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51 house rentals

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Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

2 bedrooms
3 bathrooms

sleeps 6

Match: Safe Swimming pool

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Price per night from

$344

Lazy Daze Beach House 5 Star Modern Oceanfront Islamorada Townhome on the Beach!

Islamorada townhouse

2 bedrooms
3 bathrooms

sleeps 6

Match: Safe Swimming pool

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Price per night from

$446

Paradise at Islamorada

Islamorada townhouse

2 bedrooms
2 bathrooms

sleeps 8

Match: Safe Swimming pool

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Price per night from

$161

EXECUTIVE BAY ISLAMORADA BY SoFLA VACATIONS

Islamorada townhouse

2 bedrooms
2 bathrooms

sleeps 6

Match: Safe Swimming pool

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Price per night from

$286

Executive Bay Club- great unit, great location!,

Islamorada villa

2 bedrooms
2 bathrooms

sleeps 4

Responds fast! avg. 20 minutes

1 of 2 match: Safe, Swimming pool

1 of 2 filters match

Price per night from

$205

Bay and Beach Beauty

Islamorada house

3 bedrooms
2 bathrooms

sleeps 8

Responds fast! avg. 2 hours 10 minutes

1 of 2 match: Swimming pool, Safe

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Price per night from

$532

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

2 bedrooms
3 bathrooms

sleeps 6

1 of 2 match: Safe, Swimming pool

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Price per night from

$377

ISLAMORADA 3bd in WATERFRONT COMMUNITY w BEACH!!

Islamorada apartment

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Safe, Swimming pool

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Price per night from

$363

2 BDR ISLAMORADA HOME in WATERFRONT - FREE DOCK!!

Islamorada studio

Studio
2 bathrooms

sleeps 2

1 of 2 match: Safe, Swimming pool

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Price per night from

$286

Bayview house with bayviews. Pool with Spa, dock center of town great fishing !!

Islamorada house

2 bedrooms
1 bathroom

sleeps 6

1 of 2 match: Safe, Swimming pool

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Price per night from

$819

Reel Paradise Islamorada

Lower Matecumbe Key condo

1 bedroom
1 bathroom

sleeps 4

1 of 2 match: Safe, Swimming pool

1 of 2 filters match

Price per night from

$212

ISLAND DREAM

Lower Matecumbe Key house

4 bedrooms
3 bathrooms

sleeps 8

1 of 2 match: Safe, Swimming pool

1 of 2 filters match

Price per night from

$773

Come relax in Islamorada, the tropical jewel of the Florida Keys!!

Islamorada apartment

1 bedroom
1 bathroom

sleeps 4

1 of 2 match: Safe, Swimming pool

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Price per night from

$201

WATERFRONT TOWNHOME IN ISLAMORADA K1

Islamorada apartment

3 bedrooms
3 bathrooms

sleeps 6

1 of 2 match: Safe, Swimming pool

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Price per night from

$184

Islamorada trop paradise pool, fishing, 2fls luxury with a filet stationn

Islamorada house

4 bedrooms
2 bathrooms

sleeps 8

1 of 2 match: Safe, Swimming pool

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Price per night from

$784

New Upscale, private pool, Dockage, kayaks, bikes, downtown Islamorada locale

Islamorada house

3 bedrooms
4 bathrooms

sleeps 6

1 of 2 match: Safe, Swimming pool

1 of 2 filters match

Price per night from

$911

New Listing! Charming Angler's Reef Home with Pool, Dockage

Islamorada house

2 bedrooms
3 bathrooms

sleeps 6

1 of 2 match: Safe, Swimming pool

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Price per night from

$458

Islamorada Escape - Executive Bay w/Pool, Fishing Dock, Beach, Tennis/Pickleball

Islamorada house

3 bedrooms
2 bathrooms

sleeps 8

1 of 2 match: Safe, Swimming pool

1 of 2 filters match

Price per night from

$206

Newly refinished condo open water views very nice

Islamorada condo

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Safe, Swimming pool

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Price per night from

$229

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 52 minutes

1 of 2 match: Swimming pool, Safe

1 of 2 filters match

Price per night from

$982

Oceanfront 2/2 Condo in Beacon Reef - Free boat dock

Islamorada condo

2 bedrooms
2 bathrooms

sleeps 4

1 of 2 match: Swimming pool, Safe

1 of 2 filters match

Price per night from

$1,489

Cozy Keys Cottage Islamorada FL.

Islamorada house

3 bedrooms
3 bathrooms

sleeps 6

Responds fast! avg. 2 hours 10 minutes

1 of 2 match: Swimming pool, Safe

1 of 2 filters match

Price per night from

$408

Boater's Paradise

Lower Matecumbe Key house

4 bedrooms
3 bathrooms

sleeps 10

1 of 2 match: Swimming pool, Safe

1 of 2 filters match

Price per night from

$377

"Irish Ayes" Elegant Waterfront Home with Pool

Islamorada house

4 bedrooms
4 bathrooms

sleeps 10

1 of 2 match: Safe, Swimming pool

1 of 2 filters match

Price per night from

$802

Experience the Florida Keys like never before!!!

Islamorada condo

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Safe, Swimming pool

1 of 2 filters match

Price per night from

$245

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!

1 of 2 match: Safe, Swimming pool

1 of 2 filters match

Price per night from

$253

Gorgeous Vacation Home with Beach Access!

Islamorada townhouse

3 bedrooms
2 bathrooms

sleeps 7

1 of 2 match: Safe, Swimming pool

1 of 2 filters match

Price per night from

$602

Vacation in Tropical Paradise with the Family! Waterfront Townhome in Islamorada

Islamorada townhouse

2 bedrooms
3 bathrooms

sleeps 5

1 of 2 match: Safe, Swimming pool

1 of 2 filters match

Price per night from

$602

Beautiful Waterfront Townhome in Islamorada! Perfect for Florida Keys Vacation!

Islamorada house

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Safe, Swimming pool

1 of 2 filters match

Price per night from

$602

Islamorada Waterfront Townhome w Priv. Beach! Comfortable Family Vacation Rental

Islamorada townhouse

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Safe, Swimming pool

1 of 2 filters match

Price per night from

$602

Venetian Tropics 3 bedroom pool home on sailboat canal weekly vacation rental

Islamorada house

3 bedrooms
3 bathrooms

sleeps 8

“Comfortable home for family get-together” Positive experience overall: Our family of six adults had a tropical-feeling destination Christmas here. The house easily accommodated all of us, and we enjoyed the wrap-around porch and pool. We appreciated the commodious kitchen with a two-tier dishwasher and side-by-side refrigerator with ice/water dispenser. Having a washer and dryer on the premises was very helpful, since guests are requested to wash linens and towels before departing. Some drawbacks: the house did not come equipped with adequate staples, such as paper products, laundry detergent, and garbage bags, so be prepared to purchase these. There are no beaches or stores within walking distance. On a couple of nights, noisy neighbors talking on the street woke us up. (In general, though, the area is quiet.)

Responds fast! avg. 1 hour 0 minutes

1 of 2 match: Safe, Swimming pool

1 of 2 filters match

Price per night from

$670