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$66

1 BR / 1 BA / Sleeps 4

1 Reviews

$66

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Artist cottage with hot tub

1 BR / 1 BA / Sleeps 4 | Quick view
“ Poor ” 1 Reviews

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Reviews

(1)

The artist cottage is mainly used as a residence for visiting artist that are in town doing shows at my gallery. The cottage is very quiet and secluded with lots of privacy,situated amongst 100 year old trees and lush tropical foliage. The cottage was built in 1913 and is a true piece of old key west. The property is…
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Wonderful little cottage, not so wonderful owner

Left on Apr 07, 2014 for a stay in June 2013

First, let me say that I intended not to review this property simply because I didn't want to leave a negative review but today I got a letter in the mail that made me change my mind.The cottage was great, clean,neat,location great, and a great place for our little dogs, who were welcome. First there was no washing machine which didn't seem a problem because David assured us that our laundry …

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$110

1 BR / 1 BA / Sleeps 4

Key West Cottage - Key West vacation rentals
1 / 4

$110

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Key West Cottage

1 BR / 1 BA / Sleeps 4 | Quick view

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Key West Cottage located in Mid-town away from the maddening crowd when you want to be and close enough to join in when you're ready. Our cottage is surrounded by lush vegetation including: coconuts trees, mango trees, tamarind trees, banana plants, guava plants, Spanish lime trees and many more. In late summer …
  • A/C or climate control
  • Central heating
  • Linens Provided
  • Towels Provided

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$265

2 BR / 2 BA / Sleeps 4

34 Reviews

$265

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Leeward Isle Key West Retreat

2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 34 Reviews

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Reviews

(34)

LEEWARD ISLE KEY WEST RETREAT: Small gated compound with only 13 properties, this townhome community is quiet and private right in the heart of Old Town. 2-bedroom 2-bath townhome remodeled from top to bottom. Decorated with Key West flair, this is truly a unique property. Flatscreen TVs, stereo, CD player and …
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Parking
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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Reviews

(34)

Family getaway

Left on Nov 07, 2008 for a stay in July 2007

The property and the condo was perfect. Very close to Duval St. and ample parking both on lot and street. On property staff not friendly and rental staff a bit stuffy as friends were discouraged to visiting. When they say no more than 4 people staying at one time they mean it. Although the unit has ample space for more people and isn't this a vacation. A bit pricey but the unit has everything…

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$83

1 BR / 2 BA / Sleeps 4

6 Reviews

$83

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Fishtail Hideaway - Monthly Rental

1 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 6 Reviews

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Reviews

(6)

***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** This cottage features a cozy master suite which encompasses the entire 2nd floor. This bedroom features a pillow top King bed, large flat screen TV, en-suite bath with shower. The living room has a queen murphy bed for …
  • Internet Access
  • A/C or climate control
  • Deck
  • Fitness Room
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(6)

Deception

Left on Feb 03, 2011 for a stay in January 2011

I rent Fishtail and not azul,for the second time you send me that form ! Even if i tell you, Key West Vacation Rental, the reasons of my deception, I think you really don't care. When I tried to tell Michelle about some of the things about this house (ask the owner to buy a real kitchen table, a new mattress, wool sheet, etc), she looked at the sky and didn't care. So i won't take a minute of my …

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$150

3 BR / 2 BA / Sleeps 8

30 night minimum stay requirement.  Manatee Manor - Key West vacation rentals
1 / 8

$150

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30 night minimum stay requirement. Manatee Manor

3 BR / 2 BA / Sleeps 8 | Quick view

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Just 10 miles from Old Town you’ll find a seaside neighborhood that recalls Lower Keys life in the good old days, when you would go fishing in the morning, have lunch and a beer (or two) at Geiger Key Marina, fish some more in the afternoon then cook some of the catch out on your deck with a few cold ones. And while…
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Deck
  • Linens Provided
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$200

2 BR / 2 BA / Sleeps 4

30 night Minimum Stay Heart of Historic downtown  2 bedroom 2 1/2 Bathroom - Key West vacation rentals
1 / 12

$200

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30 night Minimum Stay Heart of Historic downtown 2 bedroom 2 1/2 Bathroom

2 BR / 2 BA / Sleeps 4 | Quick view

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This unit offers the perfect way to visit Key West, park your car and walk everywhere. Sunset celebration is only steps away. This town home is complete luxury with viking appliances, custom kitchen cabinets, granite counter tops, beautifully furnished, and Westin Hotel heavenly beds. The amenities include one …
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Linens Provided
  • Dishwasher
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$215

