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Key West Rentals

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Key West Rentals

About Key West

336 house rentals

$277

1/2 Block to Duval, World of its own -Nassau Suite

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Our wedding family stayed here awesome” Fabulous. Clean roomy pool fantastic. Short walk to schooners Wharf Both inside and outside area were excellent

$277

1 / 17

$326

Steps to Duval, Old Town Charm -Grand Bahama Suite

Key West apartment

3 bedrooms / 2 bathrooms / sleeps 8

“Can't wait to return” We loved staying at the Grand Bahama suite. It was spacious, clean and centrally located just a street from all the action. We loved the courtyard and pool. I was a little concerned about parking but it worked out fine for us.

$326

1 / 11

$212

Casa Del Sol, a Key West Vacation (Truman Annex)

Key West house

2 bedrooms / 3 bathrooms / sleeps 6

“awesome” the condo was beautiful. very good location. 2 suggestions. the grill did not have gas . the bed that opens up to king. not so much, mattress is 2 different heights and slides if you try to sleep on it. very very uncomfortable.

Responds fast! avg. 2 hours 39 minutes

$212

1 / 26

$159

Sunrise At Seaside Condo 2 bedroom 2 bath

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 5

“Exactly what we needed.” Owner responded in timely manner and was pleasant and answered all questions. The unit was easy to find and close to the airport. We worried about airport traffic noise interfering with sleep, but never heard them inside the

$159

1 / 12

$124

Spectacular Atlantic Ocean View Condo (MONTHLY)

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Amazing Views And A Great Condo” My wife and I stayed here on our honeymoon and were absolutely 100% pleased with the condo. I have to honestly say it was the nicest condo either of us have stayed in. The view was amazing and the patio was very tranqu

$124

1 / 26

$257

Best Location, 1/2 Block to Duval, Bimini Suite

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 5

“Perfect!” This was the perfect size suite for 4 adults, with a little pool oasis right off our doorstep, in the center of it all without the noise of Duval. Loved every second of my stay!

$257

1 / 17

$332

Key West Island Vacation

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

$332

1 / 14

$100

PARKING,2bd/2bth,20yrd TO DUVAL,FREE OLD TOWN SHUTTLE,MAJOR ATTRACTIONS NEARBY

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 30 minutes

$100

1 / 41

$247

Center of It All - Paradise Island Suite

Key West apartment

2 bedrooms / 1 bathroom / sleeps 6

“Great location in the heart of Old Town Key West, just a block off Duval..” We stayed in the Paradise Suite. Great front porch to hang out on, pool in back with pergola for lounging. Place was set up perfect, pool towels hanging by the door, bathroom

$247

1 / 14

$475

Havana Moon ~ Weekly Rental

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

“Great spot, great pool” This place was great for my spouse & me and grown daughter & friend to stay during our visit to Key West this summer. the two bedrooms are big, comfortable and have their own bathrooms. The kitchen is well equipped; there is no

$475

1 / 11

$100

Private and Immaculate 2 Bedroom Home with Private Fenced Yard

Key West house

2 bedrooms / 1 bathroom / sleeps 4

$100

1 / 13

$360

Atlantic Oasis Penthouse on the Ocean C420

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

$360

1 / 54

$372

Key West Beachfront Luxury 2/2 Condo A212 No Hurricane Damage

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Perfect place to experience Key West” This is a lovely condo with a tropical, quiet view. Many extras are included: beach towels, bikes, and kitchen supplies. The pool area was our favorite spot, and we had coffee every morning on the balcony with cha

Responds fast! avg. 1 hour 12 minutes

$372

1 / 39

$229

Coconut Beach

Key West apartment

1 bedroom / 2 bathrooms / sleeps 4

$229

1 / 6

$88

1BR Restored Conch House w/ Pool & Deck

Key West house

1 bedroom / 1 bathroom / sleeps 3

$88

1 / 24

$360

Hemingways Atlantic Retreat C339

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

$360

1 / 50

$288

Shelleys Rooftop Hideaway

Key West apartment

2 bedrooms / 3 bathrooms / sleeps 4

“great place to stay” Close to every thing in Key West Walking distance to all of down town stores and bar my personal favorite

$288

1 / 15

$476

By The Beautiful Sea ~ A Key West Beach Front Condo ~ Weekly Rental

Key West house

3 bedrooms / 2 bathrooms / sleeps 6

$476

1 / 24

$165

Elegant, upscale home w/ heated pool moments from beach!

