Key West Vacation Rentals

(81 rentals)
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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

This wonderful property has just received a major face lift and has been beautifully renovated. King bed in the master bedroom, 2 twins in the 2nd bedroom that can be converted to a King .memory foam luxury queen sleeper in the living room will comfortably accommodate your party.Watch the sunrise ...

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Property Type

Key West Condo

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

This delightful 2 Bedroom Cigar Maker's Cottage at 1008 Whitehead was built in the 1880's, where there was once a Cigar Factory across the street on Truman Ave. It's history also includes the previous owner, David Kaufelt, a well-known Key West writer. Quaint and charming, with a view ...

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Property Type

Key West Apartment

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront

About this property

Beautifully appointed 3rd floor ocean-view condo at the prestigious 1800 Atlantic Complex in Key West. This unit is an extra large floor plan with a nice ocean view. This property features 2 queen beds in the master bedroom and a king in the guest bedroom. Full size washer/ dryer and 1 assigned private ...

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Property Type

Key West Condo

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

About this property

3 bedroom, 2 bath in private Beachside Resort, yet close to Old Town Key West, just steps to the beach, just a bike ride to all that Key West has to offer. Keys to Paradise will not disappoint. Direct ocean front condo that features 1 master suite with a king size bed, jacuzzi and luxurious walk in shower. ...

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Property Type

Key West Condo

"Amazing, Heaven, Can't wait to go back"

THE KEYS TO PARADISE CONDO IS SO WONDERFUL. The view is Breathtaking. The condo is well kept and clean. It has beautiful furnishings and distinctive artwork on the walls. The condo is in the perfect location,facing ...

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2 BR | 2 BA | Sleeps 6 | Quick View

2

Distance to beach: 800 yards to Ft. Zachary Taylor State Park

$379

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Rentals by owner

About this property

Envision yourself relaxing in a beautiful wood framed conch cottage with overhead fans lazily turning below the sloping tin roof in the heart of Old Town in Key West. This is the best value in Key West as it is no cookie cutter small rental condo but a private town home (one of only seven available for ...

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Property Type

Key West Cottage

"Island Magic"

Great location! Great people! Very nice place that gave us memories of a lifetime! I’ll be returning soon!

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Key Amenities

  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool

About this property

Beautifully renovated 2 bedroom 2 bath condo at the exclusive 1800 Atlantic Condo's. Each bedroom has a king size bed and plenty of closet space. Both have access to the private balcony that faces the nature preserve in a quiet tranquil location at the property. The unit is located across from the ...

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Property Type

Key West Condo

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

A gorgeous 3 bedroom / 2 bathroom vacation rental home with high vaulted ceilings and french doors that bring the outside in. The backyard features a large covered patio and an in-ground heated swimming pool, perfect for relaxing anytime of the year. New outside table with seating and gas bbq grill ...

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Property Type

Key West House

"Wonderful Retreat"

This house was truly a private haven. It was so quiet and peaceful but yet so centrally located in the island. Quick golf cart rides to Duval and local shops plus near beaches. The house was very neat and ...

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen

About this property

Fantastic 3rd floor ocean-view condominium. Unit features a full size fully equipped kitchen. Washer dryer. King in the master bedroom, 2 twins in the guest bedroom and a queen size sleeper sofa in the living room.. Totally renovated fall of 2017, Custom Kitchen and bathrooms. Tiled throughout.All ...

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Property Type

Key West Condo

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

About this property

Bluegrass Seabbatical is a Spectacular 3 bedroom 2 bath oceanfront condominium at 1800 Atlantic. Enjoy the incredible ocean front view from all 3 bedrooms and the living room. This property is close to 2000 sq feet and can be your fantastic home away from home. Available for extended stays during the ...

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Property Type

Key West Condo

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

About this property

Beautifully renovated 2 bedroom 2 bath ocean view condo at 1800 Atlantic available for monthly rentals. King in the master, queen in the second bedroom and a double pull out in the living room. The unit is tiled throughout. The bathrooms have been nicely upgraded and did we mention the view from Poolside ...

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Property Type

Key West Condo

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront

About this property

Beautifully renovated 2 bedroom 2 bath penthouse overlooking the Atlantic Ocean and Smathers Beach. Fabulous kitchen with stainless appliances and granite counter tops. Enjoy the amazing sunrise from the balcony of Awaken to Morning reflections. Recently renovated the master suite has a luxurious walk ...

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Property Type

Key West Condo

"beautiful ocean view condo"

condo was very clean and on the top floor with vault ceilings. Check in process was seamless as well as checkout.

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2 BR | 2 BA | Sleeps 4 | Quick View

$158

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool

About this property

Luxury island resort style living in Key West. 1800 Atlantic offers a private sandy sunning beach, Olympic style pool, gym, three tennis courts (one is clay), fitness center, community clubhouse, picnic areas and more. This condominium is updated and turnkey . Open living and dining spaces, eat-in kitchen ...

