Key West Vacation Rentals

(86 rentals)
Beach Club #304

2 BR | 2 BA | Sleeps 4 | Quick View

$275

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water as few do in Key West. The breathtaking view can be seen as soon as you enter this spacious 2 bedroom condo. It has just been purchased and newly refurnished ...

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Property Type

Key West Condo

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Casa de Cuba

3 BR | 2 BA | Sleeps 6 | Quick View

$501

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Location! Style! Elegance! This beautiful home is the fabulous combination of everything a great vacation property should be. One half block to Duval Street in the historic district, the location can't be beat. The home's history is rich; neighboring the historic Gato Cigar factory which is now restored ...

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Property Type

Key West House

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Southard Street - Queen Conch

4 BR | 4 BA | Sleeps 8 | Quick View

$750

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

On a lovely tree-lined residential street in the heart of the historic Old Town district, this quiet, historic compound offers three separate vacation suites sharing a lush, large, sunny pool, or combines for a wonderful four bedroom retreat.Downstairs there is a large, open floor plan with living ...

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Property Type

Key West House

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Beautiful Key West Golf Club -- Paradise Found

$180

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

Relax with family and friends in your own tropical paradise at this spacious townhome in Key West's beautifully landscaped & maintained Golf Club. Located in a private gated community with resort style amenities, it is just minutes away from the beaches, world class restaurants, water sports and ...

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Property Type

Key West Townhome

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Brass Palm Villa -Private Luxury Key West Home with Heated Pool

3 BR | 2.5 BA | Sleeps 6 | Quick View

1

Distance to beach: 0.5 miles to Higg's Beach

$213

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • 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

"“It’s a Magic Kind of Medicine”"
Reviewed December 30, 2017

Now I know where J.Buffett got the inspiration for those lyrics! Just the right blend of tranquility and fun! It was love at first sight. The pool, surrounding outdoor living spaces were just perfect. I ...

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Louisa's Hideaway

3 BR | 3 BA | Sleeps 6 | Quick View

$551

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Tucked away near the quite end of Duval Street, you'll find this stylish, newly renovated, three bedroom, three bath home. Thoughtful details are luxuriously appointed to appeal to the traveler looking for privacy, style and elegant design.Walk up the brick drive and enter the gate to the palm tree-lined ...

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Property Type

Key West House

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Paradise Place Duval Square

2 BR | 2 BA | Sleeps 4 | Quick View

$275

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Open the door to Paradise Place and find yourself transported to a peaceful sanctuary.The downstairs living area is decorated with warm wood floors, blue and sand accents and provides plenty of space for entertaining. French doors lead out to a large covered and private patio area. The kitchen features ...

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Property Type

Key West Condo

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Casa Atlantica One Bedroom

1 BR | 1 BA | Sleeps 2 | Quick View

$201

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Located just steps from the White Street Pier and Higgs Beach, Casa Atlantica truly lives up to its name: a home perched on the very edge of the turquoise waters of the Atlantic. Located on the quiet end of a waterfront townhome community, this property features simply the best views you will find in ...

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Property Type

Key West Condo

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Southard Horse Conch Suite

1 BR | 1 BA | Sleeps 2 | Quick View

$202

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

The Horse Conch is a one bedroom one bathroom suite in a house consisting of three vacation suites. Decorated with tropical color palette and has a queen bed. Accessed from the second floor covered porch that overlooks the shared gardens and pool below.

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Property Type

Key West House

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Upscale Home in Truman Annex!

1 BR | 1 BA | Sleeps 3 | Quick View

Distance to beach: 0.3 miles to Ft. Zachary Taylor

$178

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Pool
  • Rentals by Owner

About this property

Beautifully Remodeled -1BR/1BA End Unit Shipyard Condo in Truman Annex Location, Beauty and Comfort! Southard Breezes has what you are looking for! This gorgeous home has been meticulously renovated with our guests' complete comfort in mind. Located in the gated community of Truman Annex: a popular and ...

