Vacation Rentals & House Rentals in Islamorada

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ISLAND DREAM

Lower Matecumbe Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Private outdoor pool (unheated) Swimming pool

All filters match

Price per night from

$772

Match: Private outdoor pool (unheated) Swimming pool

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Price per night from

$909

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Executive Bay Club- great unit, great location!,

Islamorada villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 20 minutes

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$205

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$377

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$818

Reel Paradise Islamorada

Lower Matecumbe Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$212

2 BDR ISLAMORADA HOME in WATERFRONT - FREE DOCK!!

Islamorada studio

  • Studio
  • 2 bathrooms
  • sleeps 2

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$286

ISLAMORADA 3bd in WATERFRONT COMMUNITY w BEACH!!

Islamorada apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$363

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

Islamorada apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$201

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

Islamorada house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$783

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

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$458

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$206

WATERFRONT TOWNHOME IN ISLAMORADA K1

Islamorada apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$184

Newly refinished condo open water views very nice

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$229

"Irish Ayes" Elegant Waterfront Home with Pool

Islamorada house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$801

Experience the Florida Keys like never before!!!

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), 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: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$253

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

Islamorada townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$602

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$602

Gorgeous Vacation Home with Beach Access!

Islamorada townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

1 of 2 match: Private outdoor pool (unheated), 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: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$602

LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF

Islamorada villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$355

“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: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$669

Paradise at Islamorada

Islamorada townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$161

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

Islamorada house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$602

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

Islamorada townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$659

Townhome in Beachfront Community: Perfect for Florida Keys Vacation!

Islamorada townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$659

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

Islamorada townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$203

Gorgeous Florida Keys Vacation Home with Beach Access in Islamorada!

Islamorada townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$602

Luxury condo overlooking harbor with ocean view

Islamorada condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$390

Beautiful Captain's Cove

Islamorada villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$572

Oceanfront Anglers Reef Islamorada Florida Keys

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$457

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

Islamorada condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$158

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$343

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: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$1,144

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$2,124

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$1,470

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

1 of 2 match: Private outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$229

Viewing 38 of 44
rentals in Islamorada

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