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Property Type

Key West Condo

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool

About this property

Anchor Drop 307 is an ocean view totally renovated top of the line unit. We have a brand new King mattress in the master bedroom, 2 twins in the guest bedroom (which can also be converted to a King bed upon request) and a queen sleeper sofa in the living room.Anchor Drop is beautifully renovated ...

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Property Type

Key West Condo

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen

About this property

Casa Papa Del Mar Two Bedroom Premiere Ocean View With a complete 2023 renovation, the décor is inspired by the life and travels of “Papa” Earnest Hemingway. This is a beautiful top floor two-bedroom ocean-view unit at 1800 Atlantic condos. It has pristine ocean-views from all rooms ...

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Property Type

Key West Condo

"SIMPLY DIVINE"

BEST PLACE WE EVER STAYED AT. THERE WERE FOUR OF US. BEAUTIFUL LOCATION. SO COMFORTABLE. KIRK WAS SO HELPFUL TO HELP US GET SETTLED IN. ALL THE TREATS OF HOME. VIEW INCREDIBLE. WANTED OUR TIME THERE TO ...

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3 BR | 2 BA | Sleeps 8 | Quick View

2

Distance to beach: 2 miles to Smarthers Beach and Higgs Beach

$175

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

This home sits in Key Lime Grove Subdivision which I was born and raised in. It is a neighborhood rich in history and conveniently located on the Island. This home welcomes you with a white picket fence! It has been nicely upgraded down to the wood floors and crown molding trim. Open living room and ...

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Property Type

Key West House

"Great getaway"

This house has everything we need. The best part is the private backyard with lovely gardens and a pool and an outdoor shower. Inside is also wonderful with 3 bedrooms, a big kitchen, a dedicated office, ...

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Key Amenities

  • Air conditioning
  • Kid friendly

About this property

This is a beautifully renovated high end luxurious monthly rental at 1800 Atlantic. The moment you walk in you will appreciate the attention to detail. Enjoy the lovely views of the complex and Atlantic ocean from the private balcony. The master bedroom suite has a king size bed. The renovated bathroom ...

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Property Type

Key West Condo

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen

About this property

Lovely 2nd floor unit. Beautifully renovated, This unit has luxurious finishes. Both bedrooms and the living room open onto the 40 ft private balcony that has views of the nature preserve and Atlantic ocean. Fully equipped with all the modern conveniences you would need for an enjoyable vacation. This ...

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Property Type

Key West Condo

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

3 Bedroom 3 bath Partial Ocean Viewhis is the only 3 bedroom 3 bath unit in the complex. The unit is about 2000 sq feet. It will accommodate 8. 2 Master suites each with a king bed, The 3rd bedroom has 2 twin beds and there is a queen sleeper sofa in the living room. Large private balcony opens off ...

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Property Type

Key West Condo

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Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

About this property

A beautiful historic cottage, in the complex of Sirena Blue=Blue Mermaid, located in a great area of old town Key West, within walking distance of Duval St. and beaches, available to rent for short term. Recently fully remodeled May of 2023. High end furnishings. 2 bedrooms or an office and bedroom, ...

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Property Type

Key West Cottage

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool

About this property

Atlantic Paradise Found C232 at 1800 Atlantic Condominiums is a beautifully appointed spacious condominium with a lovely view of the Atlantic OceanAtlantic Paradise Found is one of the premium luxury rental properties at 1800 Atlantic Complex. Beautifully decorated with higher end furnishings. Top ...

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Property Type

Key West Condo

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool

About this property

Great top floor 2 bedroom Condo on the Atlantic ocean with views of the ocean and courtyard. The property has a full size fully equipped kitchen with a washer/dryer. Both bedrooms and the living room have impact doors open to your private balcony. There is a King bed in the master bedroom and a queen ...

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Property Type

Key West Condo

"New Year’s vacation"

Wanted to go to the Florida Keys, but this place popped up several times during my search. I’m so glad I chose this place. Breathe taking is the best word to use. Beautiful beach (7miles of it), nice ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

The k2 escape is the very best in indoor/ outdoor living. The full size heated pool is surrounded by lush mature tropical landscaping with your very own backyard poolside sandy beach. Tiki hut bar, outside cabana living room, zen outdoor shower and sun deck enhance this Centrally located Key West retreat. ...

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Property Type

Key West House

"Highly Recommend!"

My husband and I recently rented this home for a month and we couldn’t have enjoyed it more! Let me start with our favorite space… the backyard. From the heated pool, to the outdoor shower, guest house, ...