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Property Type

Key West Condo

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Pete's Cottages

4 BR | 2 BA | Sleeps 8 | Quick View

$477

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

These twin homes have the charming original style of the Key West "shot gun" cottages and have been restored with a beautiful natural cypress exterior. Each cottage opens to it's own semi-private deck and lounge area with access to a large free-form pool with waterfall.Inside, the comfortable ...

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Property Type

Key West House

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Artist's House Duval Square

2 BR | 2 BA | Sleeps 6 | Quick View

$275

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

This 2 bedroom, 2.5 bath rooftop town home is located within the quaint community of Duval Square. Beautifully decorated with bright colors and unique art work, this property will give you a great Key West experience and is perfectly located right in the heart of old town Key West. Park your car in the ...

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Property Type

Key West Condo

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Beach Club #103

2 BR | 2 BA | Sleeps 6 | Quick View

$275

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Oceanfront
  • Pool

About this property

Unique oceanfront living only 65 feet from the Atlantic!The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water. The breathtaking view can be seen as soon as you enter the unit.This spacious 2 bedroom unit features a large oceanfront balcony accessed ...

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Property Type

Key West Condo

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Southard Queen Conch Suite

2 BR | 2 BA | Sleeps 4 | Quick View

$280

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Southard Street Downstairs Queen Conch is a two bedroom two bathroom retreat in a house consisting of three vacation suites. Open floor plan with French doors that open to the large shared sunny pool surrounded by beautiful landscaped garden.

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Property Type

Key West House

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Villa Serena Duval Square

2 BR | 2 BA | Sleeps 4 | Quick View

$275

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Open the door to Villa Serena and find yourself transported to a peaceful sanctuary. Recently renovated in February 2018, Villa Serena is the perfect space for your relaxing vacation.The downstairs living area is decorated in soothing cobalt and beachy sand tones and provides plenty of space for ...

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Property Type

Key West Condo

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Coconut Cabana

3 BR | 2 BA | Sleeps 6 | Quick View

$425

per night

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Key Amenities

  • Air Conditioning
  • Private Pool

About this property

A quintessential "Old Town Key West" home, located in the Historic District and just one half a block off Duval Street.This charming home is within walking distance of dozens of restaurants, the Atlantic Ocean, the Southernmost Point and the sunset pier. Lovingly restored and cared for, ...

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Property Type

Key West House

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New Listing! Beautiful Townhouse Awaiting Your Tropical Escape

2 BR | 2.5 BA | Sleeps 6 | Quick View

Distance to beach: 0.3 miles to Ft. Zachary Taylor Beach

$275

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Pool
  • Rentals by Owner

About this property

2 Story 2 Bedroom 2 1/2 Bath Townhome in Truman Annex Location, Beauty and Comfort! Kokomo Key has what you are looking for! This upscale home has been meticulously designed with our guests' complete comfort in mind. Located in the gated community of Truman Annex: a popular and beautifully landscaped ...

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Property Type

Key West Townhome

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Key West Old Town Sanctuary- Huge Private Pool- Quiet Lane- Monthly Rental

$183

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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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Ocean View condo steps to Beach, rates include all tax and fees

$189

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Rentals by Owner

About this property

The Jungle Breeze condo at LaBrisa Condominiums is a 1 bedroom, 1 bath apartment * Rates include all taxes and fees * King size bed in the bedroom * queen size sleeper sofa in the living area *accommodates 2 adults of family of 4 * WiFi inlcuded * Parking included *Central AIr Conditioning * ...

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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

1

Distance to beach: 0.5 miles to South Beach

$138

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Rentals by Owner

About this property

This Simonton Studio is neat, sweet and complete. * Pet friendly for additional flat fee of $45 * 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

"Excellent location - would definitely stay there again!"
Reviewed April 7, 2018

This little gem had everything we needed and was just perfect for a getaway for two. We appreciated the tips left by the owner, giving recommendations for dining and activities, and it was fun to have ...

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Colony Sunset Suite

1 BR | 1 BA | Sleeps 2 | Quick View

$180

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Pool

About this property

Located in The Colony, a secluded compound just steps from Duval Street, Colony Sunset is a colorful and relaxing retreat. Walk up the flagstone path and enter the home through the vivid and cheerful living space, accented with cerulean blue walls and splashes of tropical art. A vaulted ceiling with ...

