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$290

2 BR / 2 BA / Sleeps 6

18 Reviews

$290

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Beach Club #103 - Unique oceanfront living with breathtaking views

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 18 Reviews

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Reviews

(18)

Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water. The breathtaking view can be seen as soon as you enter the unit. This spacious 2 bedroom unit features a large oceanfront balcony accessed from both the …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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Reviews

(18)

Great Location

Left on Jun 27, 2009 for a stay in April 2009

We are very satisfied with Rent Key West Vacations. The staff was very helpful. We stayed at Key West Beach Club. We were extremely pleased with the Condo we rented, very comfortable, beautiful views of the ocean, it was better than we expected. The kitchen was nicely equipped. We could have used a better vacuum and the washer & dryer combo was very noisy. The pool and grill area were …

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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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$215

2 BR / 1 BA / Sleeps 6

The Banyan Resort at Key West - Key West vacation rentals
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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$750

4 BR / 4 BA / Sleeps 8

27 Reviews

$750

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Southard Street Queen Conch - A Historic compound with large sunny pool

4 BR / 4 BA / Sleeps 8 | Quick view
“ Excellent ” 27 Reviews

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Reviews

(27)

On a lovely tree-lined residential street in the heart of the historic Old Town district, this quiet, historic compound offers three separate vacation suites sharing a lush, large, sunny pool or combines for a wonderful four bedroom retreat. Downstairs enjoys a large, open floor plan with living and dining room, …
  • Internet Access
  • A/C or climate control
  • Deck
  • Parking
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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Reviews

(27)

What a lovely property

Left on Jun 18, 2009 for a stay in May 2008

This is a great home in a great location. All of the rooms are wonderfully furnished and clean. The backporch and sun deck are truly amazing and relaxing. I especially enjoyed the privacy of the pool and backyard for relaxing and resting. I would stay here again over and over again.

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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

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(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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$270

2 BR / 2 BA / Sleeps 6

21 Reviews

$270

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Vista Fresco : Oceanside condominiums with resort-style amenities

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 21 Reviews

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Reviews

(21)

Enjoy the resort-style amenities of 1800 Atlantic Condominiums while relaxing in a residential setting amongst neighbors. 1800 Atlantic sits on 400 feet of oceanfront property. An expansive pool and spa sits oceanside surrounded by a lushly landscaped garden of native Key West plants and trees. Plan a picnic or …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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Reviews

(21)

The appart was fantastic but it was impossible to use the pool.

Left on Aug 12, 2009 for a stay in July 2009

If there wasn't any pool at this condo, we'd never rent it. Unfortunatly, the pool
was broken and it was impossible to use it. We arrived on thurdays and friday,
the pool was broke. We ask to know when it would be repare, they told us it
would be the next monday but when we left on thursday night, the pool was
still broke... This point realy desapoint us.

For the condo, everything was …

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$290

2 BR / 2 BA / Sleeps 6

15 Reviews

$290

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Beach Club #201 - Unique Oceanfront living

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

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Reviews

(15)

Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water. The breathtaking view can be seen as soon as you enter the unit. This 2 bedroom, 2 bath unit features a huge oceanfront balcony accessed from both the living/…
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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Reviews

(15)

Key West Wedding Vacation

Left on Jun 18, 2009 for a stay in June 2008

We loved staying at the condo.. It fit 5 of us very comfortably. We were down for a wedding. The view was great, the securty made me feel safe. We used the pool almost daily and actually had a couple of friends over for a cookout by the pool. I would stay with Rent Key West Vacations again and would recommend it to a friend.

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$850

4 BR / 4 BA / Sleeps 8

15 Reviews

$850

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Villa Tropicale: A lush, secluded estate in the Casa Marina District

4 BR / 4 BA / Sleeps 8 | Quick view
“ Excellent ” 15 Reviews

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Reviews

(15)

Tropical seclusion best describes this oasis in the Casa Marina District. Enter the splendor of this large estate through a private gate; stroll down brick pathways, meandering by the cottage until you reach the two story main home. The gardens are lush and abundant featuring various species of mature palms, birds of …
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Parking
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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(15)

The coolest house ever!

