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$117

2 BR / 2 BA / Sleeps 6

Amazing Grace - Key West vacation rentals
1 / 17

$117

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Amazing Grace

2 BR / 2 BA / Sleeps 6 | Quick view

Details

***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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$838

6 BR / 5 BA / Sleeps 16

ESCAPE 2 PARADISE - 2 Beautiful 3-Story Homes w/ Pvt Pools. Steps From Duval - Key West vacation rentals
1 / 25

$838

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ESCAPE 2 PARADISE - 2 Beautiful 3-Story Homes w/ Pvt Pools. Steps From Duval

6 BR / 5 BA / Sleeps 16 | Quick view

Details

Located in the luxury townhome complex "Echo Gardens," "Escape 2 Paradise" consists of two homes, units #3 and #4 - A Key Escape and Absolutely Paradise - which are right next door to each other. Equipped with two private pools, two private parking spaces, and enough room to sleep 16 people, "Escape 2 Paradise" truly…
  • Internet Access
  • A/C or climate control
  • Patio
  • Grill
  • Stereo or CD player
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$150

3 BR / 3 BA / Sleeps 8

Higgs Beach Hacienda - 3 Bed 2.5 Bath Monthly Rental Near Beach. Huge Yard! - Key West vacation rentals
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

Details

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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$127

2 BR / 2 BA / Sleeps 4

2 Reviews

$127

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Angela Cottage: A hideaway in Old Town

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

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Reviews

(2)

30 DAY MINIMUM RENTAL This cute cottage just off of Frances Street is a great hideaway, still in Old Town, but a good central location to get to the Historic seaport or new town. The light & airy combined living/dining area with its soft color toned furnishings, hardwood floors & many windows create a relaxing Key …
  • Internet Access
  • A/C or climate control
  • Deck
  • Grill
  • Linens Provided
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Outstanding

Left on Jun 26, 2009 for a stay in March 2009

I have rented the Angla Cottage for the past three seasons. The house is very comfortable with space for guests in a separate portion of thje house. Swimming pool is great, and outdoor dining area is outstanding for any meal. The kitchen is new and all the necessary pots and pans are present.

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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

Details

"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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$133

3 BR / 2 BA / Sleeps 6

1 / 25

$133

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"SEMINARY ST HIDEAWAY" 3 Bd 2 Bth Home w/ Private Pool

3 BR / 2 BA / Sleeps 6 | Quick view

Details

***Due to licensing restrictions, this home requires a minimum stay of 28 nights*** This newly renovated 3 bedroom "home away from home" sits right smack in the middle of the Key West island and is a short distance to everywhere you will want to go during your vacation! Located on Seminary St, in a quiet …
  • Internet Access
  • A/C or climate control
  • Grill
  • Linens Provided
  • Satellite or cable TV
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$1,048

6 BR / 6 BA / Sleeps 22

1 / 33

$1,048

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"PAPA'S HIDEAWAY - NIGHTLY GROUP UNIT" Guesthouse - Sleeps up to 22!

6 BR / 6 BA / Sleeps 22 | Quick view

Details

Papa's Hideaway is a Guesthouse property comprised of Garden of Eden , Torrents of Spring , Sun Also Rises , For Whom the Bell Tolls , Islands in the Stream Minimum Stay: Please contact Key West Vacation Rentals regarding minimum stays and special rates. Minimum stay requirements apply on weekends (at least…
  • 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

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$83

2 BR / 2 BA / Sleeps 2

1 / 10

$83

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Minimum 90 day rental - 1 bedroom 1 Bathroom Condo at Las Salinas

2 BR / 2 BA / Sleeps 2 | Quick view

Details

Located in New Town featuring 1 bedroom with a queen sized bed and one bathroom. The unit has a private balcony and offers covered parking. There is a shared swimming pool. It is just a short walk to the beach. Being located on the Atlantic side of the island which offers great sunrise views. This unit is great for …
  • Shared outdoor pool (unheated)
  • 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

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$200

2 BR / 2 BA / Sleeps 4

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

Details

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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$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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$180

1 BR / 1 BA / Sleeps 2

16 Reviews

$180

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Key West Garden House

1 BR / 1 BA / Sleeps 2 | Quick view
“ Excellent ” 16 Reviews

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Reviews

(16)

Experiance the laid back life of the tropics in this light and airy 1 bedroom, 1 bath private home. Located on a quiet lane in the heart of Old Town, The Key West Garden House features a large covered back porch, outdoor living and dining area, gas barbeque and heated pool in a lush tropical setting. The yard is …
  • Internet Access
  • Washing Machine
  • Outdoor Dining Area
  • Grill
  • Satellite or cable TV
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(16)

Great Experience!

