Matecumbe Key Rentals

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166 Houses

ISLAMORADA WATERFRONT PARADISE with FREE DOCKAGE

Matecumbe Key studio

  • Studio
  • 1 bathroom
  • sleeps 2

“Relaxing Weekend Getaway” We love this home! It is on a private dead-end street, and everything is just perfect. Kept the boat right at the dock, fished right there at night, took some nice boat rides through the back country, and relaxed in paradise. Wifi is good and fast (I had to do some work while we were there), and we can't wait to go back.

Price per night from

$172

The Caribbean Resort - Royal Palm North

Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 31 minutes

Price per night from

$1,432

The Caribbean Resort - Hemingway House North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 31 minutes

Price per night from

$630

The Caribbean Resort - Canary Island Palm North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 31 minutes

Price per night from

$745

The Caribbean Resort - Malayan Palm East

Matecumbe Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 31 minutes

Price per night from

$401

Island Conch Cottage

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$155

The Caribbean Resort - Princess Palm South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 31 minutes

Price per night from

$630

The Caribbean Resort - Harbor House

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 31 minutes

Price per night from

$859

The Caribbean Resort - Royal Palm South

Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 31 minutes

Price per night from

$1,432

The Caribbean Resort - Malayan Palm North

Matecumbe Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 1 hour 31 minutes

Price per night from

$630

The Caribbean Resort - Bird of Paradise - One Bedroom One Bath

Matecumbe Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 31 minutes

Price per night from

$573

The Caribbean Resort - Hemingway House South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 31 minutes

Price per night from

$630

The Caribbean Resort - Canary Island Palm South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 31 minutes

Price per night from

$630

The Caribbean Resort - Jamaican Palm House

Matecumbe Key cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Responds fast! avg. 1 hour 31 minutes

Price per night from

$1,088

The Caribbean Resort - Fish Tail Palm

Matecumbe Key house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 31 minutes

Price per night from

$573

The Caribbean Resort - Princess Palm North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 31 minutes

Price per night from

$630

Great rentals within 20 miles that match your search

Responds fast! avg. 3 hours 34 minutes

Price per night from

$1,607

Price per night from

$373

Fabulous " Sea Breeze 41 ", 3 / 2 Condo located Oceanside in Islamorada

Islamorada apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$192

Luxurious Oceanfront Condo

Tavernier apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$299

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

Islamorada house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$1,475

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

Islamorada house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$785

Coastal Key Largo Townhome with Ocean Views, Pool & Dock

Key Largo townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$391

Reel Paradise Islamorada

Lower Matecumbe Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$213

Modern house in the heart of Key Largo

Key Largo house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$345

Luxury 3-Bedroom Home with Resort Privileges

Key Largo house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Price per night from

$1,549

Luxury 4-Bedroom Home with Resort Privileges

Tavernier villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 9

Price per night from

$1,664

Price per night from

$150

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

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$459

Price per night from

$207

Paradise in Key largo

Key Largo house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$287

The Mermaid House

Key Largo house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 2 minutes

Price per night from

$342

Private and comfortable four bedrooms, three bath, private oasis

Key Largo house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$322

Ocean view condo with balcony

Tavernier condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$316

Beautiful condo with ocean view(distant)

Tavernier condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$259

Tranquil Oceanview Penthouse Paradise

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$373

The Nest Villa and Marina at Holiday House Resort, Islamorada

Upper Matecumbe Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$343

Beachfront Islamorada Villa with Dockage and Bay Views

Lower Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$349

Viewing 38 of 166
rentals in Matecumbe Key

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Top Destination reviews

ISLAMORADA WATERFRONT PARADISE with FREE DOCKAGE
Quick Getaway

I only stayed one night, but wanted to stay much longer! The room was beautiful, clean and well stocked. The dock was peaceful and a perfect place to relax. The owner was friendly and accomodating, and very quick to respond to my inquiries. Would definitely return! Highly recommend! … see more

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