Key West House Rentals

(18 rentals)
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Julia's Secret. Julia's Secret in Old Town Key West

$239

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

This beautiful house is a two bedroom, two bathroom located in the best area in Key West! Just steps from the world class shops and restaurants of world famous Duval Street. There are so many great attractions nearby like the Hemingway House, Light House Museum, Southernmost Point. The bedrooms each have ...

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Property Type

Key West House

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Hidden Cottage

3 BR | 3 BA | Sleeps 6 | Quick View

1

$466

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

Down a very quite lane the house has one off street parking spot.Enter from gate through lush and colorful walk to front door of main house . Enter into the living room with smart tv ,through to the right into the dinning area. The kitchen is off to the left. There is a large working counter with seating ...

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Property Type

Key West House

"Perfect pet-friendly vacation cottage"
Reviewed March 2, 2021

The house is tucked away on a lane in Old Town within walking distance to everywhere. It is very private with lush plantings and a variety of outdoor spaces to sit. The house is well equipped and the owners ...

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Bougainvillea Villa Key West MONTHLY RENTALS ONLY

3 BR | 2 BA | Sleeps 6 | Quick View

1

Distance to beach: 4 miles to Smathers

$494

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pets allowed
  • Private pool
  • Rentals by owner

About this property

COVID-19 UPDATE: Key West restaurants and bars are open. Masks are required at all times unless you are seated at a table in a bar or restaurant.MONTHLY RENTALS ONLY We purchased Bougainvillea Villa as our future retirement home. Since we are unable to visit as often as we’d like, we are ...

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Property Type

Key West House

"Beautiful Bougainvillea Villa"
Reviewed February 27, 2018

Nothing is missing from this very clean and very well organized beautiful home situated on a wide lagoon. For us, the highlight is the superb view of the wide lagoon from the window wall across the entire ...

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Private beach estate,gated,dock,and pool

$911

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Oceanfront
  • Private pool
  • Rentals by owner

About this property

2 rental homes within 5 private gated acres of scenic beauty in the heart of the Florida Keys and 15 minutes to Key West. Located within the keys wildlife preserve, Sea View Estate is just a 15 minute drive to the shopping and nightlife of Key West and just minutes to some of the finest restaurants ...

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Property Type

Key West House

"Wonderful property wonderful hosts!"
Reviewed March 15, 2021

I just got back from taking my family and a friend's family to Troy and Carol's property for a week. The houses were just as described, the location was just what we wanted, quiet and peaceful and away ...

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Private beach estate.Dock and pool

$515

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Private pool
  • Rentals by owner

About this property

The Sand dollar is a 3 bedroom, 2 bath home built within feet of the Atlantic Ocean with 180 degree ocean views.The property is a 5 acre gated private estate located within the Florida Keys National Wildlife Refuge.Fishing and diving just steps outside your door. Then at night, Key West is just ...

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Property Type

Key West House

"Loved it!!!!"
Reviewed April 21, 2021

We thought the accommodations were great, there were some minor things that could have helped but overall we give a glowing review. The pool and outdoor tiki bar were amazing and the owners were wonderful. ...

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Cockadoodledo Vacation Rental. Featured On Hgtv***multiple Month Discount***updated

$457

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Cock-a-doodle-do Vacation Rental, named for Key West's beloved chicken population, is a mid-town oasis! 5 minute drive to Old Town or take Uber for just $10!A meticulously updated pool home with beautifully lush landscaped grounds and plenty of space for everyone! The main house is a 3/3 (1 King, ...

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Property Type

Key West House

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Private beach estate. Gated, tropical peace and quiet. Dock

$459

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Rentals by owner

About this property

The Sea View Cottage is a 2 bedroom, 1 bath home built within feet of the Atlantic Ocean with 180 degree ocean views.The property is a 5 acre gated private estate located within the Florida Keys National Wildlife Refuge.Fishing and diving just steps outside your door. Then at night, Key West is ...

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Property Type

Key West House

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Key West Old Town Sanctuary- Huge Private Pool- Quiet Lane- Monthly Rental

$293

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

Looking to ​ Relax Renew Recharge? We got you. Your own Key West Sanctuary awaits! Escape to a classic Conch family home perfectly tucked away for privacy yet, only 5 Blocks from famous Duval Street. The best of both worlds! Morning yoga class on the deck, late night dip in the pool, and sunset ...

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Property Type

Key West House

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Tropical Seclusion On Old Town Lane With Pool And Detached Bungalow.

$335

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

2/2 Main House, 1/1 Bunglow, Large Pool And Hot Tub On Beautiful Old Town LaneHidden at the end of one of the most beautiful lanes in Old Town, Casa Escondida awaits you with its tropical seclusion and quiet serenity. Nestled amongst mature tropical landscaping, the main 2/2 house features an indoor/outdoor ...

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Property Type

Key West House

"Perfect place!"
Reviewed August 21, 2021

This house is in the perfect location that is quiet and private. It’s literally in the center of old town and just a short walk to everything. It is very comfortable and has a great layout. The cabana ...

