Upper Matecumbe Key Vacation Rentals

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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Upper Matecumbe Key Vacation Homes

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

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
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
Beach nearby, sun loungers, beach towels

Beachside Retreat w/ Pool, Boat Ramp Dock for Rent

9.6 out of 10, Exceptional, (35)
"Beautiful place. Our stay was quiet and wonderful. Very clean and comfortable. "
The price is CA $100
CA $380 total
includes taxes & fees
Aug 21 - Aug 22
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards
A heated pool

OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards

10.0 out of 10, Exceptional, (183)
"We had such a nice time at the Windley Cottage. The owners effectively communicated information about the home and check in before the stay, making arrival very easy. The home was very clean and had everything that we needed. The Anglers Reef area was nice and quiet. We enjoyed walks to the docks, kayaking, and swimming in the pool. We absolutely loved Islamorada and hope to visit again!"
OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards
Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball
Outdoor pool, a heated pool

Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball

9.6 out of 10, Exceptional, (18)
"Clean , beautiful location and pools . "
Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball
Florida Keys Townhouse For Rent 2/2
Property grounds

Florida Keys Townhouse For Rent 2/2

9.4 out of 10, Exceptional, (171)
"We used this as accommodation to explore the keys for 6days and it did not disappoint. Very accurate description of the house. Nice, clean and tidy. Thank you"
Florida Keys Townhouse For Rent 2/2
Waterfront Beach, Pool, Dock, Kayaks, Paddleboards
Outdoor dining

Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

9.6 out of 10, Exceptional, (116)
"Best sunrise site."
The price is CA $217
CA $582 total
includes taxes & fees
Aug 25 - Aug 26
Waterfront Beach, Pool, Dock, Kayaks, Paddleboards
OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars
Exterior

OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars

10.0 out of 10, Exceptional, (193)
"Great location. Beautiful, comfortable accommodations. Would absolutely return. "
OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars
Charming Home in Key Largo
Fridge, microwave, oven, stovetop

Charming Home in Key Largo

9.8 out of 10, Exceptional, (22)
"Amazing spot in the Keys. Stayed there the weekend for a wedding in Tavernier and was close to everything we needed. Would definitely stay here again when I come back. "
The price is CA $201
CA $570 total
includes taxes & fees
Aug 13 - Aug 14
Charming Home in Key Largo
Waterfront Tiny House w Pool, Beach, and Boat Dock
Marina

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 $161
CA $510 total
includes taxes & fees
Aug 21 - Aug 22
Waterfront Tiny House w Pool, Beach, and Boat Dock
Best Deals in Duck Key . 2 Bedroom /2 Bath w/40' 'Dock, Trailer Storage Incl,
Marina

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

10.0 out of 10, Exceptional, (177)
"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 - Oceanfront FL Keys Home w/Pool, Free Dockage, Gameroom, Private Balcony
Terrace/patio

NEW - Oceanfront FL Keys Home w/Pool, Free Dockage, Gameroom, Private Balcony

10.0 out of 10, Exceptional, (1)
"This property was amazing basically brand new definitely recommend "
NEW - Oceanfront FL Keys Home w/Pool, Free Dockage, Gameroom, Private Balcony
7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks
Outdoor pool, a heated pool

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
Immaculate oceanfront townhouse with ocean view & private beach access
Exterior

Immaculate oceanfront townhouse with ocean view & private beach access

8.0 out of 10, Very good, (25)
"Great location of home. Easy to find. Quiet neighborhood. Plenty of parking spots available. Great views from both decks. Two clean bedrooms and 2 bathrooms. Plenty of stocked towels. Washer and dryer convenience with laundry soap available Very clean kitchen with soaps for dishes. Was missing pot holders and kitchen dish towel. Living area space and dining area a plus.Can’t wait to come back. "
Immaculate oceanfront townhouse with ocean view & private beach access
Waterfront, saltwater lagoon, 2 pools, ocean access, marina, tennis, pickleball
Property grounds

Waterfront, saltwater lagoon, 2 pools, ocean access, marina, tennis, pickleball

9.8 out of 10, Exceptional, (102)
"beautiful and quite neighborhood. "
Waterfront, saltwater lagoon, 2 pools, ocean access, marina, tennis, pickleball
Restful waterfront townhome with deck, great water views & washer/dryer
Exterior

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
Property grounds

Beautiful Key Largo Town Home Fully Renovated Top to Bottom

9.8 out of 10, Exceptional, (163)
"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
New Mariners Club Listing, Preferred Partner, Great Location, Epic Amenities
Outdoor pool, a heated pool

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

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

10.0 out of 10, Exceptional, (8)
"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!
Single Family Home In Angler's Reef Gated Community, Beaches,Marina,Heated Pool
A heated pool

Single Family Home In Angler's Reef Gated Community, Beaches,Marina,Heated Pool

9.8 out of 10, Exceptional, (93)
"This is the best location we have stayed at in Islamorada. The community was safe and quiet, plenty to do right on site with swimming, private beach, kayaks and paddleboards, fishing off dock. We saw manatees most days in the marina. The house is exactly as listed, the owners were quick to respond and fix any issues we had. Would definitely rent again! "
Single Family Home In Angler's Reef Gated Community, Beaches,Marina,Heated Pool
NEW! Stunning 2-acre Oceanfront Estate with Private Pool ~ Beach. Very private
Smart TV, books, stereo, printers

NEW! Stunning 2-acre Oceanfront Estate with Private Pool ~ Beach. Very private

NEW! Stunning 2-acre Oceanfront Estate with Private Pool ~ Beach. Very private
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

La Siesta Resort & Villas

La Siesta Resort & Villas

10/10 Excellent
"Very nice stay. Only problem was the smell of the seaweed cooking in the hot sun. Not the fault of the resort. "
Merrill 2-night trip
Posted 9 hours ago
La Siesta Resort & Villas