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Studio | 1 BA | Sleeps 2 | Quick View

5

Distance to beach: 0.5 miles to South Beach

$223

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Rentals by owner

About this property

This Simonton Studio is neat, sweet and complete. * Pet friendly for additional flat fee of $90 *Cleaning fee of $70 is additional. * WiFi included * King size bed * Outdoor table and two chairs * spacious shower * excellent loctaion for walking Old Town * Duval Loop bus passes this adress ...

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Property Type

Key West Condo

"Fantasic studio unit and a great location."

Very clean and well-equipped unit. It comes with cable tv and great internet. It is a great location, one block from Duval st.

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Key Amenities

  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

About this property

Beautiful top floor ocean front 2 bedroom 2 bath condo at La Brisa in Key West. The property has a queen bed in each bedroom and the master has an en suite bathroom. Totally renovated Kitchen and a balcony with amazing Sunrise Views across Smathers Beach. The living room has a flat screen smart TV ...

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Property Type

Key West Condo

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

About this property

This is a spectacular 3 bedroom 2 bath ocean front unit in a premier location in the complex. Conveniently located close to the elevator with covered secure parking in the garage for a vehicle under 6ft 4 inches. Around 2000 sq feet, each bedroom and living room have sliding glass doors that open onto ...

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Property Type

Key West Condo

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

About this property

MAR Y Sol is a Beautiful 3 Bedroom Two and a half Bath ocean-front condominium at 1800 Atlantic. Enjoy the balmy breezes from your 60 foot private wrap around balcony with a fabulous view of the Atlantic ocean.Mar Y Sol has renovated kitchen and bathrooms.Mar y Sol is in high demand so during ...

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Property Type

Key West Condo

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • 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 *accommodates 2 adults only * WiFi inlcuded * Parking included *Central AIr Conditioning * Check-out cleaning is $120 * This is not a hotel; it is a privately owned condo facing the ...

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Property Type

Key West Condo

"The perfect location that has everything..."

Just finished a 2 week stay and I have been renting from Pam for over a decade and she continues to make a great condo even better with her constant upgrades to the unit and she is a wonderful host. The ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

3 Bedroom 1 & half bath Historic Conch House in the Heart of Old Town Key West Queen in the Master, 1 Queen in 1st guest bedroom and 2 queen's in the 2nd guest bedroom. Nicely renovated Kitchen & Wonderful Outside Living Area with Hot Tub & Sun Deck. There is an outside shower and full ...

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Property Type

Key West House

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Key Amenities

  • Air conditioning
  • Kitchen

About this property

Best Deal in Truman Annex - Céad Míle Fáilte (Irish) 2 Bedroom 1 bathroom Condo - sleeps up to 5Here's Céad Míle Fáilte to friend and to rover That's a greeting that's Irish as Irish can be It means you are welcome a thousand times over Wherever ...

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Property Type

Key West Condo

"Perfect location! Beautiful property!"

This was an amazing spot for a vacation! The condo was walking distance to everything! Beautiful beaches, amazing parks, Hemingway House, Duval Street, the aquarium. The property within the gated community ...

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2 BR | 1 BA | Sleeps 4 | Quick View

1

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

$368

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Private pool
  • Rentals by owner

About this property

HALF PRICE. JUST HAD A CANCELLATION TWO WEEKS JUNE 1-15 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 ...

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Property Type

Key West Condo

"A touch is all you need…"

A touch of Cuba was the perfect little spot. We are now spoiled to the conveniences of renting direct with the owner, having Class A rated efficiencies, Beach, Bikes, Pool, very quiet and well kept area ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Rentals by owner

About this property

Escape to the laid-back charm of Key West with The Gumbo Limbo Cottage, a beautiful and beachy vacation rental. Nestled in the heart of the island, this charming 1933 shotgun house has been impeccably restored and uniquely decorated, creating a tranquil and inviting atmosphere for your month-long getaway.As ...

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Property Type

Key West Cottage

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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's vacation rentals call to beach bums and other likeminded travelers 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!


FAQ

How many vacation rentals are there in/around Key West?

There are 81 Key West acation rentals available on FloridaRentals.com. From condo rentals to house rentals and beyond, find a unique vacation rental for you to enjoy a memorable vacation in Florida.

How much does it cost to rent a vacation rental in Key West?

There are vacation rentals available in Key West for as low as $117 per night with an average price per night of $400.

Can I find a vacation rental in Key West?

Yes, you can find vacation rentals in Key West close to Dry Tortugas National Park, Ernest Hemingway Home, and Ley West Butterly and Nature Conservatory. Don't forget to stop in to Mallory Squrre or Duval Street.

Do any vacation rentals in Key West have a pool?

Yes, there are 29 vacation rentals with a pool in Key West on FloridaRentals.com. Search using our filters and book one for your next vacation!

Are any Key West vacation rentals on the ocean?

There are 20 oceanfront rentals in Key West available on FloridaRentals.com. Use our filters to search and book yours today!