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Joe's Place. A+ Location in Old Town Key West

$264

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

This beautiful house is a two bedroom, two bath with a pullout sofa. The house has beautiful vaulted high ceilings. Along with the en-suite there is also another bathroom on the 1st floor and an outdoor shower. The kitchen and living room area is open. Very well air conditioned for those hot days. A nice ...

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Property Type

Key West House

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Brass Palm Villa -Private Luxury Key West Home with Heated Pool

3 BR | 2.5 BA | Sleeps 6 | Quick View

2

Distance to beach: 0.5 miles to Higg's Beach

$326

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pets allowed
  • Private pool
  • Rentals by owner

About this property

Private Luxury Key West Home with Private Pool, surrounded by lush tropical landscaping in the Casa Marina neighborhood of Old Town.The fusion of a mid-century Florida home with dramatic Caribbean design, has created an ideal contemporary “Floribbean” style villa in the Casa Marina district ...

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Property Type

Key West House

"Great home to enjoy Key West!"
Reviewed February 20, 2020

Four of us , and our dog, stayed at Lynda’s beautiful home in Casa Marina area. We had a wonderful month there. The location was great and quiet. We spent most of our time enjoying the covered deck ...

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A Thousand Hidden Hemingways

4 BR | 3 BA | Sleeps 10 | Quick View

1

$623

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pets allowed
  • Private pool
  • Rentals by owner

About this property

The home (also known as Margaux's Hideaway) was built in 1890's, with a farmhouse charm, and porches off of every bedroom. It is light and airy, with gorgeous and comfortable indoor and outdoor living spaces. It's perfect for family gatherings, or just a quiet escape. Each room is sunny and bright, ...

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Property Type

Key West House

"Perfection in every way"
Reviewed May 4, 2021

This home is beautifully appointed, spacious, quiet, comfortable and perfectly located. The pool is a haven on hot afternoons, the upper deck is amazing on warm nights for stargazing and the kitchen has ...

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

$150

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Private home located in New Town available for 4 week minimum rental. Beautifully landscaped yard with secure private back yard and pool. Use of bicycles and four passenger electric car provide flexible transportation all over the island. The home features a modern kitchen with all appliances and granite ...

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Property Type

Key West House

"Best Vacation Yet!"
Reviewed July 6, 2021

We had the pleasure of having stayed at this beautiful Key West home this past month of June 2021. We can not say enough about how wonderful our stay was. Between the location, cleanliness, amenities and ...

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Olivia House-Downtown Historic District

$256

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pets allowed

About this property

This home has been beautifully upgraded with attention to detail. In it's day it was a well known flower shop to the locals. This historic home living room is wider than most "conch homes" with traditional wood floors and vaulted ceilings. The kitchen is a cooks dream with nicely stocked cookware, ...

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Property Type

Key West House

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Dos Casas - A 2 House Compound in Old Town -- A Monthly Rental

$331

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pets allowed
  • Private pool
  • Rentals by owner

About this property

Dos Casas can be the answer to your fabulous Old Town Key West vacation. We've been renting to discriminating travelers for over 15 years. Our guests come back over and over, finding the comfortable spaces, stocked with amenities and ideal location the perfect spot to enjoy all that Key West has to offer.Why ...

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Property Type

Key West House

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"Southard Comfort"

2 BR | 2 BA | Sleeps 6 | Quick View

5

Distance to beach: 1 miles to Fort Zachery Taylor State Park

$289

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pets allowed
  • Private pool
  • Rentals by owner

About this property

924 Southard Street... an Old Town cottage made famous by Country Home magazine! Featured in Country Home , in June 2001, this one-of-a-kind cottage was formerly owned and decorated by well known decorator Mary Emmerling. Southard Comfort is perfect for the guest who wants to feel like a local and enjoy ...

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Property Type

Key West House

"I wish I didn't write this review."
Reviewed February 25, 2021

Mainly because it will lessen our chances to get back here. My wife and I used to live in Key West for close to 10 years. We had our house and a couple of rental properties and vacation properties. Then ...

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Bay Pointe

3 BR | 3 BA | Sleeps 6 | Quick View

1

$164

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pets allowed
  • Private pool

About this property

Tropical seclusion and privacy at its very best. Located just 15 miles from Key West. This luxury rental consists of 2 full suites. The first floor has a roomy living room, huge screen porch, queen sleeper sofa, bath and bedroom connected by an exterior staircase to the second floor. The second floor ...

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Property Type

Key West House

"Soon to be there"
Reviewed January 3, 2021

I have not stayed there yet, but will gladly take $5 for this review. I hope is as nice as it its described

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Historical Tropical Hideaway -September Discount

4 BR | 2.5 BA | Sleeps 8 | Quick View

Distance to beach: 600 yards to Simonton Street Beach

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

Take 30% off for any 30day period between September 1 - October 10, 2021. Enjoy an unforgettable stay at a one-of-a-kind ship-builder's home in the heart of Old Town Key West. You will be on a quiet lane in the most desirable neighborhood, just a few short blocks from dining, boating, fishing, galleries, ...

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Property Type

Key West House

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