2 BR / 1 BA / Sleeps 6

1 / 6

$215

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The Banyan Resort at Key West

2 BR / 1 BA / Sleeps 6 | Quick view

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Experience a world full of lush and fragrant gardens on a Caribbean Estate tucked away in the heart of Old Town, Key West. Stay in a 2 bedroom unit in a restored historic wrecker's home and wander through the extensive gardens as time transcends you to an era long ago. You can relax and indulge yourself at this …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Outdoor Dining Area
  • A/C or climate control
  • Central heating
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask

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$600

6 BR / 7 BA / Sleeps 12

1 / 31

$600

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Seaport Treasure Estate ~ Monthly Rental

6 BR / 7 BA / Sleeps 12 | Quick view

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While you won’t need a treasure map to find this exclusive resort-style estate, you’ll know you’ve discovered a rare island gem from the moment you walk through the private gates. Hidden by white picket fences and mature tropical landscaping, this spacious Seaport Treasure Estate is cleverly …
  • Housekeeping Optional
  • Grill
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$199

2 BR / 1 BA / Sleeps 6

15 Reviews

$199

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Center of It All - Paradise Island Suite

2 BR / 1 BA / Sleeps 6 | Quick view
“ Excellent ” 15 Reviews

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Reviews

(15)

Relax of the Island Style front porch and enjoy Key West at it's finest. Centrally located, less than a block from Duval - this Completely updated 2 Bedroom, 1 Bath will simply amaze you! High Ceilings, tall windows, full kitchen with separate dining room and plenty of space to make your Key West vacation memorable…
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for children - ask
  • Suitable for the elderly

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Reviews

(15)

Great Locaction!!

Left on Nov 08, 2013 for a stay in October 2013

Great location! loved the apartment, will definitely rent there rent it again. If I had to complain about 1 thing, the beds where awful!!!
But I was told there changing all the furniture so the place is perfect! loved it!

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$400

2 BR / 2 BA / Sleeps 4

2 Reviews

$400

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Quilted Giraffe

2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 2 Reviews

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Reviews

(2)

This home has a unique pricing structure. While it can rent for less than 30 days, the owner prefers Monthly rentals. Because of this, this home offers substantial (25% off) Monthly Rental discounts. Your space. Your vacation lifestyle. The Quilted Giraffe provides both. This two-bedroom, two full bath home welcomes …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for the elderly - ask

Details

Reviews

(2)

Relaxing respite

Left on Mar 05, 2010 for a stay in February 2010

The heated pool and lush backyard foliage were the draw to this well appointed home. Parking was a nightmare, the neighbor to the right facing the house was most unpleasant. A parking spot in the front yard would be recommended. The location was excellent for walking anywhere. The service was good once we met Bill. Prior to him, Corey and Libby both seemed disorganized and inattentive to our …

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$230

2 BR / 2 BA / Sleeps 5

2 Reviews

$230

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Royal Palm

2 BR / 2 BA / Sleeps 5 | Quick view
“ Very Good ” 2 Reviews

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Reviews

(2)

There's no better way to experience "Island Time"-that slow shifting of hours that makes Key West such an ideal vacation spot-than staying at Royal Palm. Located in the prestigious Foundry building within the exclusive Truman Annex gated community, this two-bedroom, three-story brick townhouse offers privacy and …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Central heating
  • Suitable for the elderly - ask

Details

Reviews

(2)

Really Great Experience

Left on Mar 15, 2013 for a stay in February 2013

Had a great time. Historic Hideaways was very helpful. Our place was central to everything, very clean. Perfect for our needs.

Thank you.

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$83

1 BR / 1 BA / Sleeps 6

1 / 17

$83

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Providence Suite - Monthly Rental

1 BR / 1 BA / Sleeps 6 | Quick view

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***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Nestled in tropical, flowering gardens, the Providence Suite is perfectly located, 1/2 block from Duval Street Downstairs is the living room with Queen sleeper sofa, dining room and fully equipped kitchen. Outdoor table and…
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Deck
  • Fitness Room
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$255

2 BR / 2 BA / Sleeps 5

10 Reviews

$255

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Havana Hideaway

2 BR / 2 BA / Sleeps 5 | Quick view
“ Excellent ” 10 Reviews

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Reviews

(10)