Left on Jun 18, 2009 for a stay in November 2008

I would highly recommend this property to anyone looking for a place to stay in Key West with a group of friends. It offers the best of both worlds....You could never leave the property and have a wonderful time or a quick cab ride and you're at Duval Street. Our group ventured off on a day trip to the Dry Tortugas, which was set up by the properties conceier service...and that was awesome...…

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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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$227

3 BR / 3 BA / Sleeps 6

2 Reviews

$227

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"VILLA AZUL" Luxurious Monthly Home w/ Pvt Pool, Deck & Gorgeous Interior.

3 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 2 Reviews

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Reviews

(2)

***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** You will certainly enjoy this wonderful historic home with recent renovations, perfectly placed pool, and plenty of outdoor living space located at 1116 Curry Lane. This home is situated in the heart of Old Town, just 4 blocks …
  • Internet Access
  • A/C or climate control
  • Deck
  • Fitness Room
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Beautiful and comfortable home

Left on Jan 27, 2011 for a stay in December 2008

Villa azul is a wonderfully decorated and appointed home in the historic Old Town section of Key West. The home and grounds were beautiful, serene, private and cozy. It is hard to imagine that this property would not exceed anyone's expectations.

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$320

2 BR / 2 BA / Sleeps 4

30 Reviews

$320

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Havana Lane: A classic conch cottage with rustic charm

2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 30 Reviews

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Reviews

(30)

Thoughtfully restored, Havana Lane, hearkens back to a time when cigar makers lived in the neighborhood, gathering on porch stoops to pass on the latest news. Near the notorious Key West Cemetery this classic conch cottage, embodies the essence of rustic charm while offering modern amenities and style. Centrally …
  • Internet Access
  • A/C or climate control
  • Deck
  • Grill
  • Linens Provided
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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Reviews

(30)

Gorgeous surroundings, comfortable Key West home

Left on Jun 18, 2009 for a stay in April 2009

As soon as we unlocked the gate to the high wooden fence surrounding 1
Havana Lane, we knew we had picked a gem of a place to stay for Spring Break.
My husband and I came to Key West with our 15 year-old daughter and her
friend. The home was perfect for us four, and we enjoyed being there almost
as much as going out and about the island. We called the yard our "Secret
Garden." It was so lush…

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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

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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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$290

2 BR / 2 BA / Sleeps 6

9 Reviews

$290

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Beach Club #112 - Unique Oceanfront living

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 9 Reviews

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Reviews

(9)

Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water. The breathtaking view can be seen as soon as you enter the unit. This comfortable 2 bedroom unit features a huge oceanfront balcony accessed from both the …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(9)

Fabulous view

Left on Jun 19, 2009 for a stay in May 2009

This unit was just lovely, the view off the terrace was amazing. We had the pool (one of 2) to ourselves everyday. We never heard any of our neighbors. Although the beach was not manicured, the unit was very close to 2 beaches, if you want to sit in the sand.
We could see cruise ships and parasailing right off the pation. I can't say enough, it was GREAT.

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$340

3 BR / 2 BA / Sleeps 8

8 Reviews

$340

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Hemmingway's Retreat

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

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Reviews

(8)

Welcome To Paradise!!! Located in the heart of Key West this charming 3 bedroom, 2 bathroom house has been completly renovated and includes 50", 42", and 27" flat screen TVs, DVR, and wireless high speed internet. The interior has just been furnished with custom designer furniture by Domestic Home Furnishings. The …
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly

    Details

    Reviews

    (8)