Left on Jul 23, 2013 for a stay in May 2013

We stayed at the Garden House with our maltese in May. Susan was terrific and her place felt like a home away from home in the Keys. It is such an adorable historic house, we just loved it.
I hope to go back soon and stay at the Garden House again.
Maureen B.

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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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$188

1 BR / 1 BA / Sleeps 4

23 Reviews

$188

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"VERDE SUITE" - Quiet & Affordable 'Old Town' Cottage - Shared Pool

1 BR / 1 BA / Sleeps 4 | Quick view
“ Excellent ” 23 Reviews

Details

Reviews

(23)

The location is ideal in that it is just two blocks from the action of Duval street, yet has the tranquility and peacefulness to nap on the outside deck. This immaculately clean and comfortable air conditioned suite features beautiful vaulted ceilings and pastel colored walls as well as a top of the line flat screen …
  • 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

(23)

Verde Suite relaxation

Left on Jun 25, 2009 for a stay in April 2009

Glorius week in a great little suite with almost everything you would want. The only thing missing was the availability of authorized parking although there are parking spaces adjacent to the complex that remained vacant the entire week
Everything else ranks high. Cleanliness, secluded, close to everything in Old Town.

Would I do it again? In a heartbeat....as a matter of fact I am planning a …

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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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    $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

    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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    $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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    $183

    2 BR / 2 BA / Sleeps 6

    1 / 20

    $183

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    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

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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

    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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    $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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    $468

    4 BR / 2 BA / Sleeps 12

    1 Reviews

    $468

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    "SEAPORT SUITE" - Great Party House w/ Hot Tub! 1 Min Walk to Sloppy Joe's

    4 BR / 2 BA / Sleeps 12 | Quick view
    “ Poor ” 1 Reviews

    Details

    Reviews

    (1)

    Seaport Suite is available for daily or weekly vacation rentals and located on the second floor of 219 Simonton in Old Town Key West. The location is as close to perfect as you can get, being one block off Duval Street and within walking distance to every single thing you could possibly want to do. With four bedrooms …
    • Hot Tub/Jacuzzi
    • Internet Access
    • A/C or climate control
    • Balcony or terrace
    • Parking
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (1)

    Seaport Suite not the place to stay

    Left on Dec 02, 2014 for a stay in November 2014

    Rental agents were very helpful can't complain about them or the maintenance staff. The property was not in the best shape. washer dryer didn''t work , had to have it replaced. One bathroom did not drain properly so when showering you could also take a bath. Ants all over the kitchen and bathrooms. Not impressed for the price I paid.

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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

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    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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    $157

    3 BR / 3 BA / Sleeps 8

    1 / 26

    $157

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    "BEACH CLUB BREEZE" Monthly Rental - Two Story Home w/ Sun Deck & BBQ Grill

    3 BR / 3 BA / Sleeps 8 | Quick view

    Details

    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** This well-manicured, "home away from home" is two stories of wonderful! It has 3 bedrooms, 3 baths and has a colorful, comfortable style. The traditional white picket fence greets you when you arrive. Though, it's only a …
    • Internet Access
    • A/C or climate control
    • Patio
    • Fitness Room
    • Grill
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $138

    4294967295 BR / 1 BA / Sleeps 2

    1 Reviews

    $138

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    "DECKSIDE SUITE" Studio w/ Shared Hot Tub Steps To Duval St

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

    Details

    Reviews

    (1)

    Part of Conch Republic Cottages Efficiency at its finest! The Deckside Suite is the perfect vacation rental in Key West for those who are trying to get the most bang for their buck. You have everything you need in this cozy, studio-style unit, including a fully-stocked kitchen, cable TV, free wireless internet, and a…
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (1)

    Rats Rats and Rats

    Left on Jan 21, 2015 for a stay in January 2015

    this is a very small unit... in need of a total make over. and yes there are rats all over the deck and in the walls. We could hear them at night and in the moring we saw 4 run across the deck.... Management (Key West Vacation Rentas)was not concerned simply saying there are rats everwhere in Key West.. It appears that one side of the unit is rented to locals and they helped entertain us by …

