Matecumbe Key Rentals

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165 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

$173

The Caribbean Resort - Royal Palm North

Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 45 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. 1 hour 45 minutes

Price per night from

$745

The Caribbean Resort - Canary Island Palm North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 45 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 45 minutes

Price per night from

$487

Island Conch Cottage

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$156

The Caribbean Resort - Harbor House

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 45 minutes

Price per night from

$916

The Caribbean Resort - Princess Palm South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 45 minutes

Price per night from

$745

The Caribbean Resort - Royal Palm South

Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 45 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. 1 hour 45 minutes

Price per night from

$687

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

Matecumbe Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 45 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 45 minutes

Price per night from

$745

The Caribbean Resort - Canary Island Palm South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 45 minutes

Price per night from

$745

The Caribbean Resort - Jamaican Palm House

Matecumbe Key cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Responds fast! avg. 1 hour 45 minutes

Price per night from

$1,145

The Caribbean Resort - Fish Tail Palm

Matecumbe Key house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 45 minutes

Price per night from

$630

The Caribbean Resort - Princess Palm North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 45 minutes

Price per night from

$745

Great rentals within 20 miles that match your search

Gorgeous waterfront home

Islamorada house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$460

Motel Room #1, Private Entrance, Beach and Marina

Key Largo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 37 minutes

Price per night from

$213

Diving, Fishing, Snorkeling, Kayaking Paradise

Key Largo townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 20 minutes

Price per night from

$403

Luxury condo overlooking harbor with ocean view

Islamorada condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$392

Executive Bay Club- great unit, great location!,

Islamorada villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 20 minutes

Price per night from

$206

"Irish Ayes" Elegant Waterfront Home with Pool

Islamorada house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$805

Very Nice 3 Bedroom Home With Large Lot!

Tavernier house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$81

Keys Kottage

Islamorada villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$317

Islamorada cottage on deep water canal

Islamorada house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$288

Beautiful Captain's Cove

Islamorada villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$575

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$379

Sunrise Waterfront Home

Key Largo house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$489

Islamorada Waterfront Paradise 2

Islamorada house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$518

AZALEA WARTERFRONT

Islamorada house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Price per night from

$391

Oceanfront Anglers Reef Islamorada Florida Keys

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$459

Waterfront Key Largo Bayside Cottage Paradise

Key Largo cottage

  • 1 bedroom
  • 2 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. 56 minutes

Price per night from

$253

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

$159

Newly refinished condo open water views very nice

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$230

Cozy Couple Getaway! or Great Family Home

Key Largo house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$144

Unique Houseboat on Dry Lot

Key Largo houseboat

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Quaint and unique rental” The houseboat was everything I expected and needed it to be. It slept our family of four comfortably - which was all we really needed. The weather was good so really the only thing we did at the houseboat was shower and sleep. We did also do a few loads of wash - having a full size washer and dryer was convenient. I bet if we spent more time there, we would have used the back yard, it is really neat and welcoming. Maggie was a gracious hostess and everything was exactly where and how she described it. All in all a great value.

Price per night from

$98

Spacious 1 Bedroom Duplex, Full Kitchen, Beach and Marina

Key Largo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 37 minutes

Price per night from

$282

Viewing 38 of 165
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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