Call it casual luxury. Call it tropical chic. This two bedroom/two full bath Harbour Place condominium is a part of Key West's prestigious Truman Annex community. From the luxurious pool area below, you can enjoy breathtaking views just steps from the Gulf of Mexico. Watch passing tall ships, cruise ships, pleasure …
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for the elderly - ask

Details

Reviews

(10)

Week in Paradise

Left on Jan 16, 2013 for a stay in December 2012

This was one of the greatest stays that we have had. Condo was within walking distance to everything block to most. Very nice place to stay. Easy check in and check out process. This place has a great view from pool. We were here in December with about 80 degree temps each day so we shut down the air and had the doors open most of the time the only draw back to this is the chickens will wake…

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$150

3 BR / 3 BA / Sleeps 8

1 / 25

$150

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Higgs Beach Hacienda - 3 Bed 2.5 Bath Monthly Rental Near Beach. Huge Yard!

3 BR / 3 BA / Sleeps 8 | Quick view

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Tucked into a quiet residential neighborhood, this renovated home is the perfect getaway for a family or group of friends looking to experience the Key West island life! This 3 bedroom home is on Patricia St, just a block from the scenic biking bath that runs along the Atlantic side of the island; very close (less …
  • Internet Access
  • A/C or climate control
  • Linens Provided
  • Dishwasher
  • Microwave
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$367

2 BR / 2 BA / Sleeps 4

1 / 32

$367

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Steam Plant - Luxurious 2/2 Condo w/ Amazing Views & Private Hot Tub

2 BR / 2 BA / Sleeps 4 | Quick view

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Key West regulars know that one of the best parts of downtown is actually a few blocks of the main street at the Historic Key West Seaport. The Seaport is a big part of the heart of Key West where dingy captains, commercial fisherman, sports anglers, pleasure seeking vessels, and those that admire it all come together…
  • Hot Tub/Jacuzzi
  • Internet Access
  • Balcony or terrace
  • Parking
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$167

2 BR / 2 BA / Sleeps 4

1 / 30

$167

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"ROYAL OASIS" - Beautiful 2/2 Monthly Rental w/ Private Heated Pool

2 BR / 2 BA / Sleeps 4 | Quick view

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***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Beautifully decorated with abstract art throughout, this 2 bed 2 bath monthly rental is the perfect "get away" spot for individuals looking to fully immerse themselves in Key West culture. This house is located in on Royal St. …
  • Internet Access
  • A/C or climate control
  • Deck
  • Linens Provided
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$598

4 BR / 5 BA / Sleeps 10

1 / 35

$598

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"SIMONTON COURT COTTAGES" 4 Units in 1! Sleeps up to 10 Only 1 Block To Duval

4 BR / 5 BA / Sleeps 10 | Quick view

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"Simonton Court Cottages" consists of the 4 nightly units "Audubon House," "Truman Efficiency," "Monroe Efficiency," and "Mallory Efficiency." In total, this group rental sleeps 8 - 10 comfortably. Perfect for cost-conscious, larger, groups who are looking for great a location. Take advantage of this fantastic …
  • A/C or climate control
  • Microwave
  • Refrigerator
  • Toaster
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$117

2 BR / 2 BA / Sleeps 6

1 / 17

$117

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Amazing Grace

2 BR / 2 BA / Sleeps 6 | Quick view

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***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Amazing Grace is nestled in the middle of the island on Seidenberg Avenue that dead ends into Salt Run Canal that divides Key West in half. With 2 bedrooms, 2 bathrooms, off street parking and a hot tub you may find that you …
  • Dishwasher
  • Microwave
  • Refrigerator
  • Toaster
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$139

1 BR / 4 BA / Sleeps 2

6 Reviews

$139

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Share New 5 Star $2.4m Home in Old Town Key West

1 BR / 4 BA / Sleeps 2 | Quick view
“ Excellent ” 6 Reviews

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Reviews

(6)

Beautiful New large modern Home on very quiet street . Location , Location Location ! Share .5 Star $2.4m Home in Old Town Key West.. Own fully furnished bedroom with Queen size bed for 1 - 2 max ( see photos ) with large flat screen t.v. and 2 french doors leading onto private balcony overlooking Tropical …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer

Details

Reviews

(6)

Fabulous Spot

Left on Sep 02, 2014 for a stay in April 2014

This was such a rare find. We will be back and refer our friends. Loved that we had access to the pool. Absolutely the perfect spot!

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$280

1 BR / 2 BA / Sleeps 2

1 / 21

$280

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Namaste : A blissful one bedroom cottage designed with relaxation in mind.