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    $300

    3 BR / 2 BA / Sleeps 8

    1 / 23

    $300

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    Oceanside Key West's Best Luxury Penthouse Condo

    3 BR / 2 BA / Sleeps 8 | Quick view

    Details

    WOW Oceanside Voted #1 Key West's Best Luxury Penthouse Marina/Condo/Pool Direct Oceanfront 1490 Sq Ft Condo, 3 Bedrooms, 2 Baths, (Sleeps 6) Oceanside Marina is one of the newest and one of the most prestigious communities offering breath taking water views and large, open units. The amenities are rounded out …
    • Waterfront
    • Ocean or water views
    • Wireless Internet
    • Housekeeping Optional
    • Washing Machine
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly - elevator access
    • Wheelchair accessible

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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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    $350

    3 BR / 2 BA / Sleeps 8

    12 Reviews

    $350

    Inquire

    Key West - Libra

    3 BR / 2 BA / Sleeps 8 | Quick view
    “ Excellent ” 12 Reviews

    Details

    Reviews

    (12)

    Come stay aboard our FABULOUS houseboat Libra! Docked in one of Key West's most exclusive yacht club marinas, our guests have free access to a host of "members only" amenities including a swimming pool, private beach, tiki bar, fitness facility, sauna, clubhouse, onsite restaurant, free parking and much more! This …
    • Waterfront
    • Ocean or water views
    • Shared outdoor pool (unheated)
    • A/C or climate control
    • Balcony or terrace
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (12)

    Fantastic time

    Left on Mar 28, 2013 for a stay in October 2012

    We all had a great time. It was far away from everything yet close to everything at the same time. Restaurant had excellent food and pool was great. On the downside the boat was not cleaned when we got there and the hammock I so looked forward to was not there. All n all it was a great time n we rented it again this year. Hope it's clean n ready this year when we get there

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    $418

    3 BR / 3 BA / Sleeps 8

    8 Reviews

    $418

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    "CASA MARGARITA" Amazing Location w/ Pvt Pool & Huge Deck. Pvt Parking

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

    Details

    Reviews

    (8)

    Casa Margarita is located on the 300 block Margaret Street in one of Old Town Key West’s most desirable locations. This 3 bedroom/3 bathroom home features a large backyard with lush tropical landscaping placed for an ultimate privacy that is rarely seen in Old Town. The heated pool is flanked by a large covered …
    • Internet Access
    • A/C or climate control
    • Grill
    • Linens Provided
    • Microwave
    • Pet friendly
    • Suitable for children - ask
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    • Wheelchair accessible - ask

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    Reviews

    (8)

    Walk to everywhere, but feels very private .

    Left on Nov 30, 2013 for a stay in November 2013

    My family including our havanese puppy (Reggie)just finished a great week stay in key west. Casa Margarita is within a hundred yards of every restaurant of the harbor .Many places are within crawling distance like harpoon harry's,( 3 doors down)or Pepe's (6 doors down).

    You wont hear any noise even the traffic out front is quiet as its on a quiet street ( margaret ave )in a residential …

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    $888

    5 BR / 4 BA / Sleeps 12

    1 / 32

    $888

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    "ABBEY ROAD" Great for Big Parties! - 4 Luxury Units - 4 Private Hot Tubs

    5 BR / 4 BA / Sleeps 12 | Quick view

    Details

    Abbey Road - Gated Compound, Sleeps up to 12! Lennon's Lodge (Sleeps 6 with 8 person hot tub), McCartney's Manor (Sleeps 2 with 2 person hot tub), Starr's Suite (Sleeps 2 with 2 person hot tub) and Harrison's Hideaway (Sleeps 2 with 2 person hot tub) and will accommodate up to 12 persons for the ultimate in …
    • Hot Tub/Jacuzzi
    • Internet Access
    • A/C or climate control
    • Balcony or terrace
    • Grill
    • Pet friendly
    • Suitable for children - ask
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    • Wheelchair accessible - ask

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    $217

    5 BR / 3 BA / Sleeps 18

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    $217

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    "BAY HARBOR VIEW" - Waterfront Monthly Rental w/ Spectacular Views

