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Vacation Rentals & House Rentals in Key West

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206 house rentals

Sunrise Suite Key West 2 Bed Rooms 2 Full Baths

Key West condo

2 bedrooms / 2 bathrooms / sleeps 6

“Great condo” Great condo - nicely decorated and most well stocked kitchen ever. Everything was so neat and clean and there was an abundance of supples. Would highly recommend

Responds fast! avg. 2 hours 34 minutes

Price per night from

$297

A Castle on An Island Your Santuary Retreat Key West Sleeps up to 20

Key West house

8 bedrooms / 8 bathrooms / sleeps 20

Responds fast! avg. 2 hours 35 minutes

Price per night from

$1,799

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. 1 hour 26 minutes

Price per night from

$257

Real World MTV House Key West

Key West house

10 bedrooms / 6 bathrooms / sleeps 20

“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 were complaining.and wore sweaters (haha). Everything was great and we laughed as we watched the weather on the TV at night up north. The 2 houses (main and Racket ball) are absolutely perfect for 20 guests. The property is huge . No complaints, we loved the paddle boards and kayaks, and how easy it was to put in the ocean behind the house and go!! Aric, the caretaker, gave us a few good tips for riding the paddle boards, fishing holes and restaurants. A nice quiet guy!!!

Responds fast! avg. 2 hours 35 minutes

Price per night from

$2,199

Truman Annex-Steps to Famous Duval Street

Key West townhouse

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$393

Oceanfront 2 Bedroom 2 Bath Condo Key West Florida

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Perfect location and great value!” From the moment we arrived, this condo was everything we wanted without breaking the bank. We spent days looking for a place in Key West for Christmas week. What was available was crazy expensive, so to be honest when we found this place for the price we were slightly apprehensive. It is close to everything, the check-in and check-out were easy, the people who live in the complex were very friendly and welcoming and always willing to offer advice on where to go and what to do. Everything worked and was clean and we could not have asked for a better vacation. Can't wait to go back!

Price per night from

$320

Ocean Vista

Key West condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$343

Key West Suites Hotel unit 201

Key West apartment

1 bedroom / 1 bathroom / sleeps 6

Price per night from

$343

Sunrise at Seaside Condo 2 Bedroom

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 5

“Key West Adventure” We were two couples on our first visit to explore the keys. The condo was nice for four people. Not fancy but adequate. Could use a little updating to make it nicer. Located quite aways from Duval atreet and the action. Uber costs about $20 one way to get downtown. Too far to walk. The pool was amazing. No complaints.

Responds fast! avg. 3 hours 28 minutes

Price per night from

$315

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

3 bedrooms / 3 bathrooms / sleeps 7

Price per night from

$1,946

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 away from Duval St. The unit inside was decorated very lovely and had all the amenities one would need. I found the owners were nice to do business with, especially Deb who I mostly communicated with. My family and I enjoyed our stay in Key West immensely, we had so much fun! We met many very friendly people out and about town. We would love to visit again, if we do, we would like to stay in this condo or the Bella Vita, the owner's other condo.

Responds fast! avg. 3 hours 4 minutes

Price per night from

$229

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 condo. Condo was clean and had washer and dryer inside the unit. It was amazing to be able to do laundry when I wanted. Pool was clean, heated, and refreshing. Loved having private covered parking. It kept the car nice and cool when you got in. We'll definitely visit again in the future!

Responds fast! avg. 3 hours 28 minutes

Price per night from

$258

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Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$516

Keys to Paradise luxury at its finest on the on the ocean front.

Key West apartment

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$344

*Key West Morning Reflections Paradise Awaits April - Sep 2022*

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$153

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Key West apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$144

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Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$172

** Boat House Harbor August & September 2021 **

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$144

Clean Apartment in Old Town Key West (Best Downtown Locations)

Key West apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$384

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 chairs for all 6 of us. My husband enjoyed watching March Madness on the large T.V. Kathy did a fantastic job with all communications and provided great tourist tips. We would definitely stay here again!

Responds fast! avg. 2 hours 22 minutes

Price per night from

$602

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Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$192

* Winter in Paradise Available Jan 1st - April 1st 2021 - Discounts *

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$172

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Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$287

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Key West house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$544

KEY WEST LA BRISA CONDO - North Building

Key West condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$263

Lovely 2 bedroom, 2 bath condo at La Brisa.

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$161

"Little Paradise" Historic Seaport Old Town Key West

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 18 minutes

Price per night from

$492

Ocean front Condo

Key West condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$138

Beautiful Home Located In Quiet neighborhood

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$339

Key West Gulf front Home with private dock and pool.

Key West house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$327

Downtown, Affordable & Clean available Winter of 2021- Extended stay discount

Key West apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$192

One-bedroom suite in the heart of Old Key West

Key West condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 10 minutes

Price per night from

$218

Key West, Private Beach, Fishing Pier, Old Town, Galleon Resort

Key West condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 28 minutes

Price per night from

$573

Private Pool with Atlantic Ocean View- 20 minutes away from Key West

Key West house

4 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 3 hours 35 minutes

Price per night from

$602

Eleanor's Place in Key West Old Town - Dogs Ok

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$184

* Key West Beach Condo Casa Coastal East Open Nov-Feb2021 *

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$306

Sweet Caroline Seaport Floor 2

Key West house

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$189

Ocean Front Key West Oasis. Tropical paradise awaits

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$192

Viewing 38 of 206
rentals in Key West

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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

Top Destination reviews

Sunrise at Seaside Condo 2 Bedroom
Convenient stay

Clean and quiet. Balcony overlooks pool. Easy parking and access to building with an elevator. Condo could use some paint updating. … see more
Sunrise Suite Key West 2 Bed Rooms 2 Full Baths
Perfect!

This place is absolutely amazing! Very clean and spacious. So beautiful inside and out. I can't say 1 bad thing about this condo. I would definitely go back here and I recommend it to everybody. … see more
LA DOLCE VITA, OLD TOWN KEY WEST!! STEPS TO DUVAL!! SLEEPS 2-4, 3 BLKS TO BEACH
Wonderful Experience

Beautiful decor! Perfect location - just off the beaten path but out of the hustle and bustle. Convenient to everything we wanted to do! I whole heartedly recommend this condo for a couple. Also would work nicely for three people. Might be a bit tight for four adults, but it was perfect for my husband and me.see more
Casa Del Sol, a Key West Vacation (Truman Annex)
Casa Del Sol

We absolutely loved this place! We were two short blocks away from Duval street, close to everything we needed. The place was very clean and well stocked. The owners were very friendly and helpful. I would highly recommend this place and we look forward to coming back! … see more
HISTORIC KEY WEST - Main House - Sleeps 8
Excellent location, old Key West ambience

The Bahama Gardens main house was clean and comfortable and very well located in old Key West, 2 blocks from Duval St. We especially loved the private pool and jacuzzi. There were a lot of roosters around that gave us several concerts a day, but we loved it! Would stay again. … see more
Real World MTV House Key West
Fun trip

We had a great time. Andrew was really great to work with. The fishing was awesome. My husband wouldn’t leave the deck the entire time we were there. There were 20 of us staying there and there was plenty of room and so much to do. We would definitely go back. … see more

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