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$133

2 BR / 2 BA / Sleeps 4

30 night minimum stay requirement.  The Pearl in Paradise - 2 Bedroom House w - Florida Keys vacation rentals
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$133

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30 night minimum stay requirement. The Pearl in Paradise - 2 Bedroom House w

Key West house
2 BR / 2 BA / Sleeps 4 | Quick view

Details

Located on a quiet street in Key West, a tranquil residential neighborhood located just behind the Key West Historical district. Close to downtown and the beaches. Perfect for two couples looking for Old Town and peace and quiet. This home offers a two bedroom, two bathroom and was nicely remodeled with hardwood …
  • 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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$200

2 BR / 2 BA / Sleeps 10

Executive Bay Condo Islamorada Florida Keys - Florida Keys vacation rentals
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$200

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Executive Bay Condo Islamorada Florida Keys

Islamorada condo
2 BR / 2 BA / Sleeps 10 | Quick view

Details

Make yourself at home in your own private paradise in the Fabulous Florida Keys! The exclusive Executive Bay Club is a gated community with 24 hour security situated waterfront on the Florida Bay in Islamorada, just an hour from the hussle and bustle of Miami, yet a world away. Enjoy five-star amenities such as a …
  • Wireless Internet
  • A/C or climate control
  • Central heating
  • Parking
  • Grill

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$250

3 BR / 3 BA / Sleeps 8

Three story home 100 feet deep water dock big pool - Florida Keys vacation rentals
1 / 9

$250

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Three story home 100 feet deep water dock big pool

Islamorada house
3 BR / 3 BA / Sleeps 8 | Quick view

Details

Please contact us if you have any policy questions since we do not agree with this website forcing us to choose policies they dictate. We have our own polices so please ignore what's posted in the policies section on this website. Also please visit our website at www.KeysRentalHouse.com Beautiful three story luxury …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly

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$795

3 BR / 3 BA / Sleeps 6

9 Reviews

$795

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Cloud 9-Private Pool - 1/2 Block from Duval - Five Star Luxury - Parking

Key West house
3 BR / 3 BA / Sleeps 6 | Quick view
Excellent9 Reviews

Details

Reviews

(9)

Just a half block off Duval you’ll find your secret paradise awaiting you at Cloud 9. When you pass through the whimsical custom wrought iron gate decorated with palm fronds and a welcoming gecko, you’ll find yourself in the private brick courtyard facing the home with its French doors and balconies. As …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(9)

Residence is superb. Location is great.

Left on Apr 28, 2014 for a stay in March 2014

Our stay was excellent with superb support provided by Carlos throughout our visit. The house is spectacular although the kitchen equipment (skillets etc) were a bit lacking and was fixed by Carlos. We had a problem with the pool filtration system that basically had it non operational for a couple days although maintenance support was superb. We thought residence was a bit on the pricey side.

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$175

3 BR / 3 BA / Sleeps 8

1 Reviews

$175

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BLUE WATER RETREAT

Islamorada house
3 BR / 3 BA / Sleeps 8 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

Minimum Rental: 1 Month Location, location, location! This home has it all - ocean side Lower Matecumbe location, totally remodeled in 2009. Relax by the cocktail pool or sunbathe in the private roof top sunning area. There are blue water ocean views from almost every room in this home. It is located on a canal …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Patio
  • Parking
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

Blue Water = Everything that you want

Left on Jul 15, 2013 for a stay in July 2013

This place delivers.

You never really know what you are going to get from looking at a website and photos. I just stayed there July/2013 and this place is great, everything is new and clean. Most of all the house is on a peninsula that looks at the ocean from all sides and is just a few miles south of most of that main attractions in Islamorada giving the home a calm but close feel. Also working…

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$500

4 BR / 3 BA / Sleeps 8

5 Reviews

$500

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Ocean Front-Heated Pool-View Over The Atlantic

Cudjoe Key house
4 BR / 3 BA / Sleeps 8 | Quick view
Excellent5 Reviews

Details

Reviews

(5)

Unwind and take a deep breath, you have finally found your tropical paradise vacation home. This 4 vacation home is the perfect getaway from the hustle and bustle of everyday life. Only 20 minutes from Key West! If you are ready to kick off your shoes and sit by the pool or grab that fishing pole and hop the next boat…
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(5)

What a clean, relaxing and fun place to stay!