    5 BR / 3 BA / Sleeps 18 | Quick view

    Details

    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** a passport tucked away off of mile marker 15. While relaxing in the 20x12 free form lagoon pool, the surrounding scenery makes you feel like you are on your own deserted island. Around the back of the home, the large …
    • Waterfront
    • Internet Access
    • A/C or climate control
    • Patio
    • Fitness Room
    • Pet friendly
    • Suitable for children - ask
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    • Wheelchair accessible - ask

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    $350

    3 BR / 2 BA / Sleeps 8

    12 Reviews

    $350

    Inquire

    Key West - MV Coconuts

    3 BR / 2 BA / Sleeps 8 | Quick view
    “ Excellent ” 12 Reviews

    Details

    Reviews

    (12)

    The M/V Coconuts is a completely unique home with 360 degree water views, it also happens to be a 50-foot trawler, permanently docked at the Key West Harbor Marina. This is more than a boat. It really is a very comfortable home, with proper living area, bedrooms and large sundecks. There is over 1100 sq ft of indoor …
    • Waterfront
    • Ocean or water views
    • Shared outdoor pool (unheated)
    • A/C or climate control
    • Balcony or terrace
    • Pet friendly
    • Suitable for children - ask
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    Reviews

    (12)

    awesome stay in Key West

    Left on Apr 04, 2013 for a stay in September 2012

    Great large space to share with friends, yet you all have privacy with multiple floors and decks. The beds could use some new mattresses and sheets, but otherwise it was much better than a b & b. The marina is just outside of town and provides a safe quiet stay. The club house has great food and services. During our stay, our a/C went out and our host worked into the wee hours of the morning …

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    $190

    3 BR / 3 BA / Sleeps 6

    1 Reviews

    $190

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    "CLUB CLARK" Gorgeous 3 Bd 3 Bth Home w/ Pvt Pool. Close to Dante's!

    3 BR / 3 BA / Sleeps 6 | Quick view
    “ Excellent ” 1 Reviews

    Details

    Reviews

    (1)

    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** The main dwelling includes a beautiful, newly-renovated kitchen, a master bedroom with en-suite, a second bedroom with twin beds (which can be made into a king upon request), a full guest bathroom including a tub and full …
    • Internet Access
    • A/C or climate control
    • Patio
    • Grill
    • Linens Provided
    • Pet friendly
    • Suitable for children - ask
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    • Wheelchair accessible - ask

    Details

    Reviews

    (1)

    Club Clark

    Left on Apr 10, 2014 for a stay in March 2014

    The place was really nice and the staff was very easy to work with. It was a very good vacation and would definitely like to stay there again.

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    $128

    4294967295 BR / 1 BA / Sleeps 2

    5 Reviews

    $128

    Book

    "CORAL COVE" Affordable Old Town Efficiency - Patio and BBQ Grill

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

    Details

    Reviews

    (5)

    This wonderful unit that has been completely remodeled in July 2013 has a private entrance in to the quaint efficiency on the back side of the complex. Featuring hardwood floors, Dade County Pine walls and a high-end, fully stocked kitchenette, this secluded hideaway offers the finest of appointments and one of the…
    • Internet Access
    • A/C or climate control
    • Patio
    • Fitness Room
    • Grill
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (5)

    Great Value.

    Left on Aug 17, 2013 for a stay in August 2013

    Very Small but a great value if it will only be one or two staying. Not a bad location either. My wife and I rent from Key West vacation rentals every year and they are a pleasure to work with. No surprises!

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    $233

    2 BR / 2 BA / Sleeps 4

    2 Reviews

    $233

    Book

    Pinder House - Monthly Rental

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

    Details

    Reviews

    (2)

    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Located at 516 Elizabeth Street, the Pinder House is an address and house of distinction! Previously owned by Theopolis Pinder of the historic Pinder Family, whose roots go back to the 1850’s, this historic Eyebrow home has …
    • Hot Tub/Jacuzzi
    • Internet Access
    • A/C or climate control
    • Central heating
    • Balcony or terrace
    • Pet friendly
    • Suitable for children - ask
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    Details

    Reviews

    (2)

    Live in an 1830's house w / 2014 conveniences

    Left on Jan 23, 2014 for a stay in January 2014

    B+ no Choices in cable channels no prkg
    On site , parrot sanctuary adjacent
    Property's remote pool. Access. K

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    $788

    5 BR / 4 BA / Sleeps 12

    1 / 24

    $788

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    "SOUTHERN PALMS" Historical Hideaway - Bahama Village - 2 Hot Tubs & Pvt Pool

    5 BR / 4 BA / Sleeps 12 | Quick view

    Details

    Located at 729 Whitehead St, "Southern Palms" is the group property consisting of the following homes Coconut Palm formerly Island Oasis Traveler's Palm formerly Palm Isle Royal Palm formerly Little Palm which can all be booked individually. All together, these three units have 5 separate bedrooms, 3 …
    • Pet friendly
    • Suitable for children - ask
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    $1,448

    11 BR / 9 BA / Sleeps 32

    1 / 32

    $1,448

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    TROPICAL VILLAGE 6 Homes w/ Pvt Pool & BBQ Grill. Great For Large Parties!