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Property Type

Key West Condo

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Louisa House

4 BR | 3 BA | Sleeps 8 | Quick View

$551

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Private Pool

About this property

An absolutely perfect location, just a half a block off Duval Street and within walking distance to amazing restaurants, turquoise beaches and the Southernmost Point in the United States. Louisa House has it all for the perfect Key West vacation.A historic home with elegant curb appeal, Louisa House ...

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Property Type

Key West House

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Bali Hideaway

Studio | 1 BA | Sleeps 2 | Quick View

$203

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Perfect for two, this Bali-style studio cottage has it all: comfort, privacy and location.The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within 2 blocks you'll find Key West classics ...

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Property Type

Key West Studio

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Conch Cottage Key West's only real beach house

$414

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Stay in a beautifully appointed villa or cottage located directly on the Atlantic Ocean. Only a 15 minute drive to Key West's history, restaurants and nightlife, this tropical retreat known as Sea Vista, is as serene as a private island.Enjoy full use of direct TV channels, free current video library ...

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Property Type

Key West House

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Duval Square Retreat

2 BR | 2 BA | Sleeps 4 | Quick View

$251

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Located in the heart of Old Town, Duval Square is a charming brick-paved and tree-lined courtyard complex located at the quieter end of Duval Street. The residential units are located upstairs, while quaint shops and restaurants occupy the courtyard below.This recently upgraded unit is tastefully ...

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Property Type

Key West Condo

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Duval Square Courtyard Condo

3 BR | 2 BA | Sleeps 6 | Quick View

1

$400

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

n the heart of Old Town and convenient to just about everything, this condo is set above a quaint brick and tree-lined courtyard that includes shops and restaurants. This three bedroom, two bath unit is in one of the only "stand-alone" buildings in the Duval Square complex. Simply walk down ...

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Property Type

Key West Condo

"Wedding in Key West "
Reviewed April 11, 2019

Loved the location,place was very nice and relaxing. We really enjoyed ourselves. Would stay here again in a heartbeat.

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Ann Street Cottage

1 BR | 1.5 BA | Sleeps 2 | Quick View

$237

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Tucked away in an inviting compound you'll find the perfect hideaway called Ann Street Cottage, a charming one bedroom cottage.This quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within ...

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Property Type

Key West House

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The Hamilton House

5 BR | 4.5 BA | Sleeps 9 | Quick View

$200

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool
  • Rentals by Owner

About this property

Monthly rentals only. 28 day minimum. This single family home is perfectly located in old town two blocks away from the southernmost point and one block away from Duval street. It has 4 bedrooms in the main house and a separate guest cottage with a bedroom and a full bathroom. It has two off street ...

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Property Type

Key West House

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Beach Club #104

2 BR | 2 BA | Sleeps 4 | Quick View

$275

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Unique oceanfront living only 65 feet from the Atlantic!The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water. The breathtaking view can be seen as soon as you enter the unit.The huge oceanfront balcony can be accessed from both the living/dining ...

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Property Type

Key West Condo

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Southard Rooster Conch Suite

1 BR | 1 BA | Sleeps 2 | Quick View

$202

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

On a lovely tree-lined residential street in the heart of the historic Old Town district, this quiet, historic compound offers three separate vacation suites sharing a lush, large, sunny pool or combines for a wonderful four bedroom retreat. The two one bedroom suites are located on the second floor, ...

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Property Type

Key West House

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Bougainvillea Villa Key West-monthly rental on water with private pool & dock

3 BR | 2 BA | Sleeps 6 | Quick View

1

Distance to beach: 4 miles to Smathers

$167

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Private Pool
  • Rentals by Owner

About this property

MONTHLY RENTALS ONLY We purchased Bougainvillea Villa in late 2014 as our future retirement home. The villa was built in the early 1960’s and our neighbors tell us that at one time Jimmy Buffett’s manager owned and lived in the home. It has always been a private home, and was renovated and ...