Left on Jun 06, 2013 for a stay in May 2013

The house was much bigger than it looked on the site. The pool was able to be heated and we loved being in it all hours of the day or night. Other than the food we needed for the week this house had everything! We used the kayaks provided and really enjoyed the wildlife and nature in the area. Can't wait to rent it again for next years vacation!

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$300

2 BR / 2 BA / Sleeps 6

4 Reviews

$300

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1800 Atlantic Condominiums Key West C327

Key West condo
2 BR / 2 BA / Sleeps 6 | Quick view
Average4 Reviews

Details

Reviews

(4)

Fabulous spacious two bedroom condominiums, directly on the Atlantic Ocean in Key West Florida. The Condo is fully equipped with a full size Kitchen. There is also a full size washer & dryer for your convenience. All rooms have a color cable TV and the unit has high There is an extensive private balcony that can …
    • Suitable for children - ask
    • Suitable for the elderly
    • Wheelchair accessible

    Details

    Reviews

    (4)

    Key West

    Left on Oct 31, 2010 for a stay in October 2010

    The explanation & photos on the internet were not all true. I booked this condo expecting to be able to use the beach. But the beach was not accessible. The security guard said that the last time the beach was nice was about 5-6 yrs ago. So, we had to drive downtown to a park and pay to use the public beach. There's alot of traffic 24/7. There were workers on-site re-doing the hallway walls so …

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    $208

    4294967295 BR / 1 BA / Sleeps 2

    19 Reviews

    $208

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    "HARRISONS HIDEAWAY" Luxury Cottage - Private Hot Tub - Half Block To Duval

    Key West cottage
    1 BA / Sleeps 2 | Quick view
    Excellent19 Reviews

    Details

    Reviews

    (19)

    Part of 4 exclusive units at Abbey Road, renovated January, 2010, this free standing historic cottage at 918-920 Center Street, features a king pillow-top bed, 2 lushly padded swivel chairs and a full kitchen which includes a full stove, refrigerator with ice-maker, microwave, dishwasher and soft mood lighting under …
    • Hot Tub/Jacuzzi
    • Internet Access
    • A/C or climate control
    • Deck
    • Grill
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (19)

    Relaxation

    Left on Aug 14, 2010 for a stay in June 2010

    Enjoyed a very relaxing stay in Key West. With access to the pools, hot tub and restaurants, much to chose from.

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    $275

    3 BR / 3 BA / Sleeps 8

    1 Reviews

    $275

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    Got stress?...409 Mariners Club has the power to r

    Key Largo house
    3 BR / 3 BA / Sleeps 8 | Quick view
    Average1 Reviews

    Details

    Reviews

    (1)

    Instantly feel the warmth of the island spirit as you enter this inviting 3-bedroom, 3-bath, tri-level townhouse at Mariners Club Resort. Enjoy the relaxing atmosphere the Florida Keys are known for...a perfect setting for family fun or a private romantic get-a-way. Experience the joyful gratitude of the day's …
    • Waterfront
    • Ocean or water views
    • Hot Tub/Jacuzzi
    • Internet Access
    • Washing Machine
    • Suitable for children
    • Suitable for the elderly - ask

    Details

    Reviews

    (1)

    Townhouse great, Mariner Club itself disappointing.

    Left on Mar 13, 2015 for a stay in March 2015

    Townhouse as pictures depicted which is always a relief. Outfitted fine and pretty comfortable furniture. Was very clean on arrival. Kitchen equipped with dozens of wine glasses but not 1 decent frying pan. Appreciated the shampoo/soaps in the bathrooms and the dish soap/sponge provided in the kitchen. Blinds in the living room and master bedroom the cheap plastic strips-did very little to …

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    $300

    3 BR / 3 BA / Sleeps 8

    1 / 15

    $300

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    Indigo Reef Luxury Vacation Rental - 30

