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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept
Oceanfront Private Cottage!
Guests can enjoy access to the beach and a pier from this coastal property.

Oceanfront Private Cottage!

10.0 out of 10, Exceptional, (107)
"Great location close to restaurants and everything else you may need!"
Oceanfront Private Cottage!
Mercy’s waterfront piece of paradise
Guests can enjoy a refreshing swim in the pool surrounded by a residential building.

Mercy’s waterfront piece of paradise

Mercy’s waterfront piece of paradise
Escape to a Charming 2-Bedroom Cottage in Long Key – Your Perfect Getaway!
Relax by the pool surrounded by lush surroundings and lounge in style with comfortable seating.

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!
BRING YOUR BOAT! Perfect Florida Keys Family Getaway with Activities Galore!
Guests can enjoy a tranquil marina experience with a wooden pier leading to a dock area.

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

10.0 out of 10, Exceptional, (2)
"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!
Canal-front Florida Keys Home w/ Dock!
Enjoy cooking in this well-equipped kitchen with a central island, ample counter space, and stainless steel appliances.

Canal-front Florida Keys Home w/ Dock!

3.0 star property
Canal-front Florida Keys Home w/ Dock!
Soothing Duck Key Vacation Rental!
Relax in a shaded patio area with a thatched roof, surrounded by lush greenery and a nearby pool.

Soothing Duck Key Vacation Rental!

3.0 star property
Soothing Duck Key Vacation Rental!
Close to Beach: Canal-front Home in Islamorada
Enjoy a tranquil beach experience with a picturesque pier and calm waters.

Close to Beach: Canal-front Home in Islamorada

3.0 star property
Close to Beach: Canal-front Home in Islamorada
Walk to Beach: Home 8 Mi to Key Largo!
Enjoy meals in this kitchen with a central island and dining area.

Walk to Beach: Home 8 Mi to Key Largo!

3.0 star property
Walk to Beach: Home 8 Mi to Key Largo!
Half-mi to Boat Ramp: Canal-front Florida Keys Gem
Interior

Half-mi to Boat Ramp: Canal-front Florida Keys Gem

3.0 star property
Half-mi to Boat Ramp: Canal-front Florida Keys Gem
Marathon Vacation Rental With Pool Access!
Relax on the shaded deck overlooking the pool, surrounded by natural ambiance and comfortable seating.

Marathon Vacation Rental With Pool Access!

3.0 star property
Marathon Vacation Rental With Pool Access!
Escape to a Charming 2-Bedroom Cottage in Long Key – Your Perfect Getaway!
Relax by the pool surrounded by lounge chairs and umbrellas, with steps leading down to the water.

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!
Cosy Cottage in Islamorada with private garden & pool - 6 pers.
Relax by the pool surrounded by lush greenery and palm trees.

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

Cosy Cottage in Islamorada with private garden & pool - 6 pers.
Waterfront Cottage at Tavernier, Florida Keys
Boats docked along the marina, adjacent to residential buildings with balconies.

Waterfront Cottage at Tavernier, Florida Keys

10.0 out of 10, Exceptional, (3)
"My wife and I had a wonderful stay here during the month of March escaping the cold from the Northeast. The house was immaculate and decorated very nicely inside. The kitchen and bathrooms were well stocked with essentials items. The neighborhood was very peaceful and quiet and the neighbors were very friendly. The house backs up to a canal/waterway from which we could watch the graceful pelicans gliding by from the very large back deck which is where we spent a lot of our time. Rene was a...
Waterfront Cottage at Tavernier, Florida Keys
Florida Keys Waterfront with Boat Dock
Enjoy the serene waterfront views from this sheltered outdoor space.

Florida Keys Waterfront with Boat Dock

2.0 star property
Florida Keys Waterfront with Boat Dock
Lush tropical plantings in a gated compound located directly on the Florida Bay
Relax in a serene outdoor seating area overlooking a calm body of water.

Lush tropical plantings in a gated compound located directly on the Florida Bay

Lush tropical plantings in a gated compound located directly on the Florida Bay
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 Lower Matecumbe Key Hotel Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"It was new, loved the balcony. Beach sports were nice but needed more lifejacket sizes. Pool amenities were great. Breakfast was good. "
Edgardo 1-night trip
Posted 2 days ago
Chesapeake Beach Resort