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Matecumbe Key Rentals

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308 Houses

75130 Overseas Highway

Matecumbe Key house

2 bedrooms / 2 bathrooms / sleeps 4

“The view and location was excellent.” The house had most of the amenities I would expect at a beach location. You can't beat the sunsets over the bay! We snorkeled at Key Largo and took a day trip into key West, so the location was perfect. The area had the best restaurants. We tried them all. Only complaints were: no outdoor grill, no wine glasses, sheets kept pulling off the bed and rusted beach chairs.

Price per night from

$213

Private Beachfront Paradise

Matecumbe Key house

4 bedrooms / 3 bathrooms / sleeps 8

“Nicest rental property we have ever stayed in!!” Beautiful home on spotless white beach! Property has been updated with upscale furnishings throughout. Granite, leather furniture, redone bathrooms. Well stocked for all your vacation needs -- towels, beach chairs, beach toys, kitchen full of everything you need, 2 grills. Outside patio was amazing for our meals, sunrises and after dinner activities. The backyard was the beach filled with palm trees for natural shade. Hammock and volleyball court, beautiful pool with waterfall, tables and chairs everywhere for meals or for just relaxing. We traveled as two families and there was more than enough room for all of us. We felt right at home right away. Highly recommend this paradise!

Price per night from

$827

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

$175

75691 Overseas Highway

Matecumbe Key house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$540

BEACON REEF 406

Matecumbe Key condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$100

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 4

Price per night from

$87

Cypress House 3bed/2bath with 40ft of dockage

Matecumbe Key house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 28 minutes

Price per night from

$443

Summer Sea #420

Matecumbe Key condo

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$130

Port of Call C-2

Matecumbe Key condo

2 bedrooms / 3 bathrooms / sleeps 4

Price per night from

$295

Martin Family Fish Camp

Matecumbe Key cottage

4 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$543

194 Airstream Lane

Matecumbe Key house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$306

BEACON REEF 503

Matecumbe Key condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$143

Angler's Reef #118

Matecumbe Key house

2 bedrooms / 3 bathrooms / sleeps 4

Price per night from

$385

Palms of Islamorada #403

Matecumbe Key condo

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$133

BEACON REEF 301

Matecumbe Key condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$117

The Caribbean Resort - Hemingway House North

Matecumbe Key house

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 7 minutes

Price per night from

$587

The Caribbean Resort - Malayan Palm East

Matecumbe Key house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 7 minutes

Price per night from

$374

The Caribbean Resort - Princess Palm South

Matecumbe Key house

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 7 minutes

Price per night from

$533

The Caribbean Resort - Royal Palm South

Matecumbe Key house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 7 minutes

Price per night from

$1,598

The Caribbean Resort - Malayan Palm North

Matecumbe Key house

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 3 hours 7 minutes

Price per night from

$479

The Caribbean Resort - Hemingway House South

Matecumbe Key house

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 7 minutes

Price per night from

$587

The Caribbean Resort - Canary Island Palm South

Matecumbe Key house

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 7 minutes

Price per night from

$533

The Caribbean Resort - Jamaican Palm House

Matecumbe Key cottage

3 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 3 hours 7 minutes

Price per night from

$932

The Caribbean Resort - Fish Tail Palm

Matecumbe Key house

1 bedroom / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 7 minutes

Price per night from

$479

The Caribbean Resort - Royal Palm North

Matecumbe Key house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 7 minutes

Price per night from

$1,598

The Caribbean Resort - Canary Island Palm North

Matecumbe Key house

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 7 minutes

Price per night from

$533

Island Conch Cottage

Matecumbe Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$147

The Caribbean Resort - Harbor House

Matecumbe Key house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 7 minutes

Price per night from

$692

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

Matecumbe Key house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 7 minutes

Price per night from

$426

The Caribbean Resort - Princess Palm North

Matecumbe Key house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 7 minutes

Price per night from

$533

OCEAN HARBOUR K31

Matecumbe Key condo

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$233

Great rentals within 20 miles that match your search

WELCOME TO PARADISE! In the heart of Islamorada

Islamorada condo

1 bedroom / 1 bathroom / sleeps 5

Price per night from

$168

Premier Condo in Upper Florida Keys

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$279

Very Nice 3 Bedroom Home With Large Lot!

Tavernier house

3 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$92

MM88 Best Keys Location Tranquil Wooded

Tavernier house

1 bedroom / 2 bathrooms / sleeps 8

Price per night from

$144

Keys Kottage / Bayside

Islamorada villa

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$279

Windley Key, FL Keys

Islamorada caravan/mobile home

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$131

Viewing 38 of 308
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
Private Beachfront Paradise
PARADISE....90 minutes from home

I don`t know what place the last reviewer stayed at? It wasn`t here! This house was spectacular from the moment we arrived! The house and grounds were immaculate and clean, no odors anywhere. The kitchen, bathrooms, bedrooms, all neat and clean. From the moment we arrived, we felt right at home. The pool was great! Heated too I might add. We were here in late October, and the water was delicious! The hot tub was wonderful also. As to the beach, it was just fine. The property is located about midway between Miami and Key west, so it makes a great base to explore all the keys and south Florida. Great restaurants abound in the keys, 2 notable ones being the Green Turtle inn and Lazy days very nearby. The Owner, Lisa, was very gracious and always accessible. In closing, would i recommend this property? ABSOLUTELY! I am planning to come back later this year.see more
75130 Overseas Highway
Beautiful Sunsets in Islamorada

There is a great view from the roof top deck for sunsets. The screen porch was great at night to keep the bugs away. The beach was very nice too. The setup is good for two couples or a small family. Also the staff from Freewheeler was great in getting us moved from our original rental. … see more

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