Vacation Rentals & House Rentals in Key West

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569 house rentals

Conch Haven Old Town 1/1 MONTHLY Rental

Key West apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 28 minutes

Price per night from

$93

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

Price per night from

$320

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!

Price per night from

$296

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. We just coordinated with the other tenants. We will definitely be staying here again.

Price per night from

$376

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

Key West townhouse

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$457

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. 57 minutes

Price per night from

$214

Center of It All - Paradise Island Suite

Key West apartment

2 bedrooms / 1 bathroom / sleeps 6

“Great stay for couples looking for a get away!” The Paradise Island Suite was perfect for two couples vacationing together. We had plenty of space and enjoyed all of the amenities on the property. Really enjoyed the use of the pool and grill. The location is perfect- walking distance to all attractions on the island. Will book again!

Price per night from

$285

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 tranquil. The patio faces south so you don't get blasted with the morning or evening sun making it very comfortable having your morning coffee or evening cocktail while enjoying the view. The owners have put a lot of thought into furnishing and accessorizing the unit. Tess and Mimi were wonderful to work with (Mimi met us at the condo and had great advice on where to eat, what to do...)I have stayed in several condos and this was by far my favorite, if your thinking of staying here you will not be disappointed. I will definitely be back the next time I visit the keys.

Price per night from

$330

Casa Havana

Key West house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$779

Key West Condo close to the Ocean

Key West condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 38 minutes

Price per night from

$229

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. 1 hour 57 minutes

Price per night from

$258

Studio Blue

Key West apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$229

Houseboat Trawler MV Coconuts: Once in a Lifetime Vacation With Pool Access

Key West house

3 bedrooms / 2 bathrooms / sleeps 8

“Nice alternatif for hotel” We were on the boat with only 2 people, so plenty of place ! We liked the marina and the boat very well. Something completely different than an hotelroom ... We had perfect weather so we used the different terraces on the boat depending on the wind and sun. The only point what could be better is the quality of the bedding (sheets, blankets, towels...) For this price you expect some better quality. Anyway, when we wil go back to the us I certainly will search for something similar to stay on

Price per night from

$153

Key West Island Vacation

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 45 minutes

Price per night from

$480

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

Price per night from

$401

Tropical Escape

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 5

“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.... No complaints.

Price per night from

$252

A Touch Of Havana In Key West

Key West condo

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 18 minutes

Price per night from

$351

Sunny View

Key West house

1 bedroom / 2 bathrooms / sleeps 2

Price per night from

$110

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 during your Key West experience. Ocean Paradise has gorgeous views from the 3rd level balcony, a wonderful screened-in porch on the main level (perfect for al fresco dining), and an incredible pool area with a larger than expected private pool and stunning landscaping that provides both shade and privacy. The home's interior is both spacious and functional, including lovely furnishings and everything you need for a memorable vacation in beautiful Key West. Just as important to us was the ease in managing our visit to Ocean Paradise. The owner and his staff were absolutely incredible to work with throughout the entire rental process. We had originally scheduled our visit for the 2014 Thanksgiving holiday week. However, a need arose which required us to cancel that planned stay. The property owner was gracious enough to work with us in our desire to reschedule our visit for May 2015, demonstrating a focus on and respect for his guests throughout the entire process. Our Key West vacation, and specifically our week-long stay in Ocean Paradise, was undoubtedly a memorable experience for me, my husband and our two adult children (as well as the little "furry" member of our family who also joined us for our Key West adventure). We will be returning to Key West, and when we do, Ocean Paradise will be our chosen "home away from home" during our stay!

Price per night from

$843

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 anyone fishing like we were, it's an even shorter drive to Stock Island. The apartment was very clean and quite private. We enjoyed evenings just relaxing on the rooftop deck. The only thing we were a little sad about was that the grill on the deck in the photos was not there. Otherwise, this place is exactly as it is in the pictures. We are heading back to this area again in a year and will likely try to book this place again.

Responds fast! avg. 1 hour 31 minutes

Price per night from

$189

Campbell Suite

Key West apartment

1 bedroom / 2 bathrooms / sleeps 2

“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 the unit is on the 2nd floor, and there is also a circular metal staircase to get from the living area of the unit up to the bedroom. So occupants do need to be reasonably fit to do the stairs and get their luggage up there. We had no problems with this, but others need to be aware depending on their individual circumstances. As far as improvements, we did notice that there was some water that leaked into the closet on the 2nd floor and accumulated a bit in the center of the closet floor after the heavy rain the morning of Tue. 3/25. Didn't cause any problems for us but just wanted to bring it to someone's attention to check into before it gets worse.

