Key West Florida Vacation Rentals, Hotels & Resorts

Key West Condo - 3.5 Star Review

Summary:
The Martinique Suite is set in the beautifully landscaped Sunrise Suites community, just 10 minutes away from all of the must-see Key West Attractions. Get some rest tanning by the pool or relax your muscles in the hot tub after a bike ride on some of the biking trails, or get your heart racing on the tennis court and in the gym! With a.......read more

2 Bedroom(s)
Sleeps 6
Condo

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Key West Private vacation home - 5.0 Star Review

OLD TOWN PARADISE....
Paradise awaits in a quiet Old Town location.  This four bedroom home is set on a cozy lane that is off the beaten path but close enough to walk or ride your bicycle to restaurants, museums or galleries.  Newly renovated and designer decorated to bring you a home with island details and a luxurious flare. 

DETAILS & .......read more

4 Bedroom(s)
Sleeps 8
Private vacation home

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Key West Apartment - 5.0 Star Review

WELCOME TO CASITA IN THE CLOUD!


Your search for the perfect island getaway has ended!

This large 3 story, two bedrooms, two bath apartment boasts all the amenities you’d expect from your island home. Upon entry, you’ll be greeted by a loving foyer with a set of stairs leading you to the surprisingly spacious living room, kitche.......read more

2 Bedroom(s)
Apartment

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Key West Cottage - 5.0 Star Review

WELCOME TO TRANQUILITY!



Tranquility is an adorable 3 bedroom, 3 bath pool home in a tropical setting. French doors open from the fully equipped kitchen to the spacious deck and private pool. Palm trees and tropical landscaping line the back yard for added privacy. The living room flows into the fully equipped kitchen and eat in dini.......read more

3 Bedroom(s)
Cottage

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Key West Private vacation home - 5.0 Star Review

** 20% Discounts Available for October, November, and December 2022 ** A great opportunity to stay in one of the best homes in the Key West Golf Club!!!

Monthly rentals available. Key West has strict rules for rental properties and, as such, most newer homes must be rented for 28 days or more. (I would consider longer stays as well, conta.......read more

2 Bedroom(s)
Private vacation home

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Key West Condo - 4.9 Star Review

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!

SET SAIL celebrates the experiences of the Keys, both on the water and on land. The ideal complementary home base for your water-based excursions awaits in this condo just steps from the marina. SET SAIL is a well-appointed first floor .......read more

2 Bedroom(s)
Sleeps 6
Condo

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Key West Condo - 4.5 Star Review

$25,00 Renovation completed end of 2016/beginning of 2017!! Different than ANY other Efficiency at the Galleon!! You will not be disappointed!

Location..Location...Location...this one has it all! Resort is located on the Ocean and is within steps of famous Duval Street. The Galleon Resort offers many amenities to enhance your vacation need.......read more

Studio
Sleeps 2
Condo

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Key West Private vacation home

Welcome to this Key West Tropical charmer located only 15 minutes away from Downtown Duval Street. This townhome is located in a gated community called the Key West Golf Club.
This pleasant, bright and spacious townhome comes with a large backyard space for entertaining or just lounging around and is located on a quiet cul de sac. This townhome .......read more

3 Bedroom(s)
Sleeps 6
Private vacation home

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Key West Private vacation home

Enjoy a stylish experience at this centrally-located apartment. Just a short walk from some of Key West best restaurants and shopping. This 1 bedroom, 1 bath has been beautifully furnished, features stainless steel appliances, private washer and dryer in unit, private porch with a view of a lush courtyard........read more

Studio
Sleeps 2
Private vacation home

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Key West Apartment - 4.1 Star Review

Summary:
Looking for a small studio? Matisse Manor is the perfect fit for a party of 2! It is located steps away from Key West\'s most popular attractions including the Ernest Hemingway Home and Museum, Mallory Square, and Fort Zachary Taylor Beach and Park.
When you’re not out and exploring the island, the Galleria 14-unit apartment comple.......read more