    Marathon villa
    3 BR / 3 BA / Sleeps 8 | Quick view

    Details

    This spacious three bedroom, two and a half bath Villa will make you feel right at home. Each bedroom has it’s own television, with a 60” flat screen TV in the living room. The Villa has direct sunset views looking out to the Gulf of Mexico, which can be enjoyed from the porch or upper balcony. The kitchen…
    • Waterfront
    • Ocean or water views
    • Shared outdoor pool (unheated)
    • Internet Access
    • A/C or climate control
    • Smoking allowed - ask
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $743

    3 BR / 4 BA / Sleeps 6

    1 / 22

    $743

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    The Water's Edge

    Key West house
    3 BR / 4 BA / Sleeps 6 | Quick view

    Details

    Bring more luminescence into your next vacation with evening after evening of incomparable Key West sunsets viewed from the third-floor deck of this spectacular private home. Called The Water's Edge because of its location at the edge of the Gulf of Mexico, this lovely and comfortable three-bedroom, four-bath lies …
    • Ocean or water views
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area

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    $183

    3 BR / 3 BA / Sleeps 8

    1 Reviews

    $183

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

    Key West house
    3 BR / 3 BA / Sleeps 8 | Quick view
    Excellent1 Reviews

    Details

    Reviews

    (1)

    SPRING SPECIALS! 10% off MAY & JUNE 2015! Please see Specials Page for terms, rules and limitations. 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…
    • Ocean or water views
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • Suitable for the elderly - ask

    Details

    Reviews

    (1)

    Beautiful condo.

    Left on Apr 28, 2015 for a stay in February 2015

    We very much enjoyed this condo. It is beautifully decorated and there is a high priority for safety. Each condo has a private elevator that can only be entered with a specific fob. The roof-top dipping pool was wonderful on those really hot days. We enjoy laying in the sun & it was nice to be able to dip in the pool from time to time. We walked everywhere we chose to go, it's wonderful …

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    $121

    2 BR / 2 BA / Sleeps 6

    1 Reviews

    $121

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    VO-438

    Cudjoe Key house
    2 BR / 2 BA / Sleeps 6 | Quick view
    Terrible1 Reviews

    Details

    Reviews

    (1)

    Canal front home with spacious ambiance. 35’ seawall with dock posts, cleats, fish cleaning table with hose and outdoor shower. Covered back deck with ceiling fan, drop shades and patio furniture. Living room has large Flat Screen TV with DVD, sleeper sofa, two rockers, recliner and door to covered deck. Master …
      • Suitable for children - ask
      • Suitable for the elderly - ask

      Details

      Reviews

      (1)

      Dirty!

      Left on Sep 18, 2014 for a stay in September 2014

      Upon entering the house, floors were dirty. Cabinets had roach feces all through out and live roaches in the oven drawer and in cabinets. Did not cook food in the home the last few days because the roaches were coming out. Carpets and Lazy boy chairs were stained. Put towels on chairs as a barrier so we could sit on them. Washed all linens and towels prior to use. Washed floors, counter tops, …

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      $183

      4 BR / 3 BA / Sleeps 10

      1 / 20

      $183

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      EMERALD COVE

      Islamorada house
      4 BR / 3 BA / Sleeps 10 | Quick view

      Details

      MINIMUM RENTAL: 28 NIGHTS (ONE MONTH) You'll love watching the fabulous sunsets over the tranquil waters in this semi-private lagoon setting. This is a three story single family home and offers two balconies overlooking the water and dock area. There's room to dock one 30' boat and a fish cleaning station conveniently…
      • Ocean or water views
      • Hot Tub/Jacuzzi
      • Internet Access
      • Balcony or terrace
      • Parking
      • Suitable for children - ask
      • Suitable for the elderly - 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

      Key West house
      2 BR / 2 BA / Sleeps 6 | Quick view
      Excellent8 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
      • Deck
      • Grill
      • Linens Provided
      • 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

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

      Key West house
      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
      • Grill
      • Linens Provided
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

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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

      Key West house
      1 BR / 2 BA / Sleeps 4 | Quick view
      Excellent6 Reviews

      Details

      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
      • Deck
      • Grill
      • 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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      $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.