    11 BR / 9 BA / Sleeps 32 | Quick view

    Details

    Tropical Village is comprised of 6 separate vacation rentals properties that can also be rented separately. COTTAGE @ TROPICAL VILLAGE POOLSIDE @ TROPICAL VILLAGE SOUTHERN CROSS @ TROPICAL VILLAGE TOON HALL @ TROPICAL VILLAGE RETREAT @ TROPICAL VILLAGE HIDEAWAY @ TROPICAL VILLAGE Located at 706 and…
    • Pet friendly
    • Suitable for children - ask
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    • Wheelchair accessible - ask

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    $408

    2 BR / 2 BA / Sleeps 6

    9 Reviews

    $408

    Book

    HELEN'S HIDEAWAY - Gated, Unique, 2 BR House W/ Private Heated Pool

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

    Details

    Reviews

    (9)

    This gem is located at the end of a hidden lane, just off Simonton Street, behind The Gardens Hotel. Helen's Hideaway is a step back in time to Key West during its slumbering past. Built by David Wolkowski, who built many of Key West's premier resorts, including the Pier House, this paradise reflects his passion for …
    • Internet Access
    • A/C or climate control
    • Deck
    • Fitness Room
    • Grill
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
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    Details

    Reviews

    (9)

    Quiet, private, unique concept, but big price for significant di

    Left on Sep 12, 2013 for a stay in September 2013

    Truly a hideaway! Very private-locked behind a wooden fence. Location-excellent! Fun detached bedroom w/a wall of sliders that open to the private pool. Outdoor hot/cold shower well placed amidst foliage for privacy. Sufficiently equipped kitchen, but outdated & narrow - two large people may have trouble passing each another. 3 flat screens. Lg bathroom in main bldg recently redone with huge walk…

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    $588

    4 BR / 4 BA / Sleeps 10

    46 Reviews

    $588

    Book

    "KEY WEST HIDEAWAY" Sleeps Up To 10 - Private Patio - Half Block To Duval!

    4 BR / 4 BA / Sleeps 10 | Quick view
    “ Excellent ” 46 Reviews

    Details

    Reviews

    (46)

    Two Queen bedrooms upstairs (each with a private bath) and two Queen bedrooms downstairs (each with a private bath) gives sleeping privacy and convenience for up to 8. Each bedroom has flat screen TVs, air-conditioning and ceiling fan. The two upstairs bedrooms have showers, the two downstairs bedrooms have …
    • 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

    (46)

    Second time, won't be the last time.

    Left on Jun 24, 2009 for a stay in June 2009

    This was the second year in a row that we rented the house. We absolute love staying here. We don't usually get to relax on vacations, however when we come here that is all we do and the house has all the comfort and ammenities to allow us to relax. Will be back to Key West often (live in Dallas) and will always rent this property.

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    $408

    3 BR / 2 BA / Sleeps 6

    1 Reviews

    $408

    Book

    COCONUT PALM - Bahama Village Home w/ Huge Pvt Hot Tub - Great for Families!

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

    Details

    Reviews

    (1)

    Part of Southern Palms COCONUT PALM (formerly Island Oasis). Take a lot of history and a lot of charm - mix it with a great location and you have the perfect Key West hideaway. A vacation rental home built and operated in the late 1800's as the city's hack concession and stables, has been transformed with bits and …
    • Internet Access
    • A/C or climate control
    • Ceiling Fans
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (1)

    Absolutely perfect house for our group!

    Left on Jul 29, 2014 for a stay in July 2014

    This house was awesome! Good location and very appropriate for what we used it for (bachelor party). Very nice Pool and outdoor area at a great price. The lease management company was quick with checking in/out and very nice! We are making this an annual trip and will stay here again.