    1211 Catherine St.

    Left on May 10, 2010 for a stay in April 2010

    My wife and I spent time in April at 1211 Catherine St., Key West, FL and had a marvelous time. The house is wonderful expecially the private pool. All that Key West has to offer is within easy walking or cycling distance of the house. The house is beautifully furnished and appointed so much so we spent many days just staying home and relaxing around the pool. One of the bicycles provided had to…

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    $339

    3 BR / 2 BA / Sleeps 8

    1 / 31

    $339

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    Relax In The Keys 0039

    3 BR / 2 BA / Sleeps 8 | Quick view

    Details

    April Just Became Available/Rare Opportunity...Book NOW! One of the very few & one of the largest oceanfront suites in Key West OCEANFRONT… there is nothing like it. To me, it means being directly on the shoreline with nothing between me and the sensation of the ocean. Totally different from ocean view, which …
    • Waterfront
    • Ocean or water views
    • Shared outdoor pool (unheated)
    • Hot Tub/Jacuzzi
    • Internet Access
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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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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    $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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    $270

    2 BR / 1 BA / Sleeps 4

    1 / 13

    $270

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    Pete's East Cottage: Cypress east cottage steps from Duval

    2 BR / 1 BA / Sleeps 4 | Quick view

    Details

    This property has it all! The styling of the original shot gun homes of Key West restored with a beautiful natural cypress exterior combines with the clean lines of a contemporary home. Each Twin opens to it's own semi-private deck and lounge area with steps into a large kidney shaped pool with waterfall. Inside the …
    • 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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    $1,000

    5 BR / 4 BA / Sleeps 12

    19 Reviews

    $1,000

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    DREAMING ON DUVAL- Luxury 5 Bed & Private Pool- As seen on HGTV House Hunters

    5 BR / 4 BA / Sleeps 12 | Quick view
    “ Excellent ” 19 Reviews

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    Reviews

    (19)

    Luxury on Duval Street in historic Key West? Luxury is not what most people visiting Key West associate with Duval Street until you look at Dreaming On Duval! There are very few private homes on Duval, let alone a single family vacation rental that is steps away from everything Key West has to offer and accommodates …
    • Hot Tub/Jacuzzi
    • Internet Access
    • A/C or climate control
    • Balcony or terrace
    • Parking
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (19)

    Fabulous...

    Left on May 24, 2010 for a stay in May 2010

    Dreaming in Duval is a beautiful, spacious home. The home is very well equipt,and accomodated 10 people easily.
    The location was perfect, we could walk to everything.
    Dean and Paul were both great and very helpful.
    One of our best vacations ever, we are already planning a return trip.

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    $103

    1 BR / 1 BA / Sleeps 4

    1 / 16

    $103

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    Topsail Cottage Key West ~ Monthly Rental

    1 BR / 1 BA / Sleeps 4 | Quick view

    Details

    Island living is made easy in this tropical one bedroom, 2-story Key West cottage. A classic-contemporary Key West style, this attractive rental home is designed with a graceful spiral stair case that connects the 1st and 2nd floors and a romantic gingerbread Juliet-style 2nd floor balcony overlooking a private …
    • Internet Access
    • Housekeeping Optional
    • A/C or climate control
    • Satellite or cable TV
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $133

    2 BR / 5 BA / Sleeps 4

    1 / 14

    $133

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    Buoy's Backyard

    2 BR / 5 BA / Sleeps 4 | Quick view

    Details

    MONTHLY RENTAL ONLY Buoy's Backyard - an authentic Key West retreat in the historic district just a block from upper Duval (the quiet end), two blocks from Hemingway House, and three blocks to Southernmost Buoy and Beach. Brick driveway provides private gated parking for two cars. This home has 2 buildings …
    • Wireless Internet
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • A/C or climate control
    • Pet friendly - ask
    • Suitable for children - over five
    • Wheelchair accessible

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    $83

    1 BR / 2 BA / Sleeps 4

    6 Reviews

    $83

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    "PARADISE SUITE" Monthly Villa In Gated Complex w/ Pool. Steps to Duval St

