Old Town (Key West, Florida) Vacation Rentals

(15 rentals)
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Iguana Suite, Townhouse 1/2 block from Duval**

Key Amenities

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

About this property

**Available for rent by the month. Although you rent it for a month, you may of course come late and/or leave early. The monthly price will generally be the same as for a comparable unit rented by the day for 10-14 days. It does however give you a lot more options and freedom.Located on a side ...

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Property Type

Key West Townhome

"Beautiful Stay!"
Reviewed September 6, 2020

This unit is in a tucked away little oasis one street over from all the action on Duval street. If is a very peaceful and unique spot. The unit itself is exceptionally clean and well appointed. It has ...

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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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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.

$333

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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Superb Location, Affordably Priced - The TwoSim Suite

Studio | 1 BA | Sleeps 2 | Quick View

1

Distance to beach: 0.5 miles to South Beach

$239

avg/night

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Key Amenities

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

About this property

This Studio is a lovely charmer nestled in a 6 unit compound in a residential neighborhood in the center of Old Town Key West. * Pet Friendly for flat fee of $90 * King size bed * WiFi included * check-out cleaning included * 2 wall AC units * flat screen TV * Shared gas grill * porch with ...

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Property Type

Key West Condo

"Perfect Place to Stay"
Reviewed September 9, 2020

This was our 3rd time staying in Pam's wonderful little cottage. My husband and I really love this place. Pam is awesome to work with, she always answers all my questions quickly. It was great being close ...

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The 6 bedroom Duval Street Compound

6 BR | 7 BA | Sleeps 16 | Quick View

2

Distance to beach: 0.3 miles to Ft Zachary Taylor

$1762

avg/night

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Key Amenities

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

About this property

Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theaters and shops, this sprawling six bedroom, seven bath compound has two private heated swimming pools, endless porches, terraces and a huge, fabulous decks that overlooks the action on ...

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Property Type

Key West Villa

"Best place we have ever stayed!"
Reviewed August 1, 2020

What an amazing 6 bedroom property in the heart of Old Town Key West. We did not move the car once, We would not rent one next time as you can walk to everything. It is all so close. The pools were simply ...

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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

$288

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

$330

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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A Thousand Hidden Hemingways

4 BR | 3 BA | Sleeps 10 | Quick View

1

$621

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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Olivia House-Downtown Historic District

$255

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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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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A Touch Of Cuba In Key West

2 BR | 1 BA | Sleeps 4 | Quick View

1

Distance to beach: 0.5 miles to Ft. Zachary Taylor State Park

$327

avg/night

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Key Amenities

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

About this property

Welcome to Key West and the Shipyard section of the Truman Annex. You have many choices of accommodations and since I am not a real estate salesman or property manager, allow me let the photos and description speak for themselves. My over sized two bedroom, one bathroom condominium end unit (cross ventilation) ...

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Property Type

Key West Condo

"A touch is all you need…"
Reviewed September 10, 2021

A touch of Cuba was the perfect little spot. We are now spoiled to the conveniences of renting direct with the owner, having Class A rated efficiencies, Beach, Bikes, Pool, very quiet and well kept area ...

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Ocean View condo steps to Smathers Beach

$276

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

The Jungle Breeze condo at LaBrisa Condominiums is a 1 bedroom, 1 bath apartment * King size bed in the bedroom *accommodates 2 adults only * WiFi inlcuded * Parking included *Central AIr Conditioning * Check-out cleaning included * This is not a hotel; it is a privately owned condo facing the ...

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Property Type

Key West Condo

"AMAZING"
Reviewed January 30, 2019

There truly aren't enough adjectives to describe the level of service Pam provided. At the very beginning, she answered all my questions, in less than an hour. Her customer service was amazing. She provided ...

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Simonton Studio, an Old Town get-away for 2

Studio | 1 BA | Sleeps 2 | Quick View

4

Distance to beach: 0.5 miles to South Beach

$239

avg/night

View Details

Key Amenities

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

About this property

This Simonton Studio is neat, sweet and complete. * Pet friendly for additional flat fee of $90 * WiFi included * King size bed * Check-out cleaning included * Outdoor table and two chairs * spacious shower * excellent loctaion for walking Old Town * Duval Loop bus passes this adress for free ...

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Property Type

Key West Condo

"A perfect stay"
Reviewed September 7, 2021

This little piece of paradise was everything we expected and then some. Perfect for the two of us during our week long stay. Within walking distance to Duval and a beautiful church where mass is offered ...

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Duval Balcony Rentals - Suite Mischief

1 BR | 1 BA | Sleeps 4 | Quick View

1

Distance to beach: 1 miles to Fort Zachary Taylor, Higgs Beach, Smathers Beach

Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

About this property

Located in the heart of Key West, this unique property offers a central location to the Key West landmarks and sights. Enjoy all Key West has to offer from a historic building with a private balcony overlooking Duval St. For Fantasy Fest, this property offers an ideal location from where you can enjoy ...

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Property Type

Key West Apartment

"Amazing!"
Reviewed November 17, 2020

Incredible property and awesome staff! Great location and amenities. Would highly recommend and will be back!

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Old Town (Key West, Florida) Vacation Rentals


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