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    $378

    3 BR / 3 BA / Sleeps 8

    6 Reviews

    $378

    Book

    "ALMOST SOUTHERNMOST TOO" - Private Pool - Half Block To Duval St! Sleeps 8

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

    Details

    Reviews

    (6)

    Part of ALMOST SOUTHERNMOST RETREAT Almost Southernmost Too in the 400 block of Truman Avenue is the perfect location, located between Duval Street and Whitehead St. Just around the corner from Hemingway's House and the Historic Lighthouse Museum, Almost Southernmost Too is a perfect example of shotgun architecture …
    • Internet Access
    • A/C or climate control
    • Balcony or terrace
    • Fitness Room
    • Grill
    • Pet friendly
    • Suitable for children - ask
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    • Wheelchair accessible - ask

    Details

    Reviews

    (6)

    Fantastic, wonderful experience.

    Left on Nov 23, 2011 for a stay in November 2011

    Great location, in the center of KeyWest. Parked the car and walked,biked,trollied everywhere. Beautiful color scheme, every room was vibrant with a South Florida palat. Fantastic new kitchen and pool. Spent many hours on the pool patio with a 6-toe cat from the Hemmingway house. Just an all around wonderful experience. We will return to this house again in 2013...Thanks for making this a …

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    $268

    2 BR / 3 BA / Sleeps 6

    23 Reviews

    $268

    Book

    "CASA DE MANGO @ DUVAL SQUARE" 2-Story Condo w/ Pvt Hot Tub & Balcony

    2 BR / 3 BA / Sleeps 6 | Quick view
    “ Very Good ” 23 Reviews

    Details

    Reviews

    (23)

    Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private, secured parking beneath the complex and security entrances gives the feeling of exclusivity unparalleled in Key West. The foyer of this Mediterranean Style unit opens to the living room, dining room, half-bath …
    • Shared outdoor pool (unheated)
    • Hot Tub/Jacuzzi
    • Internet Access
    • A/C or climate control
    • Balcony or terrace
    • Pet friendly
    • Suitable for children - ask
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    • Wheelchair accessible - ask

    Details

    Reviews

    (23)

    Refreshing Experience

    Left on Jun 25, 2009 for a stay in November 2007

    We thought the Condo was beautiful. Very clean, with nice furniture. The terrace off of the living room was nice too!
    Can't wait to visit again!

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    $408

    3 BR / 2 BA / Sleeps 10

    13 Reviews

    $408

    Book

    "POOLSIDE PARADISE" Amazing Home 1/2 Block to Duval w/ Pool and Pvt Parking

    3 BR / 2 BA / Sleeps 10 | Quick view
    “ Excellent ” 13 Reviews

    Details

    Reviews

    (13)

    POOLSIDE PARADISE is made up of POOLSIDE RETREAT and POOLSIDE SUITE With 3 bedrooms (K, 2 Q, plus 2 Q sleeper), 2 full baths and 2 full kitchens, this historic home is perfect for up to 10 persons. The front portion features a King bedroom, a Queen bedroom and a Queen sleeper sofa in the living room. The bath with …
    • 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

    (13)

    Enjoyed our Stay

    Left on Oct 14, 2011 for a stay in September 2011

    The place was perfect for our group. My husband and I traveled with my parents and another couple. It worked out great because the parents stayed with us and our friends had their own little apartment which gave us all our privacy if needed. The location was pretty nice as well. We were one block off Duval. Even though we were down on the end closest to SouthernMost everything was within …

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    $268

    2 BR / 2 BA / Sleeps 6

    1 Reviews

    $268

    Book

    SOUTHERN CROSS @ TROPICAL VILLAGE - Beautifully Updated Home w/ Shared Pool.

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

    Details

    Reviews

    (1)

    Part of TROPICAL VILLAGE Southern Cross: Sitting next to the lily pond with fountain or lounging in the shade of your own Royal Poinciana tree, Southern Cross is the perfect place to relax in paradise. This one and a half story vacation cottage is surrounded by exotic gardens, and situated in the Tropical Village …
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    Reviews

    (1)

    Tropical Perfection

    Left on Oct 07, 2014 for a stay in October 2014

    The property was clean, the kitchen was equipped with all the necessities, great private porch and shared pool. Location is great - just a couple blocks from Duval and a 15 minute walk to the Mallory Square. Higgs Beach was a close, great market nearby, and a CVS, you really couldn't have asked for a better location! The trip was epic, relaxing and wild from start to finish. I can't wait to come …

