Key West Vacation Rentals

(74 rentals)
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Key West Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

$1784

avg/night

$1,784
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pool
  • WiFi

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

Featured review

"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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Key West Condo
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms
2 reviews

$1043

avg/night

$1,043
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

Keys to Paradise: A 5-Star Beachside RetreatThis beautiful 3-bedroom, 2-bath condo is located in a private beachside resort, conveniently close to Old Town Key West and just steps away from the beach. It's also an easy bike ride to all that Key West has to offer.Keys to Paradise is a direct ...

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Property Type

Key West Condo

Featured review

"Absolutely Amazing"

The condo was beautiful, offering stunning views of the harbor and boat races. It was conveniently located near Duval Street but far enough awayeace and quiet. Alice and Charli to enjoy some pe were fantastic ...

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Key West Condo
Studio | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 0 bedrooms, 1 bathroom
5 reviews

Distance to beach: 0.5 miles to South Beach

$259

avg/night

$259
avg per night
View Details

Key Amenities

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

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

Featured review

"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 West Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$164

avg/night

$164
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

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 West Mobile home
2 BR | 2 BA | Sleeps 7 | Quick View
Sleeps 7, 2 bedrooms, 2 bathrooms
1 review

$200

avg/night

$200
avg per night
View Details

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Located just 10 miles from Key West on beautiful Geiger Key. Cozy and comfortable canal front getaway perfect for the fisherman eager to explore the crystal blue waters of the Keys or the person wanting to experience all that Key West has to offer. Deep water with quick direct access to Atlantic Ocean. ...

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Property Type

Key West Mobile Home

Featured review

"Awesome Key West Getaway-We'll be back!"

This location is amazing just minutes to downtown Key West and a few minute idle by Boat to the Ocean(we brought our own boat and docked out back!) Had fun Snorkeling in crystal clear water, and even tried ...

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Key West Cottage
2 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1 bathroom

$400

avg/night

$400
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Perfectly situated in Old Town Key West. This quaint pool cottage is perfect for a couple with occasional visitors. beautifully decorated with amazing outside space to enjoy our island breezes and cool off in our pool. This beautiful property has been well maintained with a newly renovated Kitchen. Queen ...

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Property Type

Key West Cottage

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Key West House
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$186

avg/night

$186
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

Welcome to our paradise please enjoy our modern 1400 square foot 2 bedroom 2 bathroom totally renovated condo. This condo is one of the nicest you will find in the complex. There is music available in every room even the master bathroom. We have thought of everything there is even a flat screen tv in ...

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Property Type

Key West House

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Key West Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$500

avg/night

$500
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

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 West House
3 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 3 bathrooms
1 review

$1390

avg/night

$1,390
avg per night
View Details

Key Amenities

  • Pool
  • WiFi

About this property

3 Bedrooms, 3 Full Bathrooms, Backs to Community Pool, Sleeps up to 6This home was built in 2004. It has been well maintained and is ready for you to enjoy on your next vacation in Key West. You can stay in this 3 Bedroom home for less than the cost of one room in some local hotels. There is a nice ...

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Property Type

Key West House

Featured review

"Southern Charm with a boat slip!"

Our family had a wonderful time staying in this townhome style rental. We relaxed and enjoyed the views of the bay and marina from the back porch. The boat slip worked great for our rental boat. This ...

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Key West Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$550

avg/night

$550
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pool
  • WiFi

About this property

Fantastic 2rd Floor Ocean View Condominium at 1800 AtlanticCompletely renovated, this unit features an entirely custom tiled unit. Fully equipped kitchen, washer dryer, high-speed internet and cable.Primary bedroom with a King, 2 twins in the guest bedroom and a queen sleeper sofa in the living ...

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Property Type

Key West Condo

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Key West Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$1860

avg/night

$1,860
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Blue Haven: An Exquisite Oceanfront Penthouse – Complete Remodel with Direct Ocean Views and Massage Chair – Premier Unit on Property Blue Haven is the premiere property in this complex. This luxury penthouse condominium is unbelievable. You will not want to leave. Nestled on the shore of ...