1 BR / 2 BA / Sleeps 2 | Quick view

Details

Tucked away in an inviting compound you'll find a blissful retreat called Namaste; a tranquil and relaxing one bedroom cottage. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within 2 blocks you'll …
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Patio
  • Linens Provided
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$350

1 BR / 2 BA / Sleeps 4

38 Reviews

$350

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Poinciana House

1 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 38 Reviews

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Reviews

(38)

Poinciana House, a one-bedroom, two-full bath conch cottage, is a standout in authentic Florida design and guest friendliness. The private pool area and tropical garden is where you find the namesake Royal Poinciana tree complete with a chair hammock beckoning from one enormous branch. Swinging back and forth, you can…
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for the elderly - ask

Details

Reviews

(38)

Awesome pool and patio, flowers everywhere!

Left on Aug 15, 2008 for a stay in June 2008

I can't say enough about how beautiful this property is. Lots of flowers, the Royal Poinciana tree is very unique. The pool is awesome and the patio on the back of the house leads right into the pool. The decor is very Key West and I loved it. We did have one problem, the AC went out in the living room/kitchen area ON MY WEDDING DAY! There is an AC unit in the bedroom that still worked. It …

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$167

2 BR / 2 BA / Sleeps 6

8 Reviews

$167

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"CASA 625" Monthly Rental w/ Private Pool. Beautiful Interior

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 8 Reviews

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Reviews

(8)

***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** The superb location at the top of Solares Hill, three blocks to the Historic Seaport and Duval Street, one block to the Public Library; Casa 625 will amaze you with the detailing, decorating and attention to detail! Sit on the …
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Fitness Room
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(8)

Always love 625

Left on Jan 27, 2011 for a stay in November 2010

This is a nice property I have stayed at multiple times. If it were my house, I would enhance it by making the master suite upstairs private (not wide open to the rest of the house) and I would put a TV in the master that's a reasonablt size (there was a 17" or so TV in a beautiful MBR!). Put the small TV downstairs in the BR there and get a new flatscreen that fits the property and the MBR.

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$286

2 BR / 2 BA / Sleeps 4

20 Reviews

$286

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Foundry's Corner

2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 20 Reviews

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Reviews

(20)

Thoroughly Key West and designed for easy living, this three-story town home is located in the Foundry, part of the residences within the prestigious Truman Annex gated community only a block from Duval and the Historic Seaport. While the impressive brick structure that houses this residence was built around 1845 as …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for the elderly - ask

Details

Reviews

(20)

Awesome Hideaway

Left on Nov 19, 2008 for a stay in October 2008

I was absolutely thrilled with this property, the townhouse was well appointed and beyond comfortable. The location cant be beat as its just a minutes walk to the north end of Duval St. and all its bars and restaurants. We were there for Fantasy Fest and having a secluded, quiet place to come back to away from all the madness that is FF was quite wonderful. I suppose if I had to rate this …

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$700

4 BR / 4 BA / Sleeps 8

2 Reviews

$700

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Hermitage South

4 BR / 4 BA / Sleeps 8 | Quick view
“ Excellent ” 2 Reviews

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Reviews

(2)

The name Hermitage invokes the sense of secluded residence or private retreat that aptly describes this inspiring four-bedroom, four-bath home in the heart of Old Town Key West. You'll know the minute you walk through the front door that an artist with considerable flair has decorated Hermitage South to be a one-of-a-…
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for the elderly - ask

Details

Reviews

(2)

Family Vacation in Key West

Left on Aug 11, 2012 for a stay in July 2012

The staff at Historic Hideaways was absolutely wonderful in assisting with the long distance scheduling of this vacation. In addition they were very responsive to any question related to the property both before arrival and during our stay.

The home was exactly as described...Clean...and stocked with all the items needed for a home away from home vacation rental. This home was close to …

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$183

3 BR / 2 BA / Sleeps 6

1 / 13

$183

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On Hemingway's Rounds ~ Monthly Rental

3 BR / 2 BA / Sleeps 6 | Quick view

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Key West has long been loved for its playful spirit, forever attracting all genres of fun-loving artists, musicians, and writers. In recognition for the island’s historical humor, we have fondly named this beautiful upscale home, On Hemingway’s Rounds. Paying tongue-in-cheek homage to Papa’s …
  • Housekeeping Optional
  • A/C or climate control
  • Stereo or CD player
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$288

3 BR / 2 BA / Sleeps 6

1 / 10

$288

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Southernmost Retreat- 1 Block from Duval

