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Matecumbe Key Rentals

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226 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

$171

BEACON REEF 406

Matecumbe Key condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$121

BEACON REEF 522

Matecumbe Key condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$156

PALMS 313

Matecumbe Key condo

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$114

Martin Family Fish Camp

Matecumbe Key cottage

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$547

BEACON REEF 503

Matecumbe Key condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$151

BEACON REEF 301

Matecumbe Key condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$134

The Caribbean Resort - Royal Palm North

Matecumbe Key house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$1,384

The Caribbean Resort - Hemingway House North

Matecumbe Key house

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$577

The Caribbean Resort - Canary Island Palm North

Matecumbe Key house

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$577

The Caribbean Resort - Malayan Palm East

Matecumbe Key house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$404

Island Conch Cottage

Matecumbe Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$154

The Caribbean Resort - Princess Palm South

Matecumbe Key house

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$577

The Caribbean Resort - Harbor House

Matecumbe Key house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$750

The Caribbean Resort - Royal Palm South

Matecumbe Key house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$1,384

The Caribbean Resort - Malayan Palm North

Matecumbe Key house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$490

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

Matecumbe Key house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$404

The Caribbean Resort - Hemingway House South

Matecumbe Key house

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$577

The Caribbean Resort - Canary Island Palm South

Matecumbe Key house

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$577

The Caribbean Resort - Jamaican Palm House

Matecumbe Key cottage

3 bedrooms / 2 bathrooms / sleeps 9

Price per night from

$980

The Caribbean Resort - Fish Tail Palm

Matecumbe Key house

1 bedroom / 2 bathrooms / sleeps 4

Price per night from

$462

The Caribbean Resort - Princess Palm North

Matecumbe Key house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$577

OCEAN HARBOUR K31

Matecumbe Key condo

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$302

Great rentals within 20 miles that match your search

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 6 minutes

Price per night from

$125

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

$568

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

$190

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

$67

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

Tavernier house

3 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$245

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. 54 minutes

Price per night from

$273

Private Beachfront -Perfect for Families and Events Historic Shadow Point Estate

Key Largo house

6 bedrooms / 5 bathrooms / sleeps 16

“Fantasic wedding on paradise!!” We picked Shadow Point because of it's fabulous secluded view and beautiful gardens on 2.5 acres. The house and cottage held up to 16 of us and was wonderfully decorated with period antiques. Our guests loved playing at their beach and kayaking and swimming around Key LargoSound. Our wedding was perfect with the full moon rising over our reception. We danced the night away in paradise.

Price per night from

$2,045

Buttonwood Bay Key Largo Waterfront Townhouse

Key Largo apartment

2 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 15 minutes

Price per night from

$199

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.

Price per night from

$137

Oceanfrontparadise: 209

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$284

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. 3 hours 28 minutes

Price per night from

$974

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!!

Responds fast! avg. 2 hours 24 minutes

Price per night from

$251

LICENSED MANAGER - MODERN 4/3.5 VILLA - AREA'S MOST LUXURIOUS OCEANFRONT RESORT

Key Largo villa

4 bedrooms / 4 bathrooms / sleeps 10

“The most relax g vacation..Awesome” We stayed at Mariners Run Key Largo.the place was beautiful,clean, state of the art appliances.there was nothing Fernanado didn't think us. my entire family raved about the rental.the pool was beautiful .we had two adjoining townhouses so it work put perfect ,more than enough room.

Price per night from

$512

Bayside Retreat. Pool, Boat and Beach

Key Largo house

5 bedrooms / 4 bathrooms / sleeps 10

“SPLENDID VACATION” I had the opportunity to stay here with my family in March. The house was spacious and the beach and pool were exactly what we wanted for a private family vacation. The house manager, Kevin, could not have been more accomodating in seeing that all of our vacation needs were taken care of. I could have sat on the porch and watched the sunset views forever. Watch for the manatees when you are there, they are a lifetime experience.

Price per night from

$1,250

Waterfront Condo with Boat

Key Largo apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$438

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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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