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460 houses

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$339

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Gorgeous waterfront home

Islamorada house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Private indoor pool, Rental types

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$459

Room with Shared Bath in Coconut Grove Cottage

Miami house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private indoor pool, Rental types

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Price per night from

$287

Comfortable South Miami Getaway

Miami house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

1 of 2 match: Private indoor pool, Rental types

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$345

"Irish Ayes" Elegant Waterfront Home with Pool

Islamorada house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$804

Very Nice 3 Bedroom Home With Large Lot!

Tavernier house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

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$81

Fisherman's Paradise in the Heart of Big Pine Key

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private indoor pool, Rental types

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Price per night from

$114

Islamorada cottage on deep water canal

Islamorada house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private indoor pool, Rental types

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Price per night from

$287

30% off now till March!!! Direct Atlantic Ocean front private boat ramp dock.

Summerland Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private indoor pool, Rental types

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$161

The Mermaids House, Historic Old Town Key West

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Beautiful Home in Old Town Key West” Mermaid House is conveniently located in the heart of Old Town yet when you are there you are in your own private paradise. The house is beautifully appointed with anything you could need during your stay and has ample space for four people. It was the perfect spot for our stay in Key West and we plan to stay again when we return to the area. Thanks to Barbara for making us feel welcome and for sharing her beautiful home with us.

1 of 2 match: Private indoor pool, Rental types

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Price per night from

$329

Islamorada Waterfront Paradise Getaway!

Islamorada house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Wonderful Romantic Get-Away” We absolutely enjoyed our stay here and would recommend it to others. The owners were very friendly and pleasant, and the apartment was incredibly clean. The tiki hut over the private lagoon was amazing. We kept finding little things all over the apartment while we were there - drinks, books, games, etc. It was a totally wonderful time, and we want to go back!

1 of 2 match: Private indoor pool, Rental types

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Price per night from

$574

Waterfront Home In Florida Keys

Tavernier house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Perfect Holiday in Tavernier” We had a wonderful time at Dan and Penny's home. They were very accommodating! The home is absolutely pristine and in a nice neighborhood. There wasn't a day that we did not see manatee and tarpon in the canal in front of the house. Perfect location for restaurants, shopping and activities either by land or water. Beautiful home with everything you need for a perfect vacation in the Keys!

Responds fast! avg. 1 hour 17 minutes

1 of 2 match: Private indoor pool, Rental types

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Price per night from

$210

Beautiful Private Home with Beach Access

Key Largo house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

“Great place for a family” Wonderful place to stay! My family of 5 enjoyed the clean rooms and full kitchen. Easy access to private beach, restaurants, grocery store. Very safe neighborhood. The house was fully provided for our stay, Great access to John Pennycamp and the Everglades. We would definitely stay here again. Daniel A. was very easy to work with. We enjoyed coming home after a busy day of snorkeling to make supper and lounge on our own deck or wander down to the private beach to enjoy the evening. Having this home made our vacation very relaxing and enjoyable.

1 of 2 match: Private indoor pool, Rental types

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Price per night from

$86

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Price per night from

$247

Fandango

Cudjoe Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

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Price per night from

$622

“Fantasic wedding on paradise!!” We picked Shadow Point because of it's fabulous secluded view and beautiful gardens on 2.5 acres. The house and cottage held up to 16 of us and was wonderfully decorated with period antiques. Our guests loved playing at their beach and kayaking and swimming around Key LargoSound. Our wedding was perfect with the full moon rising over our reception. We danced the night away in paradise.

1 of 2 match: Private indoor pool, Rental types

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Price per night from

$2,410

Casa Del Sol, a Key West Vacation (Truman Annex)

Key West house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

“awesome” the condo was beautiful. very good location. 2 suggestions. the grill did not have gas . the bed that opens up to king. not so much, mattress is 2 different heights and slides if you try to sleep on it. very very uncomfortable.