    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.*** Nestled in extensive tropical and flowering gardens, complete with aviaries with singing cockatiels lays the Paradise Suite. Paradise Suite (renovated for January 2013) is a bi-level suite with one bedroom upstairs. The …
    • Shared outdoor pool (unheated)
    • Internet Access
    • A/C or climate control
    • Patio
    • Fitness Room
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (6)

    Great time in Keys at Esperanza

    Left on Jan 28, 2011 for a stay in October 2009

    Very Nice! Great location for Fantasy Fest and the Parrothead music week that follows. Separate upstairs bedroom and a couch downstairs with its own bathroom was great for a short term friend to stay. Very private with the courtyard and gate. We really liked it...

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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

    Details

    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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    $83

    0 BR / 1 BA / Sleeps 2

    2 Reviews

    $83

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    "SAILMAKER'S STUDIO" Monthly- Seaport- Old Town

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

    Details

    Reviews

    (2)

    28 NIGHT MINIMUM STAY REQUIREMENT - THE STUDIO AT THE SAILMAKER'S HOUSE Beautifully Renovated Second Floor Studio for Two - Incredible Location in Historic Old Town Gorgeous studio apartment on the second floor of the historic Sailmaker's House. This 28 night minimum vacation rental is located only 1.5 blocks from …
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • A/C or climate control

    Details

    Reviews

    (2)

    great place, great location, great stay!

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

    I really enjoyed my stay at the sailmaker's studio. The staff as well as the owner were very easy to work with and very helpful. My small dog was with me and he enjoyed it too. It is just blocks away from the wharf and restaurants, shops, grocery stores, sailing/boating trips are also just short walks away. It has all the typical amenities you could want: 2 balconies (1 is shared with another apt…

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    $400

    2 BR / 2 BA / Sleeps 4

    10 Reviews

    $400

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    Casa Camilla

    2 BR / 2 BA / Sleeps 4 | Quick view
    “ Excellent ” 10 Reviews

    Details

    Reviews

    (10)

    You'll know you've found island heaven--the term heaven meaning transcendence or going beyond the ordinary--when you enter Casa Camilla. This two-bedroom, two-bathroom home located in the lovely Meadows neighborhood of Old Key West is extraordinary inside and out. The outside rear half of the property is beautifully …
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • A/C or climate control
    • Suitable for the elderly - ask

    Details

    Reviews

    (10)

    absolutely gorgeous!

    Left on Dec 07, 2011 for a stay in November 2011

    The house is absolutely beautiful and in a great location; easy to get to Duval street. Very quiet neighborhood. The house had everything except internet access and a heated pool/jacuzzi.

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    $175

    2 BR / 2 BA / Sleeps 5

    7 Reviews

    $175

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    Sunrise at Seaside Condo 2 Bedroom

    2 BR / 2 BA / Sleeps 5 | Quick view
    “ Excellent ” 7 Reviews

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    Reviews

    (7)

    Tropical 2 bedroom, 2 bath Key West Condo. Large balcony overlooking pool. Full kitchen and living room with all the amenities of home. Large heated pool and Jacuzzi. Tennis court and gym. Washer and dryer in unit. Great condo complex on quiet side of island. Located 1 mile from Smathers Beach. Plenty of …
    • Hot Tub/Jacuzzi
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • A/C or climate control
    • Suitable for children
    • Suitable for the elderly

    Details

    Reviews

    (7)

    OK

    Left on Feb 14, 2014 for a stay in February 2014

    when we arrived the condo smelled cigarette smoke, there was no notation if there is wi-fi and if there was no code was provided until we called the following day.

    i know this is Key West where smoking is allowed everywhere. when i looked at the ad smoking was not mentioned. i just assumed that the condo would be smelling great since the rent was top notched. it is about 4 miles to the heart of …

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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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    $83

