Matecumbe Key Rentals

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496 Houses

(13) Very Good 

32

75731 Overseas Highway

Florida Keys / Matecumbe Key

Matecumbe Key house

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Swimming pool
  • Child Friendly
“Relaxing!” The Florida Keys are so much fun and so very casual. The house was a great way to get our family together for a week and we all enjoyed ourselves, I could have stayed for a month. The guys all went fishing and the rest of us floated in the
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Price per night from

$1,045

Price per night from

$1,045

(5) Excellent 

19

75130 Overseas Highway

Florida Keys / Matecumbe Key

Matecumbe Key house

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Child Friendly
  • Pet Friendly
“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 h
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Price per night from

$186

Price per night from

$186

(12) Very Good 

47

Private Beachfront Paradise

Florida Keys / Matecumbe Key

Matecumbe Key house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
“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
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Price per night from

$500

Price per night from

$500

(9) Excellent 

16

ISLAMORADA WATERFRONT PARADISE with FREE DOCKAGE

Florida Keys / Matecumbe Key

Matecumbe Key studio

Studio 2 30 nights min

  • Studio
  • sleeps 2
  • 30 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 mi
  • Air conditioning
“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
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Price per night from

$200

Price per night from

$200

15

CRYSTAL CLEAR BAY HOME

Florida Keys / Matecumbe Key

Matecumbe Key house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Ask about children

Price per night from

$250

Price per night from

$250

32

75691 Overseas Highway

Florida Keys / Matecumbe Key

Matecumbe Key house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly

Price per night from

$482

Price per night from

$482

14

Future Townhome 707

Florida Keys / Matecumbe Key

Matecumbe Key condo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly

Price per night from

$169

Price per night from

$169

25

BEACON REEF 406

Florida Keys / Matecumbe Key

Matecumbe Key condo

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Ask about children

Price per night from

$100

Price per night from

$100

25

BEACON REEF 522

Florida Keys / Matecumbe Key

Matecumbe Key condo

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Ask about children

Price per night from

$146

Price per night from

$146

24

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

Florida Keys / Matecumbe Key

Matecumbe Key house

3 8 30 nights min

  • 3 bedrooms
  • sleeps 8
  • 30 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$388

Price per night from

$388

(2)  

23

Islamorada Yacht Life

Florida Keys / Matecumbe Key

Matecumbe Key yacht

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Air conditioning
  • Ask about pets

Price per night from

$574

Price per night from

$574

42

Tropical getaway at Executive Bay Club with heated pool, sandy sun deck and near

Florida Keys / Matecumbe Key

Matecumbe Key house

2 6 28 nights min

  • 2 bedrooms
  • sleeps 6
  • 28 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$4,200

Responds fast!
avg. 2 hours 2 minutes

Price per night from

$4,200

29

Summer Sea #420

Florida Keys / Matecumbe Key

Matecumbe Key condo

1 3 min stay varies

  • 1 bedroom
  • sleeps 3
  • min stay varies
  • Swimming pool
  • Child Friendly

Price per night from

$127

Price per night from

$127

25

87200OH-A7. Beautiful Florida Keys 3 Bedroom Town Home with Private Beach Access

Florida Keys / Matecumbe Key

Matecumbe Key house

3 8 28 nights min

  • 3 bedrooms
  • sleeps 8
  • 28 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$199

Price per night from

$199

Great rentals within 20 miles that match your search

Distance approx 3.21 km from Matecumbe Key Show on Map

(1) Excellent 

13

Islamorada Tropical Canalfront Paradise

Florida Keys / Islamorada

Islamorada house

2 6 28 nights min

  • 2 bedrooms
  • sleeps 6
  • 28 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$250

Price per night from

$250

Distance approx 3.52 km from Matecumbe Key Show on Map

9

Seas the Day in this Waterfront Home on Oceanside MM90

Key Largo / Tavernier

Tavernier house

5 14 30 nights min

  • 5 bedrooms
  • sleeps 14
  • 30 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$175

Price per night from

$175

Distance approx 3.94 km from Matecumbe Key Show on Map

56

Islamorada Oceanfront Estate, Pool, Beach Cottages-- Sea Ranch -- Florida Keys

Florida Keys / Islamorada

Islamorada house

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$1,177

Price per night from

$1,177

Distance approx 5.76 km from Matecumbe Key Show on Map

(22) Excellent 

Certificate of Excellence

17

OCEANFRONT CONDO WITH ALL AMMENITIES!

