe

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$400

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Southard Getaway

Key West apartment

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$195

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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

Responds fast! avg. 1 hour 52 minutes

Price per night from

$949

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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!

Price per night from

$700

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Campbell Suite

Key West apartment

1 bedroom / 2 bathrooms / sleeps 2

“Comfortably furnished and decorated with a very convenient locat” We really enjoyed staying at the Campbell Suite. It served our requirements nicely. The amenities and location were excellent. Potential visitors do need to note that the entrance to th

Price per night from

$200

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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 enou

Price per night from

$285

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Coconut Beach

Key West apartment

1 bedroom / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 28 minutes

Price per night from

$228

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Admiral's Lane

Key West house

4 bedrooms / 3 bathrooms / sleeps 8

“Fabulous family rental” We have stayed in Key West for four years now. This was the best rental property so far. The location is perfect for beach days and walking both ends of Duval at night. The property itself had all the amenities we needed and wa

Price per night from

$700

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Island Style

Key West house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$770

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Isle Of View II

Key West boathouse

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 38 minutes

Price per night from

$174

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The Mermaid's Garden

Key West house

4 bedrooms / 5 bathrooms / sleeps 8

Price per night from

$770

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Newton's Nest

Key West apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$75

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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. bo

Price per night from

$250

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Grande Dame Key West - 'The Watson House' ~ Weekly Rental

Key West house

7 bedrooms / 7 bathrooms / sleeps 16

“One of the best vacations I've taken.” There were a total of 16 people staying in the main house and the cottage. We were there celebrating a friends 50th birthday. The houses were wonderful!! They were clean andthe amenities were great!! The kitc

Price per night from

$1,590

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Bed, Breakfast & Beyond Sailing in Key West

Key West yacht

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$695

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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 amenit

Price per night from

$900

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First Breath

Key West house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$107

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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 w

Responds fast! avg. 3 hours 31 minutes

Price per night from

$277

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