    4294967295 BR / 1 BA / Sleeps 2

    1 / 34

    $83

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    "HARBOUR LIGHTS" - Monthly Studio- Historic Seapor

    1 BA / Sleeps 2 | Quick view

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    Beautifully Renovated First Floor Studio for Two - Incredible Location in Historic Old Town Gorgeous studio apartment on the first floor of the historic Sailmaker's House. This 28 night minimum vacation rental is located only 1.5 blocks from the Historic Seaport and 4.5 blocks from Duval Street. You will be living …
    • Waterfront
    • Wireless Internet
    • Housekeeping Optional
    • Washing Machine
    • Clothes Dryer
    • Suitable for children - ask
    • Suitable for the elderly
    • Wheelchair accessible - ask

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    $269

    0 BR / 1 BA / Sleeps 2

    1 / 16

    $269

    Inquire

    Key West Beach Front rental Your Ocean View Studio

    0 BR / 1 BA / Sleeps 2 | Quick view

    Details

    See if this unit is for you! RATE – BOOK – POLICY right here in description. Last min. Specials for Ocean view studio 7 days prior. Come have breakfast lunch or dinner in your hidden GEM of a suite overlooking the beach! Please read this ad to expedite Q'S at booking! All rates are base rates unless stated …
    • Waterfront
    • Ocean or water views
    • Housekeeping Optional
    • Outdoor Dining Area
    • A/C or climate control
    • Suitable for the elderly - ask

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    $83

    1 BR / 1 BA / Sleeps 2

    1 Reviews

    $83

    Inquire

    "SOUTHARD SQUARE HIDEAWAY" Monthly- Parking & Pool

    1 BR / 1 BA / Sleeps 2 | Quick view
    “ Very Good ” 1 Reviews

    Details

    Reviews

    (1)

    This vacation home is only licensed for stays of 28 nights or more. Southard Square Hideaway is a newly renovated first floor corner condo perfect for 2 plus space for visiting friends and family! Monthly Rental A surprise awaits you inside the gates of the Southard Square village. Nestled in the heart of Historic …
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • A/C or climate control
    • Central heating
    • Suitable for the elderly

    Details

    Reviews

    (1)

    Great location...Relax and enjoy!

    Left on Apr 27, 2014 for a stay in January 2014

    Very nice condo with huge pool area. Very clean and neat. We loved the location! We would love to go back again some day. The only negative was the living room furniture. It seem really inexpensive and quite uncomfortable...it did looked nice. No table in condo...only counter with two small bar stools. Wish it had a small table with 4 chairs. Condo manager Carlos was wonderful.

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    $93

    1 BR / 1 BA / Sleeps 2

    1 / 48

    $93

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    "TREETOP APARTMENT" Monthly - Sleeps 2 - Seaport

    1 BR / 1 BA / Sleeps 2 | Quick view

    Details

    28 NIGHT MINIMUM STAY REQUIREMENT - THE TREETOP APT AT THE SAILMAKER'S HOUSE Beautifully Renovated Second Floor Apartment for Two - Incredible Location in Historic Old Town Gorgeous one bedroom apartment on the second floor of the historic Sailmaker's House. This 28 night minimum vacation rental is located only 1.5 …
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • A/C or climate control

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    $378

    3 BR / 2 BA / Sleeps 6

    1 / 10

    $378

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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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    $229

    2 BR / 2 BA / Sleeps 6

    5 Reviews

    $229

    Book

    1/2 Block to Duval, World of its own -Nassau Suite

    2 BR / 2 BA / Sleeps 6 | Quick view
    “ Excellent ” 5 Reviews

    Details

    Reviews

    (5)

    The Nassau Suite is one of the largest suites in The Bahama House. Featuring 2 King Bedrooms, 2 Bath and 2 Day-rooms with Futons. Quietly Tucked away in a world of it's own, yet literally only steps away from all that Key West has to offer. Whether your looking for a place to meditate or find an endless party, The …
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • A/C or climate control
    • Suitable for the elderly - ask

    Details

    Reviews

    (5)

    Wish I had found this place 15 years ago.

