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$167

4 BR / 3 BA / Sleeps 10

30 night minimum stay requirement.  Key Haven Retreat - 4 Bedroom House with - Florida Keys vacation rentals
1 / 31

$167

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30 night minimum stay requirement. Key Haven Retreat - 4 Bedroom House with

4 BR / 3 BA / Sleeps 10 | Quick view

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This 4 Bedroom Key Haven open-water home has it all!! Enjoy the custom in-ground pool, barbeque and dine in at your waterside gazebo. You can relax upstairs in the custom finished open porch which features a beautiful open water view. This home also offers a downstairs porch which includes a bar area where you can …
  • 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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$400

4 BR / 3 BA / Sleeps 12

Ocean Front Split Level Keys House - Florida Keys vacation rentals
1 / 29

$400

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Ocean Front Split Level Keys House

4 BR / 3 BA / Sleeps 12 | Quick view

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Beautiful four bedroom, Ocean Front home with private beach in sunny Islamorada (near Key Largo). Welcome to our little slice of paradise in the Florida Keys! Come and relax at our beautiful ocean front home with breathtaking, panoramic views of the Atlantic ocean. This spit level home is located in Islamorada; the …
  • Private Beach
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Suitable for children
  • 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 - Florida Keys 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

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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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$400

4 BR / 5 BA / Sleeps 8

2 Reviews

$400

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74920 Overseas Hwy

4 BR / 5 BA / Sleeps 8 | Quick view
“ Excellent ” 2 Reviews

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Reviews

(2)

One of a kind bay front estate! This is an absolutely gorgeous estate home offering a gated entrance paved brick driveway, 3,500 sf, 3 bedrooms, 3.5 bathrooms upstars and a bonus 1 bedroom, 1 bathroom apartment downstairs. Enjoy ocean & lagoon views, deep water protected dockage, 2 Great rooms, private master suite, …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • A/C or climate control
  • Telephone
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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Reviews

(2)

The Best

Left on May 29, 2012 for a stay in April 2012

Everything about this property was exactly as represented by Freewheeler. It was spotless and completely ready for our group despite last minute changes to the schedule. We will certainly consider this property and Freewheeler for our future visits to the Keys.

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$500

4 BR / 3 BA / Sleeps 8

9 Reviews

$500

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Private Beachfront Paradise

4 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 9 Reviews

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Reviews

(9)

Beautiful two story home ......four bedroom three baths.....on your private white sandy Beachfront property with large pool facing the ocean. First floor is independent with a very large one bedroom, bar with wine cooler full bath, living, dinning and new kitchen. The covered patio is huge at 60X15. The second floor…
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

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Reviews

(9)

Great House and Great Property Owner

Left on Dec 06, 2013 for a stay in November 2013

My family and I had the pleasure of staying at this home during Thanksgiving week. Not only did the house beat our expectations, but the communication with the owner was also fantastic. She was so helpful with every inquiry we had and went well above what we expected to make sure our time in Islamorada was as well as it could be.

The house itself was extremely clean, beautiful and very …

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$598

4 BR / 5 BA / Sleeps 10

1 / 35

$598

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

4 BR / 5 BA / Sleeps 10 | Quick view

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

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$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

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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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$490

4 BR / 4 BA / Sleeps 8

39 Reviews

$490

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Louisa House: A comfortable four bedroom vacation hideaway

4 BR / 4 BA / Sleeps 8 | Quick view
“ Excellent ” 39 Reviews

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Reviews

(39)

Great location, just half a block off Duval Street, walking distance to restaurants, the Atlantic beaches and the Southernmost Point. Casually decorated in soft pine and white, wicker furnishings and sofa sleeper in living room, this four bedroom, three and a half bath home provides a comfortable vacation hideaway. …
  • Internet Access
  • A/C or climate control
  • Deck
  • Parking
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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Reviews

(39)

Great House, Family Friendly

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

This is the second time I have stayed at this house and we have loved it both times. The house is within walking distance to everything we needed and wanted to do and offered many amentities. The pool area is very nice and the house is very spacious. The only downfall is I wish the pool area had more than 2 lounge chairs and that the trees were cut back a little more so some sunshine could …

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$470

4 BR / 2 BA / Sleeps 8

1 / 28

$470

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Pete's Cottages: Twin Cypress cottages steps from Duval

