Key West Florida Vacation Rentals, Hotels & Resorts

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)
Sleeps
Private vacation home

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Key West Private vacation home

Exquisitely designed and perfectly located in Old Town Key West Southernmost Point area, Artist’s Retreat is a breathtaking Key West hideaway.

This double lot home expands approximately 1800 square feet and was custom built to perfection!

Offering 3 bedrooms, 2 bathrooms, vaulted ceilings and custom hardwood floors throughout. The .......read more

3 Bedroom(s)
Private vacation home

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Key West Private vacation home - 3.0 Star Review

The Tipsy Mermaid

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

Nestled in a peaceful gated community, this two-level townhome is located right on a golf course in the gated grounds of the Key West Golf Club, only a few miles from those pristi.......read more

3 Bedroom(s)
Sleeps 6
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 - 5.0 Star Review

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

Nestled under the branches of a majestic Banyan tree, BANYAN ROSE is a classic mid-century modern, ranch-style home set in the Beachside district of Key West, just a couple blocks from Smathers Beach on Rose Street. BANYAN ROSE was desig.......read more

4 Bedroom(s)
Sleeps 8
Private vacation home

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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 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 Private vacation home - 4.0 Star Review

LOCAL LIVING....
Spend time relaxing in Paradise in the perfect home. Serenity is a beautifully decorated,  4 bedroom home, with 3 baths in an amazing location.  Enjoy sunny Key West weather by spending time relaxing outdoors or soaking in the private pool.

FURNISHINGS..
Newly designer decorated!  The modern and stylish furnishings add.......read more

4 Bedroom(s)
Sleeps 8
Private vacation home

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Key West Private vacation home - 5.0 Star Review

Welcome to Bottom’s Up Bungalow located The Meadows subdivision in Old Town Key West.

This pristine Florida Bungalow is 2 bedrooms, 2 bathroom single family home and offers all the amenities you need to make this your perfect vacation. Including off-street parking, swimming pool, quaint gazebo equipped with wet bar and custom seating. The .......read more

2 Bedroom(s)
Sleeps 6
Private vacation home

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Key West Condo - 5.0 Star Review

KEY WEST IS STILL AN OASIS IN FLORIDA SO Welcome to Conch Republic 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 oversized two bedroom, one bathroom condominium is located on pict.......read more

2 Bedroom(s)
Sleeps 4
Condo

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Key West Private vacation home - 5.0 Star Review

~~7 DAY MINIMUM~~​Experience the famous island city of Key West and stay at the Treasure Cove Townhouse in the private President\'s Lane area of the prestigious Truman Annex.  Offering exquisite amenities, pool access, and an unbeatable location close to Duval Street, Truman Waterfront Park, and Ft. Zachary Taylor Beach provides a fantastic Sunshin.......read more

2 Bedroom(s)
Sleeps 6
Private vacation home

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Key West Private vacation home - 4.9 Star Review

Family home for over 20 years, we would like to share our home to those that want to relax, see an amazing sunset, and enjoy the life in Key West. It’s fully renovated, beautiful and peaceful. Enjoy, relax, and Vacation. The house is a true Key West home built in 1918, and one of the few that remains typical KW style. This home is located in histor.......read more

2 Bedroom(s)
Sleeps
Private vacation home

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Key West Private vacation home - 5.0 Star Review

Flagler Station

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

Recline next to a shimmering pool, with a banana tree and avocado tree completing your view! This pleasant home is designed for guest comfort from top to bottom, with everything fro.......read more

3 Bedroom(s)
Sleeps 8
Private vacation home

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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 Condo

Welcome to the Hyatt Beach House, a Hyatt Residence Club, your own private sanctuary amongst the lush landscape of Key West. Envision old-fashioned screen-enclosed porches, gardens bursting with tropical flowers and crystal-clear water views. Enjoy the privilege of a private white sand beach, furnished with thick-cushioned chairs, picnic tables, ba.......read more

2 Bedroom(s)
Sleeps 6
Condo

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Key West Condo - 4.6 Star Review

Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The condos are located 2 blocks from Duval Street and all the Old Town Key West attractions. The properties are also ¼ mile from Fort Zachary Taylor State Park. The property is outfitted with washer/dryer, pots/pans, towels, linens, .......read more

2 Bedroom(s)
Sleeps 4
Condo

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Key West Condo - 4.6 Star Review

Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The condos are located 2 blocks from Duval Street and all the Old Town Key West attractions. The properties are also ¼ mile from Fort Zachary Taylor State Park. The property is outfitted with washer/dryer, pots/pans, towels, linens, .......read more

Studio
Sleeps 4
Condo

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Key West Private vacation home

Mpnthly rental PLEASE CONTACT ME FIRST BEFORE YOU MAKE A RESERVATION. THANK YOU !. I advertise on multiple sites. Your best life begins with a home that inspires you! Living on the water just outside of Key West, this Mediterranean style 4 bedrooms/2 1/2 baths home just might be the perfect muse. The imposing Spanish Colonial façade of the entry op.......read more

4 Bedroom(s)
Sleeps 8
Private vacation home

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Key West Private vacation home - 4.9 Star Review

This mid-town Key West home is recently refreshed with light colors and beautiful British Colonial furnishings. It features three bedrooms and three baths. The open living/kitchen area is decorated with light colored walls with striking tropical tones in the accent furnishings and tile, and soft fabrics. The dining room is outside in the attached p.......read more

3 Bedroom(s)
Sleeps 6
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!

While Old Town Key West has its fair share of impressive homes, few can compare to ENVY OF THE ISLAND a freshly built two-story private home that combines the appearance and charm of a historic Keys home with all of the modern convenienc.......read more

5 Bedroom(s)
Sleeps 10
Private vacation home

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Key West Hotel

Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of three sparkling pools, and enjoy the fresh modern design of the newly built property.

ATTENTION: The Resort Fee is not included in the daily r.......read more

4 Bedroom(s)
Sleeps 8
Hotel

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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 Private vacation home - 4.8 Star Review

This Foundry townhouse is a Bostonian style 3 level home located in Old Town Key West. This home has been recently renovated to accommodate an individual couple, family, or vacationing couples that each desires the privacy of their own bedroom suite with full, private baths. This two bedroom, two and one half unit will comfortably sleep up to six i.......read more

2 Bedroom(s)
Sleeps 6
Private vacation home

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Key West Private vacation home - 4.0 Star Review

Discover a piece of paradise with a beautiful conch home located in the historic district of Key West.

4-bedrooms, 2 baths and an open concept kitchen/dining area. Enjoy a nice sunny day on the patio or a rainy night on the front porch. Multiple fruit trees with outdoor security cameras for peace of mind.

Guests will be given their sp.......read more

4 Bedroom(s)
Sleeps 8
Private vacation home

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Key West Hotel

Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few minutes\' walks to several local attractions. An onsite restaurant serves Latin-inspired tapas with local ingredients. The refreshing pool and pool bar are a relaxing spot to spend an afternoon in the sun. Hourly shuttle services .......read more

Studio
Sleeps 3
Hotel

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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!

SOUTHERN STAR is a modern Key West home nestled in the quiet Meadows neighborhood of Old Town that combines the island way and the sweet life of the South. With wide porches, a breezy interior, cathedral ceilings, and an apparent souther.......read more

4 Bedroom(s)
Sleeps 8
Private vacation home

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Key West Villa - 5.0 Star Review

Bring the whole family to this great place with lots of room for fun...enjoy the heated pool, spacious backyard, kayaks and paddleboards, ping-pong table, outside kitchen, little beach, tiki hut bar and open water views........read more

6 Bedroom(s)
Sleeps 17
Villa

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Key West Hotel

Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of three sparkling pools, and enjoy the fresh modern design of the newly built property.

ATTENTION: The Resort Fee is not included in the daily ra.......read more

Studio
Sleeps 2
Hotel

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Key West Private vacation home - 4.9 Star Review

ALLOW THE PERFECT VACATION TO UNFOLD...
The epitome of laid-back, island living is found within this classic, Conch style home bringing endless charm to your tropical vacation. Steps from high end galleries, bars and restaurants, yet tucked away on a quaint and colorful lane, this home entails all the desired amenities that will truly immerse y.......read more

2 Bedroom(s)
Sleeps 6
Private vacation home

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Key West Private vacation home - 4.8 Star Review

Summary:
Coconut Palm is the perfect place for your beautiful tropical getaway in Key West. It is located just one block away from the world famous Duval Street and is within walking distance of many Key West attractions including Fort Zachary Taylor Beach and Park, Ernest Hemingway Home and Museum, and local shops and restaurants.

The Sp.......read more

3 Bedroom(s)
Sleeps 8
Private vacation home

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