      Key West house
      3 BR / 3 BA / Sleeps 6 | Quick view
      Excellent2 Reviews

      Details

      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
      • Grill
      • Linens Provided
      • 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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      $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

      Key West house
      3 BR / 3 BA / Sleeps 6 | Quick view
      Excellent4 Reviews

      Details

      Reviews

      (4)

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

      Details

      Reviews

      (4)

      Perfect in Every Way!

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

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

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

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      $83

      2 BR / 2 BA / Sleeps 4

      1 / 23

      $83

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      Playa Royale - Monthly Rental

      Key West condo
      2 BR / 2 BA / Sleeps 4 | Quick view

      Details

      ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Playa Royale is located on South Roosevelt Blvd., directly across from Key West's largest beach (Smathers) on the Atlantic Ocean. You can choose to join in activities held in the club house overlooking the pool, tennis courts …
      • Shared outdoor pool (unheated)
      • Hot Tub/Jacuzzi
      • Sauna
      • Internet Access
      • A/C or climate control
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

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      $83

      2 BR / 2 BA / Sleeps 6

      1 / 30

      $83

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

      Key West house
      2 BR / 2 BA / Sleeps 6 | Quick view

      Details

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

      Key West cottage
      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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      $93

      1 BR / 1 BA / Sleeps 4

      1 / 14

      $93

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      "BOARDWALK LOFT" - Monthly Rental - Newly Renovated Condo w/ Shared Pool.

      Key West condo
      1 BR / 1 BA / Sleeps 4 | Quick view

      Details

      ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Beautiful Getaway Spot w/ Pool! Boardwalk Loft is the perfect getaway spot for families, or for individuals that just need some peace and quiet. The interior exudes elegance from top to bottom. You will fall in love with …
      • Shared outdoor pool (unheated)
      • Internet Access
      • A/C or climate control
      • Deck
      • Grill
      • Pet friendly
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

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      $1,448

      11 BR / 9 BA / Sleeps 32

      1 / 33

      $1,448

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

      Key West house
      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
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

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      $200

      3 BR / 3 BA / Sleeps 6

      1 / 19

      $200

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      Eliza's Jewel is a charming property close to White Street.

      Key West house
      3 BR / 3 BA / Sleeps 6 | Quick view

      Details

      30 DAY MINIMUM Two charming Conch houses are joined together at Eliza’s Jewel, an elegant three-bedroom home in Old Town Key West. Located in a quaint neighborhood just steps from the restaurants, shops and art galleries of White Street, Eliza’s Jewel combines beautifully preserved historical architecture with …
      • 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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      $83

      2 BR / 2 BA / Sleeps 6

      1 / 29

      $83

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      "SEASIDE HIDEAWAY" Beautiful Key West Condo w/ Shared Pool & Tennis Courts

      Key West condo
      2 BR / 2 BA / Sleeps 6 | Quick view

      Details

      ***Due to licensing restrictions, this property requires minimum stay of 28 nights*** This condominium is located right near the entrance of Key West and offers unparalleled seclusion and privacy. Although it is on the opposite side of the island from world famous Duval St, it is only about a 10 minute drive away. …
      • Shared outdoor pool (unheated)
      • Internet Access
      • A/C or climate control
      • Balcony or terrace
      • Grill
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

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      $198

      2 BR / 2 BA / Sleeps 6

      1 / 27

      $198

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      SAINT THOMAS SUITE #302 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach

      Key West condo
      2 BR / 2 BA / Sleeps 6 | Quick view

      Details

      Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped …
      • 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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      $198

      2 BR / 2 BA / Sleeps 6

      1 / 22

      $198

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      SAMANA CAY SUITE #405 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach

      Key West condo
      2 BR / 2 BA / Sleeps 6 | Quick view

      Details

      Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped …
      • Shared outdoor pool (unheated)
      • Hot Tub/Jacuzzi
      • 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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      $540

      3 BR / 2 BA / Sleeps 6

      1 / 18

      $540

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      Casa de Cuba:Beautiful home loaded with style and elegance

