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Matecumbe Key Rentals

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235 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 4

Price per night from

$113

Martin Family Fish Camp

Matecumbe Key cottage

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$543

BEACON REEF 503

Matecumbe Key condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$143

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 20 minutes

Price per night from

$1,598

The Caribbean Resort - Hemingway House North

Matecumbe Key house

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 20 minutes

Price per night from

$587

The Caribbean Resort - Canary Island Palm North

Matecumbe Key house

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 20 minutes

Price per night from

$533

The Caribbean Resort - Malayan Palm East

Matecumbe Key house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 20 minutes

Price per night from

$374

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 20 minutes

Price per night from

$533

The Caribbean Resort - Harbor House

Matecumbe Key house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 20 minutes

Price per night from

$692

The Caribbean Resort - Royal Palm South

Matecumbe Key house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 20 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 20 minutes

Price per night from

$479

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

Matecumbe Key house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 20 minutes

Price per night from

$426

The Caribbean Resort - Hemingway House South

Matecumbe Key house

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 20 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 20 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 20 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 20 minutes

Price per night from

$479

The Caribbean Resort - Princess Palm North

Matecumbe Key house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 20 minutes

Price per night from

$533

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

Tropical Island Getaway-Keys

Key Largo condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$272

Waterfront in Key Largo, Terrific 1/1 Apt, 2nd Floor, Pet Friendly, Sleeps 4

Key Largo apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 5 minutes

Price per night from

$92

Islamorada Waterfront Paradise Getaway!

Islamorada house

1 bedroom / 1 bathroom / sleeps 2

“AMAZING!!!!!!!” Ewa and Peter were incredible hosts at this beautiful property. We felt right at home immediately and had so many activities to do plus Ewa and Peter had loads of great tips when we asked. The studio was so well stocked with all the essentials and then even the ones you forgot! It was wonderful to see a manatee swim up past the dock our first morning there. A very magical spot with generous hosts. It had everything we wanted and then some. After a week there and driving around the whole Keys it was 100% the most perfect choice for us. I miss those hammocks!

Price per night from

$258

Waterfront Home In Florida Keys

Tavernier house

2 bedrooms / 2 bathrooms / sleeps 4

“Perfect Holiday in Tavernier” We had a wonderful time at Dan and Penny's home. They were very accommodating! The home is absolutely pristine and in a nice neighborhood. There wasn't a day that we did not see manatee and tarpon in the canal in front of the house. Perfect location for restaurants, shopping and activities either by land or water. Beautiful home with everything you need for a perfect vacation in the Keys!

Price per night from

$192

Beautiful Private Home with Beach Access

Key Largo house

2 bedrooms / 1 bathroom / sleeps 6

“Great place for a family” Wonderful place to stay! My family of 5 enjoyed the clean rooms and full kitchen. Easy access to private beach, restaurants, grocery store. Very safe neighborhood. The house was fully provided for our stay, Great access to John Pennycamp and the Everglades. We would definitely stay here again. Daniel A. was very easy to work with. We enjoyed coming home after a busy day of snorkeling to make supper and lounge on our own deck or wander down to the private beach to enjoy the evening. Having this home made our vacation very relaxing and enjoyable.

Price per night from

$77

Clean Keys 3/3 w/Davits Clear Canal Bay Side/Views Fenced 2Level Tavernier Home

Tavernier house

3 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 2 hours 55 minutes

Price per night from

$206

OCEANFRONT CONDO WITH ALL AMMENITIES!

Tavernier apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Great place for a comfortable vacation” We had a wonderful time at this Ocean Pointe condo. The facilities are fantastic. The pool is very clean. The condo was like new. The complex is staffed 24/7. We felt very safe and comfortable. The ocean side view is great. We would not hesitate to return another time.

Responds fast! avg. 1 hour 35 minutes

Price per night from

$281

Key Largo 2/2 Tropical Daze Oceanfront Condo

Key Largo apartment

2 bedrooms / 2 bathrooms / sleeps 4

“Couldn't be better!!!” If you are looking to rest and relax, look no further.