Key Largo / Tavernier

Tavernier apartment

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Immaculate, with lovely views!” Our first impression of this place was that it was very, very clean and cared for. Next, the view was wonderful. Third, they had everything we really needed, including cooking utensils, laundry facilities right in the c
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Certificate of Excellence

Price per night from

$235

Responds fast!
avg. 2 hours 39 minutes

Price per night from

$235

Distance approx 3.89 km from Matecumbe Key Show on Map

22

Tavernier Dreams

Key Largo / Tavernier

Tavernier house

2 6 30 nights min

  • 2 bedrooms
  • sleeps 6
  • 30 nights min
  • Nearest beach 5 mi
  • Child Friendly
  • Air conditioning

Price per night from

$150

Responds fast!
avg. 2 hours 39 minutes

Price per night from

$150

Distance approx 12.38 km from Matecumbe Key Show on Map

(6) Excellent 

20

Luxury condo overlooking harbor with ocean view

Florida Keys / Islamorada

Islamorada condo

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Nearest beach 2 mi
  • Swimming pool
  • Child Friendly

Price per night from

$269

Responds fast!
avg. 1 hour 7 minutes

Price per night from

$269

Distance approx 1.77 km from Matecumbe Key Show on Map

24

Keys home in Anglers Reef with ocean view, dock, community pool & private beach

Florida Keys / Islamorada

Islamorada house

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.25 mi
  • Child Friendly

Price per night from

$364

Price per night from

$364

Distance approx 1.84 km from Matecumbe Key Show on Map

(1) Excellent 

25

LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF

Florida Keys / Islamorada

Islamorada villa

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$279

Price per night from

$279

Distance approx 1.22 km from Matecumbe Key Show on Map

17

"Irish Ayes" Elegant Waterfront Home with Pool

Florida Keys / Islamorada

Islamorada house

4 8 28 nights min

  • 4 bedrooms
  • sleeps 8
  • 28 nights min
  • Pet Friendly

Price per night from

$701

Responds fast!
avg. 40 minutes

Price per night from

$701

Distance approx 11.11 km from Matecumbe Key Show on Map

(2) Excellent 

43

100' Private Beach Front Ocean Front Estate

Florida Keys / Islamorada

Islamorada house

4 12 7 nights min

  • 4 bedrooms
  • sleeps 12
  • 7 nights min
  • Nearest beach 0 mi
  • Swimming pool
  • Child Friendly

Price per night from

$828

Responds fast!
avg. 2 hours 18 minutes

Price per night from

$828

Distance approx 1.87 km from Matecumbe Key Show on Map

(26) Excellent 

29

Luxurious Anglers Reef with Boat Slip, Pool, Ocean

Florida Keys / Islamorada

Islamorada house

2 5 7 nights min

  • 2 bedrooms
  • sleeps 5
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“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 ever
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Price per night from

$229

Responds fast!
avg. 2 hours 27 minutes

Price per night from

$229

Distance approx 5.59 km from Matecumbe Key Show on Map

74

5BR home directly on the Ocean-- Ultra luxurious estate in Islamorada, Fl Keys

Florida Keys / Islamorada

Islamorada house

5 12 7 nights min

  • 5 bedrooms
  • sleeps 12
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$1,463

Price per night from

$1,463

Distance approx 11 km from Matecumbe Key

14

Private Key Largo Bayside Canalfront home

Florida Keys / Key Largo

Key Largo house

2 4 28 nights min

  • 2 bedrooms
  • sleeps 4
  • 28 nights min
  • Nearest beach 10 mi
  • Child Friendly
  • Air conditioning

Price per night from

$145

Price per night from

$145

Distance approx 3.7 km from Matecumbe Key Show on Map

24

Oceanfront Islamorada Condo with Huge T-Dock

Florida Keys / Islamorada

Islamorada condo

2 4 30 nights min

  • 2 bedrooms
  • sleeps 4
  • 30 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$133

Price per night from

$133

Distance approx 12.52 km from Matecumbe Key Show on Map

25

Lower Mat Canal Front Home w/ 60' dock and access to private beach on the bay!