      Key West house
      3 BR / 2 BA / Sleeps 6 | Quick view

      Details

      Location! Style! Elegance! This beautiful home is the fabulous combination of everything a great vacation property should be. One half block to Duval Street in the historic district, the location can't be beat. The home's history is rich; neighboring the historic Gato Cigar factory which is now restored and used as …
      • Internet Access
      • A/C or climate control
      • Patio
      • Parking
      • Grill
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

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      $117

      2 BR / 2 BA / Sleeps 6

      1 / 17

      $117

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      Amazing Grace

      Key West house
      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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      $133

      2 BR / 2 BA / Sleeps 4

      1 / 30

      $133

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

      Key West house
      2 BR / 2 BA / Sleeps 4 | Quick view

      Details

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

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      $714

      4 BR / 3 BA / Sleeps 10

      1 / 38

      $714

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      82754 Overseas Highway

      Islamorada house
      4 BR / 3 BA / Sleeps 10 | Quick view

      Details

      OSPREY BAY VILLA! Wonderful bayfront home in the heart of Islamorada in the fabulous Florida Keys for rent by the week or monthly. Offering 5 bedrooms and 3 full baths on 2 living levels overlooking the Florida Bay with its incredible sunset views. Sleeps 10 people comfortably. Spacious fully equiped kitchen with the …
      • Waterfront
      • Ocean or water views
      • Hot Tub/Jacuzzi
      • Internet Access
      • Fireplace
      • Suitable for children
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

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      $215

      1 BR / 1 BA / Sleeps 3

      43 Reviews

      $215

      Inquire

      Ann Street Gardens

      Key West cottage
      1 BR / 1 BA / Sleeps 3 | Quick view
      Excellent43 Reviews

      Details

      Reviews

      (43)

      (Ann Street Gardens is a 16+ compound. Regretfully, no children under 16 allowed.) The cottage is a cozy hideaway. The poolside area is picture-postcard perfect. The location is in the very heart of Key West's Old Town, a half a block off the world-famous Duval Street. In short, Ann Street Gardens offers the …
      • Shared outdoor pool (unheated)
      • Internet Access
      • Washing Machine
      • Clothes Dryer
      • Outdoor Dining Area
      • Suitable for the elderly - ask

      Details

      Reviews

      (43)

      The Great Escape

      Left on May 02, 2009 for a stay in March 2009

      Location, Location, Location: One block from Duval Streets north end, three blocks to Mallory Square, The Westin,The Hyatt and Pier House, Historic Seaport Boadwalk, multiple wonderfull musuems. No need for any form of city transportation. The best of Key West is 10 minutes(at most)away by foot..even a beautiful public beach at the end of Simenton, two well equiped grocery stores and a …

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      $100

      1 BR / 1 BA / Sleeps 4

      1 / 23

      $100

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      "FRANGIPANI OASIS" Beautifully Decorated Featured Home w/ Pvt Pool

      Key West house
      1 BR / 1 BA / Sleeps 4 | Quick view

      Details

      ***Due to licensing restrictions, this home requires a minimum stay of 28 nights*** This inviting HGTV Featured Home (Bang for Your Buck, 2010) surrounds you with luxury, comfort and history. Originally a Cuban Cigar Maker’s Cottage (circa 1920’s), this vacation home has been updated with no expense spared. …
      • 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

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      $471

      3 BR / 3 BA / Sleeps 6

      1 Reviews

      $471

      Inquire

      Maison Matecumbe 304

      Islamorada condo
      3 BR / 3 BA / Sleeps 6 | Quick view
      Excellent1 Reviews

      Details

      Reviews

      (1)

      This three bedroom, three bathroom condominium sits on a lushly landscaped property, offering the Florida Keys you've always imagined. Enjoy beautiful oceanfront vistas from one of two balconies. Take a dip in the spacious pool that sits right at the foot of the condo staircase. Or journey a few yards further to the …
      • Ocean or water views
      • Shared outdoor pool (unheated)
      • Internet Access
      • A/C or climate control
      • Porch
      • Suitable for children
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

      Details

      Reviews

      (1)

      Relaxing in Islamorada

      Left on Jul 14, 2010 for a stay in June 2010

      Everything was beautiful. Very nice property. Private but very close to fishing charters.

