Search All Cottages in Islamorada, FL

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Islamorada, FL cottages
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23 Cottages at the best price in Islamorada, FL

Explore Family-Friendly Holiday Cottages in Islamorada, FL

These family-friendly cottages in Islamorada, FL offer easy beach access and plenty of room to spread out.

Cottage ∙ 4 Bedrooms ∙ 8 Guests - Islamorada, FL
8.0 1 review

Cottage ∙ 4 Bedrooms ∙ 8 Guests

cottage, Islamorada, Village of Islands
This oceanfront holiday home in Islamorada, Village of Islands, is located at Mile Marker 83 and offers direct access to the Atlantic Ocean and a private sandy beach, with a skiff dock suitable for shallow draft boats.
This spacious 4-bedroom, 3-bathroom villa accommodates up to 8 guests and features a heated beachside swimming pool, a separate spa, a garden cottage, and is a noted destination for weddings, providing excellent amenities and activities for families and pets.
Cottage ∙ 1 Bedroom ∙ 4 Guests - Islamorada, FL
No reviews

Cottage ∙ 1 Bedroom ∙ 4 Guests

cottage, Islamorada, Village of Islands
Little Bay Cottage is located directly on Florida Bay in Islamorada, just off Overseas Highway at Mile Marker 82.2, within easy reach of attractions like John Pennekamp Coral Reef State Park and Robbie's Marina. The cottage is part of a gated compound offering privacy and security, and has a unique floor plan with a spacious living area, two bedrooms and two bathrooms, comfortably sleeping up to four guests.
The cottage features a modern kitchen with new appliances and granite countertops, as well as a full-size washer and dryer, central air conditioning, and WiFi. Guests can also enjoy a variety of outdoor spaces for relaxation, including a sunning area with lounge chairs, hammocks, a pergola and a tiki hut, as well as a protected dock for boats up to 10 metres long.
Oceanfront Private Cottage! - Islamorada, FL
10 117 reviews

Oceanfront Private Cottage!

cottage, Islamorada, Village of Islands
This charming cottage is situated in the Matecumbe district of Islamorada, just a short distance from Florida Keys Brewing Co. and Bud n' Mary's Dive Center, making it ideal for exploring the area's attractions. The cottage has received excellent reviews from previous guests, highlighting its comfortable and well-equipped nature.
The cottage is a single-bedroom property with a fully equipped kitchen and a private terrace, perfect for enjoying the fresh air and stunning ocean views. Guests can enjoy a range of amenities including a private boat dock, kayaks, and bicycles, allowing them to explore the local area and experience the beauty of the Florida Keys.

Best Islamorada, FL cottages with a garden

Cottage ∙ 2 Bedrooms ∙ 6 Guests - Islamorada, FL
No reviews

Cottage ∙ 2 Bedrooms ∙ 6 Guests

cottage, Islamorada, Village of Islands
This conch-style dwelling is situated directly on Florida Bay on Upper Matecumbe Key, approximately 30 meters from the water, within a native hammock extending from US 1, placing it in the "Sportfishing Capital of the World."
This two-bedroom, two-bathroom holiday home accommodates up to six guests and offers a protected boat basin for vessels up to 8 meters, a boat launching ramp, and access to Founders Park's Olympic-size pool and beach, with opportunities for fishing, snorkelling, and kayaking.
Oceanfront Private Cottage! - Islamorada, FL
10 117 reviews

Oceanfront Private Cottage!

cottage, Islamorada, Village of Islands
This charming cottage is situated in the Matecumbe district of Islamorada, just a short distance from Florida Keys Brewing Co. and Bud n' Mary's Dive Center, making it ideal for exploring the area's attractions. The cottage has received excellent reviews from previous guests, highlighting its comfortable and well-equipped nature.
The cottage is a single-bedroom property with a fully equipped kitchen and a private terrace, perfect for enjoying the fresh air and stunning ocean views. Guests can enjoy a range of amenities including a private boat dock, kayaks, and bicycles, allowing them to explore the local area and experience the beauty of the Florida Keys.
Cottage ∙ 4 Bedrooms ∙ 8 Guests - Islamorada, FL
8.0 1 review

Cottage ∙ 4 Bedrooms ∙ 8 Guests

cottage, Islamorada, Village of Islands
This oceanfront holiday home in Islamorada, Village of Islands, is located at Mile Marker 83 and offers direct access to the Atlantic Ocean and a private sandy beach, with a skiff dock suitable for shallow draft boats.
This spacious 4-bedroom, 3-bathroom villa accommodates up to 8 guests and features a heated beachside swimming pool, a separate spa, a garden cottage, and is a noted destination for weddings, providing excellent amenities and activities for families and pets.

