Vacation Rentals & House Rentals in Key Largo

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

Islamorada apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Private outdoor pool (heated) Swimming pool

All filters match

Price per night from

$201

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: Private outdoor pool (heated) 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: Private outdoor pool (heated) Swimming pool

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Price per night from

$344

Beautiful Captain's Cove

Islamorada villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Private outdoor pool (heated) Swimming pool

All filters match

Price per night from

$574

"Irish Ayes" Elegant Waterfront Home with Pool

Islamorada house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Private outdoor pool (heated) Swimming pool

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Price per night from

$803

Match: Private outdoor pool (heated) Swimming pool

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Price per night from

$2,130

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

Islamorada house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Private outdoor pool (heated) Swimming pool

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Price per night from

$1,147

Match: Private outdoor pool (heated) Swimming pool

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Price per night from

$912

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

Islamorada house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Private outdoor pool (heated) Swimming pool

All filters match

Price per night from

$1,474

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

Islamorada house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Private outdoor pool (heated) Swimming pool

All filters match

Price per night from

$785

These homes match some but not all of your filters. Clear all filters

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 (heated), Swimming pool

1 of 2 filters match

Price per night from

$206

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$378

Kawama Tower Unit 512

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$339

Luxurious Oceanfront Condo

Tavernier apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$299

Luxury 4-Bedroom Home with Resort Privileges

Tavernier villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 9

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

1 of 2 filters match

Price per night from

$1,663

Reel Paradise Islamorada

Lower Matecumbe Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

1 of 2 filters match

Price per night from

$213

Beautiful condo with ocean view(distant)

Tavernier condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

1 of 2 filters match

Price per night from

$258

The Mermaid House

Key Largo house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 2 minutes

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

1 of 2 filters match

Price per night from

$342

Tranquil Oceanview Penthouse Paradise

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$373

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

1 of 2 filters match

Price per night from

$820

ISLAMORADA 3bd in WATERFRONT COMMUNITY w BEACH!!

Islamorada apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$364

BEAUTIFUL YATCH IN THE KEYS ONCE IN A LIFETIME EXPERIENCE

Tavernier boathouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

1 of 2 filters match

Price per night from

$253

2 BDR ISLAMORADA HOME in WATERFRONT - FREE DOCK!!

Islamorada studio

  • Studio
  • 2 bathrooms
  • sleeps 2

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

1 of 2 filters match

Price per night from

$286

ISLAND DREAM

Lower Matecumbe Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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

1 of 2 filters match

Price per night from

$774

FALL IN LOVE with your home away from home!

Tavernier house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$207

Paridise Found

Tavernier house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 13

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

1 of 2 filters match

Price per night from

$764

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 (heated), Swimming pool

1 of 2 filters match

Price per night from

$459

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

1 of 2 filters match

Price per night from

$207

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

1 of 2 filters match

Price per night from

$373

WATERFRONT TOWNHOME IN ISLAMORADA K1

Islamorada apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$230

Luxury 3-Bedroom Home with Resort Privileges

Key Largo house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

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

1 of 2 filters match

Price per night from

$1,548

Islamorada Waterfront Paradise | 5br | Dock | Pool

Tavernier house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

Responds fast! avg. 3 hours 58 minutes

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

1 of 2 filters match

Price per night from

$344

Luxury beachfront home with pool in Islamorada

Layton house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 30 minutes

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

1 of 2 filters match

Price per night from

$589

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 (heated), Swimming pool

1 of 2 filters match

Price per night from

$254

Rent a Piece of Paradise in Key Largo

Key Largo caravan/mobile home

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

1 of 2 filters match

Price per night from

$229

Gorgeous Vacation Home with Beach Access!

Islamorada townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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

1 of 2 filters match

Price per night from

$602

BEACHFRONT PARADISE

Sunset Point house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

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

1 of 2 filters match

Price per night from

$2,519

Viewing 38 of 79
rentals in Key Largo

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