Upper Matecumbe Key Vacation Rentals

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Browse Select Upper Matecumbe Key Vacation Homes

Piece of Paradise located at Hawks Cay in Duck Key

9.4 out of 10, Exceptional, (3)
"Amazing place. "
Piece of Paradise located at Hawks Cay in Duck Key

Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

9.8 out of 10, Exceptional, (67)
"Such a great, gated location with access to a variety of amenities. "
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball

9.6 out of 10, Exceptional, (19)
"Clean , beautiful location and pools . "
Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball

Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

9.6 out of 10, Exceptional, (31)
"Nice property . Well kept. Good management "
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

Sea La Vie – Key Largo Retreat in Mariner’s Club - Labor Day & Fall Specials

10.0 out of 10, Exceptional, (138)
"You would be very hard presses to find a better Key Largo location. Especially for family, boating and fishing!"
Sea La Vie – Key Largo Retreat in Mariner’s Club - Labor Day & Fall Specials

Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal

9.6 out of 10, Exceptional, (58)
"The property is central location in Islamorada, best location....The outdoor area is perfect,pool heated very enjoyable.. great neighborhood..Friendly Host JoAnn is amazing, and prompt response, a delightful person, and a wonderful host!"
Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal

Oceanfront 165ft beach-Dock-Heated pool-4K sq.ft 4 bed/5 bath-Next avail 8.9.25

10.0 out of 10, Exceptional, (84)
"Everything just great except need better vaccum"
Oceanfront 165ft beach-Dock-Heated pool-4K sq.ft 4 bed/5 bath-Next avail 8.9.25

Charming Home in Key Largo

9.8 out of 10, Exceptional, (25)
"loved it!!"
The price is CA $236
CA $615 total
includes taxes & fees
Aug 27 - Aug 28
Charming Home in Key Largo

7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks

10.0 out of 10, Exceptional, (57)
"We have stayed in one of this Hosts properties for 5 years in a row. Always clean, always great communication and we always have a great time. We highly recommend."
7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks

Resort-Style Living at Mariner's Club – Steps from Pools, Marina, & Ocean Views!

10.0 out of 10, Exceptional, (9)
"We stayed at this property for our spring break trip and thoroughly enjoyed our stay. The home was clean, comfortable, and well-equipped with everything we needed. The location was great—close to local attractions yet peaceful enough for a relaxing getaway. The host was responsive and accommodating, making the entire experience seamless. We would definitely stay here again!"
Resort-Style Living at Mariner's Club – Steps from Pools, Marina, & Ocean Views!

Amazing Florida Keys Retreat!

10.0 out of 10, Exceptional, (70)
"Great location and quiet. Very clean and had all the amenities for a great relaxing stay. "
Amazing Florida Keys Retreat!

Spectacular Ocean Front Home In Beautiful Islamorada!Slip,Com Pool, & Prv Bch

10.0 out of 10, Exceptional, (44)
"Loved the time with family- great location "
Spectacular Ocean Front Home In Beautiful Islamorada!Slip,Com Pool, & Prv Bch

Best Deals in Duck Key . 2 Bedroom /2 Bath w/40' 'Dock, Trailer Storage Incl,

10.0 out of 10, Exceptional, (178)
"Beautiful place in the keys, and felt larger than the photos showed. Owner is very communicative! "
Best Deals in Duck Key . 2 Bedroom /2 Bath w/40' 'Dock, Trailer Storage Incl,

New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

9.6 out of 10, Exceptional, (74)
"The house is great, tidy little spot to start all your Keys adventures from!"
The price is CA $160
CA $510 total
includes taxes & fees
Sep 16 - Sep 17
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

Waterfront, dog-friendly home with beautiful canal view & 2 shaded porches

9.8 out of 10, Exceptional, (21)
"It was perfect for my family- had everything we needed. Nice area to avoid crowds, but fast to drive to stores/restaurants as needed. "
Waterfront, dog-friendly home with beautiful canal view & 2 shaded porches

Charming Canal-Front House | WiFi+Swim+Kayak+Fish

10.0 out of 10, Exceptional, (3)
"Great house and very responsive host."
Charming Canal-Front House | WiFi+Swim+Kayak+Fish

4 Bedroom 3 Bathroom Sanctuary Villa W/ Private Pool & 35ft dock upon request

8.0 out of 10, Very good, (2)
"Property was spacious and meticulously maintained. Frank is very informative, absolute pleasure to deal with."
The price is CA $812
CA $1,629 total
includes taxes & fees
Sep 1 - Sep 2
4 Bedroom 3 Bathroom Sanctuary Villa W/ Private Pool & 35ft dock upon request

Tranquility Cove Beautiful Remodeled home in the heart of Islamorada.

7.6 out of 10, Good, (5)
"Three generations stayed very comfortably in this great house. It was located great for food and activities!"
Tranquility Cove Beautiful Remodeled home in the heart of Islamorada.

Ocean-View 3BR/3BA Cottage 5004 with Private Pool: Village at Hawks Cay Villas

10.0 out of 10, Exceptional, (9)
"The house was amazing and in a great location "
Ocean-View 3BR/3BA Cottage 5004 with Private Pool: Village at Hawks Cay Villas

Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)

10.0 out of 10, Exceptional, (202)
"This property was very clean and comfortable, and the property manager was super responsive when we had questions. I would definitely recommend this rental to family and friends!"
Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Upper Matecumbe Key Hotel Reviews

Find out more about Upper Matecumbe Key

Find out more about Upper Matecumbe Key

Upper Matecumbe Key Vacation Homes information

Number of reviews
794
Accommodation
690 Vacation Homes
Lowest Price
CA $160
Highest Price
CA $812

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