3 BR / 2 BA / Sleeps 6 | Quick view

Details

Just 1 short block from Duval Street the Southernmost Retreat is a recently renovated and decorated 3 bedroom, 2 bath house located Simonton Street. The Southernmost Retreat is located in the Simonton Historic Cottages enclave and is surrounded by fine restaurants, art galleries, shopping and in the center of the Old…
  • Internet Access
  • Housekeeping Optional
  • Outdoor Dining Area
  • A/C or climate control
  • Porch
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly

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$225

2 BR / 2 BA / Sleeps 4

9 Reviews

$225

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President's Lane

2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 9 Reviews

Details

Reviews

(9)

If any residence deserves the location-location-location mantra, it's this two-bedroom, two-bath townhouse in Truman Annex. The first "location" is the island of Key West, a world-class vacation destination. The second is Truman Annex, a premiere gated waterfront community named for President Harry Truman. The third "…
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Central heating
  • Suitable for the elderly - ask

Details

Reviews

(9)

great location

Left on Aug 16, 2008 for a stay in April 2008

The location of the townhouse in Truman annex was perfect for us. I walked to the Fort Zachary beautiful beach every morning for yoga on the beach and sunbathing and snorkeling. We were able to walk to town and most everywhere we wanted to go. The house was clean,beautifully appointed and comfortable for two couples. We would definitely stay here again.

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$250

2 BR / 2 BA / Sleeps 6

25 Reviews

$250

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Duval Street Suite

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 25 Reviews

Details

Reviews

(25)

Everybody knows it's all about location: in this case, a dream vacation location in the heart of Old Town Key West. Duval Street Suite is a two-bedroom, two-full-bath townhouse in a small rooftop community overlooking the island's main artery for fun and entertainment. From your private and expansive Bahamian-style …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Central heating

Details

Reviews

(25)

Beth was great!

Left on Apr 06, 2011 for a stay in March 2011

It was a great location. Any problems we had Beth got it taken care of very quick...even one of the tvs went out and they replaced that day. It could use internet was the only thing we missed.

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$232

3 BR / 3 BA / Sleeps 6

1 / 21

$232

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Blackbeard's Treasure - MONTHLY Rental (30 night min.)

3 BR / 3 BA / Sleeps 6 | Quick view

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Save 3% off published rates if you pay by cash/check. To say this townhouse condominium is worth the amassed treasure of Blackbeard, one of the most notorious and wealthy pirates in seafaring history, is a major understatement. The 1950's era art deco Steamplant at water's edge has been quintessentially transformed …
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for the elderly - ask

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$175

3 BR / 3 BA / Sleeps 6

1 / 17

$175

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Mediterranean Caribbean Villa ~ Monthly Rental

3 BR / 3 BA / Sleeps 6 | Quick view

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Tucked behind a breathtaking tropical garden wall this spectacular Mediterranean Caribbean vacation rental home reflects a dynamic blend of contemporary Mediterranean with Caribbean architectural design. Located along one of Key West's most desirable residential streets this "Casa el Paradiso" most …
  • Housekeeping Optional
  • A/C or climate control
  • Stereo or CD player
  • Telephone
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$214

2 BR / 2 BA / Sleeps 4

8 Reviews

$214

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"Shipyard Perch" Weekly or Monthly (Truman Annex) - Gourmet Appointed Kitchen

2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 8 Reviews

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Reviews

(8)

***Due to licensing restrictions, this property requires a minimum stay of 7 nights.*** The Shipyard’s Perch is a great place to stay and play near the water and Old Town Key West! Located in Truman Annex, a secure enclave of historic and exclusive residences, Truman Annex is the most exclusive and …
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Deck
  • Fitness Room
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(8)

Wonderful trip!

Left on Jan 27, 2011 for a stay in April 2010

Something to do every day, perfect location, nice condo.

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$83

2 BR / 2 BA / Sleeps 6

1 / 30

$83

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"HOWE STREET HIDEAWAY" Newly Renovated 2 Bed Two Bath Home.