Frequently asked questions about cottages in Islamorada, FL

Popular destinations

Find the Best Cottages with a Hot Tub in Islamorada, FL

Unwind after a coastal adventure with a private hot tub soak at your Islamorada, FL cottage.

Lush Tropical Plantings In A Gated Compound Located Directly On The Florida Bay - Islamorada, FL
No reviews

Lush Tropical Plantings In A Gated Compound Located Directly On The Florida Bay

cottage, Islamorada, Village of Islands
This Islamorada holiday home is conveniently located within a 2.4km walk of the Islamorada Brewery & Distillery, Keys History & Discovery Centre, and History of Diving Museum.
The two-bedroom, two-bathroom property sleeps four guests and boasts a fully equipped kitchen, swimming pool, spa, on-site water park, BBQ grills, and in-unit laundry facilities.

Discover Dog-Friendly Holiday Cottages in Islamorada, FL

Book a dog-friendly cottage in Islamorada, FL for a relaxing break that welcomes the whole family.

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 beachfront cottage in Islamorada's Matecumbe district is situated less than 2.4km from Indian Key Historic State Park and Bud n' Mary's Dive Center, and under 1.6km from the Hurricane Monument and Florida Keys Brewing Company.
This 42 square metre self-catering property sleeps four, featuring a bedroom, bathroom, private balcony with potential ocean views, and amenities including air conditioning, Wi-Fi, a swimming pool, and parking.
Cottage ∙ 4 Bedrooms ∙ 8 Guests - Islamorada, FL
8.0 1 review

Cottage ∙ 4 Bedrooms ∙ 8 Guests

cottage, Islamorada, Village of Islands
This oceanfront holiday home in Islamorada, Village of Islands, is located at Mile Marker 83 and offers direct access to the Atlantic Ocean and a private sandy beach, with a skiff dock suitable for shallow draft boats.
This spacious 4-bedroom, 3-bathroom villa accommodates up to 8 guests and features a heated beachside swimming pool, a separate spa, a garden cottage, and is a noted destination for weddings, providing excellent amenities and activities for families and pets.
Cottage ∙ 2 Bedrooms ∙ 6 Guests - Islamorada, FL
No reviews

Cottage ∙ 2 Bedrooms ∙ 6 Guests

cottage, Islamorada, Village of Islands
This conch-style dwelling is situated directly on Florida Bay on Upper Matecumbe Key, approximately 30 meters from the water, within a native hammock extending from US 1, placing it in the "Sportfishing Capital of the World."
This two-bedroom, two-bathroom holiday home accommodates up to six guests and offers a protected boat basin for vessels up to 8 meters, a boat launching ramp, and access to Founders Park's Olympic-size pool and beach, with opportunities for fishing, snorkelling, and kayaking.
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 pet-friendly cottage in Islamorada's Matecumbe district is conveniently located less than 1km from Bud n' Mary's Dive Center and Indian Key Historic State Park.
Sleeping up to four guests, this one-bedroom, one-bathroom self-catering property offers a private balcony, shared swimming pool, free Wi-Fi, and access to kayaks and bicycles, ideal for exploring the surrounding area.

Find the Best Seaside Cottages in Islamorada, FL

Book a refreshing coastal getaway at comfortable shoreside cottages in Islamorada, FL located near the beach.

Cottage ∙ 2 Bedrooms ∙ 6 Guests - Islamorada, FL
No reviews

Cottage ∙ 2 Bedrooms ∙ 6 Guests

cottage, Islamorada, Village of Islands

Browse Luxury Cottages in Islamorada, FL

Coastal elegance defines our luxury cottages in Islamorada, FL, where every detail is considered for your stay.

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

Popular Cottages with a Pool in Islamorada, FL

Take a dip whenever the mood strikes with an on-site pool at your waterside cottage in Islamorada, FL.

Oceanfront Private Cottage! - Islamorada, FL
10 117 reviews

Oceanfront Private Cottage!

cottage, Islamorada, Village of Islands

Top Holiday Cottages with Free Parking in Islamorada, FL

Enjoy hassle-free seaside trips with private parking included at every Islamorada, FL cottage near the beach.

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

Search Holiday Cottages with Spa Facilities in Islamorada, FL

Experience waterside wellness with full spa bath access at a spa-equipped cottage in Islamorada, FL.

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
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