Upper Matecumbe Key Vacation Rentals

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Browse Select Upper Matecumbe Key Vacation Homes

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

Charming Home in Key Largo

9.8 out of 10, Exceptional, (25)
"loved it!!"
The price is CA $201
CA $563 total
includes taxes & fees
Aug 13 - Aug 14
Charming Home in Key Largo

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

9.4 out of 10, Exceptional, (72)
"The house is great, tidy little spot to start all your Keys adventures from!"
The price is CA $140
CA $478 total
includes taxes & fees
Aug 14 - Aug 15
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

New Mariners Club Listing, Preferred Partner, Great Location, Epic Amenities

2.5 star property
10.0 out of 10, Exceptional, (18)
"This condo and the club is awesome. The pool is wonderful. We loved everything about or stay would come back! "
New Mariners Club Listing, Preferred Partner, Great Location, Epic Amenities

208 Mariners Club Key Largo | 3 Bed, 3 Bath

9.8 out of 10, Exceptional, (89)
"We had a Wonderful time! There was plenty of space for our family of five. We had a few minor issues with ants, but it did not impact our comfortable stay. We loved the pool and Pickleball court! Would highly recommend. "
208 Mariners Club Key Largo | 3 Bed, 3 Bath

Mariners Club Unit 904, Brand New Completely Remodeled Preferred Partner Listing

10.0 out of 10, Exceptional, (1)
"Beautiful property with a lot of space. Very well stocked with more than what you even think you need. Mariners Club is very nice with two great pools, a game room, marina, and pickleball courts. Only thing to note is there’s no beach access if that’s what you are looking for."
Mariners Club Unit 904, Brand New Completely Remodeled Preferred Partner Listing

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

9.8 out of 10, Exceptional, (66)
"Such a great, gated location with access to a variety of amenities. "
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

Palm Villa - Sleeps 6, Boat Slip Available

9.8 out of 10, Exceptional, (138)
"Great trip. Very comfortable for family of 5. Cabana club lovely and great recommendations!"
Palm Villa - Sleeps 6, Boat Slip Available

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

Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

9.6 out of 10, Exceptional, (117)
"Best sunrise site."
The price is CA $195
CA $547 total
includes taxes & fees
Aug 14 - Aug 15
Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

Catch your last summer glow at Mariners Club 606 w resort style amenities & more

10.0 out of 10, Exceptional, (137)
"Nice location with lots of restaurant choices, pools and especially the Grotto were awesome, Tarpon feeding was our favorite nearby activity."
The price is CA $412
CA $1,229 total
includes taxes & fees
Aug 17 - Aug 18
Catch your last summer glow at Mariners Club 606 w resort style amenities & more

Waterfront Tiny House w Pool, Beach, and Boat Dock

9.6 out of 10, Exceptional, (57)
"My wife and I stayed here for our honeymoon , and we were absolutely thrilled with everything. We loved that the house had a bunch of mini splits to keep it nice and chilly. We also loved that the house was very clean and well kept. The tiki hut on the water with the tv and great lighting at night makes a perfect place to relax at the end of a fun filled day. All around this was a fantastic place to stay!"
The price is CA $167
CA $508 total
includes taxes & fees
Sep 8 - Sep 9
Waterfront Tiny House w Pool, Beach, and Boat Dock

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

9.6 out of 10, Exceptional, (19)
"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

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,

VOTED BEST KEY LARGO VACATION RENTAL

10.0 out of 10, Exceptional, (81)
"We had a great stay! We loved having kayaks, snorkels, a lagoon and the ocean and everything nearby. We loved feeding the fish on the property. The kitchen is well stocked with everything we needed for making meals. Nice restaurants nearby! Thanks for meeting us, Norman - that was very helpful!!"
VOTED BEST KEY LARGO VACATION RENTAL

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

10.0 out of 10, Exceptional, (55)
"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

Manatee Bay: Escape to this 2BR Duck Key Villa, Private Patio, Dip Pool & Easy Access to Marathon

9.8 out of 10, Exceptional, (38)
"Excellent location off the main drag with quiet stay and perfect place to have as a base of operation for sightseeing and fishing."
Manatee Bay: Escape to this 2BR Duck Key Villa, Private Patio, Dip Pool & Easy Access to Marathon

Immaculate oceanfront townhouse with ocean view & private beach access

8.0 out of 10, Very good, (25)
"The upper deck has a great sunset view. Great area for walks. Very quiet and peaceful neighborhood. Would definitely stay again next time in the Keys"
Immaculate oceanfront townhouse with ocean view & private beach access

Restful waterfront townhome with deck, great water views & washer/dryer

9.2 out of 10, Wonderful, (85)
"Quiet, clean, neighborhood feel."
Restful waterfront townhome with deck, great water views & washer/dryer

Beautiful Key Largo Town Home Fully Renovated Top to Bottom

9.8 out of 10, Exceptional, (164)
"The porperty had everything we needed for a great family spring break. The kids especially enjoyed trips to the jetty on the golf cart!"
Beautiful Key Largo Town Home Fully Renovated Top to Bottom
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