Islamorada Rentals with Pools

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80 house rentals in Islamorada with pools

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

Islamorada apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Swimming pool

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Price per night from

$201

Newly refinished condo open water views very nice

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$230

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

Match: Swimming pool

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Price per night from

$172

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$344

“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

Match: Swimming pool

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Price per night from

$671

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!

Match: Swimming pool

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Price per night from

$254

Beautiful Captain's Cove

Islamorada villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$573

LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF

Islamorada villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$356

Luxury condo overlooking harbor with ocean view

Islamorada condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$391

Experience the Florida Keys like never before!!!

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$246

"Irish Ayes" Elegant Waterfront Home with Pool

Islamorada house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Swimming pool

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Price per night from

$802

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

Islamorada condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Swimming pool

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Price per night from

$158

Match: Swimming pool

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Price per night from

$2,128

Blue Dolphin Private Oceanfront 1.8 acre Estate on Millionaire's Row with Pool

Islamorada house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Swimming pool

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Price per night from

$1,146

Oceanfront Anglers Reef Islamorada Florida Keys

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$457

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

Islamorada townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$446

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$377

Paradise at Islamorada

Islamorada townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Swimming pool

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Price per night from

$161

Executive Bay Club- great unit, great location!,

Islamorada villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 20 minutes

Match: Swimming pool

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Price per night from

$205

Gorgeous Florida Keys Vacation Home with Beach Access in Islamorada!

Islamorada townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$602

WATERFRONT TOWNHOME IN ISLAMORADA K1

Islamorada apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$184

Match: Swimming pool

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Price per night from

$207

Townhome in Beachfront Community: Perfect for Florida Keys Vacation!

Islamorada townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Swimming pool

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Price per night from

$659

EXECUTIVE BAY ISLAMORADA BY SoFLA VACATIONS

Islamorada townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$286

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

Islamorada townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

Match: Swimming pool

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Price per night from

$602

Match: Swimming pool

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Price per night from

$819

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

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$459

Match: Swimming pool

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Price per night from

$602

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

Islamorada house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Swimming pool

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Price per night from

$784

Reel Paradise Islamorada

Lower Matecumbe Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Swimming pool

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Price per night from

$212

ISLAMORADA 3bd in WATERFRONT COMMUNITY w BEACH!!

Islamorada apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$364

Islamorada Townhome w/Beach View, Pool, Marina,Tennis! Perfect Family Getaway!!

Islamorada townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$203

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

Islamorada townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$602

2 BDR ISLAMORADA HOME in WATERFRONT - FREE DOCK!!

Islamorada studio

  • Studio
  • 2 bathrooms
  • sleeps 2

Match: Swimming pool

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Price per night from

$286

Gorgeous Vacation Home with Beach Access!

Islamorada townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Match: Swimming pool

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Price per night from

$602

Remodeled Townhome in Waterfront Community - 20% for Spring/Summer!

Islamorada house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Swimming pool

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Price per night from

$602

ISLAND DREAM

Lower Matecumbe Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Swimming pool

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Price per night from

$774

Perfect Family Getaway! Waterfront Vacation Home in Islamorada, Florida Keys!

Islamorada townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$659

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