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“Relaxing Weekend Getaway” We love this home! It is on a private dead-end street, and everything is just perfect. Kept the boat right at the dock, fished right there at night, took some nice boat rides through the back country, and relaxed in paradise. Wifi is good and fast (I had to do some work while we were there), and we can't wait to go back.
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$172
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$155
Great rentals within 20 miles that match your search
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$459
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$803
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$316
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$287
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$574
“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!
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$574
“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.
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$86
Clean Keys 3/3 w/Davits Clear Canal Bay Side/Views Fenced 2Level Tavernier Home
Tavernier house
- 3 bedrooms
- 3 bathrooms
- sleeps 12
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$247
Private Beachfront -Perfect for Families and Events Historic Shadow Point Estate
Key Largo house
- 6 bedrooms
- 5 bathrooms
- sleeps 16
“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.
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$2,408
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$488
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$390
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$458
“Hidden Treasure” This cottage is one of our favorite place to stay. Clean, well equipped, private, and so relaxing. A great place to spend a relaxing vacation. We love the outdoor kitchen and sitting area.
Responds fast! avg. 56 minutes
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$253
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$144
“Quaint and unique rental” The houseboat was everything I expected and needed it to be. It slept our family of four comfortably - which was all we really needed. The weather was good so really the only thing we did at the houseboat was shower and sleep. We did also do a few loads of wash - having a full size washer and dryer was convenient. I bet if we spent more time there, we would have used the back yard, it is really neat and welcoming. Maggie was a gracious hostess and everything was exactly where and how she described it. All in all a great value.
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$98
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$201
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$774
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$574
Blue Dolphin Private Oceanfront 1.8 acre Estate on Millionaire's Row with Pool
Islamorada house
- 5 bedrooms
- 4 bathrooms
- sleeps 12
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$1,147
San Roc - Private 150 Ft Oceanfront 2.5 Acre Millionaire Row Estate, Pool, Spa,
Islamorada house
- 4 bedrooms
- 3 bathrooms
- sleeps 8
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$2,130
Come relax in Islamorada, the tropical jewel of the Florida Keys!!
Islamorada apartment
- 1 bedroom
- 1 bathroom
- sleeps 4
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$201
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$264
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$207
Paradise Found - Sandy Beach, Beachside Bar, Great Views, And Dock
Islamorada villa
- 3 bedrooms
- 3 bathrooms
- sleeps 6
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$1,147
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$764
Responds fast! avg. 2 hours 10 minutes
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$532
Waterfront Home; Private 50ft Concrete Boat Dock Pet-friendly Tropical vacation
Key Largo house
- 2 bedrooms
- 1 bathroom
- sleeps 6
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$373
Majestic estate, 200' of private oceanfront beach & pool, 3,600sqft tiki
Islamorada house
- 3 bedrooms
- 3 bathrooms
- sleeps 8
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$1,474
Islamorada trop paradise pool, fishing, 2fls luxury with a filet stationn
Islamorada house
- 4 bedrooms
- 2 bathrooms
- sleeps 8
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$785
Relax in newly remodeled home just minutes away from marinas, parks and beaches
Key Largo house
- 4 bedrooms
- 3 bathrooms
- sleeps 8
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$149
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$344
New Listing! Charming Angler's Reef Home with Pool, Dockage
Islamorada house
- 2 bedrooms
- 3 bathrooms
- sleeps 6
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$459
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$287
Islamorada Escape - Executive Bay w/Pool, Fishing Dock, Beach, Tennis/Pickleball
Islamorada house
- 3 bedrooms
- 2 bathrooms
- sleeps 8
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$207
Responds fast! avg. 2 hours 15 minutes
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$172
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$316