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Featured Cottages in Upper Matecumbe Key

Beachfront Retreat w Pool, Boat Ramp & Dock Rental

8.8 out of 10, Excellent, (29)
"Nice facilities. Wish we had better weather. Always enjoy our home away from home. KEYS LIFE FOR ME!!!!"
The price is AU$615
includes taxes & fees
5 Apr - 6 Apr
Beachfront Retreat w Pool, Boat Ramp & Dock Rental

RELAX in your PRIVATE Oceanfront Cottage!

10.0 out of 10, Exceptional, (103)
"Our third time staying here was as wonderful as the first two. So peaceful and comfortable. All the comforts of home, close to grocery, restaurants and pharmacy if needed. It’s just the best place to stay when escaping the northern states for a little warmth and sunshine in mid winter. I can’t imagine staying anywhere else in the Keys.This place is our favorite of favorites!"
RELAX in your PRIVATE Oceanfront Cottage!

Kampground Escape w/ Kayaks, Heated Pool & Marina!

10.0 out of 10, Exceptional, (8)
"Everything was absolutely perfect! We highly recommend this property!!"
Kampground Escape w/ Kayaks, Heated Pool & Marina!

Escape to a Charming 2-Bedroom Cottage in Long Key – Your Perfect Getaway!

Escape to a Charming 2-Bedroom Cottage in Long Key – Your Perfect Getaway!

3BR/3BA Sunset Cottage located at The Villages of Hawks Cay

10.0 out of 10, Exceptional, (195)
"Was perfect for our family. Views and convenience were great."
3BR/3BA Sunset Cottage located at The Villages of Hawks Cay

Luxury cottage in the heart of paradise

9.6 out of 10, Exceptional, (26)
"Enjoyed our stay. Location is perfect although there is no beach access just the marina. Close to everything and the place is very nice and clean"
Luxury cottage in the heart of paradise

Mercy’s waterfront piece of paradise

Mercy’s waterfront piece of paradise

Cottage w/ Bay View FREE Kayaks, Snorkel`

Cottage w/ Bay View FREE Kayaks, Snorkel`

Great location -pool-boat ramp-marina-golf cart

10.0 out of 10, Exceptional, (2)
"Good!"
Great location -pool-boat ramp-marina-golf cart

Key Largo Cozy Cottage! Paradise Awaits you! Private Beach& Boat Ramp

10.0 out of 10, Exceptional, (3)
"Super host,very comfortable,clean,well equipped kitchen and the whole place was well equipped. Wonderful place to stay. "
Key Largo Cozy Cottage! Paradise Awaits you! Private Beach& Boat Ramp

BRING YOUR BOAT! Perfect Florida Keys Family Getaway with Activities Galore!

10.0 out of 10, Exceptional, (1)
"We had an awesome time! The house was perfect for us and the host is fantastic! Loved the community and amenities! We would definitely stay again "
BRING YOUR BOAT! Perfect Florida Keys Family Getaway with Activities Galore!

Kayaking, sailing, snorkeling Free w/ Cottage

Kayaking, sailing, snorkeling Free w/ Cottage

Cottage w/ FREE Sailboat, Kayak, Bikes & More

Cottage w/ FREE Sailboat, Kayak, Bikes & More

1 Mi to Dtwn: Oceanfront Gem w/ Resort Amenities!

3.0 star property
1 Mi to Dtwn: Oceanfront Gem w/ Resort Amenities!

Bungalow w/ FREE Kayaks, Sailboat, Bicycle Use

Bungalow w/ FREE Kayaks, Sailboat, Bicycle Use

Large House w/ FREE Sailboat, Kayaks, Snorkel and Fishing Gear

Large House w/ FREE Sailboat, Kayaks, Snorkel and Fishing Gear

Free sailing, kayaking, water toys etc w/ Cottage

Free sailing, kayaking, water toys etc w/ Cottage

Bayside view Cottage , Free kayaks and sailboat

Bayside view Cottage , Free kayaks and sailboat

Cottage w/ Full Kitchen FREE sailboats and kayaks

Cottage w/ Full Kitchen FREE sailboats and kayaks

Cosy Cottage in Islamorada with private garden & pool - 6 pers.

Cosy Cottage in Islamorada with private garden & pool - 6 pers.
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, (421)
"We visited Breezy Palms for our 20th wedding anniversary. We took advantage of the boat rental on site, had a great day on the water. Played cards on our lanai. Used the lovely pool, walked to local restaurants, and had a memorable time. Definitely will be back!"
The price is AU$360
includes taxes & fees
6 Apr - 7 Apr
Breezy Palms Resort

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (52)
"Everything was lovely except I felt rushed on my departure date. A front desk representative knocked around 9am to find out what time I was leaving. If your check out policy is 11am, you should not knock on people’s door to find out what time they are planning on leaving. It doesn’t feel like a luxurious experience when you do. In addition to the early knock, the entire housekeeping staff was waiting by my front door when I checked out at 10:25. What if I wasn’t checking out at 10:25 and was...
The price is AU$1,121
includes taxes & fees
6 Apr - 7 Apr
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."
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.