Vacation Rentals & House Rentals in Islamorada

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

Islamorada townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated) Swimming pool

All 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

Match: Shared outdoor pool (unheated) Swimming pool

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Price per night from

$601

WATERFRONT TOWNHOME IN ISLAMORADA K1

Islamorada apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated) Swimming pool

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Price per night from

$184

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

Islamorada townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated) Swimming pool

All filters match

Price per night from

$601

2 BDR ISLAMORADA HOME in WATERFRONT - FREE DOCK!!

Islamorada studio

  • Studio
  • 2 bathrooms
  • sleeps 2

Match: Shared outdoor pool (unheated) Swimming pool

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Price per night from

$285

Townhome in Beachfront Community: Perfect for Florida Keys Vacation!

Islamorada townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Shared outdoor pool (unheated) Swimming pool

All filters match

Price per night from

$658

EXECUTIVE BAY ISLAMORADA BY SoFLA VACATIONS

Islamorada townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated) Swimming pool

All filters match

Price per night from

$285

Gorgeous Vacation Home with Beach Access!

Islamorada townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Match: Shared outdoor pool (unheated) Swimming pool

All filters match

Price per night from

$601

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

Islamorada house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Shared outdoor pool (unheated) Swimming pool

All filters match

Price per night from

$601

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

Islamorada townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

Match: Shared outdoor pool (unheated) Swimming pool

All filters match

Price per night from

$601

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

Islamorada townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated) Swimming pool

All filters match

Price per night from

$658

Match: Shared outdoor pool (unheated) Swimming pool

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Price per night from

$601

Reel Paradise Islamorada

Lower Matecumbe Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared outdoor pool (unheated) Swimming pool

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Price per night from

$213

ISLAMORADA 3bd in WATERFRONT COMMUNITY w BEACH!!

Islamorada apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated) Swimming pool

All filters match

Price per night from

$363

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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: Shared outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$206

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

1 of 2 filters match

Price per night from

$821

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$378

ISLAND DREAM

Lower Matecumbe Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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

1 of 2 filters match

Price per night from

$775

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

Islamorada apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

1 of 2 filters match

Price per night from

$785

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

1 of 2 filters match

Price per night from

$912

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

1 of 2 filters match

Price per night from

$207

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

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$459

Newly refinished condo open water views very nice

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$230

"Irish Ayes" Elegant Waterfront Home with Pool

Islamorada house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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

1 of 2 filters match

Price per night from

$803

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: Shared outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$254

Experience the Florida Keys like never before!!!

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$246

“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: Shared outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$671

LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF

Islamorada villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$356

Paradise at Islamorada

Islamorada townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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

1 of 2 filters match

Price per night from

$161

Beautiful Captain's Cove

Islamorada villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$574

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$345

Oceanfront Anglers Reef Islamorada Florida Keys

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$458

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

Islamorada condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

1 of 2 filters match

Price per night from

$159

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

1 of 2 filters match

Price per night from

$2,131

Majestic estate, 200' of private oceanfront beach & pool, 3,600sqft tiki

Islamorada house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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

1 of 2 filters match

Price per night from

$1,474

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: Shared outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$1,148

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: Shared outdoor pool (unheated), Swimming pool

1 of 2 filters match

Price per night from

$172

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rentals in Islamorada

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