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Islamorada, FL cottages
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23 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.

Oceanfront Private Cottage! - Islamorada, FL
10 117 reviews

Oceanfront Private Cottage!

cottage, Islamorada, Village of Islands
This oceanfront cottage is situated in Matecumbe, a neighborhood in Islamorada, Village of Islands, offering easy access to nearby attractions. It has excellent user ratings and features one bedroom and one bathroom.
The cottage has been newly renovated and decorated with modern and stylish interior, all new appliances and furnishings. It includes amenities like a private boat dock and ramp, kayaks and bicycles, a tiki hut, and fishing charter options.
Cottage ∙ 1 Bedroom ∙ 4 Guests - Islamorada, FL
No reviews

Cottage ∙ 1 Bedroom ∙ 4 Guests

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.
Cottage ∙ 2 Bedrooms ∙ 5 Guests - Islamorada, FL
No reviews

Cottage ∙ 2 Bedrooms ∙ 5 Guests

cottage, Islamorada, Village of Islands
The Green Cottage is located in Turtle Cove, a private community of five vacation homes in Islamorada, Florida, offering pool and ocean views.
This 2-bedroom, 1-bathroom cottage accommodates up to 5 guests and features a queen bed in the master bedroom and a full/twin bunk bed in the second bedroom, with shared amenities including a pool, boat basin, kayaks, and paddleboards.

Best Islamorada, FL cottages with a garden

Oceanfront Private Cottage! - Islamorada, FL
10 117 reviews

Oceanfront Private Cottage!

cottage, Islamorada, Village of Islands
This oceanfront cottage is situated in Matecumbe, a neighborhood in Islamorada, Village of Islands, offering easy access to nearby attractions. It has excellent user ratings and features one bedroom and one bathroom.
The cottage has been newly renovated and decorated with modern and stylish interior, all new appliances and furnishings. It includes amenities like a private boat dock and ramp, kayaks and bicycles, a tiki hut, and fishing charter options.
Serene Cozy Cottage In Islamorada With Heated Pool - Islamorada, FL
9.6 161 reviews

Serene Cozy Cottage In Islamorada With Heated Pool

apartment, 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.

Frequently Asked Questions about cottages in Islamorada, FL

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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
No reviews

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

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.

Ocean Front Unit In Islamorada | Enjoy Scenic Walks On Private Beach - Islamorada, FL
8.0 2 reviews

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

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.
Oceanfront Cottage In Islamorada! Swimming Pool, Pets Allowed, Free Parking! - Islamorada, FL
No reviews

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

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.
Oceanfront Private Cottage! - Islamorada, FL
10 117 reviews

Oceanfront Private Cottage!

cottage, Islamorada, Village of Islands
This oceanfront cottage is situated in Matecumbe, a neighborhood in Islamorada, Village of Islands, offering easy access to nearby attractions. It has excellent user ratings and features one bedroom and one bathroom.
The cottage has been newly renovated and decorated with modern and stylish interior, all new appliances and furnishings. It includes amenities like a private boat dock and ramp, kayaks and bicycles, a tiki hut, and fishing charter options.
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