Search All Cottages in Islamorada, FL

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.

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.

The Key Lime Cottage is situated in a peaceful neighbourhood in Islamorada, just 800 metres from Founders Park and a 5-minute drive south of Annes Beach. The cottage has consistently received excellent ratings for its location, cleanliness, and overall experience.
The property offers two bedrooms and a bathroom, comfortably accommodating up to 5 guests. Amenities include a shared heated pool, a communal kayak launch, access to the "Freebee" electric ride service, a full kitchen, outdoor seating with a grill and fire pit, and beach chairs for enjoying the nearby beaches.

Bungalow Blue is located in the Shady Palms community of Islamorada, at mile marker 76, just a short walk from the community pool and a short bike ride from Robbie's Marina. The cottage has consistently received excellent ratings for its location, cleanliness, and overall experience.
This charming two-bedroom property can comfortably accommodate up to four guests. The cottage offers a private backyard, a fully equipped kitchen with modern appliances, air conditioning, and a private heated pool, making it ideal for a relaxing and enjoyable stay in the Florida Keys.

This holiday home is situated in the Matecumbe district of Islamorada, a 3-minute walk from Islamorada Brewery & Distillery and an 11-minute walk from the History of Diving Museum.
Guests can enjoy a communal swimming pool and hot tub, with amenities including a kayak and bicycles provided for outdoor activities, alongside on-site parking and complimentary Wi-Fi.

This waterside holiday home in Islamorada, Village of Islands, is situated directly on Florida Bay at mile marker 82.2, offering protected boat dockage and close proximity to John Pennekamp Coral Reef State Park, Theater of the Sea, and Robbie's Marina.
This family-friendly bungalow accommodates up to 6 guests and features a ground-floor layout with a king bedroom, an en-suite bathroom, and an enclosed sunroom that functions as a second bedroom, alongside essential amenities like WiFi, air conditioning, and parking.

The Green Cottage is located within the Turtle Cove enclave in Islamorada, Village of Islands, offering peaceful seclusion and views of the pool and ocean.
This family-friendly holiday home sleeps five with two bedrooms and one bathroom, featuring a queen bed and bunk beds, and provides access to shared amenities including a pool, boat basin, and water sports equipment.

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.

This detached house in the Matecumbe district of Islamorada offers a beachfront location, just a 3-minute walk to Islamorada Brewery & Distillery and an 11-minute walk to the History of Diving Museum.
Guests can enjoy a family-friendly stay with amenities including air conditioning, a full kitchen, complimentary Wi-Fi, a swimming pool, jacuzzi, garden, spa, parking, and access to on-site kayaks and bicycles for exploring the Village of Islands.

This Islamorada canal-side property, minutes from the Snake Creek Bridge and close to Theatre of the Sea, Founders Park, restaurants, and shops, offers a private dock, BBQ facilities, and a hammock for enjoying the waterfront.
The two-bedroom, one-bathroom house sleeps four guests and includes a kitchen with fridge, freezer, and microwave, air conditioning, a swimming pool, garden, parking, internet access, and pet-friendly accommodation.

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.