4 BR / 2 BA / Sleeps 8 | Quick view

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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
  • Deck
  • Linens Provided
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$217

4 BR / 3 BA / Sleeps 12

1 Reviews

$217

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1108 Heron Rd - 28 Night Minimum

4 BR / 3 BA / Sleeps 12 | Quick view
“ Very Good ” 1 Reviews

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Reviews

(1)

Located in Key Largo at mile marker 95, oceanside, this pool home will really seal the deal. Just remodeled, and offering stunning Atlantic views, the home is ideal for a family seeking a combination of camaraderie and privacy. Divided into separate units on its two floors, each with its own kitchen, the home's decor …
  • Waterfront
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

We had a relaxing and complete vacation stay.

Left on Aug 05, 2013 for a stay in June 2013

The house was decorated and remodeled beautifully. The pool was a nice addition. All amenities were at the house.

I will be staying here again and again provided that it is available.

Brought my boat and there was ample space and area for fish cleaning, as well as, a couple of beers under the palms when done.

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$425

4 BR / 3 BA / Sleeps 8

10 Reviews

$425

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Luxurious oceanfront villa! 525 Mariners Club

4 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 10 Reviews

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Reviews

(10)

The Florida Keys; and Mariner's Club...not a place to live;but a way to live. Do you long for a life away from the hustle and bustle of the 'real world'; fishing every day; snorkeling exotic coral reefs; diving captivating ship wrecks; exploring mother nature's finest natural habitats and her inhabitants; old world …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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Reviews

(10)

Magnificent

Left on Aug 25, 2010 for a stay in July 2010

Very nice house and we love the view at the ocean.

My wife and me come back for sure

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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

4 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 5 Reviews

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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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$750

4 BR / 4 BA / Sleeps 8

27 Reviews

$750

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

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

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Reviews

(27)

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

Details

Reviews

(27)

What a lovely property

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

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

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$250

4 BR / 2 BA / Sleeps 8

4 Reviews

$250

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Relaxing Getaway (REDUCED) in Key Largo

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

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Reviews

(4)

SPECIAL SEPT. OCT. AND NOV RATES This brand new 4 bedroom 2 bath house is on a canal which opens up to beautiful Tarpon Basin Bay with access to the Atlantic Ocean. Minutes from beautiful Penny Camp National Underwater Park. Minutes from best fishing and diving in the world. Come to the beautiful Florida Keys where…
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children

Details

Reviews

(4)

Awesome! Will stay there again and again.

Left on Apr 29, 2014 for a stay in April 2014

What a great place in Key Largo. Plenty of room and a great location. Right across from Publix and near all of the fun. We rented a boat from Pennicamp which was a short ride away. This place is perfect for a family. Each kid had their own bedroom and my daughter loved the trundle! There is a boat ramp and beach area that is perfect for relaxing or having a picnic. The owner was so nice and …

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$850

4 BR / 4 BA / Sleeps 8

15 Reviews

$850

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

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

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Reviews

(15)

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

Details

Reviews

(15)

The coolest house ever!

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

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

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$225

4 BR / 3 BA / Sleeps 9

1 Reviews

$225

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Bliss in the Florida Keys

4 BR / 3 BA / Sleeps 9 | Quick view
“ Excellent ” 1 Reviews

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Reviews

(1)

Beautiful canal front, clean, home located on ocean side in Long Key. MM 68. 4 bedrooms 3 baths total: 3 bedroom, 2 bath upstairs, 1 bedroom/bath (studio) downstairs. Great fishing and diving moments away. This is our family's vacation hideaway. Never rented prior to December 2012. Direct TV w HBO, Regional Sports …
  • Waterfront
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(1)

Must stay! Gorgeous house with plenty of room.

Left on Jun 14, 2014 for a stay in June 2014

Currently staying here and couldn't be happier. Comfortably sleeping 9 people in our party (4 adults, 4 kids/teens and a baby). The kitchen is stocked very well. Gorgeous view of the ocean from the upper deck. Quiet neighborhood. Will definitely be back!

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$799

8 BR / 6 BA / Sleeps 20

1 Reviews

$799

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Gulf View Suites w/Docks, Pools, Kayaks -Sleeps 20

8 BR / 6 BA / Sleeps 20 | Quick view
“ Excellent ” 1 Reviews

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Reviews

(1)

WHAT IS UNIQUE ABOUT THIS VACATION RENTAL? This rental offers a great option for multi-family vacationing by providing two 4-bedroom homes side-by-side. This gives you 2 kitchens, 2 pools, 2 deep water docks, 2 gas grills, parking for 5 vehicles and 6 kayaks! These properties are non-smoking and dog friendly. HOW …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

Awesome location, close to many popular destinations.

