Key West Florida Vacation Rentals, Hotels & Resorts

Key West Private vacation home

IDEAL LOCATION IN GREAT COMMUNITY...
Enjoy your stay at the President\'s Walk at Truman Annex.  This well manicured community is set in a wonderful location which is walking distance to most that Key West offers! 

FURNISHINGS...
The first floor includes a living room, dining area, fully equipped kitchen and a half bath.  The sitting ar.......read more

2 Bedroom(s)
Sleeps 4
Private vacation home

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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 Private vacation home

This stylish Conch Home is tucked away on a quiet lane in Old Town Key West. Surrounded by distinctive neighborhoods this is the traveler\'s dream escape. Just a short stroll from the famous Duval Street, this romantic cottage has all the essentials of a modern vacation rental property. The main house consists of 2 perfectly sized bedrooms and a sh.......read more

3 Bedroom(s)
Sleeps 6
Private vacation home

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Key West Condo - 4.5 Star Review

Due to Covid 19, we thoroughly sanitize upon check-out. This luxurious condo features a wonderful tropical interior design. It includes 2 spacious BR\'s: king bed/ full bath, queen bed/ full bath). Our living room sofa bed accommodates 1 guest. A fully equipped kitchen. Patio overlooks pool. WiFi, cable, 3 TV\'s, A/C, washer-dryer, workout center, .......read more

2 Bedroom(s)
Sleeps 5
Condo

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Key West Condo - 5.0 Star Review

Great unit for boat week in Key West. Saturday to Saturday availability. 2 bedroom condo at The Galleon Resort sleeps 6 and overlooks the Bay with Sunset Key views, also. Watch the races from the balcony! All the amenities of an RCI Gold Crown rated resort. See The Galleon Resort website for property information. Other Galleon condo available for w.......read more

2 Bedroom(s)
Sleeps 6
Condo

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Key West Private vacation home - 4.6 Star Review

Beautiful gated home located in Coral Hammock just minutes away from Key West. It\'s a spacious 3 bedroom, 3 bath home with a full kitchen, living room, indoor and outdoor dining. With access to shared pool, club house and gym. Everything you need to enjoy vacation.

It would work great for a family or couples or group.

On the first f.......read more

3 Bedroom(s)
Sleeps
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

Our condo is located is in the heart of Key West\'s Old Town. This neighborhood is filled with historic homes dating from the period when Key West was the wealthiest city in the United States. The condo is in a historic home with three other condo units. The location is ideal to explore Key West by foot or bike. Great restaurants are within a f.......read more

2 Bedroom(s)
Sleeps 4
Condo

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Key West Private vacation home

Two Story Apartment in central Old Town Key West location.
Only a 5 min bike ride to Duval.
1 King size bed on 3rd floor bedroom
1 Full Size bed on 2nd floor bedroom
1 Double Pull out Sofa on 2nd floor lounge

Truman Ave, just a few blocks from Duval in Old Town. Includes 966 square feet of modern living space on two levels; gi.......read more

2 Bedroom(s)
Sleeps 6
Private vacation home

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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)
Sleeps
Private vacation home

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Key West Private vacation home - 5.0 Star Review

MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local!

THE PROPERTY: Villa Azul consists of two separate buildings - a main house and a separate pool house! The main house is a two-story historic cottage with Brazilian cherry hardwood floors. The spacious living room is finel.......read more

3 Bedroom(s)
Private vacation home

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Key West Condo - 4.9 Star Review

We understand that these are unprecedented times and no one knows what tomorrow will bring. Here in Key West we believe in One Human Family where everyone is welcome and treated like family. Let\'s protect one another.

Our condo has always received great reviews on cleanliness and the enhanced cleaning practices are just another step. There.......read more

Studio
Sleeps 4
Condo

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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

This home was built in 1933 and was an original Key West shotgun house and has been beautifully restored. The house has been decorated uniquely and has a tranquil and beachy vibe.
Upon entry you have a front closed in office space or reading room. This room looks out to the lush landscape and is perfect for an early morning coffee or an afternoo.......read more

2 Bedroom(s)
Sleeps 4
Private vacation home

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Key West Private vacation home

BAHAMA VILLAGE TREASURE...
This Old Town Key West home is just steps from the award winning restaurants and charming boutiques of Petronia Street in historic Bahama Village. The Village Rooster greets you with a charming front porch and quaint entry.