    Left on Jan 06, 2014 for a stay in December 2013

    Stayed in the Nassau the week of Christmas thru New Years. Came down with two other couples. The pictures do not do this place justice. Plenty of room for all. Having two bathrooms was also a plus. Very close to Duval street, and anywhere you really would want to go is in walking distance, minus the beach, but is a short/cheap taxi ride away. Our unit had 90% new furniture, and matresses. …

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    $450

    3 BR / 2 BA / Sleeps 6

    8 Reviews

    $450

    Book

    3 Bedroom Oceanfront Condo Key West

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

    Details

    Reviews

    (8)

    Large 3 Bedroom, 2 Bath OCEANFRONT condo. Breathtaking views of the Atlantic from every room. Tropical landscaped property with large heated pool and Jacuzzi. Just steps to Smathers Beach which has swimming, jet skis, parasailing, etc. Fully appointed condo with all the amenities of home at your fingertips. Sorry …
    • Waterfront
    • Ocean or water views
    • Hot Tub/Jacuzzi
    • Internet Access
    • Washing Machine
    • Suitable for children

    Details

    Reviews

    (8)

    Beautiful oceanfront condo

    Left on Jan 11, 2014 for a stay in January 2014

    We just rented this unit - it was wonderful!!! Beautiful kitchen,
    recently remolded. Large family room. Bedrooms nice sizes. Unit
    has a complete wrap around deck with ocean views. About 3 minute walk to Smathers beach. Really nice pool & 15 person hot tub. If you are
    a beach person this unit is for you!! Only negative - not that close
    to the down town area(5 minute car ride) - however unit …

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    $270

    2 BR / 3 BA / Sleeps 4

    3 Reviews

    $270

    Book

    Shelleys Rooftop Hideaway

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

    Details

    Reviews

    (3)

    Upper Duval is the best! A few steps away from the Southernmost pt & beaches,great restaurants,art galleries, Louies backyard,and Blue Heaven. A few more steps from Mallory sq, Sloppy Joes, Smokin tuna, the pier restaurants, entertainment day and night. Have the best of both worlds, be in the middle of all key …
    • Housekeeping Optional
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • A/C or climate control
    • Pet friendly - ask
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible - ask

    Details

    Reviews

    (3)

    Great location

    Left on Dec 31, 2013 for a stay in December 2013

    Really enjoyed staying at Shelleys Rooftop. Far enough down Duval St. to be away from the crowds but just a walk away to the crowds and popular bars. Spent Christmas with family and friends in Key West and fun time had by all. Great pool at the condo and great people watching area at the "ledge" over looking Duval St. Condo was perfect for the 5 of us especially with 2 1/2 baths. When I …

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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

    Details

    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 into Old Town Key West's most opulent vacation community…
    • Ocean or water views
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • Suitable for the elderly - ask

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    $600

    2 BR / 2 BA / Sleeps 6

    1 / 24

    $600

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    Garden Home Paradise in Midtown Key West

    2 BR / 2 BA / Sleeps 6 | Quick view

    Details

    2 bedrooms, 1 Bath, 1 Outdoor Shower and Pavillion, Tropical Garden (sleeps 4-6). Open the gate and stroll through the lush gardens of this beautiful two bedroom, one bath home, built in 1953 and entirely renovated. In addition to the updated kitchen and bath, there's a screen porch, a covered outdoor pavillion with …
    • Internet Access
    • Housekeeping Optional
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly - 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

    PreviousNext property

    $183

    2 BR / 2 BA / Sleeps 6

    1 / 20

    $183

    Book

    A Low Key Paradise- Monthly rental only

    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 …
    • Wireless Internet
    • Housekeeping Optional
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible - ask