Price per night from

$180

Private and Immaculate 2 Bedroom Home with Private Fenced Yard

Key West house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$138

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

Key West yacht

4 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$285

Southard Getaway

Key West apartment

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$195

President's Walk

Key West house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$195

Villa Deja vu Key West ~ Weekly Rental

Key West house

4 bedrooms / 3 bathrooms / sleeps 10

“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 pictures online truly do not give it justice. It is beautiful and brightly colored. The house was stocked, clean and comfortable for a large group. The grounds were in pristine condition and the location of the home was perfect for any activity on the island. We walked everywhere! Having a pool right in the backyard was such a great amenity. We used it every day. Most of the day we were even able to get a suntan there, even though it is hidden and private. We had one issue during our second day, the propane was empty for the grill. I called maintenance and they showed up within 15 minutes. The service was better than I could've asked for. My only suggestion for the property would be to add lighting out back for evenings at the house. We tended to eat dinner late, and used our phones for light over the grill.

Price per night from

$875

Real World MTV House Key West

Key West house

10 bedrooms / 6 bathrooms / sleeps 22

“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 30 minutes

Price per night from

$1,797

The Mermaid's Garden

Key West house

4 bedrooms / 5 bathrooms / sleeps 8

Price per night from

$650

Artist Garden

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

“Beautiful House, sometimes loud” We stayed at the artist's Garden for one week. There were 4 adults and an 11 month old. The house is gorgeous, lots of interesting art. Some of it we had to move out of reach of our 11 month old, but that was easy enough. The only downside to this house is that it's located across the street from the post office. It wouldn't be bad except the bedroom windows face the post office. Some mornings the postal trucks banged around starting at 4:52 am! I finally had to put on a white noise app every night to drown them and the roosters out. (The roosters is a Key West issue, not this houses's ;-) ) .. It was in a great location, easy to access all the restaurants, Duval Street and Mallory square. The pool is very close and well maintained. We definitely would consider staying here again, but if a different house in Truman annex were available not close to the post office, we'd probably choose that first. We would definitely go through at Home in Key West, though! They were wonderful and helpful. They also recommended using The Hip Tourist for renting baby equipment and it was perfect!!!

Price per night from

$285

Island Style

Key West house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$700

Hidden Treasure

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$78

Admiral's Lane

Key West house

4 bedrooms / 3 bathrooms / sleeps 8

“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 was run well by the property managers. The major reason we didn’t give five stars is that all of the tv’s were from the 90’s. They offered cable but on screens that are archaic. Not great for unwinding or catching up with March Madness. For this level of home/rental, the owners could spring for even just ONE flat screen.

Price per night from

$648

Big house

Key West house

5 bedrooms / 5 bathrooms / sleeps 12

“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!

Price per night from

$700

Grande Dame Key West - 'The Watson House' ~ Weekly Rental

Key West house

7 bedrooms / 7 bathrooms / sleeps 14

“One of the best vacations I've taken.” There were a total of 16 people staying in the main house and the cottage. We were there celebrating a friends 50th birthday. The houses were wonderful!! They were clean andthe amenities were great!! The kitchens saved us from having to go out every morning to eat. We put the food in the main house kitchen and had our beer and liquor in the cottage refrigerator. :) The 3 washers and dryers came in handy also. You don't have to bring as many outfits and save on the baggage fees. Loved the pool and the hot tub. Every night after coming home from our adventures, we would all take a dip in the pool or soak our aching bodies. Lol The location is wonderful!! It is one block from Duval Street and only blocks from other attractions, stores and the waterfront. We were there for 8 days and 7 nights and the value was great. You could not get a hotel room for the price it came out per person. While we were there we all talked about definately coming back and renting this property. Also, if you are looking to just come as a couple the cottage is a great place to rent alone. You still have use of the pool and the hot tub. If you do rent the house please remember to think of your neighbors after 11 at night. :)

Price per night from

$1,645

Isle Of View II

Key West boathouse

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 23 minutes

Price per night from

$228

Bayview Harbor

Key West apartment

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$160

Green Orchid

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$93

Coconut Beach

Key West apartment

1 bedroom / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 20 minutes

Price per night from

$262

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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