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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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Cockadoodledo

4 BR | 4 BA | Sleeps 10 | Quick View

$300

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

Cock-a-doodle-do Vacation Rental, named for Key West's beloved chicken population, is a mid-town oasis! 5 minute drive to Old Town or take Uber for just $ 10!A meticulously updated pool home with beautifully lush landscaped grounds and plenty of space for everyone! The main house is a 3/3 (1 King, ...

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Property Type

Key West House

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Superb Location, Affordably Priced - The TwoSim Suite

Studio | 1 BA | Sleeps 2 | Quick View

Distance to beach: 0.5 miles to South Beach

$135

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • 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 $45 * 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

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Dreaming on Duval

5 BR | 4 BA | Sleeps 10 | Quick View

$1150

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Luxury on Duval Street in historic Key West? Luxury is not a word most people associate with Duval Street... until you look at Dreaming On Duval! There are very few private homes on this famous street, let alone a single-family, free-standing vacation rental that is just steps away from everything Key ...

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Property Type

Key West House

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Ann Street Tranquility

1 BR | 1 BA | Sleeps 2 | Quick View

$236

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

This charming one bedroom cottage is the perfect hideaway.The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within 2 blocks you'll find Key West classics like The Bull, Sloppy Joe's, ...

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Property Type

Key West House

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Pete's West Cottage

2 BR | 1 BA | Sleeps 4 | Quick View

$236

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

These twin homes have the charming original style of the Key West "shot gun" cottages and have been restored with a beautiful natural cypress exterior. Each cottage opens to it's own semi-private deck and lounge area with access to a large free-form pool with waterfall.Inside, the comfortable ...

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Property Type

Key West House

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Catherine House

2 BR | 2 BA | Sleeps 4 | Quick View

$309

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Private Pool

About this property

This charming Key West cottage is just a short walk to a selection of great restaurants, art galleries, and shopping.Catherine House is located only ½ block from the quieter end of Duval Street, and better yet, just three blocks to a beach (Duval & South Streets). The house can comfortably ...

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Property Type

Key West House

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Namaste

1 BR | 2 BA | Sleeps 2 | Quick View

$260

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Tucked away in an inviting compound you'll find a blissful retreat called Namaste; a tranquil and relaxing one bedroom cottage. The quiet compound is located just one block from Duval Street combining the best of both worlds: relaxing and taking advantage of all that Key West has to offer. Within 2 blocks ...

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Property Type

Key West House

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Vista Fresco

2 BR | 2 BA | Sleeps 4 | Quick View

1

$251

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Enjoy the resort-style amenities of 1800 Atlantic Condominiums while relaxing in a residential setting amongst friendly neighbors. The 1800 Atlantic complex sits on 400 feet of oceanfront property. An expansive pool and spa sits ocean side, surrounded by a lushly landscaped garden of native Key West plants ...

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Property Type

Key West Condo

"Waterview Condo"
Reviewed February 18, 2019

The condo was as advertised. It had a spacious kitchen and was nicely decorated. We had a beautiful view of the ocean and sunrises. You will need a car or bicycle to get to town. The bed we slept in ...

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Truman Annex unit202-3

2 BR | 1 BA | Sleeps 4 | Quick View

$307

per night

View Details

Key Amenities

  • Air Conditioning
  • Pool

About this property

Truman Annex unit202-3This upstairs unit has beautiful views and offers a private front and back porch. There is a queen bed in the master bedroom and 2 twins in the second bedroom.

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Property Type

Key West Condo

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CasaBella Duval Square

2 BR | 2 BA | Sleeps 4 | Quick View

$300

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Located just steps from famous Duval street, this two-story town home is located in quaint, cobble stoned Duval Square. You are within the heart of the historic district and can walk almost everywhere. Although close to Duval, the home is a quiet escape from the hustle bustle.This town house community ...

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Property Type

Key West Condo

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Colony Poolside

1 BR | 1 BA | Sleeps 2 | Quick View

$200

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Located in The Colony, a secluded compound just steps from Duval Street, Colony Poolside is a peaceful retreat. Enter the home through the serene and inviting living space, accented with blue and white decor, wood floors and pops of color from nautical-themed accents and artwork. A vaulted ceiling with ...

