Vacation Rentals & House Rentals in Key West

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47 house rentals

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

Key West townhouse

2 bedrooms / 3 bathrooms / sleeps 6

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$572

Top floor, two bedroom,two bath condo with private balcony,close to the Ocean

Key West condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 45 minutes

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Price per night from

$229

Conch Haven Old Town 1/1 MONTHLY Rental

Key West apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 56 minutes

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Price per night from

$105

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!

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Price per night from

$842

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.

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$246

Coconut Beach

Key West apartment

1 bedroom / 2 bathrooms / sleeps 4

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$262

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 other guests were warm and welcoming! The unit was very spacious and comfortable and you can"t beat the location. It's within walking distance of all attractions and Fort Zachary Taylor State Park. The owner was very responsive to all of my questions and a pleasure to work with and we look forward to being repeat guests at The Banyan Resort.

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$263

Walk or Bike!! Truman Annex: 3 BIKES, 2 PORCHES, A POOL, WIFI, & PARKING

Key West condo

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 47 minutes

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Price per night from

$196

Key West Hyatt Windward Pointe

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$229

Luxury 3BD/3B Penthouse Condo at Galleon Resort, Old Key West

Key West condo

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 0 minutes

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Price per night from

$915

Old Town Eyebrow:Luxurious/Private Home

Key West house

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$492

Truman Treasure

Key West apartment

3 bedrooms / 3 bathrooms / sleeps 5

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Price per night from

$557

MAJESTIC PARADISE - Truman Annex - Downtown

Key West condo

2 bedrooms / 1 bathroom / sleeps 5

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Price per night from

$258

Sunrise off Southard- A Tropical Sanctuary Newly Remodeled in May

Key West condo

1 bedroom / 1 bathroom / sleeps 3

“Sunrise on Sourhard” A beautifully decorated condo fitting all our needs. We especially appreciate the the 2 brand new bikes to get us around the the island, as it saved us from renting any other transportation!! The back deck is spacious and comfortable as well!

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Price per night from

$327

Live the Dream - S/V Take It Easy 2014 Premium Lagoon Catamaran Resort Amenities

Key West boathouse

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$338

The Tree House Old Town 2 Bedroom MONTHLY Rental

Key West house

2 bedrooms / 1 bathroom / sleeps 7

“Wonderful” Close to everything! Furnishings just the best. We stayed upstairs in the 2 bedroom 1 large bath. Great wrap around porch up stairs and down. Our key Westies were welcomed which was a plus for us! Overall Stephanie has done a great job and her sister was really helpful. Planning on returning!!!!

Responds fast! avg. 1 hour 56 minutes

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Price per night from

$117

Seaport Sanctuary in Old Town, Key West, FL (Beach-Pool-BBQ)

Key West condo

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$637

Seaport Panorama in Old Town, Key West, FL (Beach-Pool-BBQ)

Key West condo

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$638

LOCATION LOCATION LOCATION HYATT SUNSET HARBOR 1 WEEK RENTAL Sept 27-Oct 4 202

Key West condo

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$294

Seaside Condo 2 pools JANUARY SPECIAL

Key West condo

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 55 minutes

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Price per night from

$100

Old Town *Pink Conch House" with Pool

Key West house

4 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$287

Seaport Penthouse in Old Town, Key West, FL (Beach-Pool-BBQ)

Key West condo

2 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$637

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Price per night from

$229

2 Bedroom, 2 Bath Condo with private balcony and Close to the Ocean

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

“We'll be back...” We found this condo to be very clean and comfortable. We enjoyed sitting at the pool as well. Paul, the caretaker, was very pleasant and most accommodating. We shared the condo with another couple for our two night stay. It was wonderful to have our privacy (2 BR/2 baths) but still be able to share the kitchen/living room area with our friends. We had a rental car so found the location easy for shopping, dining, sightseeing on other keys and, of course, Duval Street.

Responds fast! avg. 1 hour 45 minutes

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Price per night from

$315

Beachfront Villa Ambriana, Luxury Upscale Home Right on the Beach

Key West house

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$744

6 bedroom Duval Street Compound - Pool, Hot Tub, 2 parking spots - A++ Location

Key West villa

6 bedrooms / 7 bathrooms / sleeps 16

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Price per night from

$2,004

Great rentals within 20 miles that match your search

Dog-friendly Sunrise Suites condo w/ shared pool, & hot tub!

Stock Island house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 39 minutes

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Price per night from

$189

Restored historic home w/ private pool & reserved off-street parking - Dogs OK!

Stock Island house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 39 minutes

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Price per night from

$605

Tranquility in Paradise - Sugarloaf Key (17 miles to Key West)

Sugarloaf house

5 bedrooms / 3 bathrooms / sleeps 9

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Price per night from

$323

Sprawling condo w/ ocean views, dock, & shared pool - dog-friendly!

Stock Island house

2 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 39 minutes

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Price per night from

$140

Family Friendly! Shared pool, hot tub, tennis, parking, full kitchen- dogs ok

Stock Island house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 39 minutes

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Price per night from

$187

Shared pool, hot tub, tennis courts, & balcony - dogs OK! Family friendly!

Stock Island house

2 bedrooms / 2 bathrooms / sleeps 6

“Great Place!!” Very nice place!! I would stay here again when returning to Key West. The location was great!! The property was well maintained and had a great pool.

Responds fast! avg. 3 hours 39 minutes

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Price per night from

$194

Comfortable, dog-friendly studio w/ shared pool, patio & nearby beach access!

Stock Island studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 39 minutes

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$165

Sunny condo w/ shared pool & entertainment - central location!

Stock Island house

1 bedroom / 1 bathroom / sleeps 2

“Quiet street, near Duval” Lovely home in The Colony on Olivia Street. We found everything to our liking - clean and comfortable. Daily maid service was a bonus.

Responds fast! avg. 3 hours 39 minutes

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Price per night from

$195

Dog-friendly home w/ private pool - walk to the beach and restaurants!

Stock Island house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 39 minutes

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Price per night from

$521

Peaceful, dog-friendly home in a residential neighborhood w/ a shared pool

Stock Island house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 39 minutes

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Price per night from

$291

Charming house w/ private patio - great central location, dogs OK

Stock Island house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 39 minutes

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Price per night from

$257

Family-friendly home w/ private pool, furnished patio, and parking - Dogs OK!

Stock Island house

2 bedrooms / 2 bathrooms / sleeps 6

“Perfect getaway!” I would highly recommend this property. It's bigger than we expected and incredibly clean. Maid service was a pleasant surprise too! The location was close enough to the center of it all but also far enough where we didn't hear any of it. Loved it and would definitely return.

Responds fast! avg. 3 hours 39 minutes

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Price per night from

$524

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