Vacation Rentals & House Rentals in Key West

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27 house rentals

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.

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Price per night from

$330

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

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Price per night from

$401

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

Shipyard-1/2 Block Duval Street

Key West townhouse

2 bedrooms / 1 bathroom / sleeps 6

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Price per night from

$245

Coconut Beach

Key West apartment

1 bedroom / 2 bathrooms / sleeps 4

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Price per night from

$262

Tiki Too Townhouse, 2 blocks from Duval,Pool, Bikes

Key West townhouse

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 3 hours 52 minutes

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Price per night from

$359

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

3 bedrooms / 2 bathrooms / sleeps 7

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Price per night from

$1,259

Key West Hyatt Windward Pointe

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$229

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

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

MAJESTIC PARADISE II Luxury living in Truman Annex. Downtown, pool, 2 blks

Key West townhouse

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$344

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

$636

Ocean Vista

Key West condo

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$342

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

The Tiki Suite - soon to be a Key West icon

Key West houseboat

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$572

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

Key West's only Real Beach House

Key West guest house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$392

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Price per night from

$2,455

Great rentals within 20 miles that match your search

NEW LISTING! Waterfront condo w/ shared pool and hot tub & amazing water views

Stock Island house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 39 minutes

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Price per night from

$214

Spacious, waterfront condo w/ a full kitchen, shared pool, & furnished balcony

Stock Island condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 39 minutes

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Price per night from

$267

NEW Listing! Brand-new waterfront home on Stock Island w/furnished deck

Stock Island house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 39 minutes

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Price per night from

$181

Comfortable condo w/ shared pool, private balcony, and beach access

Stock Island house

2 bedrooms / 2 bathrooms / sleeps 6

“Relaxing and Fun” Very good location..steps away from Smathers beach. Parked car then rode bikes, scooters, and walked around the entire Key. Condo was very nice and comfortable with everything needed for a week or more stay. The only negative is that the in laid wood bedroom floors creek on every step--annoying at night. Maybe a few rugs could solve this issue. We really enjoyed the hot tub--relaxing.

Responds fast! avg. 3 hours 39 minutes

Match: Sea view

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Price per night from

$299

New home w/ private pool & rooftop patio - ideal location & steps from beach!

Stock Island house

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 3 hours 39 minutes

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Price per night from

$158

Spectacular, oceanfront, dog-friendly home w/ private pool & boat docks

Sugarloaf Key house

5 bedrooms / 3 bathrooms / sleeps 18

Responds fast! avg. 3 hours 39 minutes

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Price per night from

$250

NEW LISTING! Ocean-view condo w/shared pool, close to beach-free airport shuttle

Stock Island house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 39 minutes

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Price per night from

$188

Colorful beachfront condo w/ ocean view balcony & shared hot tub/pool/tennis!

Stock Island condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 39 minutes

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Price per night from

$243

Waterfront townhouse w/ pool, fenced backyard & deck - dogs ok

Stock Island house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 39 minutes

Match: Sea view

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Price per night from

$302

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