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Matecumbe Key Rentals

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389 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

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

$233

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!

Responds fast! avg. 1 hour 20 minutes

Price per night from

$610

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

$147

75691 Overseas Highway

Matecumbe Key house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$540

Waterfront 3BR w/ Private Beach & Dock - Near Epic Diving & Everglades

Matecumbe Key house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$390

PALMS 313

Matecumbe Key condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$73

Angler's Reef #118

Matecumbe Key house

2 bedrooms / 3 bathrooms / sleeps 4

Price per night from

$266

Spacious, oceanfront condo w/ ocean views, shared pool & dock! Tennis on-site!

Matecumbe Key condo

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$97

NEW LISTING! Canal front home with private boat ramp, and kayak!

Matecumbe Key house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$157

NEW LISTING! Newly-renovated condo w/shared pool, beach access, & private grill

Matecumbe Key condo

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$152

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

Matecumbe Key house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 34 minutes

Price per night from

$288

194 Airstream Lane

Matecumbe Key house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$306

149 Stromboli Drive

Matecumbe Key house

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$764

75651 Overseas Hwy Islamorada Fla Keys Oceanfront

Matecumbe Key apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$134

FISH WHISTLE

Matecumbe Key villa

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$500

Martin Family Fish Camp

Matecumbe Key cottage

4 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$543

Summer Sea #420

Matecumbe Key condo

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$130

BEACON REEF 503

Matecumbe Key condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$143

Palms of Islamorada #403

Matecumbe Key condo

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$134

Port of Call C-2

Matecumbe Key condo

2 bedrooms / 3 bathrooms / sleeps 4

Price per night from

$229

BEACON REEF 301

Matecumbe Key condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$117

NEW LISTING! Bayfront townhouse in FYC w/ a shared pool, boat slip, & tennis

Matecumbe Key townhouse

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$233

Great rentals within 20 miles that match your search

Waterfront Condo with Boat

Key Largo apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$375

Price per night from

$116

Paradise on the water

Key Largo house

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 1 hour 17 minutes

Price per night from

$289

Paradise at Islamorada

Islamorada townhouse

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$162

Luxury condo overlooking harbor with ocean view

Islamorada condo

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 49 minutes

Price per night from

$312

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

$194

AZALEA WARTERFRONT

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$174

Large Waterfront 4 balcony Key Largo Townhouse with Oceanfront Dock

Key Largo townhouse

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$290

Good Times and Tan Lines - (New Listing) Deluxe Renovated Ocean View 2B/2B Condo

Tavernier condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$248

Relaxation in the Keys! MM 74 1/2

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$203

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. 3 hours 12 minutes

Price per night from

$174

Waterview 2 Bedroom - Marina and Beach

Key Largo house

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 35 minutes

Price per night from

$215

Luxurious Anglers Reef with Boat Slip, Pool, Ocean

Islamorada house

2 bedrooms / 3 bathrooms / sleeps 5

“A perfect retreat! Every need anticipated.” Anglers Reef is the ideal spot for a truly relaxing and enjoyable holiday. The owner was so helpful prior to our arrival that we were able settle into our vacation home immediately. It was spotless and everything we needed was at our fingertips. The grounds, pool, and ocean-side location were everything we'd hoped for. As we were travelling with a baby, we were naturally a bit anxious regarding managing the demands of caring for an infant in a new location. As a high chair and travel crib were already set up for us on arrival, as well a high quality food blender in the kitchen, we were able to proceed with a perfectly restful and fun holiday. The home is beautifully and tastefully decorated which only added to our a+ vacation. Attention to details like extra large plush beach towels, recommendations for enjoying The Keys, where to go shopping, plenty of dishes, cookware & utensils all added to our enjoyment. We look forward to returning to anglers Reef, especially when we need to get away from the winter - which seemed to be endless this year! Thanks again for making us feel so welcome.

Responds fast! avg. 59 minutes

Price per night from

$398

Athenas Hideaway Key Largo

Tavernier houseboat

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$115

Viewing 38 of 389
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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