AMENITIES AND FURNISHINGS...
Village Rooster boasts an open living area and spacious k.......read more

2 Bedroom(s)
Sleeps 4
Private vacation home

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Key West Condo - 4.8 Star Review

Relax at Villa Nomade in luxurious surroundings. Featuring a fully equipped kitchen with bar seating and dining area. The living room is furnished with comfy furniture and a 50"TV. The bedrooms have queen beds. Enjoy outdoor dining on the deck surrounded by a tropical landscape.
Villa Nomade is located in the Shipyard Condominiums at the Truman.......read more

2 Bedroom(s)
Sleeps 4
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 Condo - 5.0 Star Review

Summary:
This spacious, airy rental is the perfect location for your Key West getaway! If you are looking to kick back and relax this location is equipped with an expansive shared swimming pool, shared hot tub, several tennis courts and an outdoor shower.
There are two bedrooms and two bathrooms in this condominium allowing for a maximum occ.......read more

2 Bedroom(s)
Sleeps 4
Condo

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Key West Condo - 4.7 Star Review

Spectacular ocean views from this condo located on the top floor with 1350 sq ft of fabulous living space and a 45 ft private balcony accessible from the living and both bedrooms will make your vacation a memorable one and keep you coming back year after year. If the dates you need are not available check my other Key West vacation rental (Henry\'.......read more

2 Bedroom(s)
Sleeps 5
Condo

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Key West Private vacation home - 5.0 Star Review

PRESTIGIOUS TROPICAL RETREAT...
Indulge in this spectacular two-story home situated in the premier gated community of historic Truman Annex. Escape to a sun-kissed dream as soon you enter this picturesque community, surrounded by swaying palm trees inviting you to enter your island vacation home which is tucked away on a quiet lane. Totaling 4 b.......read more

4 Bedroom(s)
Sleeps 8
Private vacation home

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Key West Condo - 4.3 Star Review

PROFESSIONAL CLEANING PER CDC GUIDELINES BEFORE & AFTER EACH STAY
Let us help make your dreams come true: Enjoy your tranquil view of the deep blue Ocean and sparkling salt water pool within our tropical garden.....There is nothing like it...anywhere. You don\'t have to spend a fortune to enjoy a spacious, clean and comfortable Key West condo........read more

2 Bedroom(s)
Sleeps 6
Condo

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Key West Private vacation home - 4.7 Star Review

The Bonaire Suite is a bi-level suite decorated in a rich contemporary palm tree motif with two queen beds separated by a privacy curtain in the upstairs bedroom. The upstairs bath features a custom tumbled marble shower with glass door.

Downstairs is a living room with sofa that converts to a queen bed and a love seat decorated with rich pa.......read more

Studio
Sleeps 6
Private vacation home

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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 - 5.0 Star Review

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

OLD TOWN OASIS is back! After three years out of the rental program, this luxurious condo has returned, with all the same elegance enjoyed by many guests since 2004, and with many improvements.

You’ll be staying right near the oce.......read more

2 Bedroom(s)
Sleeps 6
Condo

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Key West Apartment

Summary:
This elegant, elevated 2nd story loft with vaulted ceilings is made for your next dream Key West getaway. Tastefully decorated with trendy decor, modern furnishings this property has an elegant and clean feel. Combined of two lofts - Sky Suite & Cloud Suite on Duval, this recently renovated compound is perfect for up to 12 guests.
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4 Bedroom(s)
Sleeps 12
Apartment

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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 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 Condo - 4.8 Star Review

PROFESSIONAL CLEANING PER CDC GUIDELINES BEFORE & AFTER EACH STAY
Ocean views from every room with floor to ceiling windows. Feel the warm tropical breezes as the palm trees sway to the music . It\'s a magical rhythm set into motion over a century ago by pirates, artists, writers and other champions of leisure.
Yes ... THERE STILL IS MAGIC IN.......read more

2 Bedroom(s)
Sleeps 6
Condo

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Key West Condo

NEWLY REMODELED in the Summer of 2022 this 2 bedrooms, 2-bathroom condo checks all the boxes for your vacation needs!

Located in the 1800 Atlantic condo complex with two large communal swimming pools, spa, tennis courts, fitness facilities, private beach, walking paths, BBQ area and recreation room/ library. The opportunities for entertainme.......read more

2 Bedroom(s)
Sleeps 6
Condo

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