      Toaster did not work and upstairs a/C quit working the night before we left. Other than that the condo was great.

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      $117

      3 BR / 2 BA / Sleeps 6

      1 / 1

      $117

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      258 Mohawk St - 28 Night Minimum!!!!!!!

      Islamorada house
      3 BR / 2 BA / Sleeps 6 | Quick view

      Details

      Looking for an extended stay in the Upper Keys that won't bust the bank? If so, you need not search any farther than this cozy, modern home on Islamorada's Plantation Key. Located in the popular Indian Waterways neighborhood, this three-bedroom/two-bath house is a great value at just $3,500 per month. The residence …
      • Waterfront
      • Internet Access
      • A/C or climate control
      • Porch
      • Grill
      • Suitable for children
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

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      $285

      2 BR / 1 BA / Sleeps 4

      6 Reviews

      $285

      Inquire

      Conch Key Bayfront cottage with 23' Sailboat

      Conch Key cottage
      2 BR / 1 BA / Sleeps 4 | Quick view
      Excellent6 Reviews

      Details

      Reviews

      (6)

      Our Florida Keys tradional island home is a fully furnished 2 bedroom, 1 bath plus Florida room with a deck overlooking the bay. It is surrounded by lush vegetation and large towering coconut palm trees. The house has been decorated in a nautical flavor with many fine antiques collected from around the world. This …
      • Waterfront
      • Ocean or water views
      • Internet Access
      • Outdoor Dining Area
      • A/C or climate control
      • Suitable for the elderly - ask

      Details

      Reviews

      (6)

      "One of our best Vacations"

      Left on Dec 30, 2012 for a stay in December 2012

      My wife and I sat on the back porch watching the sunset over the sailboats, and she said, "this has been one of our best vacations." We had no agenda so the pace was wonderful. We are life long sailors, so to have a 23' Compac sailboat, in great condition docked right out back made for a great way to mix the joy of sailing with the comfort of the wonderfully decorated house. If you like things…

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      $70

      2 BR / 2 BA / Sleeps 4

      1 / 18

      $70

      Inquire

      THE PALMS 214

      Islamorada condo
      2 BR / 2 BA / Sleeps 4 | Quick view

      Details

      Minimum Rental: 1 Month Gorgeous 2 bedroom, 2 bath condo. This is a gated complex located directly on the Atlantic Ocean. This unit has unobstructed views of the ocean from the master suite and the balcony. Wake up every morning, open the curtains and view a panorama of the Atlantic Ocean directly in front of you…
      • Ocean or water views
      • Shared outdoor pool (unheated)
      • Hot Tub/Jacuzzi
      • Internet Access
      • Balcony or terrace
      • Suitable for children - ask
      • Suitable for the elderly - ask

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      $245

      3 BR / 2 BA / Sleeps 9

      3 Reviews

      $245

      Book

      Tropical House at relaxing paradise !!!

      Key Largo house
      3 BR / 2 BA / Sleeps 9 | Quick view
      Excellent3 Reviews

      Details

      Reviews

      (3)

      Beautiful 2 story 3 bedroom 2 baths home. Located in Key Largo at MM 103 on the bayside and close to John Pennekamp Park, local shopping, fine restaurants, diving, charter fishing or just swimming with the dolphins! This home has an open water view overlooking the beautiful Florida Keys bay, Relax in this tropical …
      • Waterfront
      • Ocean or water views
      • Internet Access
      • Washing Machine
      • Clothes Dryer
      • Pet friendly
      • Suitable for children
      • Suitable for the elderly

      Details

      Reviews

      (3)

      A very clean, cozy and tastefully decorated house with a balcony overlooking a canal

      Left on Feb 05, 2014 for a stay in January 2014

      We stayed at the property for 4 nights. It accommodated us (5 adults and 4 kids) nicely - there were three bedrooms, all rooms being decorated very tastefully. Kind size beds in two bedrooms, a large bunk bed in one bedroom and a sofa in the living room. The kitchen was also nice and there was almost everything we needed. Only one thing - there were not enough cups for all of us so we had to buy …

