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108 house rentals

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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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Price per night from

$915

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

Key West condo

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$487

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!

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Price per night from

$659

BIG POOL! Across Street from Beach! SEASIDE PLACE, Key West - 5/5 w/parking

Key West house

5 bedrooms
6 bathrooms

sleeps 12

“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 amenities you'll ever need and then some, from a kitchen that Julia Child would not have found wanting, gorgeous, large rooms each with its very own character, spacious communal dining areas and a beautiful large pool with romantic lighting, a soothing waterfall feature and total privacy. The owners' love for providing the best experience is evident in every detail, from the painstaking labeling of all switches and outlets to the folders of carefully compiled information about where to go, and what to do and see. The house is just a block from the quiet end of Duval Street (there is such a thing), yet far enough removed from the Key West bar scene responsible for the prevailing serious shortage of liver donors. We thoroughly enjoyed every minute of our stay and can't wait to return soon. And we can't help but think that if Hemingway had stayed here he might still be alive today

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Price per night from

$2,119

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

Key West townhouse

2 bedrooms
1 bathroom

sleeps 6

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Price per night from

$916

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

3 bedrooms
3 bathrooms

sleeps 7

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Price per night from

$1,946

One-bedroom time share suite in the heart of Old Key West

Key West condo

1 bedroom
1 bathroom

sleeps 4

Responds fast! avg. 26 minutes

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Price per night from

$338

HISTORIC KEY WEST - Cigar House - Sleeps 4

Key West house

1 bedroom
1 bathroom

sleeps 4

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Price per night from

$1,144

Tee by the Sea - Luxury 2/2 1/2, WIFI, pool, parking, Bikes, 3 night min.

Key West townhouse

2 bedrooms
3 bathrooms

sleeps 6

“Absolutely Perfect!!!” I chose this place to rent because it looked nice and it was affordable. I knew going in that it was not located on the Key West island, which was fine considering the condo came with bikes you could ride onto the island...What I experienced during my stay here is nothing short of Perfect!!! The entire condo was clean and spacious, everything inside the condo worked, the beds and all furniture were clean and comfortable, plenty of towels and linens, the showers, water presure and plumbing were excellent, the pool was clean, relaxing and private, the nights were quiet for sleeping and the gated community within the condo were friendly and fun. The bikes were the best part...10-15 minutes and you were on Duval Street, or the Southernmost Point, or Fort Zachery beach with no hassles what so ever, and I got some good exercise!!! I will definately stay here again!!!

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Price per night from

$344

KEY WEST and 3 Bikes or Walk Everywhere! 2 Porches, Pool, Parking & WIFI

Key West condo

2 bedrooms
1 bathroom

sleeps 4

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Price per night from

$342

HISTORIC KEY WEST - Conch House - Sleeps 5

Key West house

2 bedrooms
1 bathroom

sleeps 5

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Price per night from

$1,144

Olivia Place

Key West house

4 bedrooms
4 bathrooms

sleeps 8

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Price per night from

$344

SEAPORT PANORAMA at Galleon Resort (Beach-Pool & Hot Tub-BBQ-55” TV-Jacuzzi)

Key West condo

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$911

Private, heated pool. Private yard.

Key West condo

1 bedroom
1 bathroom

sleeps 2

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Price per night from

$172

HISTORIC KEY WEST - Turtle House - Sleeps 6

Key West house

2 bedrooms
1 bathroom

sleeps 6

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Price per night from

$1,488

SEAPORT SERENITY in Old Town—Beach-Pool-BBQ-Hot Tub

Key West condo

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$911

Seaside Condo 2 pools. sunny, quiet, near Old Town

Key West condo

1 bedroom
1 bathroom

sleeps 2

Responds fast! avg. 3 hours 48 minutes

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Price per night from

$107

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.

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Price per night from

$487

Single Family Home, 3 Bedroom, 2 Baths, and Pool. Great Value!

Key West house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$165

Ambrosia - OLD TOWN/HISTORIC SEAPORT, large POOL, wrap around porch, washer/dry

Key West condo

1 bedroom
1 bathroom

sleeps 2

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Price per night from

$155

Artist Cottage

Key West apartment

2 bedrooms
1 bathroom

sleeps 4

“Key West, Spring 2012” In a word,our stay with you was ”wonderful”. We have been to Key West on several occasions and have loved every visit. Staying in Truman annexe was even more special. We all felt like we were at home with everything we needed. You must feel blessed to live in that part of the world. We will be looking for a job for our 19 year old son,Tom. He wants to come and work over in Key West. We have just arrived home and everything seems grey, and much colder than Key West. Depending on finances( the pound-dollar rate is not too good just now) we hope to come back soon. We will definitely be giving you a call.I would recommend your accommodation and company to future holiday makers. Love and blessings John,Jayne,Jack and Tom

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Price per night from

$379

HISTORIC KEY WEST - Main House - Sleeps 8

Key West house

4 bedrooms
2 bathrooms

sleeps 8

“February visit to Key West” Our family stayed at the Main House for 4 nights and loved it. The location was fabulous! Loved the houses and gardens!!! The owner was very nice and considerate of us. If we get back that is where we would want to be!!

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Price per night from

$2,060

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

Harbor Walk Hideaways

Key West b&b

4 bedrooms
3 bathrooms

sleeps 8

“Location, Location, Location” We were a group of 8 and rented the entire compound! The place was in an amazing location that was easily accessible to everything. We had everything we needed onsite and if we had any questions, Phyllis was always just a phone call away. The music and talking at night from the cigar lounge was a bit loud, but nothing we couldn't tolerate. The only suggestion I'd make is to buy an ionizer for the first two units to help with the cigar smell....again, nothing intolerable, but could make a world of difference. Can't wait to come back for another visit! THANK YOU!

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Price per night from

$1,300