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

My husband and I really enjoyed our vacation to Marathon Fl. Our vacation home was very clean and close to many great restaurants and beaches. We used the kayaks, swam in our own pool and sat out on the deck to just watch the world go by.

We would highly recommend Rent My Island.

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$1,184

12 BR / 8 BA / Sleeps 30

2 Reviews

$1,184

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Twelve Bedrooms! Up to 30 peoplePools-Docks-Kayaks

12 BR / 8 BA / Sleeps 30 | Quick view
“ Excellent ” 2 Reviews

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Reviews

(2)

WHAT IS UNIQUE ABOUT THIS VACATION RENTAL? This rental offers a great option for multi-family vacationing by providing three 4-bedroom homes side-by-side. This gives you 3 kitchens, 3 pools, 3 deep water docks, 3 gas grills, parking for 8 vehicles and 6 kayaks! These properties are non-smoking and two of the three …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(2)

50th Wedding anniversary Celebration

Left on Dec 29, 2013 for a stay in June 2013

27 of us rented 3 houses(Gulf Shore Suites)in Marathon for my parents' 50th wedding anniversary. We really enjoyed the waterfront property with the option to swim in the ocean or pools. We loved the kayaks and outdoor dining with grills, too. The docks were wonderful for fishing in your own backyard; we enjoyed several dinners that were freshly caught! The houses were roomy and afforded us plenty…

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$625

4 BR / 4 BA / Sleeps 8

3 Reviews

$625

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4 ROOM LUXURY HOME IN MARATHON FL

4 BR / 4 BA / Sleeps 8 | Quick view
“ Very Good ” 3 Reviews

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Reviews

(3)

Amazing 4 Room 4 Bath New Luxurious Florida keys house. Completely newly built house equipped with state of the art appliances and modern furniture available for rent as of right now. Sleeps 10ppl, less then 0.5 miles from Sombrero Beach, Less then 1 mile from supermarket and shopping centers. Close to most of the…
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Pet friendly - ask
  • Suitable for children

Details

Reviews

(3)

Beautifully Presented new home

Left on Mar 24, 2014 for a stay in March 2014

This is a new rental property, only finished building in December 2013. So everything is brand new and clean and beautifully presented. A couple of wires still to attach, but this did not detract. Loads of space, great pool and hot tub (pay $25 a day extra to heat) , and great bbq and bar area next to the pool. Walking distance to Sombrero Beach, but need car to get to restaurants and shops. Wifi…

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$858

4 BR / 4 BA / Sleeps 12

2 Reviews

$858

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Turtle Nest

4 BR / 4 BA / Sleeps 12 | Quick view
“ Very Good ” 2 Reviews

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Reviews

(2)

Village Permit VR-062 You can not rent this property for less than one week. This luxurious new oceanfront estate is located in Islamorada. Enjoy the island's year-round sunny weather on the home's exotic wood deck surrounding a custom pool - all overlooking a private sugar sand beach on the Atlantic Ocean. New …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(2)

This house is simply amazing, best vacation ever!

Left on Oct 29, 2012 for a stay in September 2012

I stayed in the turtle nest with my mother, father, and sister my father has stage 4 lung cancer and has been giving only months to live, this was our last vacation together and ill tell you this was the best one ever, it's a beautiful house right on the beach, it is the dream house I have always wanted :)

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$141

4 BR / 3 BA / Sleeps 12

1 / 11

$141

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Paradise Can Be Cheap!!!