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    $408

    3 BR / 2 BA / Sleeps 6

    31 Reviews

    $408

    Book

    "CASA SERENDIPITY" - World Class Comfort in Lush, Tropical Paradise

    3 BR / 2 BA / Sleeps 6 | Quick view
    “ Excellent ” 31 Reviews

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    Reviews

    (31)

    Located on one of old town's prettiest historic streets, Frances Street. Casa Serendipity is one of the finest examples of the 'conch cottage' style architecture that Key West is famous for. Designed to accommodate a family, this three-bedroom home has two full baths, one full bath upstairs and one full bath …
    • Internet Access
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    • Patio
    • Fitness Room
    • Grill
    • Pet friendly
    • Suitable for children - ask
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    • Wheelchair accessible - ask

    Details

    Reviews

    (31)

    Very quaint

    Left on Jun 24, 2009 for a stay in March 2008

    Loved the house, nicely decorated and well kept. Lots of room except you
    need to watch your head going down the stairs - low clearance. Nice wrap
    around porch and yard with small pool (too cold for me but the kids loved it).
    The walk to town (Duval St area) was longer than expected especially since the
    house is across from the cemetary (above ground).

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    $748

    4 BR / 4 BA / Sleeps 16

    1 / 30

    $748

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    Palm Gardens - Great for Big Groups! 4 Condos 4 Hot Tubs 1 Pool. Sleeps 16!

    4 BR / 4 BA / Sleeps 16 | Quick view

    Details

    The Condos are tied together in a lushly landscaped garden setting with a spa pool in the rear. Booking all 4 condos gives you a great alternative to booking a single house as you are offered privacy and closeness at the same time. Call to book your Island Paradise while there is still time! Palm Gardens is …
    • Hot Tub/Jacuzzi
    • Internet Access
    • A/C or climate control
    • Balcony or terrace
    • Fitness Room
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $268

    2 BR / 2 BA / Sleeps 6

    1 / 31

    $268

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    THE COTTAGE @ TROPICAL VILLAGE - Spacious Home w/ Shared Pool. Close To Beach

    2 BR / 2 BA / Sleeps 6 | Quick view

    Details

    Part of TROPICAL VILLAGE Tropical Village Cottage - is a two bedroom, two bath vacation cottage that overlooks a large shared seasonally heated pool, sun-deck and pool-side grilling station. With all the amenities of contemporary living set in island style and decor. Tropical Village Cottage is your ticket to a …
    • Pet friendly
    • Suitable for children - ask
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    • Wheelchair accessible - ask

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    $198

    2 BR / 2 BA / Sleeps 6

    1 / 24

    $198

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    GRAND CAYMAN SUITE #309 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach

    2 BR / 2 BA / Sleeps 6 | Quick view

    Details

    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

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    $178

    4294967295 BR / 1 BA / Sleeps 2

    17 Reviews

    $178

    Book

    "STARR'S SUITE" Luxury Cottage - Private Hot Tub - Half Block to Duval St!

    1 BA / Sleeps 2 | Quick view
    “ Excellent ” 17 Reviews

    Details

    Reviews

    (17)

    Part of 4 exclusive units at Abbey Road, renovated January, 2010, this suite is at 918-920 Center Street. Featuring a king pillow-top bed and marble floors, the state-of-the-art kitchen includes granite counter top, a 2 burner cook top, dishwasher, under counter refrigerator, microwave and soft mood lighting under …
    • 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

    (17)

    Not Sure

    Left on Jan 19, 2011 for a stay in November 2010

    While I loved the room in and place in most ways, I didn't like that there was no chair, comfortable or otherwise in the room or the fact that there were no night light for reading while in bed.

    I felt same staying in abby Lane and loved the updated room. Other friends who had traveled at the same time loved my room also.

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    $388

    2 BR / 3 BA / Sleeps 6

    1 / 34

    $388

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    "HAVANA HIDEAWAY" - Beautiful Home w/ Pvt Pool Just Steps To Duval

    2 BR / 3 BA / Sleeps 6 | Quick view

    Details

    The Beach Boys on one of their many trips to Key West (they are Mojito buds with Jimmy Buffett) stayed at our vacation rental called Havana Hideaway, where they wrote the song Kokomo - according to a very reliable source at the Pink Cab Company. This vacation rental is a modern two-story, built in the best conch …
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask
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