Vacation Rentals & House Rentals in Key West

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475 house rentals

(19) Excellent 

26

Spectacular Atlantic Ocean View Condo (MONTHLY)

Florida Keys / Key West

Key West apartment

2 6 28 nights min

  • 2 bedrooms
  • sleeps 6
  • 28 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“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
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Price per night from

$330

Price per night from

$330

(3) Very Good 

12

Conch Haven Old Town 1/1 MONTHLY Rental

Florida Keys / Key West

Key West apartment

1 4 30 nights min

  • 1 bedroom
  • sleeps 4
  • 30 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Car not necessary

Price per night from

$93

Price per night from

$93

(63) Excellent 

26

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

Florida Keys / Key West

Key West house

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“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.
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Price per night from

$228

Responds fast!
avg. 1 hour 13 minutes

Price per night from

$228

(65) Very Good 

Certificate of Excellence

11

Steps to Duval, Old Town Charm -Grand Bahama Suite

Florida Keys / Key West

Key West apartment

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Car not necessary
“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.
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Certificate of Excellence

Price per night from

$376

Price per night from

$376

(49) Very Good 

Certificate of Excellence

17

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

Florida Keys / Key West

Key West apartment

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Car not necessary
“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!
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Certificate of Excellence

Price per night from

$296

Price per night from

$296

(34) Excellent 

Certificate of Excellence

17

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

Florida Keys / Key West

Key West apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Car not necessary
  • Air conditioning
“Our wedding family stayed here awesome” Fabulous. Clean roomy pool fantastic. Short walk to schooners Wharf Both inside and outside area were excellent
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Certificate of Excellence

Price per night from

$319

Price per night from

$319

19

Key West Townhouse in stunning 5 Star Resort * Close to Duval Street and beach

Florida Keys / Key West

Key West townhouse

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$455

Price per night from

$455

(33) Excellent 

Certificate of Excellence

14

Center of It All - Paradise Island Suite

Florida Keys / Key West

Key West apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Car not necessary
“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
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Certificate of Excellence

Price per night from

$284

Price per night from

$284

(7) Excellent 

15

Shelleys Rooftop Hideaway

Florida Keys / Key West

Key West apartment

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“great place to stay” Close to every thing in Key West Walking distance to all of down town stores and bar my personal favorite
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Price per night from

$333

Price per night from

$333

(4) Excellent 

48

Key West Condo close to the Ocean

Florida Keys / Key West

Key West condo

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$297

Responds fast!
avg. 2 hours 11 minutes

Price per night from

$297

24

1BR Restored Conch House w/ Pool & Deck

Florida Keys / Key West

Key West house

1 3 30 nights min

  • 1 bedroom
  • sleeps 3
  • 30 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$93

Price per night from

$93

(3) Average 

24

Casa Havana

Florida Keys / Key West

Key West house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$777

Price per night from

$777

(85) Very Good 

26

Tropical Escape

Florida Keys / Key West

Key West apartment

2 5 3 nights min

  • 2 bedrooms
  • sleeps 5
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Very comfortable and all around great place to stay.” It was very clean, comfortable and homey. The pool was great and it's very close to Key West and a beach. We really enjoyed our stay. Provided plenty of towels, pool accessories, kitchenware, etc.
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Price per night from

$251

Price per night from

$251

13

Private and Immaculate 2 Bedroom Home with Private Fenced Yard

Florida Keys / Key West

Key West house

2 4 28 nights min

  • 2 bedrooms
  • sleeps 4
  • 28 nights min
  • Nearest beach 2 mi
  • Child Friendly
  • Air conditioning

Price per night from

$137

Price per night from

$137

(40) Excellent 

39

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

Florida Keys / Key West

Key West apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
“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
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Price per night from

$399

Responds fast!
avg. 2 hours 5 minutes

Price per night from

$399

38

Shark Key Home with beach 10 Min from Duval St

Florida Keys / Key West

Key West house

3 8 21 nights min

  • 3 bedrooms
  • sleeps 8
  • 21 nights min
  • Child Friendly
  • Ask about pets

Price per night from

$333

Responds fast!
avg. 2 hours 58 minutes

Price per night from

$333

(4) Excellent 

22

Key West Florida Beachfront Condo

Florida Keys / Key West

Key West condo

2 6 5 nights min

  • 2 bedrooms
  • sleeps 6
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“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
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Price per night from

$371

Price per night from

$371

(1) Excellent 

16

Studio Blue

Florida Keys / Key West

Key West apartment

1 2 30 nights min

  • 1 bedroom
  • sleeps 2
  • 30 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 mi
  • Car not necessary

Price per night from

$229

Price per night from

$229

(1) Excellent 

24

President's Walk

Florida Keys / Key West

Key West house

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Swimming pool
  • Child Friendly