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Key West Condo - 4.7 Star Review

PROFESSIONAL CLEANING PER CDC GUIDELINES BEFORE & AFTER EACH STAY
You feel the excitement the moment you arrive. The warm tropical breezes, the blue green water. It\'s a rhythm. A rhythm set into motion over a century ago by pirates, artists, writers and other champions of leisure. Today that same rhythm beckons you to discover the charm and gra.......read more

2 Bedroom(s)
Sleeps 6
Condo

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Key West Apartment - 4.1 Star Review

Summary:
Andy\'s Inn is the perfect little studio for two! Location is key to discovering all things “Key West” - Just 2.5 blocks from Duval Street, Andy’s Inn is just steps away from Key West\'s most popular attractions. This is the perfect spot if you want to be out on the town and all you need for a cozy place to sleep!

This 14-unit ap.......read more

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Key West Condo - 4.9 Star Review

Enjoy the New and Completely Renovated bathrooms to this tropical residence. This is quiet, peaceful living on the Atlantic Ocean. The spectacular view can be seen immediately upon entering the condo. The floor to ceiling glass walls provide a full sea panorama from the living room, dining room, kitchen and master bedroom. The 31 foot oceanfront ba.......read more

2 Bedroom(s)
Sleeps 4
Condo

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Key West Private vacation home

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!

It is not so often that something new is built in Old Town, the historic district of Key West known for quintessential conch homes and walkable streets. But recently a spectacular development called Old Town Villas was constructed smack .......read more

3 Bedroom(s)
Sleeps 8
Private vacation home

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Key West Condo - 4.5 Star Review

Summary:
Sea Breeze is the perfect location for your tropical getaway! This two bedroom is located in the heart of Old Town Key West, just steps away from the world famous Duval Street\'s shops, bars and restaurants! With off-street parking and 1-block from Duval, this property has everything you need and more!

The Space:
This quaint t.......read more

2 Bedroom(s)
Sleeps 6
Condo

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Key West Private vacation home - 4.7 Star Review

Newly renovated town home located on a charming lane in the Truman Annex. The generous open floor plan features 10 foot ceilings both on the first and second levels with hardwood floors and crown molding. Enjoy the theater style kitchen with new quartz counter tops and stainless-steel appliances with a gas cook top. The large living and dining are.......read more

2 Bedroom(s)
Sleeps 4
Private vacation home

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Key West Private vacation home - 5.0 Star Review

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!

In Key West, every day is a celebration of what makes Summer such a beloved season - warm weather, no agendas, and spending quality time with family and friends. SUMMER SOLSTICE provides the perfect setting for a large group looking to e.......read more

9 Bedroom(s)
Sleeps 22
Private vacation home

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Key West Condo - 4.4 Star Review

Minimum 28 day stay required per county regulations.

A 2-bedroom 2.5 bath townhome in the private gated community of Coral Hammock, this home offers the finest accommodations for you and your family. Furnished with comfort in mind with a fully equipped kitchen and a gas grill on the porch.

Master bedroom with bath en-suite offers a n.......read more

2 Bedroom(s)
Sleeps 6
Condo

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Key West Private vacation home - 4.9 Star Review

The William Skelton "Pink House" is located just steps from Duval Street in the heart of Old Town Key West. At this very spacious and historic home, you\'ll enjoy 6 comfortable bedrooms, a private backyard pool, two spacious living rooms, shaded outdoor patios and porches, and so much more.