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Property Type

Key West House

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Key West Beach Front Rental! Beach Studio Ocean views

Studio | 1 BA | Sleeps 3 | Quick View

1

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

$249

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Oceanfront
  • Rentals by Owner

About this property

Welcome to your Ocean Views Studio! Get yourself dates before flights! Art studio is smaller available monthly till excluding October phone for inquiry,, Key West has wind! Upon request Happy to hold you first in queue- a short while! Ocean view studios 2? In town, of Key West? YES! Best Stay ...

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Property Type

Key West Studio

"Breathtaking!!"
Reviewed April 28, 2019

We chose this listing because we wanted to have the true key west experience!! The house definitely makes you feel like a true local. Each morning enjoying coffee on the patio and the ocean waves lull us ...

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Casa Atlantica Studio

Studio | 1 BA | Sleeps 2 | Quick View

$200

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Located just steps from the White Street Pier and Higgs Beach, Casa Atlantica truly lives up to its name: a home perched on the very edge of the turquoise waters of the Atlantic. Located on the quiet end of a waterfront townhome community, this property features simply the best views you will find in ...

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Property Type

Key West Condo

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The 6 bedroom Duval Street Compound

6 BR | 6.5 BA | Sleeps 16 | Quick View

Distance to beach: 0.3 miles to Ft Zachary Taylor

$1250

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • 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

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Shipyard Palms

2 BR | 1.5 BA | Sleeps 4 | Quick View

$203

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

In the heart of old town Key West, nestled within the secluded and lush community of private homes and condominiums of Truman Annex, this Shipyard Condominium has convenient access to both the gorgeous Fort Zachary State Park Beach and historic old town Key West.This colorful and whimsically decorated ...

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Property Type

Key West Condo

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Parrot Dice --"MONTHLY," 2 bedroom (+den), 3 bath, Pool & Hot Tub, Private Drive

2 BR | 3 BA | Sleeps 6 | Quick View

Distance to beach: 0.5 miles to Higgs Beach

$150

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool
  • Rentals by Owner

About this property

"MONTHLY" RENTAL ONLY: Old Town Tropical Oasis, Private Pool, Hot Tub, Private Driveway. Meticulously restored and maintained home featuring: 2 bedrooms + den with sleep sofa (can be a 3rd bedroom) and 3 full en suite bathrooms. Our favorite part of this property is the lush & extremely ...

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Property Type

Key West House

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Pete's East Cottage

2 BR | 1 BA | Sleeps 4 | Quick View

$233

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

These twin homes have the charming original style of the Key West "shot gun" cottages and have been restored with a beautiful natural cypress exterior. Each cottage opens to it's own semi-private deck and lounge area with access to a large free-form pool with waterfall.Inside, the comfortable ...

View all property information

Property Type

Key West House

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Beach Club #204

2 BR | 2 BA | Sleeps 4 | Quick View

$275

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Unique oceanfront living only 65 feet from the Atlantic!The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water. The breathtaking view can be seen as soon as you enter the unit.This is one of the most elegant and colorful 2 bedroom units in the Key ...

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Property Type

Key West Condo

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Colony Calypso

1 BR | 1 BA | Sleeps 2 | Quick View

$200

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Located in The Colony, a secluded compound just steps from Duval Street, Colony Calypso is a peaceful retreat. Enter the home through the tranquil and inviting living space, accented with sage green walls, new tile floors and pops of color from local artwork and photography. A vaulted ceiling with exposed ...

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Property Type

Key West House

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Key West Vacation Rentals

Key West Weather

 | 

7524°  6518°
JANUARY
Ocean 7122°
7624°  6619°
FEBRUARY
Ocean 7122°
7926°  6921°
MARCH
Ocean 7323°
8228°  7222°
APRIL
Ocean 7825°
8529°  7624°
MAY
Ocean 8127°
8831°  7926°
JUNE
Ocean 8329°
8932°  8027°
JULY
Ocean 8530°
9032°  7926°
AUGUST
Ocean 8731°
8831°  7926°
SEPTEMBER
Ocean 8530°
8529°  7624°
OCTOBER
Ocean 8328°
8127°  7222°
NOVEMBER
Ocean 7826°
7725°  6719°
DECEMBER
Ocean 7524°

Stay steps from the sand in your Key West vacation rental

Relaxing, laid-back Key West calls to beach bums who prefer their landscape pristine and untouched. Key West is famous for watersports, nightlife, beaches and historic sites. Don’t miss Duval Street, one of the most energetic strips of shops, bars and cafes in Florida. Whether you prefer culture or the outdoors, Key West has plenty to offer in a relaxed, welcoming atmosphere.