Price per night from

$195

Price per night from

$195

19

A Touch Of Havana In Key West

Florida Keys / Key West

Key West condo

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Nearest beach 0.5 mi
  • Swimming pool
  • Child Friendly

Price per night from

$352

Responds fast!
avg. 3 hours 27 minutes

Price per night from

$352

14

Key West Island Vacation

Florida Keys / Key West

Key West house

2 6 30 nights min

  • 2 bedrooms
  • sleeps 6
  • 30 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$479

Price per night from

$479

(49) Very Good 

291

Real World MTV House Key West

Florida Keys / Key West

Key West house

10 22 min stay varies

  • 10 bedrooms
  • sleeps 22
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Haha Buffalo, New York” This year while my friends and neighbors froze to death in Buffalo, my extended family and a few friends escaped the cold at the Real World MTV House in Key West. It was cold in Key West as well just 78 degrees, all the locals
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Price per night from

$1,795

Responds fast!
avg. 1 hour 48 minutes

Price per night from

$1,795

(3) Very Good 

17

KeyWestStay.com

Florida Keys / Key West

Key West apartment

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning
“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
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Price per night from

$189

Responds fast!
avg. 3 hours 24 minutes

Price per night from

$189

24

Southard Getaway

Florida Keys / Key West

Key West apartment

2 5 7 nights min

  • 2 bedrooms
  • sleeps 5
  • 7 nights min
  • Swimming pool
  • Child Friendly

Price per night from

$195

Price per night from

$195

(15) Very Good 

25

Campbell Suite

Florida Keys / Key West

Key West apartment

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“Comfortably furnished and decorated with a very convenient locat” We really enjoyed staying at the Campbell Suite. It served our requirements nicely. The amenities and location were excellent. Potential visitors do need to note that the entrance to th
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Price per night from

$234

Price per night from

$234

(2) Excellent 

24

Sunny View

Florida Keys / Key West

Key West house

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Child Friendly

Price per night from

$110

Price per night from

$110

(2) Excellent 

51

Welcome Aboard! Relax, unwind, enjoy the water! in key west

Florida Keys / Key West

Key West yacht

4 6 2 nights min

  • 4 bedrooms
  • sleeps 6
  • 2 nights min
  • Nearest beach 1 mi
  • Swimming pool
  • Air conditioning

Price per night from

$455

Price per night from

$455

(2) Excellent 

27

The Water's Edge

Florida Keys / Key West

Key West house

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“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
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Price per night from

$840

Price per night from

$840

25

Island Style

Florida Keys / Key West

Key West house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$767

Price per night from

$767

23

Bayview Harbor

Florida Keys / Key West

Key West apartment

2 5 7 nights min

  • 2 bedrooms
  • sleeps 5
  • 7 nights min
  • Swimming pool
  • Child Friendly

Price per night from

$180

Price per night from

$180

(3) Excellent 

25

Quilted Giraffe

Florida Keys / Key West

Key West house

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$399

Price per night from

$399

(1) Excellent 

24

The Mermaid's Garden

Florida Keys / Key West

Key West house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$767

Price per night from

$767

24

Hidden Treasure

Florida Keys / Key West

Key West apartment

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Pet Friendly

Price per night from

$78

Price per night from

$78

(5) Excellent 

24

Big house

Florida Keys / Key West

Key West house

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Bachelorette in Key West” I rented this house for my sister-in-law's bachelorette weekend in Key West. The house was spacious, clean, and overall the best place I've ever stayed! It was worth every penny!
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Price per night from

$698

Price per night from

$698

(8) Very Good 

36

Villa Deja vu Key West ~ Weekly Rental

Florida Keys / Key West

Key West house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“Great stay over the 4th of July” The Villa Deja Vu was the perfect place for our group of 10. We were on vacation in Key West for a 30th birthday celebration and had a great experience. The house was wonderful, more than we could have imagined. The pi
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Price per night from

$873

Price per night from

$873

6

Coconut Beach

Florida Keys / Key West

Key West apartment

1 4 7 nights min

  • 1 bedroom
  • sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$262

Responds fast!
avg. 2 hours 45 minutes

Price per night from

$262

(23) Very Good 

20

Admiral's Lane

Florida Keys / Key West

Key West house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“Fabulous family rental” We have stayed in Key West for four years now. This was the best rental property so far. The location is perfect for beach days and walking both ends of Duval at night. The property itself had all the amenities we needed and wa
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Price per night from

$770

Price per night from

$770

(40) Excellent 

24

Seaside Place Key West FL 5 Bedroom House 4 Baths

Florida Keys / Key West

Key West house

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Nearest beach 0.1 mi
  • Swimming pool
  • Child Friendly
“Paradise in Paradise” Just returned from a marvelous vacation in Key West. While the tan is already starting to fade, the memories of our stay at Seaside Place remain vivid. We absolutely loved this house. It is very charming and offers all the amenit
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Price per night from

$897

Price per night from

$897

About Key West

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