Responds fast! avg. 2 hours 7 minutes

1 of 2 match: Private indoor pool, Rental types

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Price per night from

$344

The Tree House Old Town 2 Bedroom MONTHLY Rental

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

“Wonderful” Close to everything! Furnishings just the best. We stayed upstairs in the 2 bedroom 1 large bath. Great wrap around porch up stairs and down. Our key Westies were welcomed which was a plus for us! Overall Stephanie has done a great job and her sister was really helpful. Planning on returning!!!!

1 of 2 match: Private indoor pool, Rental types

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$134

Florida Keys Splendor at Hammer Point

Tavernier house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Winter Paradise!” My wife and I stayed at this great place in January 2014 and it was wonderful. It was very clean and well maintained. The canal was great to watch the fish jump and we saw Manatees almost every day. We especially liked the kayak and did a lot of site seeing from the ocean side. Migdy was great to work with and very accommodating. We would highly recommend this place to anyone.

1 of 2 match: Private indoor pool, Rental types

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Price per night from

$158

SANCTUARY IN PARADISE

Islamorada house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

“What Florida dreams are made of” Growing up in South Florida and the Keys but now moved farm away, I wanted to show my husband and young children the Florida I remembered as a child. This my friends was more than my dreams could have asked for! We were tremendously blessed to have had the opportunity to share this paradise! Private, gated estate with coral wooded hammocks to stroll through, palm trees clicking in the breeze, flocks of ibis that grazed through the lush green yard that ended at the private water front. Orchids blooming in the trees welcomed us to the hammocks where we had our morning coffee to stunning colored sunrises. It had everything: super clean Keys styled house with a cute kitchen (that saved us on meal expenses), bedrooms and bathrooms that were perfect size and accommodations, and wifi. It was quiet yet welcoming to my kids. We kayaked and swam on Christmas morning! The hosts were gracious and really made us feel as we were family. It was a Christmas we will always cherish. "Give and it will be given to you. A good measure, pressed down, shaken together and running over, will be poured into your lap." Luke 6:38 Truly, after giving us the chance to come share your slice of heaven, our cup runneth over.

Responds fast! avg. 2 hours 42 minutes

1 of 2 match: Private indoor pool, Rental types

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Price per night from

$984

Kokomo Cove Boat House

Marathon house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

“Boat ramp and beautiful pool in the heart of the Keys” We wanted a house on a canal in the Marathon area, where we have been vacationing for years. This house had its own boat ramp, so we rented kayaks for a week and launched effortlessly right on site. The pool is lovely and relaxing. The house is well equipped and centrally located so trips up to Key Largo and down to Key West are quick.

1 of 2 match: Private indoor pool, Rental types

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Price per night from

$401

Royal Palm House

Marathon house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Beautiful Home in Marathon” We truly loved this place, the home was clean, spacious and very comfortable! My husband still claims to this day that was the best sleep he has had in years and that's a big compliment coming from him! We loved having water access (although we didn't have a boat) it really made for some beautiful sunsets and sunrises! We found a couple of amazing restaurants that we visited on several occasions, the first and our favorite was Tarpon Creek following as a very close second was The Sunset Grill and Raw Bar, also our favorite breakfast spot became Juice Paradise Cuban Cafe (the best coffee). I'm only just now getting around to reviewing this place because we are planning another trip to the Keys in December and I was checking this place out and i didn't see our review and ask my husband about it (I thought he posted it and he thought I posted it), so finally 2 yrs later I'm giving our review!!! Unfortunately I see it's booked for our time frame and we are very disappointed about that but I know whoever booked it WILL NOT be disappointed! Thanks so much for an amazing experience, Gina & Scott PS we actually stayed Sept 2014 but it would only let me go back to Oct 2014! :-)