4 BR / 3 BA / Sleeps 12 | Quick view

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This Amazing Beach Home Has All That You Need!!! This House Has 3 Floors With Balconies With An Amazing View Of The Bay. It Has An Outdoor/Covered Space That Can Be Used To Hang Out And Cook. It Has An Outside Island Kitchen That Is Fully Stocked With Cooking Gadgets. The Private Beach And Boat Ramp Is 2 Blocks Down …
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for children
  • Suitable for the elderly

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$467

4 BR / 3 BA / Sleeps 8

1 / 21

$467

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Lazy Daze (28 Day Minimum)

4 BR / 3 BA / Sleeps 8 | Quick view

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****Due to a County Ordinance this property cannot rent for less than 28 days**** LAZY DAZE………….Imagine sitting on your lounge or palm hanging hammock, toes in the warm sugar sand, next to your heated pool, silence (except for a few birds), viewing the John Pennekamp State Park Marine Sanctuary waters. This …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask

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$600

4 BR / 0 BA / Sleeps 8

1 Reviews

$600

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76190 Overseas Highway - Casa Dorado

4 BR / Sleeps 8 | Quick view
“ Very Good ” 1 Reviews

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Reviews

(1)

Casa Dorado is a premier rental vacation home on Lower Matecumbe Key in Islamorada, Florida. Completely renovated in 2014, the spacious living and dining areas, four bedrooms, and three and a half bathrooms will make for a very comfortable stay during your visit to the Florida Keys. The house is located on the Florida…
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Casa Dorado delivers!

Left on Dec 26, 2014 for a stay in December 2014

The house is newly remodeled and in great condition. Very clean- which was a must for me! The views are wonderful. We thouroghly enjoyed the week we spent there (myself, my husband, our 24yr old daughter and her friend). It was a great location for biking, walking, kayaking and paddle boarding. The home has a pool, but we did not use it because it was not heated. We highly recommend Casa Dorado.

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$1,279

5 BR / 7 BA / Sleeps 10

1 / 13

$1,279

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Kara-Pan

5 BR / 7 BA / Sleeps 10 | Quick view

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You can not rent this property for less than one week. The ultimate island experience awaits you at Kara-Pan I. This exquisite, private, two story, Plantation Style home is located on a pristine natural white sand beach with oceanviews that inspire relaxation. The 5 bedroom 7 bath home with a wrap around porch, is …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • Suitable for children
  • Suitable for the elderly

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$1,000

5 BR / 4 BA / Sleeps 12

19 Reviews

$1,000

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

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

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Reviews

(19)

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

Details

Reviews

(19)

Fabulous...

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

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

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$643

4 BR / 3 BA / Sleeps 8

1 / 1

$643

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50 Schooner Bay Rd - Aguazul

4 BR / 3 BA / Sleeps 8 | Quick view

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How about sipping coffee and watching the sun come up as you fish off the end of your very own 300 foot pier? Sounds good, right? Well, that's just one reason to stage your upcoming vacation at this lovely, hacienda-style home on a quaint and private oceanfront street in Islamorada. CLICK HERE to view photos on a …
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$600

4 BR / 3 BA / Sleeps 8

1 Reviews

$600

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Latitude

4 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 1 Reviews

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Reviews

(1)

****This house cannot rent for less than 28 days, per County Ordinance**** Latitude: Freedom of thought or action. No word could better described this Keys Vacation Home. Embrace the serenity of the azure Atlantic Ocean while you relax in the private heated pool. Latitude boasts 2 master suits and two guest rooms. …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

A wonderful week with extended family

Left on Jun 16, 2013 for a stay in June 2013

Our extended family of 8 had a wonderful week at Latitude. The house is modern and immaculate. There was plenty of space and privacy for everyone. We had a great time watching a huge variety of sealife from the dock. We saw nurse and bonnet-head sharks, crabs, puffer fish, a turtle, stingrays and much more. The house was convenient to several very good restaurants (Pierre's, Islamorada Fish …

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$550

4 BR / 3 BA / Sleeps 12

1 / 9

$550

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Florida Keys Tavernier Canal Front House

4 BR / 3 BA / Sleeps 12 | Quick view

Details

4 Bedroom, 3 bath, Private heated Pool, jacuzzi, barbecue, Washer/Dryer, Tiki Hut with fans, TV, and MP3 speakers. Available November-January $4,000 for whole house or $3,000 for just upstairs (2 bed, 1 bath, and 1 pool bath) Utilities not included
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$729

5 BR / 6 BA / Sleeps 12

1 / 9

$729

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OCEAN FRONT VILLA- Grand Mangrove House

5 BR / 6 BA / Sleeps 12 | Quick view

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Ocean Front - Villa Bali inspired Florida Keys beauty on Privately owned Walker's Island. This is a spacious 5 bedroom, 5.5 bath home with luxury in every detail and design. Features include cathedral ceilings, marble, stainless steel and and mahogany finishes, and fireplaces in the living room and master suite. …
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly

