Holiday Homes in Upper Matecumbe Key

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Featured Holiday Homes in Upper Matecumbe Key

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

9.4 out of 10, Exceptional, (46)
"Clean, quiet and comfortable. The only problem was the lockbox. It took us 1/2 hour to open because the button is worn down so bad. They should get a new one. It was so frustrating. Otherwise the time house was perfect"
The price is AU$695
includes taxes & fees
5 Feb - 6 Feb
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

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

10.0 out of 10, Exceptional, (180)
"Had a great time in Key Largo. This home is in a setting that allows for walking, visiting and enjoying the Florida air. Had a great time. The home is lovely and well furnished. Bathrooms are a little small. "
Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)

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

10.0 out of 10, Exceptional, (164)
"This property is well setup for those wishing to bring their boats - it's a short idle out of the canals, fish filet stations, electricity, water, etc. We had a great time and Cecelia was very prompt with communication. "
Best Deals in Duck Key . 2 Bedroom /2 Bath w/40' 'Dock, Trailer Storage Incl,

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

9.8 out of 10, Exceptional, (45)
"We spent a week uch enjoyed our visit. It's a little dated but very clean and comfortable. "
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

Tipsy Turtle: Luxurious Waterfront Villa on Duck Key with Stunning Views and Modern Upgrades!

9.8 out of 10, Exceptional, (19)
"We visited this property for an extended weekend over the Thanksgiving holiday. Upon arrival we encountered a minor setback with a missing bathroom mirror, however, the property management company was very responsive and had someone on site to replace on Thanksgiving day AND without hesitation. Overall, the property was in a great location and as described. They even included Keurig cups for coffee.I appreciate the level of cleanliness and response time!"
Tipsy Turtle: Luxurious Waterfront Villa on Duck Key with Stunning Views and Modern Upgrades!

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

9.8 out of 10, Exceptional, (22)
"Our family had an amazing trip to the Keys. We were able to drive to several different Islands in a short amount of time. Great restaurants around as well!"
Manatee Bay: Escape to this 2BR Duck Key Villa, Private Patio, Dip Pool & Easy Access to Marathon

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

9.4 out of 10, Exceptional, (89)
"We were fortunate to get just one day of rain, and otherwise had wonderful weather, which was great because the outdoor space at this property is wonderful. There is a large area to play soccer or throw a ball, as well as beach, long and low dock, and kayaks to use. The outside space is truly what makes this house special. The location is very good and easy to get to -- you're just a handful of miles from some of the more touristy things in Islamorada, making this a quiet spot that still has...
Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly

Mariners Club Townhouse, Unit 603, Epic Amenities, Tennis & Indoor Pickleball

2.5 star property
10.0 out of 10, Exceptional, (2)
"Exactly as described- great communication. Family loved it!"
Mariners Club Townhouse, Unit 603, Epic Amenities, Tennis & Indoor Pickleball

Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball

9.6 out of 10, Exceptional, (10)
"Our group was looking for a warm spot to relax and this place delivered! We had quite a few of us, so it was great to have many places to sleep and lots of living space. Mariner's Club was a beautiful spot and the pools were a beautiful place to spend relaxing days. We had no problem finding great restaurants nearby using Erick's recommendations. "
Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball

★Newly remodeled tropical townhome★ Private plunge pool close to fun activities

10.0 out of 10, Exceptional, (35)
"Loved staying in the Keys. Townhome was clean and neat and had everything we needed for the stay. Extra special touches with snacks and toiletries provided when we got there. Communication with Miguel was wonderful and information for the area and recommendations for fishing guides provided were spot on. Plunge pool and outdoor areas were really nice additions. Would highly recommend this rental. "
★Newly remodeled tropical townhome★ Private plunge pool close to fun activities

Islamorada Home with Private Beach Freshly updated Waterfront and Swimming Pool

8.8 out of 10, Excellent, (9)
"The house was perfect for our large family, different spaces for everyone to spread out. Very happy with our stay in islamorada"
Islamorada Home with Private Beach Freshly updated Waterfront and Swimming Pool

Villa 5054 on Duck Key BOAT SLIP available

9.8 out of 10, Exceptional, (39)
"Right outside Marathon close the all the needs you want. Nice drive to the Keys and back from the condo. Price was right. Complete kitchen nice common area and back porch and sunset. Rooms were a little small but workable with individual baths for each room. Quiet and lots of lizards for your entertainment in the morning on the back porch."
The price is AU$1,115
includes taxes & fees
3 Feb - 4 Feb
Villa 5054 on Duck Key BOAT SLIP available

Islamorada Boaters Paradise with 70' Dock and private beach access..