Florida Keys / Islamorada

Islamorada house

3 8 30 nights min

  • 3 bedrooms
  • sleeps 8
  • 30 nights min
  • Child Friendly

Price per night from

$133

Price per night from

$133

Distance approx 0.1 km from Matecumbe Key Show on Map

(2) Excellent 

19

Mile Marker 87 - Mina Bay - Oceanfront "Million Dollar View"

Florida Keys / Islamorada

Islamorada townhouse

2 8 30 nights min

  • 2 bedrooms
  • sleeps 8
  • 30 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$133

Price per night from

$133

Distance approx 15.71 km from Matecumbe Key

25

Fabulous and Spacious HOME!!

Florida / Ocean Reef

Ocean Reef house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$127

Price per night from

$127

Distance approx 14.61 km from Matecumbe Key

14

1/1 with Living Room plus Oceanview

Key Largo / Tavernier

Tavernier guest house

1 3 28 nights min

  • 1 bedroom
  • sleeps 3
  • 28 nights min

Price per night from

$126

Price per night from

$126

Distance approx 16.97 km from Matecumbe Key

37

Awesome pool view condo - Sunshine Vibe at Moon Bay

Florida Keys / Key Largo

Key Largo condo

2 6 5 nights min

  • 2 bedrooms
  • sleeps 6
  • 5 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$189

Price per night from

$189

Distance approx 5.79 km from Matecumbe Key Show on Map

35

2 x ISLAND VIEW 2BR/2BA SUITES FOR 12, FULL KITCHEN, PRIVATE BEACH, GRILL, POOL

Key Largo / Tavernier

Tavernier apartment

4 12 min stay varies

  • 4 bedrooms
  • sleeps 12
  • min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child Friendly

Price per night from

$339

Responds fast!
avg. 3 hours 28 minutes

Price per night from

$339

Distance approx 11.9 km from Matecumbe Key

(16) Excellent 

Certificate of Excellence

16

Tropical Retreat With Sandy Beach

Florida Keys / Key Largo

Key Largo villa

2 6 4 nights min

  • 2 bedrooms
  • sleeps 6
  • 4 nights min
  • Beach / lakeside relaxation
  • Ask about children
  • Air conditioning
“Wonderful Keys Getaway Cabin” My family thoroughly enjoyed the villa. The location was fantastic, right on the water. We used the kayaks to paddle out into the bay every night to watch the sunsets. Martha was very helpful - every time we had a ques
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Certificate of Excellence

Price per night from

$200

Price per night from

$200

Distance approx 12.86 km from Matecumbe Key Show on Map

25

Dream Home In The Keys

Florida Keys / Islamorada

Islamorada house

5 12 7 nights min

  • 5 bedrooms
  • sleeps 12
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Ask about children

Price per night from

$357

Responds fast!
avg. 3 hours 14 minutes

Price per night from

$357

Distance approx 10.43 km from Matecumbe Key

27

Beautiful One Bedroom Cottage at Riptide RV Resort in Key Largo

Florida Keys / Key Largo

Key Largo cottage

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$167

Price per night from

$167

Distance approx 5.79 km from Matecumbe Key Show on Map

(2) Very Good 

31

Right on the ocean, 2BR+2BA for 12, pool, tennis courts, restaurant. marina

Key Largo / Tavernier

Tavernier apartment

4 12 min stay varies

  • 4 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$369

Price per night from

$369