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      $250

      2 BR / 2 BA / Sleeps 8

      1 / 7

      $250

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      Kawama Yacht Club Oceanfront Beach Sunsets!! WIFI

      Key Largo condo
      2 BR / 2 BA / Sleeps 8 | Quick view

      Details

      Luxurious and spacious oceanfront condo in modern Tower building at Kawama Yacht Club, a beautifully landscaped gated resort on the Atlantic Ocean at the southern tip of Key Largo in the Florida Keys. Great West exposure and beautiful sunsets!! Brand New Pool! Free WiFi Wireless High Speed Internet! Flat Panel LCD …
      • Waterfront
      • Ocean or water views
      • Wireless Internet
      • Washing Machine
      • Clothes Dryer
      • Suitable for children
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

      PreviousNext property

      $233

      2 BR / 2 BA / Sleeps 4

      2 Reviews

      $233

      Book

      Pinder House - Monthly Rental

      Key West house
      2 BR / 2 BA / Sleeps 4 | Quick view
      Average2 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
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

      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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      $83

      2 BR / 2 BA / Sleeps 6

      1 / 24

      $83

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      "SALT POND HIDEAWAY" 2/2 Condo w/ Huge Shared Pool & Hot Tub. Close to Beach!

      Key West condo
      2 BR / 2 BA / Sleeps 6 | Quick view

      Details

      ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Salt Pond Hideaway is located right off of South Roosevelt Blvd. in the oceanfront Salt Ponds Condominium Complex. It offers a neighborly and relaxing atmosphere with the ocean breezes of the Atlantic right across the …
      • Shared outdoor pool (unheated)
      • Hot Tub/Jacuzzi
      • Internet Access
      • A/C or climate control
      • Patio
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

      PreviousNext property

      $188

      4294967295 BR / 1 BA / Sleeps 4

      12 Reviews

      $188

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      "FOR WHOM THE BELL TOLLS" - Papas Hideaway's Deluxe Studio 3, Shared Pool

      Key West condo
      1 BA / Sleeps 4 | Quick view
      Very Good12 Reviews

      Details

      Reviews

      (12)

      Located at Papa's Hideaway Feel your tensions release as you soak up the warm tropical sun. Listen to the trade winds rustling through the palms, blowing each of your cares away... This Deluxe Studio is located on the ground floor and offers a private porch just off of the pool area. The unit includes a king-…
      • Shared outdoor pool (unheated)
      • Internet Access
      • A/C or climate control
      • Balcony or terrace
      • Grill
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

      Details

      Reviews

      (12)

      The location is in a very safe, quiet, and convenient location.

      Left on Nov 28, 2013 for a stay in November 2013

      Although the property could use some upgrades, it was clean enough and the price was right (considering Key West can be very expensive.) We found a great place nearby on the beach for breakfast. We walked everywhere (except when we took the trolley tour) and so we never had to move the car. Also, parking was onsite and free.

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      $198

      2 BR / 2 BA / Sleeps 6

      1 / 38

      $198

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      SAINT BARTS SUITE #303 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach

      Key West condo
      2 BR / 2 BA / Sleeps 6 | Quick view

      Details

      Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped …
      • 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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      $248

      1 BR / 1 BA / Sleeps 2

      1 / 20

      $248

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      "BANANA SPLIT"

      Key West condo
      1 BR / 1 BA / Sleeps 2 | Quick view

      Details

      Part of Banana's Foster Guest House This one bedroom apartment is on the 2nd floor of this historic property and accessed through the shared gated courtyard, right beside the shared off street parking on Simonton. Once through the gates, walk around the shared plunge pool and BBQ grill, going upstairs to the large …
      • 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

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      $198

      2 BR / 2 BA / Sleeps 6

      1 / 24

      $198

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      PUERTO RICO SUITE #103 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach

      Key West condo
      2 BR / 2 BA / Sleeps 6 | Quick view

      Details

      Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped…
      • 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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      $650

      4 BR / 3 BA / Sleeps 10

      1 Reviews

      $650

      Inquire

      Amanda's Dream Suites ~ Weekly Rental

      Key West house
      4 BR / 3 BA / Sleeps 10 | Quick view
      Average1 Reviews

      Details

      Reviews

      (1)

      Originally built in 1938, Amanda's Dream Suites vacation rental is a charming large wooden home offering two full stories with deep porches which overlook the garden and pool. An exterior stair case on one end of the building join the first and second floor. A renovation of the home in the early 1990's …
      • 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

      Details

      Reviews

      (1)

      Comfortable but over priced, tired and in need of updating.

