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Wireless Internet
Air conditioning
Swimming pool
Private pool

Heated pool
Private indoor pool
Balcony or terrace
Washing machine
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Internet access
DVD player
Grill
Fireplace
Private tennis court
Cot available
Sea view
Safe
Dishwasher
Satellite TV
Children's pool
Games room
Clothes dryer
Pool or snooker table
Table tennis
Shared indoor pool
Private outdoor pool (unheated)
Private outdoor pool (heated)
Shared outdoor pool (unheated)
Shared outdoor pool (heated)
Cribs
Ceiling Fans
Fax machine
Swing set or jungle gym
Video player
Fridge
TV
Central heating
Stereo system
Kettle
Toaster
Iron
Hair dryer
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Freezer
Boat available
Microwave
Linen provided
Towels provided
Bicycles available
Climbing frame
Trampoline
Private fishing lake or river
Staffed property
Housekeeping Included

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Pets
Pets allowed
Parking
Car not required

Children under 5
Smoking allowed
Non-Smoking property
Smoking - Ask
Wheelchair adapted
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Beach or lakeside relaxation
City breaks
Skiing – property near ski resort
Walking trips

Tennis in town
Nightlife
Water sports
Horse riding
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Golf course on site or within 15 min walk
Mountain Views
Beach or lakeside relaxation
Golf within 30mins drive
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151 Houses

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Florida Keys at it's best

Sugarloaf house

3 bedrooms
3 bathrooms

sleeps 6

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Price per night from

$240

Oceanside, pet friendly, 5/3 smart home with paddle equip.-SUPs, kayaks & canoe

Sugarloaf house

5 bedrooms
3 bathrooms

sleeps 8

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Price per night from

$331

Paradise Point: Your Luxurious Waterfront Getaway with Pool, Tiki, Dockage, and

Sugarloaf house

4 bedrooms
4 bathrooms

sleeps 10

Responds fast! avg. 2 hours 34 minutes

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Price per night from

$463

Great rentals within 20 miles that match your search

A Change in Latitudes - TRUMAN ANNEX

Key West condo

2 bedrooms
1 bathroom

sleeps 4

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Price per night from

$172

The Mermaids House, Historic Old Town Key West

Key West house

2 bedrooms
1 bathroom

sleeps 4

“Beautiful Home in Old Town Key West” Mermaid House is conveniently located in the heart of Old Town yet when you are there you are in your own private paradise. The house is beautifully appointed with anything you could need during your stay and has ample space for four people. It was the perfect spot for our stay in Key West and we plan to stay again when we return to the area. Thanks to Barbara for making us feel welcome and for sharing her beautiful home with us.

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$327

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

$1,296

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. 14 minutes

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Price per night from

$286

Family Retreat-Ocean front home with private pool

Cudjoe Key house

6 bedrooms
4 bathrooms

sleeps 14

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Price per night from

$788

Fandango

Cudjoe Key house

5 bedrooms
3 bathrooms

sleeps 14

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Price per night from

$619

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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$485

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. 2 hours 7 minutes

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Price per night from

$342

Conch Haven Cottage Old Town Studio MONTHLY Rental

Key West apartment

1 bedroom
1 bathroom

sleeps 2

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Price per night from

$107

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!!!!

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$133

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

$378

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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$2,111

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

$2,053

HISTORIC KEY WEST - Turtle House - Sleeps 6

Key West house

2 bedrooms
1 bathroom

sleeps 6

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Price per night from

$1,482

HISTORIC KEY WEST - Cigar House - Sleeps 4

Key West house

1 bedroom
1 bathroom

sleeps 4

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Price per night from

$1,140

HISTORIC KEY WEST - Conch House - Sleeps 5

Key West house

2 bedrooms
1 bathroom

sleeps 5

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Price per night from

$1,140

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. 1 hour 58 minutes

Match: Satellite TV

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Price per night from

$319