Key West house

2 bedrooms / 3 bathrooms / sleeps 6

“ISLAND TIME” What a wonderful find! I have stayed on Sunset Key for many years now. This is the first time I experienced staying in a home located on Sunset Key. What a huge difference. First of all I traveled with three adults and two children. The l

Responds fast! avg. 2 hours 30 minutes

$165

1 / 29

$178

Truman Annex Shipyard with Tropical Garden

Key West apartment

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 1 hour 40 minutes

$178

1 / 8

$1,140

Tropical ~ Tranquility ~ Weekly Rental

Key West house

4 bedrooms / 4 bathrooms / sleeps 8

$1,140

1 / 17

$164

KeyWestStay.com

Key West apartment

2 bedrooms / 1 bathroom / sleeps 4

“A great spot just outside Key West” If you're at all like me, you like places that are close to where you want to be but not in the middle of a busy area. This place is exactly that. A quick 7 minute drive puts you at the entrance to Key West. For

$164

1 / 17

$243

Key West Condo close to the Ocean

Key West condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 28 minutes

$243

1 / 26

$107

Flagler Station

Key West house

3 bedrooms / 2 bathrooms / sleeps 8

“Little gem is right!” Can't say enough good about this place! Newly renovated 1800 square foot home;3 be king in master, queen and double Beds in third room. Loved the small private pool and gourmet kitchen, much thought, love and detail went into mak

$107

1 / 25

$248

Key West Gulf front Home with private dock and pool.

Key West house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 0 minutes

$248

1 / 29

$137

LA DOLCE VITA, OLD TOWN KEY WEST!! STEPS TO DUVAL!! SLEEPS 2-4, 3 BLKS TO BEACH

Key West apartment

1 bedroom / 1 bathroom / sleeps 4

“Fantastic Stay!” My husband and two sons (21 & 24) stayed in this condo over Christmas. This was our first stay in Key West and we wanted to be close to everything, but yet not right on Duval St. This location was perfect; literally a stones throw a

Responds fast! avg. 2 hours 21 minutes

$137

1 / 69

$305

A Touch Of Havana In Key West

Key West condo

2 bedrooms / 1 bathroom / sleeps 4

$305

1 / 19

$198

Isle Of View II

Key West boathouse

2 bedrooms / 2 bathrooms / sleeps 6

$198

1 / 24

$300

Botanical Island Delight C120

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 4

$300

1 / 46

$237

Island Oasis Garden Home ~ Weekly Rental

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

$237

1 / 13

$360

Atlantic Paradise Found C232

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

$360

1 / 48

$227

The Banyan Resort at Key West

Key West apartment

2 bedrooms / 1 bathroom / sleeps 6

“Wonderful week at The Banyan Resort!!” My husband and I recently stayed in a 2 bedroom/1Bath unit at The Banyan Resort and we were extremely pleased with everything!! Everyone we encountered from the front desk, housekeeping, grounds personnel and oth

$227

1 / 6

$325

Coral Hammock Beautiful Poolside Home

Key West house

3 bedrooms / 3 bathrooms / sleeps 6

$325

1 / 32

$225

Key West Florida Beachfront Condo

Key West condo

2 bedrooms / 2 bathrooms / sleeps 6

“Better than the photos” Condo is perfectly located at the beach. Well designed for easy living both inside and out. Great advise on where to visit and eat thanks

Responds fast! avg. 3 hours 41 minutes

$225

1 / 22

$156

Coral Garden

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

“Good Rental” Basic rental. Clean. As advertised. Did not like one car limit as there were not many places outside property to park. Understand this is HOA policy not ownwers.

