Key West Vacation Rentals

(75 rentals)
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 ...

View all property information

Property Type

Key West Condo

Show less

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 ...

View all property information

Property Type

Key West Condo

Show less

Truman Annex Shipyard Condo-1BR/1BA w/Loft

$185

per night

View Details

Key Amenities

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

About this property

1BR/1BA w/ Loft in Truman Annex close to Ft Zachary Taylor beachThis condo easily accommodates both couples and small families with its unique layout. It features a private bedroom, loft area and sleeper sofa for flexible sleeping accommodations. Located within the gated community of Truman Annex, ...

View all property information

Property Type

Key West Condo

Show less

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 ...

View all property information

Property Type

Key West House

Show less

Southard Horse Conch Suite

1 BR | 1 BA | Sleeps 2 | Quick View

$202

per night

View Details

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.

View all property information

Property Type

Key West House

Show less

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 ...

View all property information

Property Type

Key West Condo

Show less

A Touch of Paradise.. pool, close to beach & Duvall. 2 FULL baths, 7 night Min.

2 BR | 2 BA | Sleeps 5 | Quick View

Distance to beach: 0.1 miles to Ft Zachery Taylor Beach

$242

per night

View Details

Key Amenities

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

About this property

Best Location!! .. ...This Key West Getaway, with beachy decor, is so close to all the local Key West bars & restaurants and museums, just take a short stroll or jump on a bike and a way you go...google KeyWest296! 1 block to Green Parrot Music bar or Blue Heaven restaurant/bar/music , and only 2 ...

View all property information

Property Type

Key West Condo

Show less

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

Show less

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 ...

View all property information

Property Type

Key West Condo

Show less

Tropical Escape

2 BR | 2 BA | Sleeps 5 | Quick View

Distance to beach: 2 miles to Higgs/Smathers

$227

per night

View Details

Key Amenities

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

About this property

This luxurious condo/hotel features a wonderful tropical interior design. It has 2 spacious bedrooms (one room with a king-size bed and a full bath and one queen-size bed with a full bath. The unit has a fully equipped kitchen that looks onto the living room with a queen-size sofa sleeper. The patio overlooks ...

View all property information

Property Type

Key West Condo

Show less

Villa Paradiso

3 BR | 3 BA | Sleeps 6 | Quick View

$425

per night

View Details

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 ...

View all property information

Property Type

Key West House

Show less

La Brisa 405E Sea Orchid

2 BR | 2 BA | Sleeps 4 | Quick View

$203

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly

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 ...

View all property information

Property Type

Key West Condo

Show less

Vista Fresco

2 BR | 2 BA | Sleeps 4 | Quick View

$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 ...

View all property information

Property Type

Key West Condo

Show less

Luxury Shark Key waterfront home with beach 10 minutes from downtown Key West

$253

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Oceanfront
  • Private Pool
  • Rentals by Owner

About this property

Rentals are per calendar month only. WE HAVE A 28 DAY MINIMUM STAY PER MONROE COUNTY LAW, WE WILL NOT RESPOND TO REQUESTS FOR SHORTER PERIODS! 3 bedrooms 4 bath, sleeps 6 to 8, spectacular open water sunsets Enjoy the amenities of a luxury hotel in the privacy of our home located on the sunset side ...

View all property information

Property Type

Key West House

Show less

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 ...

View all property information

Property Type

Key West House

Show less

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 ...

View all property information

Property Type

Key West Condo

Show less

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 ...

View all property information

Property Type

Key West House

Show less

Key West Seashell Cottage - private home with spa, located on a quiet lane.

1 BR | 1 BA | Sleeps 2 | Quick View

Distance to beach: 0.5 miles to South Beach

$186

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Rentals by Owner

About this property

Forget that 'been there, done that' hotel room; enjoy the comforts of home in Old Town Key West at the Seashell Cottage. Located on a quiet lane, just 1 block to Duval Street, walk to the grocery store, restaurants, museums, beach, and 'Sunset Celebration'.The original local artwork throughout the ...

View all property information

Property Type

Key West Cottage

Show less

Casa Atlantica One Bedroom

1 BR | 1 BA | Sleeps 2 | Quick View

$201

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 ...

View all property information

Property Type

Key West Condo

Show less

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.

View all property information

Property Type

Key West House

Show less

Bali Hideaway

Studio | 1 BA | Sleeps 2 | Quick View

$203

per night

View Details

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 ...

View all property information

Property Type

Key West Studio

Show less

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 ...

View all property information

Property Type

Key West Condo

Show less

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 ...

View all property information

Property Type

Key West House

Show less

Beach Club #304

2 BR | 2 BA | Sleeps 4 | Quick View

$275

per night

View Details

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 ...

View all property information

Property Type

Key West Condo

Show less

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 ...

View all property information

Property Type

Key West Apartment

Show less

Expand map | Close map
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!