1 of 2 match: Private indoor pool, Rental types

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Price per night from

$215

BIG POOL! Across Street from Beach! SEASIDE PLACE, Key West - 5/5 w/parking

Key West house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

“Paradise in Paradise” Just returned from a marvelous vacation in Key West. While the tan is already starting to fade, the memories of our stay at Seaside Place remain vivid. We absolutely loved this house. It is very charming and offers all the amenities you'll ever need and then some, from a kitchen that Julia Child would not have found wanting, gorgeous, large rooms each with its very own character, spacious communal dining areas and a beautiful large pool with romantic lighting, a soothing waterfall feature and total privacy. The owners' love for providing the best experience is evident in every detail, from the painstaking labeling of all switches and outlets to the folders of carefully compiled information about where to go, and what to do and see. The house is just a block from the quiet end of Duval Street (there is such a thing), yet far enough removed from the Key West bar scene responsible for the prevailing serious shortage of liver donors. We thoroughly enjoyed every minute of our stay and can't wait to return soon. And we can't help but think that if Hemingway had stayed here he might still be alive today

1 of 2 match: Private indoor pool, Rental types

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Price per night from

$2,124

Bayside Retreat. Pool, Boat and Beach

Key Largo house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

“SPLENDID VACATION” I had the opportunity to stay here with my family in March. The house was spacious and the beach and pool were exactly what we wanted for a private family vacation. The house manager, Kevin, could not have been more accomodating in seeing that all of our vacation needs were taken care of. I could have sat on the porch and watched the sunset views forever. Watch for the manatees when you are there, they are a lifetime experience.

1 of 2 match: Private indoor pool, Rental types

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Price per night from

$1,263

HISTORIC KEY WEST - Turtle House - Sleeps 6

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Private indoor pool, Rental types

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Price per night from

$1,491

HISTORIC KEY WEST - Main House - Sleeps 8

Key West house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

“February visit to Key West” Our family stayed at the Main House for 4 nights and loved it. The location was fabulous! Loved the houses and gardens!!! The owner was very nice and considerate of us. If we get back that is where we would want to be!!

1 of 2 match: Private indoor pool, Rental types

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Price per night from

$2,065

HISTORIC KEY WEST - Conch House - Sleeps 5

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Private indoor pool, Rental types

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Price per night from

$1,147

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private indoor pool, Rental types

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Price per night from

$345

LUXURY EXECUTIVE ISLAND HOME W DOCK

Alice Town house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Private indoor pool, Rental types

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Price per night from

$632

OCEANFRONT LUXURY "Mar Azul"

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Private indoor pool, Rental types

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Price per night from

$501

Waterfront Vacation Beach House Rental Home Bayside Sunset Cove Access

Key Largo house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Abbsolutly Fantastic !!” This is our second year staying a week. Can not say enough about how much we love this house. It's not often you ca stay somewhere for this amount of time and feel like you are are coming home when you arrive for vacation. The house has all the amenities you will need to include fishing rods and 1 and 2 person Kayaks. toys for the kids etc. The location is also great near restaurants, marinas etc. The only complaint once you stay here you are hooked ! We were already ready to book for next year immediately after this vacation. If you want a stress free place for a vacation this is it.

1 of 2 match: Private indoor pool, Rental types

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Price per night from

$574

Florida Keys Beach Home Pool Fishing Diving

Marathon house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Wonderful stay” Post hurricane and still a spectacular place to stay. Office staff was great. Free use of tennis court, rackets, and balls. Pool and jacuzzi were very excellent. TG

1 of 2 match: Private indoor pool, Rental types

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Price per night from

$2,296

Everglades National Park , South East Florida Home

Homestead house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Private indoor pool, Rental types

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Price per night from

$345

Luxurious 4Bedrooms House near Miami &; the Keys.

Homestead house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Private indoor pool, Rental types

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Price per night from

$287

Sunrise Waterfront Home

Key Largo house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Private indoor pool, Rental types

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Price per night from

$488

Islamorada Waterfront Paradise 2

Islamorada house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private indoor pool, Rental types

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Price per night from

$517

AZALEA WARTERFRONT

Islamorada house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

1 of 2 match: Private indoor pool, Rental types

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Price per night from

$391

Bay Pointe

Sugarloaf house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private indoor pool, Rental types

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Price per night from

$204

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