Search Holiday Homes in Upper Matecumbe Key

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Check prices for these dates

Next weekend
4 Jul - 6 Jul
In two weeks
11 Jul - 13 Jul
In one month
25 Jul - 27 Jul
In two months
22 Aug - 24 Aug

Browse Select Upper Matecumbe Key Holiday Homes

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, (16)
"Clean , beautiful location and pools . "
Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball
Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7
Terrace/patio

Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7

10.0 out of 10, Exceptional, (82)
"Everything just great except need better vaccum"
Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7
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, (14)
"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
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
Exterior

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

9.8 out of 10, Exceptional, (60)
"Enjoyed our stay. Lots to do if you’re wanting a relaxing day or a day of swimming, tennis, walking or cycling. "
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
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, (172)
"It was the perfect place for our family while visiting the Florida Keys. "
Best Deals in Duck Key . 2 Bedroom /2 Bath w/40' 'Dock, Trailer Storage Incl,
DUPLEX IN DUCK KEY Grand 3/2 W/90' Private Dock, Trailer Storage included
Pool

DUPLEX IN DUCK KEY Grand 3/2 W/90' Private Dock, Trailer Storage included

10.0 out of 10, Exceptional, (148)
"We were in the Keys for a long weekend. This was a very convenient location and a beautiful setting. "
DUPLEX IN DUCK KEY Grand 3/2 W/90' Private Dock, Trailer Storage included
NEW OCEANVIEW CASA MAR VOTED #1! INDOOR PICKLEBALL ~ POOLS~ TENNIS~ FISH~ MARINA
Outdoor pool, a heated pool

NEW OCEANVIEW CASA MAR VOTED #1! INDOOR PICKLEBALL ~ POOLS~ TENNIS~ FISH~ MARINA

10.0 out of 10, Exceptional, (99)
"Loved the location, the decor and the pool area!"
NEW OCEANVIEW CASA MAR VOTED #1! INDOOR PICKLEBALL ~ POOLS~ TENNIS~ FISH~ MARINA
Fun For All! Key Largo 3/3 Townhome Oceanside Resort
Terrace/patio

Fun For All! Key Largo 3/3 Townhome Oceanside Resort

9.6 out of 10, Exceptional, (59)
"Great location and property."
Fun For All! Key Largo 3/3 Townhome Oceanside Resort
801 Mariners Club Key Largo | 4 Bed, 4 Bath
A heated pool

801 Mariners Club Key Largo | 4 Bed, 4 Bath

9.4 out of 10, Exceptional, (70)
"We had too much fun great central location. Good amenities!! "
801 Mariners Club Key Largo | 4 Bed, 4 Bath
Waterfront Tiny House w Pool, Beach, and Boat Dock
Dining

Waterfront Tiny House w Pool, Beach, and Boat Dock

9.6 out of 10, Exceptional, (55)
"We stayed here in April 2025 - perfect location with a great patio overlooking the waterfront harbor, perfect for us. Everything you need is a short drive - grocery Publix is close enough to walk to. The tiny house is adorable and clean, well stocked kitchen - We found great place to hike /Hamock State Park and Rowell’s was a great place to swim "
The price is £310
includes taxes & fees
30 Jun - 1 Jul
Waterfront Tiny House w Pool, Beach, and Boat Dock
Great Water Front 2 Story Townhouse With Boat Slip available at additional cost
Outdoor pool

Great Water Front 2 Story Townhouse With Boat Slip available at additional cost

8.6 out of 10, Excellent, (42)
"This was a great spot to enjoy a large part of the Keys chain. The location midway down the Keys gave us access to so much. The space was exactly what we needed. The area was lovely and the amenities on the property were fantastic. Julio was great to work with and responded to our questions and needs very quickly."
Great Water Front 2 Story Townhouse With Boat Slip available at additional cost
Waterfront, dog-friendly home with beautiful canal view & 2 shaded porches
Marina

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

9.6 out of 10, Exceptional, (17)
"Escaped the snow and single digit temps for shorts and sunshine in February. The water was every bit as beautiful as the pictures. Toms of fish to see around the dock which the kids loved. Short drive to great restaurants and dog friendly beach. Plenty of room to spread out in the like new property. Very safe area to walk around and let the kids play. Would definitely recommend for a family getaway!"
Waterfront, dog-friendly home with beautiful canal view & 2 shaded porches
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, (81)
"Quiet, clean, neighborhood feel."
Restful waterfront townhome with deck, great water views & washer/dryer
Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly
On the beach, sun-loungers, beach towels

Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly

9.4 out of 10, Exceptional, (94)
"Oceans views for miles! Great pool. "
Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly
WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!
Outdoor dining

WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!

9.6 out of 10, Exceptional, (81)
"Great stay, lovely setting and location! Our second time here!"
WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!
Key Largo Relaxing Getaway
Marina

Key Largo Relaxing Getaway

9.8 out of 10, Exceptional, (90)
"Great spot for a Key Largo get away!"
Key Largo Relaxing Getaway
Manatee Bay: Escape to this 2BR Duck Key Villa, Private Patio, Dip Pool & Easy Access to Marathon
Pool

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

9.8 out of 10, Exceptional, (31)
"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
Waterfront Beach, Pool, Dock, Kayaks, Paddleboards
Outdoor dining

Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

9.6 out of 10, Exceptional, (113)
"Best sunrise site."
The price is £349
includes taxes & fees
15 Jul - 16 Jul
Waterfront Beach, Pool, Dock, Kayaks, Paddleboards
Private Pool Home: 4BR/2.5BA Sanctuary Village Villa 7222
Pool

Private Pool Home: 4BR/2.5BA Sanctuary Village Villa 7222

8.0 out of 10, Very good, (10)
"All good "
Private Pool Home: 4BR/2.5BA Sanctuary Village Villa 7222
Beautiful Oceanside Mariner's 3 Bedroom Townhome
A heated pool

Beautiful Oceanside Mariner's 3 Bedroom Townhome

10.0 out of 10, Exceptional, (79)
"Amazing and cozy home and great location very close to the pools. "
The price is £582
includes taxes & fees
30 Jun - 1 Jul
Beautiful Oceanside Mariner's 3 Bedroom Townhome
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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