2 BR / 2 BA / Sleeps 6 | Quick view

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***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** The neighborhood is complete with conch style homes, little lanes, corner gardens and yes our famous Key West Roosters watching their chicks. Featuring a classic front porch for greeting the neighbors as they go about their day…
  • Internet Access
  • A/C or climate control
  • Patio
  • Fitness Room
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$150

2 BR / 1 BA / Sleeps 4

1 / 15

$150

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"ISLAND RENDEZVOUS" Gorgeous Old Town Home w/ Private Pool

2 BR / 1 BA / Sleeps 4 | Quick view

Details

***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** This exclusive home in the heart of the island offers optimum privacy while having an airy and open floor plan and the best of appointments throughout. Whether enjoying the heated pool flanked by meticulously maintained …
  • Internet Access
  • A/C or climate control
  • Deck
  • Fitness Room
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$215

1 BR / 2 BA / Sleeps 4

25 Reviews

$215

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Tranquility

1 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 25 Reviews

Details

Reviews

(25)

TRANQUILITY - The epitome of life in Key West, this charming cottage is full of color and creativity, lovingly restored with no detail overlooked. Fabulous artwork, fun collectables, beautiful stained glass all give this cottage the unique feel that keeps bringing visitors back to Key West. As you enter this wonderful…
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Grill
  • Television
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(25)

I needed to get away!

Left on Oct 20, 2011 for a stay in October 2011

Ladies,
I had so much stress in my life at this time. I just needed to get away! I walked into this cottage an immediately felt at home. Just enough room the extra bath is great when having guests over. The pool is perfect for short laps and the pond was a tranquil centerpiece to the front porch area.
Clean and tranquil! Will definitely come back.
M

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$400

2 BR / 2 BA / Sleeps 8

1 / 6

$400

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Hyatt Sunset Harbor Key West, FL

2 BR / 2 BA / Sleeps 8 | Quick view

Details

Please note. This is a timeshare rental and I have only 1 week allotted to me. Please do not request any dates other than available week of March 8th through the 15th. This Hyatt property is a 2 floor--2 Bedroom Caribbean furnished condo type unit situated right in the heart of Key West facing the famous sunset. …
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Balcony or terrace
  • Parking
  • Grill
  • Suitable for children
  • Suitable for the elderly - elevator access
  • Wheelchair accessible - ask

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$83

1 BR / 1 BA / Sleeps 2

1 / 9

$83

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Butterfly Garden ~ Monthly Rental

1 BR / 1 BA / Sleeps 2 | Quick view

Details

Completely hidden from the street, this recently redecorated garden flat provides you with two private entrances off a large gated manicured garden. Your own private expansive covered bricked front porch spans the width of the garden right out the front door and leads to a beautiful meditation garden. Relax and …
  • Internet Access
  • Linens Provided
  • Telephone
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$175

3 BR / 2 BA / Sleeps 8

1 / 16

$175

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Island Elegance ~ Near The Beach ~ Monthly Rental

3 BR / 2 BA / Sleeps 8 | Quick view

Details

Strikingly set in the oft-missed Key West Beachside neighborhood, we find Island Elegance ~ Near the Beach, making a seriously smart curbside statement showing a tall white privacy wall topped with shimmering green louvers. Completely renovated in summer 2012, to modern luxury standards, this island home is a fabulous…
  • Housekeeping Optional
  • A/C or climate control
  • Grill
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$600

3 BR / 3 BA / Sleeps 6

9 Reviews

$600

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Kemp House

3 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 9 Reviews

Details

Reviews

(9)

This Civil War Era home sits in Key West's most desirable Historic Seaport District, less than a block from the Gulf of Mexico. Did Abraham Lincoln sleep here? Probably not. But anyone staying today in this classic revival valued in the millions will find not only history but every creature comfort and contemporary …
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for the elderly - ask

Details

Reviews

(9)

very lovely

Left on Feb 09, 2009 for a stay in November 2008

Beautiful house. Near everything. Comfortable and well kept.

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$167

3 BR / 3 BA / Sleeps 6

4 Reviews

$167

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"TOBAGO GRANDE" Monthly Rental Home w/ Private Pool Just 1 Block To Duval

3 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 4 Reviews

Details

Reviews

(4)

***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Tobago House is just steps from restaurants, night life, Hemingway's House, and the 'Southernmost Point' of the United States. This home offers an open, airy floor plan with old style pine walls and floors, cathedral ceilings …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Patio
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(4)

Perfect in Every Way!

Left on Nov 14, 2013 for a stay in October 2013

I stayed at Tobago house for the month of October and loved it! This was my 2nd stay - my best friend rented the house for 6 weeks in the spring of 2012 - and it was even better than I remembered. The house is well appointed with all the things one needs to set up house for a few days or for several weeks.

