Key West Rentals by Owner

(26 rentals)
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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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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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A Touch of Bermuda at Truman Annex

2 BR | 2 BA | Sleeps 6 | Quick View

2

Distance to beach: 800 yards to Ft. Zachary Taylor State Park

$353

avg/night

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Key Amenities

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

About this property

Envision yourself relaxing in a beautiful wood framed conch cottage with overhead fans lazily turning below the sloping tin roof in the heart of Old Town in Key West. This is the best value in Key West as it is no cookie cutter small rental condo but a private town home (one of only seven available for ...

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Property Type

Key West Cottage

"Island Magic"
Reviewed March 25, 2021

Great location! Great people! Very nice place that gave us memories of a lifetime! I’ll be returning soon!

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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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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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2 Bedroom Townhouse Key West 10% off Available Dates Spring/Summer 2021

2 BR | 1.5 BA | Sleeps 4 | Quick View

2

Distance to beach: 2 miles to Smathers Beach

$226

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Come stay in a premier development in Key West. This would be a great location to stay with a monthly 29 day rental minimum. Yearly rates available. You would be close to everything Key West has to offer and the peaceful serenity of your temporary home in Paradise. Our house offers many amenities to ...

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Property Type

Key West Townhome

"Three months in Paradise"
Reviewed April 1, 2021

The townhouse and grounds are exactly as pictured and described! Staying on Stock Island was a great experience. Close enough to beaches and downtown Key West and the island itself offers a number of terrific ...

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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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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

$1758

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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Truman Annex, Lrg In/Outdoors Beautiful 1st Flr, 2BR KING/twins, Pool

2 BR | 1 BA | Sleeps 5 | Quick View

1

Distance to beach: 0.2 miles to Fort Zachary Beach

$351

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

TRUMAN ANNEX: SHABBY CHICKEN - come stay with the large & proud bird in town!! She's not too shabby after all. Large front yard and porch to watch Key West pass by. Beautiful and spacious in/out doors.58 5-STAR REVIEWS!!! (on our primary site on VRBO #595903)Our fantastic cleaner has been ...

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Property Type

Key West Condo

"Perfect condo for our needs"
Reviewed March 16, 2021

Location was perfect as it is closer to the entrance of Truman Annex and in turn only steps away from Duval, Mallory Square and Truman Waterfront park. Owner's were very friendly, extremely responsive ...

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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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YKNOT CHARTERS, ON AND OFF DOCK CHARTERS

$171

avg/night

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Key Amenities

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

About this property

The Space Y Knot is a 44 foot trawler yacht with 2 staterooms, a full head with walk in shower, a complete galley complimented by 2 refrigerators, freezer, stove/oven and microwave. Dining booth sits 6 adults. The v-berth stateroom has 3 double berths and 1 single birth. The small stateroom has 2 single ...

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Property Type

Key West Yacht

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Historic Studio on the Waterfront at the Red Doors

$137

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

About this property

Overlooking the Historic Key West Bight, this bright and clean studio features a fully equipped kitchen, renovated bathroom, front loading washer/dryer, 4K smart TV, and one of the best people watching front porches in Key West. Steps from the water, just 3 blocks from Duval street, and surrounded by ...

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Property Type

Key West Studio

"Key West Gem"
Reviewed April 10, 2019

We stayed at this property for 6 weeks. The location is awesome! It is steps away from the marina, a short walk to a small beach, and just several blocks from Duval Street. The location is also set in close ...

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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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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

View Details

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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Geiger Key Waterfront

2 BR | 2 BA | Sleeps 7 | Quick View

1

$133

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

About this property

Located just 10 miles from Key West on beautiful Geiger Key. Cozy and comfortable canal front getaway perfect for the fisherman eager to explore the crystal blue waters of the Keys or the person wanting to experience all that Key West has to offer. Deep water with quick direct access to Atlantic Ocean. ...

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Property Type

Key West Mobile Home

"Awesome Key West Getaway-We'll be back!"
Reviewed October 7, 2021

This location is amazing just minutes to downtown Key West and a few minute idle by Boat to the Ocean(we brought our own boat and docked out back!) Had fun Snorkeling in crystal clear water, and even tried ...

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Key West Beach Front Rental Beach Studios Ocean views

Studio | 1 BA | Sleeps 3 | Quick View

5

Distance to beach: 22 yards to Public use + Private views Waldorf Astoria Resort

$510

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Oceanfront
  • Rentals by owner

About this property

This is Key West Beach Front Rental Welcome to; Ocean view STUDIO See rates first**** save yourself some valuable ***time This is NOT A BUDGET STAY! This is truly a romantic Ocean View stay for two adults. Opposite of most Ocean View destination experiences of huge buildings, long ...

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Property Type

Key West Studio

"Amazing place to stay- spectacular view"
Reviewed June 8, 2021

This was our second time staying at here and we love it! The views and sound of the ocean are amazing! Place is clean and cozy. Host Holly is fantastic! We will definitely be returning again next year. ...

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Ocean View condo steps to Smathers Beach

$276

avg/night

View Details

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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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

View Details

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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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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