Vacation Rentals & House Rentals in Key West

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55 house rentals

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 boat depending on the wind and sun. The only point what could be better is the quality of the bedding (sheets, blankets, towels...) For this price you expect some better quality. Anyway, when we wil go back to the us I certainly will search for something similar to stay on

Match: Private outdoor pool (unheated)

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Price per night from

$258

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

$246

President's Walk

Key West house

2 bedrooms / 1 bathroom / sleeps 4

Match: Private outdoor pool (unheated)

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Price per night from

$195

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

$750

Sunshine Key West

Key West house

2 bedrooms / 3 bathrooms / sleeps 5

“Perfect Home for Key West” This place has all the amenities you need! It was our first time renting a home and it couldn't have been more perfect! Quiet neighborhood, but not too far from the action of Duval.

Match: Private outdoor pool (unheated)

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Price per night from

$107

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

First Breath

Key West house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Private outdoor pool (unheated)

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Price per night from

$107

Verandah

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

“We had a delightful stay, enjoyed meeting warm and welcoming peo” This was our second year at verandah and once again it was just perfect. Can't wait to return in 2014. Key west is definitely our happy place.

Match: Private outdoor pool (unheated)

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Price per night from

$100

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

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

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

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

House, 2 Bedrooms + Convertible bed(s), 2 Baths, (Sleeps 6)

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 11 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$716

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

$335

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

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

$167

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

$365

Poolside Paradise

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

Match: Private outdoor pool (unheated)

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Price per night from

$100

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

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

$117

A Castle on An Island Your Santuary Retreat Key West Sleeps 24

Key West house

8 bedrooms / 8 bathrooms / sleeps 24

Responds fast! avg. 2 hours 33 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$1,499

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

$316

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

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

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

$2,004

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

$900

Great rentals within 20 miles that match your search

Seafarer's Refuge

Stock Island house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 51 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$1,033

Captain's Daughter

Stock Island house

5 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 51 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$1,260

Bayview Retreat

Stock Island townhouse

4 bedrooms / 5 bathrooms / sleeps 10

Responds fast! avg. 51 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$1,033

Island Chic

Stock Island townhouse

3 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 51 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$776

Vibrant home w/hot tub & private pool blocks from the beach - dog-friendly!

Stock Island house

2 bedrooms / 3 bathrooms / sleeps 4

Responds fast! avg. 3 hours 39 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$327

Eisenhower Retreat

Stock Island house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 51 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$1,034

Lovely, dog-friendly townhouse w/ private pool, full kitchen & beach access

Stock Island house

2 bedrooms / 3 bathrooms / sleeps 6

“Fabulous” We stayed at Island Oasis for Labor Day weekend 2008. The location is perfect! The house was EXTREMELY clean & well kept, furnishings & decor modern, the private pool is perfect, the rental agency was fabulous (helpful & friendly). We would definitely stay here again & recommend it for a Key West visit.

Responds fast! avg. 3 hours 39 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$460

Dog-friendly, colorful cottages w/ pool & hot tub in a fabulous location!

Stock Island house

5 bedrooms / 4 bathrooms / sleeps 14

“Love Key West” We had a group of 10 people and we stayed at almost Southernmost Retreat. The property consisted of 2 homes that were connected with a pool and hot tub. The property was fantastic. Great location and the property was well kept and very clean. In addition, the property management personnel were great. I highly recommend this property; however, if this property is too large for your needs, I would recommend using the property management company which was Key West Vacation Rentals.

Responds fast! avg. 3 hours 39 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$711

Enchanting seaside cottage w/private pool & prime location

Stock Island house

1 bedroom / 2 bathrooms / sleeps 4

“Luxurious tropical relaxing vacation.” Fishtail Hideaway is located in a quiet neighborhood only 2 blocks from Duval St. We loved being able to walk to the beach, the Southernmost Point, plenty of shopping and the best restaurants in town. The house itself was very comfortable, clean with lots of colorful decor. This house had everything you could ask for on a vacation. A pool, full size washer/dryer, Viking and Sib zero appliances and a very comfortable king sized bed. Kw vacation rentals gave us excellent service from when we checked in, if we needed anything during our stay and when we checked out. We will definitely be back.

Responds fast! avg. 3 hours 39 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$134

Six dog-friendly homes in a quiet neighborhood w/ private pool & hot tub

Stock Island house

12 bedrooms / 9 bathrooms / sleeps 36

Responds fast! avg. 3 hours 39 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$1,594

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