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Islamorada, FL cottages
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30 Best cottages in Islamorada, FL

Our Favorite Family-Friendly Cottages in Islamorada, FL

A family cottage near the water in Islamorada, FL offers plenty of room for everyone to spread out.

Cottage ∙ 1 Bedroom ∙ 4 Guests - Islamorada, FL
Islamorada, FL
06/20 – 06/27
$616/nighttotal: $4312 (7 )

Cottage ∙ 1 Bedroom ∙ 4 Guests

1 2
cottage , Islamorada, Village of Islands
Little Bay Cottage is a secluded retreat on a lush one-acre tropical property in Islamorada, Village of Islands. It offers direct bay access, a protected dock for boats up to 34 feet, and stunning views of Florida Bay from the covered balcony.
The cottage has two bedrooms, two bathrooms, and a queen-size sleeper sofa, comfortably accommodating up to six guests. It features a modern kitchen with granite countertops and new appliances, as well as outdoor relaxation areas with hammocks, a pergola, and a tiki hut. Activities and attractions nearby include John Pennekamp Coral Reef State Park, Theater of the Sea, and Robbie's Marina.

Best Islamorada, FL cottages with a garden

2br/1ba Serene Cozy Cottage Of Shady Palms In Islamorada With Heated Pool - Islamorada, FL
9.6 155 reviews
Islamorada, FL
10/09 – 10/12
$312/nighttotal: $936 (3 )

2br/1ba Serene Cozy Cottage Of Shady Palms In Islamorada With Heated Pool

1 2
cottage , Islamorada, Village of Islands
This charming cottage is located at mile marker 76.7 in Islamorada, just a short drive from Caloosa Cove Marina and Robbie's Marina, offering a peaceful retreat away from the hustle and bustle of the main tourist areas. The cottage has consistently received excellent ratings from previous guests for its cleanliness, location, and overall experience.
The cottage has two bedrooms and comfortably accommodates four guests. Enjoy a refreshing dip in the heated swimming pool, shared exclusively with a select few cottages at Shady Palms, and take advantage of the starter pack with essential supplies, convenient parking, and family-friendly features.

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Top-Rated Cottages with a Hot Tub in Islamorada, FL

Whether you prefer a jacuzzi or a hot tub, these Islamorada, FL cottages are designed for a private soak after a day by the water.

Oceanfront Cottage In Islamorada! Swimming Pool, Pets Allowed, Free Parking! - Islamorada, FL
Islamorada, FL
07/18 – 07/22
$902/nighttotal: $3608 (4 )

Oceanfront Cottage In Islamorada! Swimming Pool, Pets Allowed, Free Parking!

1 4
cottage , Islamorada, Village of Islands
This Islamorada pet-friendly cottage, located in the Matecumbe district, offers easy access to Bud n' Mary's Dive Center (a 14-minute walk) and Indian Key Historic State Park (a 6-minute walk).
This one-bedroom, one-bathroom vacation home sleeps four and features a private balcony, shared pool access, kayaks, bicycles, free Wi-Fi, and a fully equipped kitchen; nearby attractions include Hurricane Monument and several state parks.

Explore Dog-Friendly Cottages in Islamorada, FL

Traveling with a pet to Islamorada, FL is simple at these cottages, featuring dog-friendly facilities.

Oceanfront Cottage In Islamorada! Swimming Pool, Pets Allowed, Free Parking! - Islamorada, FL
Islamorada, FL
07/18 – 07/22
$902/nighttotal: $3608 (4 )

Oceanfront Cottage In Islamorada! Swimming Pool, Pets Allowed, Free Parking!

1 4
cottage , Islamorada, Village of Islands
This Islamorada pet-friendly cottage, located in the Matecumbe district, offers easy access to Bud n' Mary's Dive Center (a 14-minute walk) and Indian Key Historic State Park (a 6-minute walk).
This one-bedroom, one-bathroom vacation home sleeps four and features a private balcony, shared pool access, kayaks, bicycles, free Wi-Fi, and a fully equipped kitchen; nearby attractions include Hurricane Monument and several state parks.
Ocean Front Unit In Islamorada | Enjoy Scenic Walks On Private Beach - Islamorada, FL
8.0 2 reviews
Islamorada, FL
06/20 – 06/27
$884/nighttotal: $6188 (7 )

Ocean Front Unit In Islamorada | Enjoy Scenic Walks On Private Beach

1 2
cottage , Islamorada, Village of Islands
This Islamorada beachfront cottage in Matecumbe offers direct ocean access, a 15-minute walk from Indian Key Historic State Park and Bud n' Mary's Dive Center, and under a mile from the Hurricane Monument and Florida Keys Brewing Co.
The 450-square-foot, one-bedroom, one-bathroom vacation home sleeps four and includes a private balcony, air conditioning, Wi-Fi, a swimming pool, parking, and concierge services.
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