Matecumbe Key Rentals

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200 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

BEACON REEF 406

Matecumbe Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$120

BEACON REEF 522

Matecumbe Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$155

PALMS 313

Matecumbe Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$113

Martin Family Fish Camp

Matecumbe Key cottage

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$542

BEACON REEF 503

Matecumbe Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$150

BEACON REEF 301

Matecumbe Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$133

The Caribbean Resort - Royal Palm North

Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 57 minutes

Price per night from

$1,775

The Caribbean Resort - Hemingway House North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 57 minutes

Price per night from

$719

The Caribbean Resort - Canary Island Palm North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 57 minutes

Price per night from

$719

The Caribbean Resort - Malayan Palm East

Matecumbe Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 57 minutes

Price per night from

$481

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. 3 hours 57 minutes

Price per night from

$719

The Caribbean Resort - Harbor House

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 57 minutes

Price per night from

$914

The Caribbean Resort - Royal Palm South

Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 57 minutes

Price per night from

$1,775

The Caribbean Resort - Malayan Palm North

Matecumbe Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 3 hours 57 minutes

Price per night from

$684

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

Matecumbe Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 57 minutes

Price per night from

$514

The Caribbean Resort - Canary Island Palm South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 57 minutes

Price per night from

$743

The Caribbean Resort - Hemingway House South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 57 minutes

Price per night from

$719

The Caribbean Resort - Jamaican Palm House

Matecumbe Key cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Responds fast! avg. 3 hours 57 minutes

Price per night from

$1,143

The Caribbean Resort - Fish Tail Palm

Matecumbe Key house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 57 minutes

Price per night from

$600

The Caribbean Resort - Princess Palm North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 57 minutes

Price per night from

$745

OCEAN HARBOUR K31

Matecumbe Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$300

Great rentals within 20 miles that match your search

1 / 1 Apartment Key Largo in Pennekamp

Key Largo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$103

Sunrise Waterfront Home

Key Largo house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$486

Islamorada Waterfront Paradise 2

Islamorada house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$514

Key Largo Kampground Vacation

Key Largo house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

“Great location and pleasantly surprised!” Romberto's Camprground vacation was definitely more than i expected. There was ample room for my husband and I, the folks were nice and the area was quiet and clean. The marina was convenient (small boats only). There was a small leak in the bathroom in the overhead skylight but it was almost negligible unless it was pouring. we will definitely be back.

Price per night from

$143

AZALEA WARTERFRONT

Islamorada house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Price per night from

$389

PALMS 309

Islamorada house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$113

Oceanfront Anglers Reef Islamorada Florida Keys

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$456

Waterfront Key Largo Bayside Cottage Paradise

Key Largo cottage

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 4

“Hidden Treasure” This cottage is one of our favorite place to stay. Clean, well equipped, private, and so relaxing. A great place to spend a relaxing vacation. We love the outdoor kitchen and sitting area.

Responds fast! avg. 2 hours 10 minutes

Price per night from

$252

Windley Key, FL Keys

Islamorada caravan/mobile home

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$115

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

Islamorada condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$158

MANATEE MANOR

Islamorada house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$248

LYONS LANDING

Islamorada house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$292

Responds fast! avg. 1 hour 46 minutes

Price per night from

$320

Newly refinished condo open water views very nice

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 5 minutes

Price per night from

$229

Cozy Couple Getaway! or Great Family Home

Key Largo house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$143

Viewing 38 of 200
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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