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$217

4 BR / 4 BA / Sleeps 9

1 / 26

$217

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152 Valencia Drive - 28 Night Minimum

4 BR / 4 BA / Sleeps 9 | Quick view

Details

This is a beautiful Venetian Shores home... It truly is a must see! The interior is clean and nicely decorated. The large porch on the back allows you to see the famous Florida Keys sunsets from your own home! Located a few houses down from Snake Creek, you'll have quick ocean and bay access. Deep water dockage, tiki …
  • Waterfront
  • Ocean or water views
  • A/C or climate control
  • Grill
  • Dishwasher
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$175

4 BR / 4 BA / Sleeps 8

1 / 36

$175

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164 Plantation Shores Drive - 28 NIGHT MINIMUM

4 BR / 4 BA / Sleeps 8 | Quick view

Details

This is a very spacious and very well-maintained 4 bedroom, 3 bathroom home toward the mouth of the canal on a quiet street in Plantation Key (Tavernier). You and your group will enjoy stunning views from the main level, master suite, & rooftop sundeck. There is approximately 20ft concrete dockage. The home sits on a …
  • Ocean or water views
  • Internet Access
  • A/C or climate control
  • Grill
  • Dishwasher
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$950

6 BR / 4 BA / Sleeps 12

1 / 23

$950

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Flower Power House ~ Weekly Rental

6 BR / 4 BA / Sleeps 12 | Quick view

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

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$600

6 BR / 7 BA / Sleeps 12

1 / 31

$600

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Seaport Treasure Estate ~ Monthly Rental

6 BR / 7 BA / Sleeps 12 | Quick view

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

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$1,072

4 BR / 4 BA / Sleeps 10

13 Reviews

$1,072

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75731 Overseas Highway

4 BR / 4 BA / Sleeps 10 | Quick view
“ Excellent ” 13 Reviews

Details

Reviews

(13)

Islamorada is the Spiritual Center of the Keys, the Sportfishing Capital of the World, and home to the largest fleet of charter boats in the Keys. Fish deep water or the back bay. Snorkeling and SCUBA sites abound. Restaurants, art galleries, and other shopping are plentiful in Islamorada. Pass through a private …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • A/C or climate control
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(13)

Paradise!!!

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

Michelle Sorell was a great help and everything was just perfect. I hated to leave. the property is well maintained and Randy was also nice with all our grandboys that came in to visit while we were there. Thanks again for making our vacation so wonderful.

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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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$1,000

5 BR / 5 BA / Sleeps 10

1 Reviews

$1,000

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Key Largo Oceanfront Luxurious Rental

5 BR / 5 BA / Sleeps 10 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

This Oceanfront home is totally re-modeled with all top of the line finishes and ready to enjoy your Keys Vacation. Oceanfront Pool Home. 3 Story 5 Bed/5.5 Bath 4300+ sq. ft. of luxury and fun. Protected deepwater Dockage & Panoramic Ocean Views. This great executive rental features Ocean Views from almost every room …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

Best House in Key Largo

Left on Jan 11, 2015 for a stay in January 2015

Thank you for allowing us to stay in your amazing property!

The pictures really do not do it justice, surely one of the finest houses in Key Largo

Absolutely first class and without doubt the best vacation home we have ever rented wonderful ocean views from everywhere delightful pool area, fantastic fixtures and fittings,

A magnificent vacation rental

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$150

4 BR / 3 BA / Sleeps 8

1 Reviews

$150

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"SEABREEZE" Monthly Rental -Sanctuary- Golf Course

4 BR / 3 BA / Sleeps 8 | Quick view
“ Very Good ” 1 Reviews

Details

Reviews

(1)

28 NIGHT MINIMUM STAY REQUIREMENT - SEABREEZE 4 Bedroom 3 Bath with Off Street Parking, Private Heated Pool, Fitness Center, Gorgeous!! A warm color scheme and meticulous design details lend an elegant tropical ambience to this spacious four bedroom, 3 bath home located in the "Sanctuary" on the Key West …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

Awesome Month!!!

