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Vacation Rentals & House Rentals in Key West

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56 house rentals

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!

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Price per night from

$696

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 47 minutes

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Price per night from

$1,998

First Breath

Key West house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$100

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

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Price per night from

$1,724

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

$325

Lighthouse Villa

Key West house

3 bedrooms / 4 bathrooms / sleeps 8

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Price per night from

$192

** Fantastic Spring& Summer Stay Downtown walk everywhere **

Key West apartment

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$287

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Key West apartment

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$395

** Totally Renovated Ocean View Condo Great Prices **

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$544

tropical Casita

Key West house

1 bedroom / 2 bathrooms / sleeps 2

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Price per night from

$107

Key West Oasis - Private Pool, Separate Cottage - Great for Couples & Families

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

“Fabulous luxury home in Fabulous Key West” Beautiful, private, historic 2 BR/2 bath home, lovely heated pool, outdoor dining & living areas in addition to most attractive indoor spaces. Wonderful Old Town neighborhood. Can walk, cycle, & Lyft everywhere (including great restaurants)--no car needed. 2nd BR is in the guest house beyond the pool--fabulous outdoor shower completes the "only-in-Key West" ambiance. The owner, Kim, is super responsive.

Responds fast! avg. 1 hour 38 minutes

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Price per night from

$640

Conch Republic Retreat

Key West cottage

2 bedrooms / 2 bathrooms / sleeps 4

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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.

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$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!.

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Price per night from

$324

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...

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Price per night from

$107

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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.

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Price per night from

$687

** New Ownerss many upgrades, Tropical retreat on the ocean**

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$413

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.

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Price per night from

$324

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.

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Price per night from

$547

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!

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Price per night from

$547

* Book today Anchor drop key west short bike ride from old Town*

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$526

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Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$413

* Amazing Ocean Front 3 Bedroom Open Winter of 2022 *

Key West apartment

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$344

Old Town Treasure, Historic Seaport, Conch House 3 Bedrooms 3.5 Baths, Pool

Key West house

3 bedrooms / 4 bathrooms / sleeps 6

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Price per night from

$469

** Totally renovated in 2019, New Kitchen & Bathrooms.. Book Now **

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$504

*Atlantic Docks Fantastic Ocean View Condo- Short bike ride to Old Town*

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$210

* Winter in Paradise Available Jan 1st - April 1st 2021 - Discounts *

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$172

Olivia Place

Key West house

4 bedrooms / 4 bathrooms / sleeps 8

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Price per night from

$343

Old Town, 5 Bdrm Home with Private Pool in Gated Backyard

Key West house

5 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 1 hour 18 minutes

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Price per night from

$361

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Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$172

Great Rates starting May 2021

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$192

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Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$487

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

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Price per night from

$133

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Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$516

* Morning Reflections open April 5th onwards Great Monthly Discounts*

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$161

Single Family Home, 3 Bedroom, 2 Bath, Pool and Electric Car, Great Value!

Key West house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$144

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Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$181

* Key West Beach Condo Casa Coastal East Open Nov-Feb2021 *

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$146

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