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Vacation Rentals & House Rentals in Key West

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23 house rentals

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.

Match: Private outdoor pool (unheated)

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Price per night from

$271

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!

Match: Private outdoor pool (unheated)

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Price per night from

$700

First Breath

Key West house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Private outdoor pool (unheated)

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Price per night from

$100

Lighthouse Villa

Key West house

3 bedrooms / 4 bathrooms / sleeps 8

Match: Private outdoor pool (unheated)

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Price per night from

$193

Coconut Cottage

Key West house

1 bedroom / 2 bathrooms / sleeps 2

Match: Private outdoor pool (unheated)

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Price per night from

$77

tropical Casita

Key West house

1 bedroom / 2 bathrooms / sleeps 2

Match: Private outdoor pool (unheated)

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Price per night from

$107

Key Lime Pie

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

“Loved Off Season Key West” Spent a month in this very secluded house within walking distance of everything, including the marina, Duval Street and my favorite Watering Hole, Finnegan's Irish Wake pub. Renting in October, the off season, meant I got to experience an uncrowded Key West. And best of all, at the end of the month, to experience Fantasy Fest in its entirety. What a rush. House was wonderful. Had it all including a hot tub. Private parking, a real plus in Key West. Plan to do it again.

Match: Private outdoor pool (unheated)

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Price per night from

$87

Conch Republic Retreat

Key West cottage

2 bedrooms / 2 bathrooms / sleeps 4

Match: Private outdoor pool (unheated)

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Price per night from

$107

Perfect Pineapple

Key West house

2 bedrooms / 1 bathroom / sleeps 4

“Kudos to Owner” The owners updated many things such as new bathroom tile, area rugs, washer and dryer area as well as painting. Still needed are more dinner and salad plates as it is necessary to run the dishwasher almost every day. The timer system for the garden lights needs to be repaired. Guests came to visit and it was very crowded with 4 people even with two bedrooms. This is a perfect place for a couple. The big negative is the Iguana's who wander from the cemetery area . A 3 1/2 foot Iguana can scare the heck out of you.

Match: Private outdoor pool (unheated)

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Price per night from

$100

Amelia Home

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

“Perfect” We loved this house! It was the perfect little getaway. It was in a great location, very convenient to everything. The house was beautiful with very nice decorating inside to the beautiful lush garden outside. If we visit Key West again, I’d stay here without hesitation. I highly recommend!.

Match: Private outdoor pool (unheated)

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Price per night from

$325

Flagler Station

Key West house

3 bedrooms / 2 bathrooms / sleeps 6

“Little gem is right!” Can't say enough good about this place! Newly renovated 1800 square foot home;3 be king in master, queen and double Beds in third room. Loved the small private pool and gourmet kitchen, much thought, love and detail went into making this a home away from home. 5 blocks from the public beach and a couple of miles from duval street. So close to so much but still have some privacy and parking.. Would love to bring bikes next time. Y'all save a place for me next summer we hope to come back! And the home away folks get an A plus for the process of renting, it was so easy...

Match: Private outdoor pool (unheated)

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Price per night from

$107

Rosalie's House

Key West house

3 bedrooms / 2 bathrooms / sleeps 8

Match: Private outdoor pool (unheated)

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Price per night from

$100

Tropical Dreaming

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

“Oasis in busy Key West” We have stayed at Tropical Dreaming several years in a row. It is a lovely setting a couple of blocks off Duval so it is its own oasis.

Match: Private outdoor pool (unheated)

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Price per night from

$325

Easy Livin'

Key West house

3 bedrooms / 4 bathrooms / sleeps 8

“Great Experience” This house was beautiful. The pictures don't do it justice. It's the perfect house for families. The location couldn't be better - walking distance to everything.

Match: Private outdoor pool (unheated)

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Price per night from

$550

The Dolphin House

Key West house

4 bedrooms / 3 bathrooms / sleeps 8

“Perfect” Perfect house. Perfect pool. Perfect location. I want to live there. Secluded but so close to everything!

Match: Private outdoor pool (unheated)

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Price per night from

$550

Papa's Cottage Retreat

Key West cottage

1 bedroom / 1 bathroom / sleeps 2

Match: Private outdoor pool (unheated)

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Price per night from

$100

A Castle on An Island Your Santuary Retreat Key West Sleeps up to 20

Key West house

8 bedrooms / 8 bathrooms / sleeps 20

Responds fast! avg. 2 hours 45 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$1,899

Here Tomorrow

Key West house

3 bedrooms / 2 bathrooms / sleeps 6

“Exceeded our expectations” We loved this house! Super location - just one block off Duval - and also near to the beach; we went to the Southernmost beach a lot. We thought that the house is bigger then it looks in the photographs. We were expecting a small little conch cottage whereas we got a nice size 3 storey house. The bedrooms in particular were very roomy and of course the main bathroom with the jacuzzi bath, the doublesize waterfall shower (with sit down area) and double vanity area was fabulous. It had all the expected amenities and we made particular good use of the ice machine for cocktails by the pool :-) Decor is modern. Very nice bed linen and lots of towels were provided. The pool area was a little small (but no smaller then we expected from the photographs). Was not great for sunbathing as the sun only hits in one spot but as I mentioned earlier we went to the beach a lot. All in all a great house. Also must mention the good service from At Home in Key West when booking. I found the Live Chat service really useful. We had no need to contact them during our stay (no issues with house etc) so cannot comment on service during our stay. Eating: We ate at out the majority of the time and aside from the fish we caught (we went fishing with Captain John's Greyhound V) we never cooked at home. Our favourite place is A&B lobster house/Alonzos, Santiagos Bodega and Firefly. Shopping: Coach and Banana Republic on Duval are probably the only two good stores - only you are looking for tee-shirts!!!! Red Gallery near Flagler Station museum is good for quirky gifts. Recommendations things to do: Custom House Museum Lighthouse tour Little White House Hemingway House Fishing with Captain John's Greyhound V is always good

Match: Private outdoor pool (unheated)

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Price per night from

$133

Luxury Condominium in Old Town | Monthly Rental at Steamplant Key West

Key West condo

3 bedrooms / 4 bathrooms / sleeps 8

Match: Private outdoor pool (unheated)

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Price per night from

$318

Under The Palms

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

Match: Private outdoor pool (unheated)

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Price per night from

$117

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

Key West villa

6 bedrooms / 7 bathrooms / sleeps 16

Match: Private outdoor pool (unheated)

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Price per night from

$2,024

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: Private outdoor pool (unheated)

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Price per night from

$1,320

Great rentals within 20 miles that match your search

Margaretaville - Live Like A Key West Local, Dog Friendly Old Town Home With Pri

Stock Island house

2 bedrooms / 2 bathrooms / sleeps 5

Match: Private outdoor pool (unheated)

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Price per night from

$232

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