Responds fast! avg. 10 minutes

Price per night from

$331

Buttonwood Bay Key Largo Waterfront Townhouse

Key Largo apartment

2 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 58 minutes

Price per night from

$177

BAYSIDE CONDO WITH BOAT

Key Largo apartment

1 bedroom / 1 bathroom / sleeps 4

“Very friendly and relaxing atmosphere!” My wife and I were really pleased with our trip. So relaxing and everyone in the area were so friendly and helpful. Thank you Jay, Sander and the crew at Sail Fish Scuba. Love having the boat to go and explore the area. Will definitely do it again!

Price per night from

$373

'SANDY BEACH' Key Largo,Fl. Luxury Vacation Rental

Key Largo house

3 bedrooms / 3 bathrooms / sleeps 10

“Amazing Place! Must See.” We had an amazing week at this Home. Very comfy, with outstanding beach and views. Close to Miami and close to paradise. I would recommend this house to any family, couple or friends who wish to get away and relax at their own private sandy beach. I would come back any time!!! Excellent deal!!

Price per night from

$2,061

Florida Keys Splendor at Hammer Point

Tavernier house

2 bedrooms / 2 bathrooms / sleeps 4

“Winter Paradise!” My wife and I stayed at this great place in January 2014 and it was wonderful. It was very clean and well maintained. The canal was great to watch the fish jump and we saw Manatees almost every day. We especially liked the kayak and did a lot of site seeing from the ocean side. Migdy was great to work with and very accommodating. We would highly recommend this place to anyone.

Responds fast! avg. 3 hours 23 minutes

Price per night from

$138

Oceanfrontparadise: 209

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$287

SANCTUARY IN PARADISE

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 10

“What Florida dreams are made of” Growing up in South Florida and the Keys but now moved farm away, I wanted to show my husband and young children the Florida I remembered as a child. This my friends was more than my dreams could have asked for! We were tremendously blessed to have had the opportunity to share this paradise! Private, gated estate with coral wooded hammocks to stroll through, palm trees clicking in the breeze, flocks of ibis that grazed through the lush green yard that ended at the private water front. Orchids blooming in the trees welcomed us to the hammocks where we had our morning coffee to stunning colored sunrises. It had everything: super clean Keys styled house with a cute kitchen (that saved us on meal expenses), bedrooms and bathrooms that were perfect size and accommodations, and wifi. It was quiet yet welcoming to my kids. We kayaked and swam on Christmas morning! The hosts were gracious and really made us feel as we were family. It was a Christmas we will always cherish. "Give and it will be given to you. A good measure, pressed down, shaken together and running over, will be poured into your lap." Luke 6:38 Truly, after giving us the chance to come share your slice of heaven, our cup runneth over.

Responds fast! avg. 2 hours 51 minutes

Price per night from

$982

Bayside Condo, marina, pool and beach

Islamorada condo

3 bedrooms / 2 bathrooms / sleeps 6

“The Best Keys Location” My family stayed at this lovely Futura Yacht Club Condo for three weeks this July. We have stayed at many other units in this complex over the years but this unit was one of the nicest we have seen. The unit has been remodeled and it has everything you would need for a great Keys vacation. Futura Yacht club has a big heated pool, tennis courts and if you are a boater a great marina with its own boat ramp which made it easy for us to enjoy our boat and jet ski's. It is a gated complex with security, centrally located to all the activities & restaurants in the area. We found the owner most helpful, accommodating and easy to deal with. We are looking forward to our next stay!!

Price per night from

$164

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rentals in Matecumbe Key

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Top Destination reviews

75130 Overseas Highway
Amazing views of the Gulf

Loved the split bedroom plan and the open common area. Older home and stairs difficult to navigate at times. So quiet and peaceful when construction not going on next door. Loved the private beach. Outdoor chairs could be updated. … see more
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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