    PreviousNext property

    $100

    2 BR / 1 BA / Sleeps 4

    1 / 34

    $100

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    "ANGELFISH COTTAGE" - Monthly - 2 Bedroom on a quiet Key West Lane

    2 BR / 1 BA / Sleeps 4 | Quick view

    Details

    28 NIGHT MINIMUM STAY REQUIREMENT - ANGELFISH COTTAGE 2 Bedroom 1 Bath Historic Conch House on a quiet Lane in Historic Old Town Key West This monthly vacation home is located in the heart of Historic Old Town Key West Florida on a very private, quiet lane. Restaurants and bars, marinas and shopping are all within …
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • A/C or climate control
    • Central heating
    • Suitable for children - ask
    • Suitable for the elderly

    PreviousNext property

    $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

    Details

    ***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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    $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

    Details

    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

    PreviousNext property

    $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

    Details

    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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    $950

    6 BR / 4 BA / Sleeps 12

    1 / 23

    $950

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    Flower Power House ~ Weekly Rental

    6 BR / 4 BA / Sleeps 12 | Quick view

    Details

    Flower Power House 5 - 6BR (Sleeping Porch) 4BA Sleeps 12+   Boho beautiful, the free-spirited presence of the Key West Flower Power House has much more in common with the real Key West than the shiny hotels around town. Kindred to memories we share about ‘the good old days,’ this 1938 …
    • Shared outdoor pool (unheated)
    • A/C or climate control
    • Linens Provided
    • Television
    • Stereo or CD player
    • Smoking allowed - ask
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    PreviousNext property

    $308

    2 BR / 2 BA / Sleeps 6

    13 Reviews

    $308

    Book

    "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.

    PreviousNext property

    $200

    1 BR / 1 BA / Sleeps 6

    1 Reviews

    $200

    Inquire

    Key West - Capt. Andy

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

    Details

    Reviews

    (1)

    Have you ever wondered what it would be like to live on a boat? Well now you can try out the liveaboard experience on board Capt Andy, a 43 ft fishing boat in Key West! This is the perfect rental for a group of boat loving friends looking for a budget friendly rental in Key West. Featuring a full galley kitchen, …
    • Ocean or water views
    • Internet Access
    • A/C or climate control
    • Balcony or terrace
    • Linens Provided
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (1)

    Worst stay for the highest price ever paid nightly.

    Left on Feb 22, 2015 for a stay in February 2015

    I worked for the airline for 13 years and travelled the world. After the taxes, cleaning fee and exchange, this was the highest price I paid for a nightly stay of $410.77cad. This marina is in the middle of a seedy area, surrounded by low income housing. There's no lock box so you have to get a hold of the captain and wait when you get there. We were not advised that the boat was under …

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    $230

    2 BR / 2 BA / Sleeps 5

    2 Reviews

    $230

    Inquire

    Royal Palm

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

    Details

    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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    $198

    1 BR / 1 BA / Sleeps 4

    1 Reviews

    $198

    Inquire

    Steps To Duval! La Dolce Vita, Luxury, Sleeps 2-4

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

    Details

    Reviews

    (1)

    La Dolce Vita is the sister unit to the Bella Vita in the same building, Flip Key listing #333914. Steps from Duval Street! "La Dolce Vita" is a totally renovated condo. Please check out our calendars for availability, photos and video. Everything is brand new from floor to ceilings! 14 foot high…
    • Housekeeping Optional
    • A/C or climate control
    • Central heating
    • Balcony or terrace
    • Linens Provided
    • Suitable for the elderly - ask

    Details

    Reviews

    (1)

    Fantastic Stay!

    Left on Mar 01, 2015 for a stay in December 2014

    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…

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    $167

    2 BR / 2 BA / Sleeps 6

    8 Reviews

    $167

    Book

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

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

    Details

    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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    $150

    2 BR / 1 BA / Sleeps 4

    1 / 15

    $150

    Book

    "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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