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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.
Match: High chair Pets allowed
All filters matchPrice per night from
$2,408
Majestic estate, 200' of private oceanfront beach & pool, 3,600sqft tiki
Islamorada house
- 3 bedrooms
- 3 bathrooms
- sleeps 8
1 of 2 match: High chair, Pets allowed
1 of 2 filters matchPrice per night from
$1,474
New Upscale, private pool, Dockage, kayaks, bikes, downtown Islamorada locale
Islamorada house
- 3 bedrooms
- 4 bathrooms
- sleeps 6
1 of 2 match: High chair, Pets allowed
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$912
Responds fast! avg. 3 hours 2 minutes
1 of 2 match: High chair, Pets allowed
1 of 2 filters matchPrice per night from
$342
The Nest Villa and Marina at Holiday House Resort, Islamorada
Upper Matecumbe Key villa
- 2 bedrooms
- 2 bathrooms
- sleeps 4
1 of 2 match: High chair, Pets allowed
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$344
1 of 2 match: High chair, Pets allowed
1 of 2 filters matchPrice per night from
$458
“Pleasant place to stay for a few days” We got off on a bad foot as the room had not been cleaned before our arrival at 4:30PM (we were told we could check in a 3PM). The management was very responsive however, and paid for a complementary dinner at a fun, nearby restaurant by way of apology. The room was well designed and comfortable, if not spacious; the kitchenette and living/bedroom are all in one layout. It was fine for 2 guests but there would be no privacy if there were more. The cabana is right on the canals; boats pass frequently but it's not noisy. This was our first visit to the Florida Keys, and this cabana was a comfortable base for seeing Key Largo. It's not as convenient if you want to go as far south as Key West.
Responds fast! avg. 2 hours 15 minutes
1 of 2 match: Pets allowed, High chair
1 of 2 filters matchPrice per night from
$172
Responds fast! avg. 2 hours 15 minutes
1 of 2 match: Pets allowed, High chair
1 of 2 filters matchPrice per night from
$172
Responds fast! avg. 2 hours 15 minutes
1 of 2 match: Pets allowed, High chair
1 of 2 filters matchPrice per night from
$172
Responds fast! avg. 2 hours 23 minutes
1 of 2 match: High chair, Pets allowed
1 of 2 filters matchPrice per night from
$402
Large Waterfront 4 balcony Key Largo Townhouse with Oceanfront Dock
Key Largo townhouse
- 3 bedrooms
- 3 bathrooms
- sleeps 8
Responds fast! avg. 2 hours 23 minutes
1 of 2 match: High chair, Pets allowed
1 of 2 filters matchPrice per night from
$402
“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: High chair, Pets allowed
1 of 2 filters matchPrice per night from
$210
Clean Keys 3/3 w/Davits Clear Canal Bay Side/Views Fenced 2Level Tavernier Home
Tavernier house
- 3 bedrooms
- 3 bathrooms
- sleeps 12
1 of 2 match: High chair, Pets allowed
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$247
“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 52 minutes
1 of 2 match: High chair, Pets allowed
1 of 2 filters matchPrice per night from
$983
“Nice get away” Beautiful and relaxing. Did alot of snorkeling right off the deck. Enjoyed the paddle boats and the kayaks. When we make it down that way again I would definitely stay here.
1 of 2 match: High chair, Pets allowed
1 of 2 filters matchPrice per night from
$401
Responds fast! avg. 2 hours 23 minutes
1 of 2 match: High chair, Pets allowed
1 of 2 filters matchPrice per night from
$402
Key Largo Ocean Front Villa with Dock and Incredible views
Key Largo villa
- 2 bedrooms
- 2 bathrooms
- sleeps 6
Responds fast! avg. 2 hours 23 minutes
1 of 2 match: High chair, Pets allowed
1 of 2 filters matchPrice per night from
$459
1 of 2 match: High chair, Pets allowed
1 of 2 filters matchPrice per night from
$488
Blue Dolphin Private Oceanfront 1.8 acre Estate on Millionaire's Row with Pool
Islamorada house
- 5 bedrooms
- 4 bathrooms
- sleeps 12
1 of 2 match: High chair, Pets allowed
1 of 2 filters matchPrice per night from
$1,147
Responds fast! avg. 3 hours 58 minutes
1 of 2 match: High chair, Pets allowed
1 of 2 filters matchPrice per night from
$344
Responds fast! avg. 2 hours 15 minutes
1 of 2 match: Pets allowed, High chair
1 of 2 filters matchPrice per night from
$149
1 of 2 match: High chair, Pets allowed
1 of 2 filters matchPrice per night from
$803
1 of 2 match: High chair, Pets allowed
1 of 2 filters matchPrice per night from
$316
1 of 2 match: High chair, Pets allowed
1 of 2 filters matchPrice per night from
$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.
1 of 2 match: High chair, Pets allowed
1 of 2 filters matchPrice per night from
$98
1 of 2 match: High chair, Pets allowed
1 of 2 filters matchPrice per night from
$201
1 of 2 match: High chair, Pets allowed
1 of 2 filters matchPrice per night from
$660
1 of 2 match: High chair, Pets allowed
1 of 2 filters matchPrice per night from
$264
1 of 2 match: High chair, Pets allowed
1 of 2 filters matchPrice per night from
$207
San Roc - Private 150 Ft Oceanfront 2.5 Acre Millionaire Row Estate, Pool, Spa,
Islamorada house
- 4 bedrooms
- 3 bathrooms
- sleeps 8
1 of 2 match: High chair, Pets allowed
1 of 2 filters matchPrice per night from
$2,130
Responds fast! avg. 2 hours 10 minutes
1 of 2 match: High chair, Pets allowed
1 of 2 filters matchPrice per night from
$409
Waterfront Home; Private 50ft Concrete Boat Dock Pet-friendly Tropical vacation
Key Largo house
- 2 bedrooms
- 1 bathroom
- sleeps 6
1 of 2 match: High chair, Pets allowed
1 of 2 filters matchPrice per night from
$373
Islamorada trop paradise pool, fishing, 2fls luxury with a filet stationn
Islamorada house
- 4 bedrooms
- 2 bathrooms
- sleeps 8
1 of 2 match: High chair, Pets allowed
1 of 2 filters matchPrice per night from
$785
1 of 2 match: High chair, Pets allowed
1 of 2 filters matchPrice per night from
$1,663
Luxury on the water-Clean remodeled Houseboat with great WiFi -Baycation
Tavernier boathouse
- 1 bedroom
- 1 bathroom
- sleeps 4
1 of 2 match: High chair, Pets allowed
1 of 2 filters matchPrice per night from
$344
1 of 2 match: High chair, Pets allowed
1 of 2 filters matchPrice per night from
$378
1 of 2 match: High chair, Pets allowed
1 of 2 filters matchPrice per night from
$459
1 of 2 match: Pets allowed, High chair
1 of 2 filters matchPrice per night from
$516