The location is prime and provides easy access to Duval street and all the shops and …

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$185

2 BR / 1 BA / Sleeps 4

21 Reviews

$185

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Shipyard

2 BR / 1 BA / Sleeps 4 | Quick view
“ Excellent ” 21 Reviews

Details

Reviews

(21)

This cozy two-bedroom, one-bath condo lies hidden behind wrought iron gates and down a winding pathway. The Shipyard, part of the Truman Annex neighborhood named for President Harry Truman, is Old Town's premiere gated waterfront community. The manicured landscaping, verdant palms, and white picket fences give the …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for the elderly - ask

Details

Reviews

(21)

Great for Boat Races!

Left on Nov 13, 2008 for a stay in November 2008

Great location for walking to watch the races and Duval Street. Quaint,clean, and spacious. Small bathroom and kitchen that need an update, but otherwise a great place! I stayed in a gated complex so the added security was a plus and I felt safe at all times. I would certainly stay again without hesitation!

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$198

2 BR / 2 BA / Sleeps 6

1 Reviews

$198

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CAT ISLAND SUITE #205 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach

2 BR / 2 BA / Sleeps 6 | Quick view
“ Terrible ” 1 Reviews

Details

Reviews

(1)

Sunrise Suites Resort is an island paradise. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped pool surrounded by lush tropical foliage where you can let your cares melt away. Please take a moment to look through our site at our many amenities, the …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Aweful

Left on Nov 11, 2014 for a stay in October 2014

Avoid this place at all costs . It is horrible ….. I would rather have stayed in my car. The apartment was disgusting . Furniture looked like it was from the early 80's and was dirty.

The walls are mirrored and broken, fixed with tape. The smoke alarms are missing but the wires are hanging out of the walls. I would never stay there again. I do have to say the girl at the front desk was nice …

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$216

2 BR / 2 BA / Sleeps 6

1 / 17

$216

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Key West Bluewater Retreat

2 BR / 2 BA / Sleeps 6 | Quick view

Details

Bluewater is a classic porch-on-porch Key West home with all the amenities to make your vacation ideal. Located in the prestigious Sanctuary of the Key West Golf Club, the house has two bedrooms each with its own private bath. The house sleeps 4 adults and two children or smaller adults. It offers a private patio, …
    • Pet friendly - ask
    • Suitable for children

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    $700

    4 BR / 3 BA / Sleeps 10

    9 Reviews

    $700

    Inquire

    Truman House

    4 BR / 3 BA / Sleeps 10 | Quick view
    “ Excellent ” 9 Reviews

    Details

    Reviews

    (9)

    The Keys have some of the most charming, top-rated vacation residences in the world. Truman House, a 1920's Conch home with four spacious bedrooms, three full baths, a dazzling pool, and ample amenities easily qualifies for the list. And as an added perk, this classic pet-friendly home is located on an upscale and …
    • Hot Tub/Jacuzzi
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • Suitable for the elderly - ask

    Details

    Reviews

    (9)

    Extremely comfortable house in a great neighborhood

    Left on May 13, 2011 for a stay in February 2011

    The Truman house is an extremely comfortable house in a great neighborhood. We rented the house two years in a row for three months. We loved the huge heated pool and the privacy afforded by the landscaping. The location gives you the opportunity to enjoy some of the best restaurants in Key West, all within walking distance. While only a few blocks from Duval Street, you are far enough away to …

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    $183

    2 BR / 2 BA / Sleeps 6

    1 / 20

    $183

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    A Low Key Paradise

    2 BR / 2 BA / Sleeps 6 | Quick view

    Details

    Located on a quiet residential street in the beautiful Key West neighborhood of Casa Marina, A Low Key Paradise has a beautiful open layout, with views of the large private patio and pool visible as soon as you enter. Guests can walk to nearby Higgs beach, and Higgs beach dog park— perfect for your family member …
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • A/C or climate control
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible - ask

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    $308

    2 BR / 2 BA / Sleeps 6

    13 Reviews

    $308

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    "GARDEN OF EDEN" - Papa's Hideaway Historic Inn's 2 BR/2 Bath Cottage

    2 BR / 2 BA / Sleeps 6 | Quick view
    “ Excellent ” 13 Reviews

    Details

    Reviews

    (13)

    Located at Papa's Hideaway , the serene grounds strike you immediately upon entering the beautifully landscaped, gated property. Located just one block off World Famous Duval Street, Garden of Eden is the perfect combination of quiet Key West living and optimum access to all of the islands best attractions. The …
    • Shared outdoor pool (unheated)
    • Internet Access
    • A/C or climate control
    • Patio
    • Fitness Room
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (13)

    Great Cottage Property

    Left on Nov 22, 2013 for a stay in November 2013

    I spent a long weekend at this property with my wife and another couple. The property was clean, well maintained, quiet (although only a short walk to Duval) and very private. The landscaping, outdoor seating and pool were also nice added features. We would definitely stay again.