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Property Type

Key West Condo

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Key West Condo
3 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 3 bathrooms

$742

avg/night

$742
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

3 Bedroom, 3 Bath Partial Ocean ViewAtlantic Sunrise is the only 3-bedroom, 3-bath unit in the complex, spanning approximately 2,000 square feet and accommodating up to 8 guests. It features two master suites, each with a king bed, while the third bedroom has 2 twin beds. Additionally, there is a ...

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Property Type

Key West Condo

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Key West Apartment
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 1 bedroom, 1 bathroom

$150

avg/night

$150
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

Galveston Porches Stylish one bedroom apartment in the heart of Old Town. Totally renovated and beautifully decorated. Everything you will need for your perfect Key West extended stay. 1 assigned parking space with the apartment. Full kitchen and washer dryer, Central AC and wifi access. The owners have ...

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Property Type

Key West Apartment

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Key West Apartment
2 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1 bathroom

$309

avg/night

$309
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

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 West House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

$333

avg/night

$333
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • WiFi

About this property

3-Bedroom, 1.5-Bath Historic Conch House in the Heart of Old Town Key WestThis charming Conch house features a queen bed in the master bedroom, a queen bed in the first guest bedroom, and two queen beds in the second guest bedroom. The kitchen has been beautifully renovated, and there is a wonderful ...

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Property Type

Key West House

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Key West House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms
2 reviews

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

$217

avg/night

$217
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

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

Featured review

"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 West Condo
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 1 bedroom, 1 bathroom
3 reviews

$322

avg/night

$322
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

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

Featured review

"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 West Condo
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms

$1904

avg/night

$1,904
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Private pool
  • WiFi

About this property

Tom's Oceanfront Penthouse is a spectacular oceanfront unit features 3 bedrooms and 2 bathrooms in a prime location within the complex. It is conveniently situated near the elevator and offers secure covered parking in the garage for vehicles under 6 feet 4 inches in height.Spanning approximately ...

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Property Type

Key West Condo

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Key West Condo
3 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2.5 bathrooms

$1786

avg/night

$1,786
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pool
  • WiFi

About this property

Mar Y Sol is a beautiful oceanfront condominium featuring three bedrooms and two and a half bathrooms, located at 1800 Atlantic. Enjoy the balmy breezes from your 60-foot private wrap-around balcony, which offers a stunning view of the Atlantic Ocean.The condominium includes renovated kitchens and ...

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Property Type

Key West Condo

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Key West Condo
2 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1 bathroom
2 reviews

$309

avg/night

$309
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

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

Featured review

"Great vacation rental!"

We really enjoyed the unit at Shipyard Condos. Very clean and well equipped. Walking distance to local restaurants and very convenient with a dedicated parking place. Pool was nice too. There were only ...

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Key West Condo
2 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1 bathroom
1 review

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

$397

avg/night

$397
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

JUNE SPECIAL. $300 OFF MY WEEKLY RATE. So 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, ...

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Property Type

Key West Condo

Featured review

"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 West Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

$1860

avg/night

$1,860
avg per night
View Details

Key Amenities

  • Oceanfront
  • Pool
  • WiFi

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

Featured review

"Vacation"

Very thing was good the condo was perfect and the pool was great the parking was close to the elevator

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Key West House
4 BR | 3.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3.5 bathrooms

$421

avg/night

$421
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Treat yourself, your family and friends to a grand Key West home ideal for an extended stay on the island. This wonderful home boasts 4 bedrooms, 3-1/2 bathrooms, a new modern kitchen, a living room, a dining room, an office nook, a 270 degree wrap around porch, a pool deck and a heated dipping pool/large ...

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Property Type

Key West House

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Key West Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Hot tub
  • Pool
  • WiFi

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 West Vacation Rentals

Key West Weather

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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 74 Key West acation rentals available on FloridaRentals.com. From house rentals to condo 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 $133 per night with an average price per night of $397.

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 33 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 17 oceanfront rentals in Key West available on FloridaRentals.com. Use our filters to search and book yours today!