From a romantic bungalow for a couple to a house that can fit your entire family and more, the Key West house rentals are endless. When staying in one of our Key West vacation rentals instead of hotel, you’ll have much more space and privacy, plus cost savings when booking a property for a large group. Some of our condos and villas even come with special amenities like a set of bicycles, chef’s kitchen, and in-home theater. Use the filters to narrow down your choices and choose the property that calls to you, just like Key West does.

Key West, Florida travel advice

Thanks to economic boom and a bustling cigar industry, this area's became quite a hot spot by the turn of the 20th century. Surrounded by the Gulf of Mexico, Key West offers visitors ample natural beauty and great swimming beaches. History buffs love the island’s maritime history and legends of its famous residents, while partygoers can’t get enough of Duval Street. Located closer to Cuba than to Miami, Key West offers endless Latin and Cuban cultural influences from the cuisine to the music and art. Running four miles long and about two miles wide at its widest, this is a small island. The popular Old Town makes up about half of this area.

Climate

Abundant sunshine and gentle breezes make Key West one of the most popular tourist destinations in Florida. With over 320 sunny days per year you’ll most likely get the weather you want, no matter when you visit. Be sure to bring plenty of sunscreen and beach umbrellas as the UV rays can be quite strong here. The sea temperature is almost bath water and you’ll love the turquoise-blue color.

Top activities and attractions

Even getting to Key West is an adventure. The Overseas Highway is one of the most beautiful drives in the country. Completed in 1938, it connects a string of cays and coral rock with 113 miles of concrete roadway. The aptly named Seven Mile Bridge is the longest and most scenic of the entire route.

Key West’s diverse and unique ecosystems are a result of the convergence of two major bodies of water. There’s endless entertainment to be had on the ocean. You’ve got the deep blue Atlantic and its Gulf Stream current to the south and the shallow flats of the Gulf of Mexico to the west. From deep sea fishing to parasailing and even just body surfing, you’ll love a day out on the water in Key West.

Hop on the Conch Tour Train for a fun way to see the surrounding area. You’ll get a narration of the city’s past from an experienced tour guide as you cruise around the streets. Walking tours are one of the best ways to see the city, too. Peek in at the area’s intriguing architecture, courtyards, and gardens.

On the presidential side of life, don't miss a tour of the Harry S. Truman Little White House, a command center during World War I and II as well as the winter home of President Harry S. Truman. Fort Zachary Taylor Historic State Park is a great place to swim, snorkel, and catch the sunset.

Dining and Nightlife

Over 300 restaurants and bars make this city one of the most fun places to be in southern Florida. For those with a sophisticated palate, try the highly-rated Bien restaurant to indulge in Latin & Cuban flavors. For great sandwiches and service, eat at the cleverly named Munch Box to break up your day of adventure. For Korean food that will make you scream “WOW”, pop in to Garbo’s Lunchbox. And lastly, for those who love to brunch, visit Key Plaza Creperie for delicious breakfast foods.

At night, Duval Street is the place to be. The Green Parrot is Key West’s oldest bar but it’s still a rockin’ atmosphere. Famed local Ernest Hemingway loved to get sauced at Sloppy Joe’s bar. (Don’t miss the Ernest Hemingway Home & Museum to get a closer look at what made this famous author tick.) For those who like the legitimate arts, take in a performance at Key West’s Fringe Theater, the Red Barn Theatre, or the Waterfront Playhouse.

For the kids, take the family to Mallory Square, where you’ll find local performers, plenty of fried food, and gorgeous sunset views.

Key West vacation homes on FloridaRentals.com

Vacation rentals in Key West on FloridaRentals.com can save you up to 20% over our competitors. Plus, we have a wide array of inventory appealing to any group size or traveler tastes. Happy planning!