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85 Houses

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ISLAMORADA WATERFRONT PARADISE with FREE DOCKAGE

Matecumbe Key studio

Studio
1 bathroom

sleeps 2

“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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Price per night from

$172

Great rentals within 20 miles that match your search

Motel Room #1, Private Entrance, Beach and Marina

Key Largo apartment

1 bedroom
1 bathroom

sleeps 2

Responds fast! avg. 1 hour 37 minutes

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$213

Diving, Fishing, Snorkeling, Kayaking Paradise

Key Largo townhouse

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 2 hours 23 minutes

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Price per night from

$402

Islamorada Ocean Views! Pool, Wi-Fi, Balcony, Gym, Covered Parking

Islamorada condo

2 bedrooms
2 bathrooms

sleeps 4

Responds fast! avg. 2 hours 44 minutes

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$172

Luxury condo overlooking harbor with ocean view

Islamorada condo

3 bedrooms
3 bathrooms

sleeps 6

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$391

Very Nice 3 Bedroom Home With Large Lot!

Tavernier house

3 bedrooms
2 bathrooms

sleeps 5

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$81

1 Bed ,Full Kitchen, Mini Split Air, Upstairs, Waterview, Beach, Marina, Apt #4

Key Largo apartment

1 bedroom
1 bathroom

sleeps 2

Responds fast! avg. 1 hour 37 minutes

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Price per night from

$316

Islamorada cottage on deep water canal

Islamorada house

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$287

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!

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$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

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$210

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

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.

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$157

Bayside Condo, marina, pool and beach

Islamorada condo

3 bedrooms
2 bathrooms

sleeps 6

“Phenomenal keys experience!” This bay front condo is the perfect destination for the entire family! The fishing ranks up with the best in the world, there are plenty of other activities, and Key West is just a short trip down the beautiful HWY 1. I've had the pleasure of staying at this condo several times and have honestly never had a bad time (even during a cat 5 Trop Storm). There is too much to do, the condo is comfy, and the weather is always beautiful. Definitely recommend this condo!

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$254

Bayfront Cottage Vacation Home Rental Bayside Beach Renovated 2019 Sunset Cove

Key Largo cottage

2 bedrooms
2 bathrooms

sleeps 6

“Perfect” Great house. Very clean and simple. You share the beach and dock with the two other houses in the property but was never an issue. Location is great in Largo. Martha was a great host and very friendly. Will definetly be going back.

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$316

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.

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$574

Key Largo Rental Fantastic Views

Key Largo condo

3 bedrooms
2 bathrooms

sleeps 8

Responds fast! avg. 2 hours 23 minutes

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Price per night from

$402

LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF

Islamorada villa

2 bedrooms
3 bathrooms

sleeps 6

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$356

Islamorada Waterfront Paradise 2

Islamorada house

2 bedrooms
2 bathrooms

sleeps 6

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$516

Oceanfront Anglers Reef Islamorada Florida Keys

Islamorada house

2 bedrooms
3 bathrooms

sleeps 6

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$458

Bay Front Beauty/ Summer Sea Must See!!!!

Islamorada condo

1 bedroom
1 bathroom

sleeps 4

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$159

Bayfront Cottage with Bay Front Screen Porch, Central Air, Beach and Marina

Key Largo cottage

1 bedroom
1 bathroom

sleeps 5

Responds fast! avg. 1 hour 37 minutes

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Price per night from

$367

Newly refinished condo open water views very nice

Islamorada condo

2 bedrooms
2 bathrooms

sleeps 6

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$230

Unique Houseboat on Dry Lot

Key Largo houseboat

2 bedrooms
1 bathroom

sleeps 4

“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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Price per night from

$98