Left on May 01, 2014 for a stay in February 2014

We rented Seabreeze for a month! It was in the Golf Course a gated community. It was a great home away from home. Very comfortable, stocked well. Had a few glitches with the pool. [the pool company not sweeping the pool} a lot of vegetation so many leaves and such in pool. Gym [we were told it was included and they tried charging us, took a few days to get key] But, I will say everything worked …

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$429

5 BR / 4 BA / Sleeps 10

8 Reviews

$429

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140 Atlantic Lane

5 BR / 4 BA / Sleeps 10 | Quick view
“ Excellent ” 8 Reviews

Details

Reviews

(8)

Amazing ocean views can be enjoyed from this beautiful stilt home with seperate mother-in-law cottage. You'll fall in love with this little piece of Heaven. Enjoy fishing, diving, and catching lobster with all the comforts of home. Best ocean views in town! Interior photos are available! Mile Marker 76.5, Oceanside. …
  • Ocean or water views
  • A/C or climate control
  • Grill
  • Dishwasher
  • Microwave
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(8)

Summer vacation 2010

Left on Sep 13, 2010 for a stay in August 2010

Overall nice place, kitchen items were not very organized, and place could use a deep cleaning

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$700

4 BR / 4 BA / Sleeps 8

2 Reviews

$700

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Hermitage South

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

Details

Reviews

(2)

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

Details

Reviews

(2)

Family Vacation in Key West

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

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

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

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$500

4 BR / 3 BA / Sleeps 8

4 Reviews

$500

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101 Palo de Oro

4 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 4 Reviews

Details

Reviews

(4)

Great pool home in desirable Venetian Shores. This 4 bedroom/3 bath home is roomy and has great porches overlooking the wide, clean canal. Lovely master suite on the top floor with it's own balcony. Comfortably furnished pool home with 90 feet of excellent deep water dockage on a wide canal leading directly to Snake …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(4)

Wonderful

Left on Jul 15, 2010 for a stay in June 2010

We have stayed at this house 2 years in a row. The house is comfortable and a great location. The area has wonderful restaurants and fishing is great. We plan on staying next year for 2 weeks.

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$758

5 BR / 3 BA / Sleeps 10

17 Reviews

$758

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87445 Old Hwy

5 BR / 3 BA / Sleeps 10 | Quick view
“ Excellent ” 17 Reviews

Details

Reviews

(17)

This oceanfront home will surely get you in a Keys state of mind. Featuring five bedrooms, a pool, and an expansive private beach, its ideal for anything from a reunion of extended family or friends, to a small wedding, to a relaxing family vacation. The 4,300 square foot house will capture your attention at the …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • A/C or climate control
  • Garage
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(17)

Great Location, house needs some nimor work

Left on Apr 07, 2011 for a stay in March 2011

Nice house, dirty carpets, screens on doors need repair, with minor cleaning and repairs this house could be great

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$300

4 BR / 4 BA / Sleeps 10

8 Reviews

$300

Inquire

4 Bedroom with guest quarters! 612 Mariners Club

4 BR / 4 BA / Sleeps 10 | Quick view
“ Excellent ” 8 Reviews

Details

Reviews

(8)

3-7 night minimum stay requirement varies by time of year. Three-story townhouse with over 2600 sq of living space...room for the whole family! Ground floor 1-bedroom (king bed) with kitchenette, open floor plan sitting area with queen sleeper sofa and a private full bath...perfect for grandma or the nanny. An …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(8)

A very comfortable place for a three generation holiday.

Left on May 29, 2012 for a stay in December 2011

The townhouse was good for all nine of us and we did not trip over each other. The kitchen was big enough for 3 or 4 to work in so meals got done in a hurry with several people helping. The swimming pool was great with its white sandy beach There were plenty of things to do close enough to keep us all happy. We had a great time and my expectations had been lower. So the only hitch was getting …

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$800

4 BR / 3 BA / Sleeps 10

6 Reviews

$800

Inquire

Pavilion Villa ~ Weekly Rental

4 BR / 3 BA / Sleeps 10 | Quick view
“ Very Good ” 6 Reviews

Details

Reviews

(6)

A Private Tropical Paradise... is the feeling you get when you enter the pavilion of this extraordinary award winning villa just a half block off Duval St. in Old Town Key West. I first visited this private home when it was featured on the prestigious Garden Home Tour of Key West which opens a few select private homes…
  • Housekeeping Optional
  • A/C or climate control
  • Parking
  • Television
  • DVD Player
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(6)

Great Stay!

Left on Jan 12, 2011 for a stay in April 2010

We stayed here with a big group in April, and had the time of our lives. GREAT PLACE!