$156

1 / 23

$425

Valhalla

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

“Best Vacation Ever” This home is really lovely and larger than we expected, having never been in a 'shotgun house'. Kitchen is small but fully functional w dishwasher etc. The house has everything you need (beach towels, laundry detergent, TP, etc)

$425

1 / 25

$765

The Water's Edge

Key West house

3 bedrooms / 4 bathrooms / sleeps 8

“Perfect for a Memorable Key West Experience!” My family and I absolutely loved staying in this beautiful Key West home. Located in Truman Annex (a quiet, private community in Old Town Key West), the location is perfect for whatever you wish to do duri

$765

1 / 25

$331

Key West Sunset Sojourn ~ Monthly Rental

Key West house

2 bedrooms / 3 bathrooms / sleeps 6

$331

1 / 40
Viewing 38 of 336

About Key West

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Located closer to Cuba than to Miami lies the island of Key West. Since its founding in the early 1800s, the island's year-round balmy, subtropical climate and unique "anything goes" flavor have made it an ideal visitor destination.

Over the years, the island has been seasoned by the rich American and Cuban culture of the 1800s, sweetened by the unabashed romantic appeal of its natural beauty, and energized by the world-renowned artistic talents of Ernest Hemingway, Tennessee Williams, Elizabeth Bishop, Robert Frost and Jimmy Buffett among others.

Residents and visitors to the island actively participate in sightseeing, touring museums, outdoor and maritime activities, and shopping by day. Later, they become part of the sunset celebration held each evening at Mallory Square, when tightrope walkers, jugglers and animal acts strive to top a more captivating performer - the fiery sun settling into the Gulf of Mexico.

The cobblestone streets of Old Town are shaded by beautiful banyan trees and lined with colorful, picturesque homes that reflect the architecture of past eras. Whether exploring these quieter streets or rocking to the vibrant beat of renowned Duval Street, visitors can savor an abundance of restaurants offering breakfast, lunch and dinner, most incorporating the Keys' fresh indigenous seafood.

Surrounding Key West are waters ranging from pastel teals to jewel-toned blues. They are home to one of the world's largest coral reefs and a bounty of shipwrecks, which make for exotic diving and snorkeling. Both novice and skilled anglers can challenge themselves to fish the Atlantic Ocean or Gulf of Mexico, targeting game fish like tarpon and marlin.

At night, the isolated island's sky is filled with stars that create a backdrop for entertainment options including jazz clubs, piano bars, drag shows and saloons. In addition, area playhouses feature Broadway-quality performances.

The tiny island has more than a dozen historic museums showing that the city's roots go deeper than picturesque palm trees and enchanting sunsets. One of the most popular is the Ernest Hemingway Home and Museum, which was the legendary author's home during the 1930s and is still home to his famous lineage of six-toed cats. The Mel Fisher Maritime Museum houses the richest single collection of 17th-century maritime and shipwreck antiquities in the Western Hemisphere, including the treasure of the Spanish galleon Nuestra Señora de Atocha.

Though the city is pedestrian friendly, there are two trolleys visitors can take as a method of transportation and for a tour highlighting the city's landmarks, restaurants, bars and historic sites.

Key West can be reached by flying into Miami International Airport and driving from the mainland down the magnificent Overseas Highway - featuring 42 bridges over open water and designated an All-American Road under the National Scenic Byways program - or by ferry from points on Florida's west coast.

The island is also accessible via Key West International Airport, which is serviced by American Eagle, Delta/Express Jet, United/Silver Air, US Airways and others.

Information provided by: The Monroe County Tourist Development Council

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