A perfect choice for family reunions, weddings, an.......read more

6 Bedroom(s)
Sleeps 14
Private vacation home

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Key West Condo - 4.8 Star Review

Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific property, take advantage of the multitude of amenities offered to make a vacation in the Florida Keys the perfect one. Guests can take in all the island has to offer, from the comfort of their own vacation rental at the new and upscale .......read more

3 Bedroom(s)
Sleeps 6
Condo

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Key West Private vacation home - 4.8 Star Review

This traditional cottage, in the heart of Old Town, was built by a shipbuilder in the early 1900’s. It has all the charms of old Key West with all the modern amenities for any couple or family to have a memorable vacation. Wake up to the sweet smells of bread and pastries from the local bakery across the street. Eaton Street has a lot to offer with.......read more

3 Bedroom(s)
Private vacation home

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Key West Condo - 4.3 Star Review

Shangri La

Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click \'Book Now!\'

This home features a 300 sq ft. private deck with a perfect pool and lush vegetation view in a great neighborhood in Key West. This is a second floor unit with wonderful shared space tha.......read more

Studio
Sleeps 2
Condo

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Key West Apartment - 5.0 Star Review

Welcome to charming Studio Royale, a monthly Vacation Rental located in quirky Old Town Key West.
Heated in ground pool. hours 12:00-6:00 PM
This 500 sq.ft. apartment is the front unit of a delightful 100+ year-old-home. Your hosts, John and Laura, live in the rear unit. Studio Royale boasts the finest touches to make your vacation super-rel.......read more

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Key West Condo - 5.0 Star Review

We want to let you know that your safety and comfort is our priority. Past reviews have always praised how clean our condo is and now we are stepping it up! Our professional cleaners are doing all of the right things making sure that we don\'t only look clean but that we are adhering to enhanced practices as laid out by the State and County! You wi.......read more

2 Bedroom(s)
Sleeps 4
Condo

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Key West Condo - 4.6 Star Review

Perfect vacation rental that allows you to enjoy breakfast on your private balcony, unwind and relax in the master bath jacuzzi, have front row seats to the variegated lights of Mother Nature\'s Sunrises, have the convenience of a fully equipped kitchen, two sitting areas for extra comfort and flexibility and for countless hours to enjoy the view.......read more

2 Bedroom(s)
Sleeps 8
Condo

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Key West Condo - 4.8 Star Review

A TRUE CARIBBEAN PARADISE! Location! Location! Location! The Conch Retreat Condo is located in the Beautiful Shipyard of Truman Annex a luxury community located in the heart of Old Town. No need for a car as you are close to everything! The condo comes with 2 bicycles for your use with helmets. There\'s free parking for one vehicle at the condo. Th.......read more

2 Bedroom(s)
Sleeps 4
Condo

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Key West Private vacation home - 5.0 Star Review

This property is a rare find! Sleeping 6 and located over 2 floors, its located in the beautiful resort of Santa Maria. The condo itself is overlooking the pool, enjoys 2 stunning balconies with its own outdoor furniture. Fully equipped kitchen, 2 1/2 bathrooms, TVs and wifi throughout. The property is located in one of the best destinations within.......read more

2 Bedroom(s)
Sleeps 6
Private vacation home

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Key West Condo - 4.6 Star Review

This 1BR 1BA condo has an extra large living room with a big screen TV. It sits nestled in the back of the Shipyard backing up to the entrance to Ft Zachary Taylor State Park, which has the nicest beach in Key West | This unit includes a Sonos WiFi speaker to be used within the unit, during your stay. Please do not unplug or move the speaker. | Dow.......read more

Studio
Sleeps 2
Condo

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Key West Condo

Louisa\'s Garden

Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click \'Book Now!\'

Book this wonderful, ground-level, Old Town getaway with all the comforts of home including central air conditioning and complimentary internet access! This vacation rental feature.......read more

Studio
Sleeps 4
Condo

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Key West Private vacation home - 5.0 Star Review

VINTAGE ISLAND PARADISE...
Tucked within luxuriant foliage lies this timeless, adult only, tropical sanctuary in the midst of Old Town Key West. Elegant architectural design with an unmatched collection of artwork, this mature retreat creates a blissful ambiance. A well known ficus tree among the infinite landscape makes this the legendary "Fic.......read more

3 Bedroom(s)
Sleeps 6
Private vacation home

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