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    $250

    2 BR / 2 BA / Sleeps 6

    34 Reviews

    $250

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    Duval Square

    2 BR / 2 BA / Sleeps 6 | Quick view
    “ Excellent ” 34 Reviews

    Details

    Reviews

    (34)

    The rooftop community of Duval Square is a prime perch from which to launch the best tropical vacation ever. The townhomes cluster on the second story above their namesake square. Winding pathways bordered by swaying palm and colorful plantings arranged in terracotta pots define the layout. Best of all, the small …
    • Hot Tub/Jacuzzi
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • Suitable for the elderly - ask

    Details

    Reviews

    (34)

    Barbecue

    Left on Aug 14, 2008 for a stay in February 2008

    The vacation week was good, except for the use of the barbecue. When we had stayed there before we had used the barbecue every other night (and gone out for dinner the other nights). We have a 6 yr. old and the deal we made with him was the above (as you know 6 yr. olds couldn't care less about eating out) and prefer barbecues and staying in. (ours does anyway). This February we were told that we…

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    $215

    1 BR / 2 BA / Sleeps 4

    1 / 6

    $215

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    Coconut Beach

    1 BR / 2 BA / Sleeps 4 | Quick view

    Details

    This Key West condo is legally listed as a one-bedroom. However it could easily accommodate two couples, or a family of 4, with privacy. The first floor includes a full kitchen, full bath, dining area, TV area with a sofa, and a Murphy Bed. The second floor (a lock-out unit) includes a "closet kitchen", a king bed…
    • Ocean or water views
    • Hot Tub/Jacuzzi
    • Internet Access
    • Outdoor Dining Area
    • A/C or climate control
    • Smoking allowed - ask
    • Suitable for children
    • Suitable for the elderly - ask

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    $87

    2 BR / 2 BA / Sleeps 4

    7 Reviews

    $87

    Inquire

    Key Lime Pie

    2 BR / 2 BA / Sleeps 4 | Quick view
    “ Very Good ” 7 Reviews

    Details

    Reviews

    (7)

    KEY LIME PIE: One block from the Historic Seaport and close enough to bike to all the sites and attractions of Old Town.Refurbished with updated kitchen cabinets, countertops, and appliances. On the first floor you will find the living room, kitchen, master bedroom and bathroom. On the second floor is the guest …
    • Hot Tub/Jacuzzi
    • A/C or climate control
    • Parking
    • Grill
    • Television
    • Pet friendly
    • Smoking allowed - ask
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (7)

    Cute & Clean

    Left on Nov 06, 2008 for a stay in March 2008

    House is very nice, well kept and supplied, cozy. Good location by Key West Bight waterfront
    Second year we stayed and there were changes in the neighborhhod. Several vacant and unkempt properties, lots of traffic in the alley, several vagrants had to be shooed away from the house. Not returning to this property in 09. A little pricey for the size also.

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    $467

    5 BR / 5 BA / Sleeps 14

    1 / 40

    $467

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    "SHARK KEY CHATEAU" Incredible 3-Story Mansion w/ Private Beach, Pool, & Spa

    5 BR / 5 BA / Sleeps 14 | Quick view

    Details

    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Shark Key Chateau is 'Grande' to say the least. With unspoiled views from every angle, to playful colors, and unrivaled decor and design, this home is a Chateau unlike any other. Shark Key Chateau is designed in true keys …
    • Private Beach
    • Waterfront
    • Ocean or water views
    • Hot Tub/Jacuzzi
    • Internet Access
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $153

    2 BR / 2 BA / Sleeps 4

    1 / 16

    $153

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    Tropical Sun Garden Retreat ~ Monthly Rental

    2 BR / 2 BA / Sleeps 4 | Quick view

    Details

    Everyone dreams of a charming Key West cottage, tucked away in a tropical sun garden where flowers and trees flourish around an outdoor living porch all year round. This private cottage has all of that and more. Situated in the Conch Grove Garden compound, in Old Town Key West, this quiet little gated community has …
    • Internet Access
    • Housekeeping Optional
    • A/C or climate control
    • Pet friendly - ask
    • Smoking allowed - ask
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask
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