      Left on Mar 16, 2014 for a stay in March 2014

      Management company was very inattentive to advertised included amenities. No beach towels to use or forks in the kitchen for three days after three requests. An added note this property is in the direct flight path of the airport so it can be deafening at times.

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      $170

      3 BR / 2 BA / Sleeps 8

      11 Reviews

      $170

      Inquire

      Casa Mar Azul - III- Luxury Home- WiFi -Prv Pool

      Key Colony Beach house
      3 BR / 2 BA / Sleeps 8 | Quick view
      Excellent11 Reviews

      Details

      Reviews

      (11)

      Welcome to our "Newly Constructed" Casa Mar Azul III, a "Brand New" upscale and luxurious 3 Bedroom, 2 Bath newer home with a private heated pool that sleeps 8 people and located at 260 Sadowski Causeway in Key Colony Beach. Do you prefer privacy and to be almost all alone on the beach?? Well we have just the ticket…
      • Waterfront
      • Ocean or water views
      • Internet Access
      • Washing Machine
      • Clothes Dryer
      • Suitable for children
      • Suitable for the elderly
      • Wheelchair accessible

      Details

      Reviews

      (11)

      Genial !!!

      Left on Jan 27, 2013 for a stay in December 2012

      Nosotros alquilamos por Internet, 2 semanas, solo vimos las fotos y realmente fue una alegría cuando recorrimos la casa. Preciosa, cómoda y funcional. Eramos 5 personas incluidos una nena y un nene de 12 años. Había que tenerlos entretenidos y activos. La piscina en la casa nos soluciono mucho, ellos se divirtieron mucho, a cualquier hora del día o de la noche cuando llegábamos de pasear, …

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      $300

      3 BR / 3 BA / Sleeps 6

      1 / 16

      $300

      Inquire

      Indigo Reef Villa 60

      Marathon villa
      3 BR / 3 BA / Sleeps 6 | Quick view

      Details

      This spacious three bedroom, two and a half bath Villa will make you feel right at home. Each bedroom has it’s own television, with a 60” flat screen TV in the living room. The Villa has direct sunset views looking out to the Gulf of Mexico, which can be enjoyed from the porch or upper balcony. The kitchen…
      • Waterfront
      • Ocean or water views
      • Shared outdoor pool (unheated)
      • Internet Access
      • A/C or climate control
      • Smoking allowed - ask
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

      PreviousNext property

      $200

      3 BR / 3 BA / Sleeps 6

      8 Reviews

      $200

      Book

      Reel Paradise - Big Pine Key

      Big Pine Key house
      3 BR / 3 BA / Sleeps 6 | Quick view
      Excellent8 Reviews

      Details

      Reviews

      (8)

      REEL PARADISE, located in Big Pine Key, Florida Keys offers a large open format Keys retreat with vaulted ceilings. 3 bedrooms – King bed master suite – Queen bed master suite and two full beds in a spacious third bedroom, 3 baths, large kitchen, dining room, family room, sitting area, large screen plasma TV in …
      • Waterfront
      • Internet Access
      • Housekeeping Optional
      • Washing Machine
      • Clothes Dryer
      • Suitable for children
      • Suitable for the elderly
      • Wheelchair accessible

      Details

      Reviews

      (8)

      Comfort & Privacy at Reel Paradise

      Left on Jul 29, 2013 for a stay in September 2012

      Reel Paradise was the perfect place for our Keys trip last year. We completely loved the layout of this house and the comfort and luxury it provided. The entire interior of the house is covered in cedar planks including the interior of the roof. The furniture is all Tommy Bahama and the kitchen has a nice big island to prep and serve all the food we made each night.

      The canal system is …

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