Key West Vacation Rentals

(87 rentals)
Pete's Cottages

4 BR | 2 BA | Sleeps 8 | Quick View

$477

per night

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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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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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Duval Square Penthouse

4 BR | 4 BA | Sleeps 8 | Quick View

$575

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

This huge penthouse condo, located just steps from the action of Duval Street, has been recently upgraded. This four-bedroom, 4.5 bath condo is in the heart of the action at Duval Square, a charming brick-paved and tree-lined courtyard just south of Truman Avenue. The residential units are on the second ...

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Property Type

Key West Condo

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A Touch Of Cuba In Key West

2 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 0.5 miles to Ft. Zachary Taylor State Park

$250

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • 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 is located on picturesque ...

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Property Type

Key West Condo

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Vista Fresco

2 BR | 2 BA | Sleeps 4 | Quick View

1

$251

per night

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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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Superb Location, Affordably Priced - The TwoSim Suite

Studio | 1 BA | Sleeps 2 | Quick View

Distance to beach: 0.5 miles to South Beach

$142

per night

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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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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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CasaBella Duval Square

2 BR | 2 BA | Sleeps 4 | Quick View

$300

per night

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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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Villa Paradiso

3 BR | 3 BA | Sleeps 6 | Quick View

$425

per night

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Key Amenities

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

About this property

This mid-town Key West home is beautifully decorated in jewel tones of the Mediterranean. It features three bedrooms and three baths. The open living/kitchen area is decorated with rich tones with tropical accents and soft fabrics. The dining room is outside in the attached pavilion with ornate iron and ...

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Property Type

Key West House

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Dreaming on Duval

5 BR | 4 BA | Sleeps 10 | Quick View

$1150

per night

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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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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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Louisa's Hideaway

3 BR | 3 BA | Sleeps 6 | Quick View

$551

per night

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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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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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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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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 ...

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Property Type

Key West House

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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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Casa Atlantica Studio

Studio | 1 BA | Sleeps 2 | Quick View

$200

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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Beach Club #408

4 BR | 3 BA | Sleeps 8 | Quick View

$400

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Welcome to your quiet and relaxing Key West vacation! The Key West Beach Club stretches along the Atlantic Ocean shores. This top floor penthouse has it all: 15 foot vaulted ceilings, a well equipped kitchen, huge oceanfront balcony, four bedrooms and three baths. Enjoy breathtaking views of the ocean ...

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Property Type

Key West Condo

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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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Louisa House

4 BR | 3 BA | Sleeps 8 | Quick View

$551

per night

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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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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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La Brisa #403E Ocean Vista

2 BR | 2 BA | Sleeps 4 | Quick View

$203

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

La Brisa Beach Condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes that flow around the pretty blue and white buildings, La Brisa is an ideal spot to enjoy your Keys vacation. Located on South Roosevelt Boulevard, this secure gated community is directly ...

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Property Type

Key West Condo

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Ocean View condo steps to Smathers Beach

$175

per night

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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 * 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 * Check-out cleaning included * This ...

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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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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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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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Havana Lane

2 BR | 2 BA | Sleeps 4 | Quick View

1

$352

per night

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Key Amenities

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

About this property

Havana Lane recalls a time in Key West's colorful history when cigar makers populated the neighborhood, gathering on their porch stoops to cool off and socialize with friends. Very close to the colorful Key West Cemetery, this classic Conch cottage embodies the essence of rustic charm while offering modern ...

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Property Type

Key West House

"Best hidden treasure in Key West!"
Reviewed July 11, 2019

We absolutely LOVED it! One Havana Lane will be forever in our best memories of our time spent in the Keys! The pool was perfect and we enjoyed the few entertaining iguanas. The house was laid out so that ...

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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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Coconut Cabana

3 BR | 2 BA | Sleeps 6 | Quick View

$425

per night

View Details

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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Townhouse, 1/2 Block from Duval in Old Town. Monthly Only**

$75

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • 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

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Catherine House

2 BR | 2 BA | Sleeps 4 | Quick View

$309

per night

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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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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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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

$269

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 - 2 Base rate room and tax- see listing info. But Before you book any dates! see listing -FAQ's, travel insurance Notes + Additional info for clarity- good knowledge - + no surprises, no refunds, 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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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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Southard Queen Conch Suite

2 BR | 2 BA | Sleeps 4 | Quick View

$280

per night

View Details

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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Artist's House Duval Square

2 BR | 2 BA | Sleeps 6 | Quick View

1

$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

"It was perfect"
Reviewed January 16, 2020

We really enjoyed the location. There were restaurants right at the door. Security was great. When u walked up the stairs to the condo it felt like u were in ur own little world. On duval but up above ...

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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 Balcony Rentals - Suite Mischief

1 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 1 miles to Fort Zachary Taylor, Higgs Beach, Smathers Beach

Key Amenities

  • Air Conditioning
  • Full 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

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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!