Long Key Rentals

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168 Houses

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Welcome to Paradise

Long Key townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

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Price per night from

$205

Luxury beachfront home with pool in Islamorada

Layton house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 30 minutes

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Price per night from

$589

Responds fast! avg. 2 hours 34 minutes

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Price per night from

$172

Great rentals within 20 miles that match your search

Beachfront Islamorada Villa with Dockage and Bay Views

Lower Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$347

Harbor Hideaway 4 Bedrooms-3 Bathrooms Waterfront- Indoor Pool

Marathon Shores house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$741

Reel Paradise Islamorada

Lower Matecumbe Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$212

Key Colony Beach Oasis

Key Colony Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$1,142

Oceanside waterfront 2/2 home with 55ft dock and paddle equipment

Marathon Shores house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$286

The Mini Coconut

Marathon Shores house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 1 hour 48 minutes

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Price per night from

$257

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

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$457

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Price per night from

$206

Hammerhead Hideaway- 2 Bed 2Bath Canal Front Home w/Cabana Club!

Key Colony Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$343

Key Colony Beach-2 Bed 2 Bath Canal Front Home with Cabana Club!

Key Colony Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$308

Oasis Canal-Front Home: Pool, 30ft Dock, BBQ, and more!

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$516

Pet Friendly Half-Duplex, Cottage with 40' Slip Option at The Boat House Marina

Marathon Shores cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$195

Boater's Paradise

Lower Matecumbe Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$377

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Price per night from

$820

Thirty Three by The Sea - Vacation Rental Key Colony Beach, FL

Key Colony Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$344

Villa Bella 3/3 with Private Pool and Dock

Key Colony Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

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Price per night from

$413

Immaculate Waterfront ~ 2 BR ~ Private Pool, Tiki on Canal! 2 Min Walk to Beach!

Key Colony Beach house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$343

Gorgeous Vacation Home with Beach Access!

Islamorada townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$602

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

Islamorada townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

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Price per night from

$602

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

Islamorada townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$659

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

Islamorada house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$602

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

Islamorada townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$602

Gorgeous Florida Keys Vacation Home with Beach Access in Islamorada!

Islamorada townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$602

Townhome in Beachfront Community: Perfect for Florida Keys Vacation!

Islamorada townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

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Price per night from

$659

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

Islamorada townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$203

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Price per night from

$602

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$377

Outstanding Oceanfront Condo on the Beach!!

Marathon condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$343

Unit 8b, small efficiency located 50 yards from Ocean

Marathon studio

  • Studio
  • 1 bathroom
  • sleeps 2

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Price per night from

$206

8c, Efficiency located 50 yards from Ocean

Marathon studio

  • Studio
  • 1 bathroom
  • sleeps 2

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Price per night from

$229

Gorgeous waterfront home

Islamorada house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$458

Manatee Bay

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$261

Luxury condo overlooking harbor with ocean view

Islamorada condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$391

Executive Bay Club- great unit, great location!,

Islamorada villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 20 minutes

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Price per night from

$205

"Irish Ayes" Elegant Waterfront Home with Pool

Islamorada house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$802

Viewing 38 of 168
rentals in Long Key

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