10.0 out of 10, Exceptional, (19)
"Everything was amazing for our stay. We were able to have the boat right at the house for easy access for sunset boat rides and our everyday fishing adventures. "
Islamorada Boaters Paradise with 70' Dock and private beach access..

Villa 5023 on Duck Key BOAT SLIP available

9.4 out of 10, Exceptional, (28)
"I stayed at a lodging in Marathon, which is in the middle of my trip to Key West. It was a quiet and comfortable place to stay. It was a little narrower than it looked in the picture, but it was fine for staying with family."
The price is AU$1,115
includes taxes & fees
4 Feb - 5 Feb
Villa 5023 on Duck Key BOAT SLIP available

Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

9.6 out of 10, Exceptional, (100)
"If you are looking for an easy place to stay near Pennekamp State Park, this is a great option. Our family of 5 (4 adults 16 year old) enjoyed the great views and convenient location. It's small but adequate and had everything we needed for a couple of nights! "
The price is AU$819
includes taxes & fees
3 Feb - 4 Feb
Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

Water View Keys Retreat: Waterfront Villa on Duck Key, Enchanting Open Water Views, Multiple Decks

2.0 star property
Water View Keys Retreat: Waterfront Villa on Duck Key, Enchanting Open Water Views, Multiple Decks

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

9.8 out of 10, Exceptional, (15)
"This cluster of cottages is a small “community” within a neighborhood off Highway 1 in the Keys. Very close to things you need like restaurants, grocery and close enough to beachy areas like Sombrero Beach on Marathon or Bahia Honda a bit farther south. Loved the quiet pool and our fire pit for those cooler January nights. The neighbors seemed to be a mix of permanent residents, boaters, renters and snowbirds. This is ideal for couples and maybe kids who don’t mind sharing a small double (full)...
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

Private Pool Home: 3BR/3BA Sanctuary Village Villa 7219

9.4 out of 10, Exceptional, (3)
"My stay was very nice. My family enjoyed our stay and got all caught up with each other. We would definatly do it again!"
Private Pool Home: 3BR/3BA Sanctuary Village Villa 7219

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

10.0 out of 10, Exceptional, (2)
"All was great we had what we needed and more it was very clean and our host communicated well. We had lots of fun and this house facilitated that!"
Charming Canal-Front House | WiFi+Swim+Kayak+Fish

4BR/4BA Mariner's Club Townhouse 607 with Oasis Pool, Marina, Game Room & More

10.0 out of 10, Exceptional, (4)
"Property was beautiful and perfectly fit our needs for our business fishing trip! "
4BR/4BA Mariner's Club Townhouse 607 with Oasis Pool, Marina, Game Room & More
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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Other property types in Upper Matecumbe Key

Breezy Palms Resort

2.5 star property
8.6 out of 10, Excellent, (403)
"nice warm pool, nice ocean views."
The price is AU$348
includes taxes & fees
13 Feb - 14 Feb
Breezy Palms Resort

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (47)
"Beautiful property with great staff! "
The price is AU$1,164
includes taxes & fees
2 Mar - 3 Mar
The Islands of Islamorada

Key Largo Cottages

2.5 star property
9.4 out of 10, Exceptional, (20)
"Love this place! Very friendly and secluded. Not your typical resort-look elsewhere if that’s what you want. But if you want a friendly private sailing camp where you hang out with other fun people and like to sail and kayak, this is absolutely it! The use of the sailboat alone more than pays for the room."
The price is AU$732
includes taxes & fees
6 Feb - 7 Feb
Key Largo Cottages
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.