We got there early, and the maid was still cleaning when we walked in. She was hesitant to let us leave our bags there because of liability reasons, which we totally understood. She let us leave them there anyway, and all was well. :)

There are actually 3 bedrooms available, but you can make it 5. My …

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$267

4 BR / 5 BA / Sleeps 8

1 / 28

$267

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"THE CORAL HOUSE" Luxury Monthly- Parking and Pool

4 BR / 5 BA / Sleeps 8 | Quick view

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28 NIGHT MINIMUM STAY REQUIREMENT - THE CORAL HOUSE Old Town / Historic Seaport Location 4 Bedrooms, 4.5 Baths, Sleeps 8 LUXURY Vacation Home located on Millionaire's Row in Historic Old Town Key West We guarantee that the Coral House will fulfill even the highest expectations. Just under 2000 square feet of …
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children - ask

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$715

4 BR / 3 BA / Sleeps 10

1 / 38

$715

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82754 Overseas Highway

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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$600

5 BR / 6 BA / Sleeps 12

1 / 42

$600

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Ultimate Key West Beach House - Sunset Key~ VIP~ Monthly Rental

5 BR / 6 BA / Sleeps 12 | Quick view

Details

Perfectly positioned on Sunset Key, ‘the islands island,’ the Ultimate Key West Beach House ~ Sunset Key VIP, is within 500 yards off-shore of the ‘main island’ of Key West. A splendid view gazing toward Mallory Dock and the famous sunset celebration, this one-of-a-kind waterfront property …
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$400

4 BR / 5 BA / Sleeps 10

19 Reviews

$400

Inquire

4/5 waterfront gated home, heated pool, boat docks

4 BR / 5 BA / Sleeps 10 | Quick view
“ Excellent ” 19 Reviews

Details

Reviews

(19)

Waterfront 4 bedroom and 5 full bathrooms private gated home, heated pool, Tiki hut, deep 135 foot boat dock, fish cleaning station, bait freezer, gourmet kitchen, 2 full size refrigerator and freezers. sleeps 10, covered parking for 4 cars. Awesome sunset views over Bonefish Bay,veranda, 3 hammock, plenty of trailer …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(19)

Perfect place for a family or group

Left on Jul 23, 2010 for a stay in February 2008

We had our family reunion in the Keys, and we ended up renting 2 houses on ave F, to be able to fit the entire group of 21 people. Everyone gathered at this house, though, to relax on the balconies, sit around the living room, cook & grill together, and use the pool area. The pictures don't come close to the real thing! There is a tremendous amount of space, and we never felt crowded. If you …

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$200

4 BR / 2 BA / Sleeps 9

6 Reviews

$200

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Key Largo Villa - Beautiful Waterfront 3/2 + Den

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

Details

Reviews

(6)

This beautiful, waterfront house in Key Largo is our 2nd home. Enjoy watching breathtaking sunsets over the Bay from the 2nd floor balcony. A short canal leads you to tranquil Sexton Cove, with ocean access only 5 minutes away via Adams Waterway. Back-country anglers can head straight west through the Boggies and …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(6)

We had a very relaxing and fun time with our boat docked right i

Left on Jun 24, 2011 for a stay in May 2011

We loved the house and would love to rent it again. We especially like that we were able to have our boat right in the canal in back of the house. The house is very comfortable, roomy and light. I found the bedroom a little too bright in the morning that would have been better with some light blocking curtains, but that is really the only thing I would change. We had a great time, and also loved …

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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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$299

4 BR / 4 BA / Sleeps 10

10 Reviews

$299

Inquire

Exquisite 4 bedroom, 4 bath! 607 Mariners Club

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

Details

Reviews

(10)

3-7 night minimum stay requirement varies by time of year. Three-story townhouse with over 2600 sq of living space...room for the whole family! Ground floor 1-bedroom (king bed) with kitchenette, open floor plan sitting area with queen sleeper sofa and a private full bath...perfect for nana or the kids! An interior …
  • Waterfront
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(10)

vacation

Left on Apr 06, 2012 for a stay in March 2012

Everything was wonderful. My only complaint was the downstairs apartment didn't even have a coffee table and the bedroom floor was full of "dust bunnies". Other than that the resort was beautiful and the condo was great.

Thank you for all your help with the rental. Debbie and annie were just terrific.

Lee Okon

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