Search All Cottages in Islamorada, FL

23 available cottage rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Islamorada, FL cottages
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

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.

Private Cottage On Bayfront Estate With Heated Pool, Deep Dockage, Kayaks And More - Islamorada, FL
10 16 reviews

Private Cottage On Bayfront Estate With Heated Pool, Deep Dockage, Kayaks And More

cottage, Islamorada, Village of Islands
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.
Charming 2br Cottage In Prime Keys Location W/pool - Islamorada, FL
9.9 147 reviews

Charming 2br Cottage In Prime Keys Location W/pool

cottage, Islamorada, Village of Islands
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.
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.
Lush Tropical Setting With Dockage - Charming Coastal Retreat - Islamorada, FL
No reviews

Lush Tropical Setting With Dockage - Charming Coastal Retreat

cottage, Islamorada, Village of Islands
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.

Best Islamorada, FL cottages with a garden

Charming 2br Cottage In Prime Keys Location W/pool - Islamorada, FL
9.9 147 reviews

Charming 2br Cottage In Prime Keys Location W/pool

cottage, Islamorada, Village of Islands
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.
Private Cottage On Bayfront Estate With Heated Pool, Deep Dockage, Kayaks And More - Islamorada, FL
10 16 reviews

Private Cottage On Bayfront Estate With Heated Pool, Deep Dockage, Kayaks And More

cottage, Islamorada, Village of Islands
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.
Cottage With Dock Space - Islamorada, FL
10 1 review

Cottage With Dock Space

cottage, Islamorada, 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.
Islamorada Bungalow 2 Bed & Pool - Islamorada, FL
9.9 104 reviews

Islamorada Bungalow 2 Bed & Pool

cottage, Islamorada, Village of Islands
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.

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.

Private Cottage On Bayfront Estate With Heated Pool, Deep Dockage, Kayaks And More - Islamorada, FL
10 16 reviews

Private Cottage On Bayfront Estate With Heated Pool, Deep Dockage, Kayaks And More

cottage, Islamorada, Village of Islands
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.

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.

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.
Private Cottage On Bayfront Estate With Heated Pool, Deep Dockage, Kayaks And More - Islamorada, FL
10 16 reviews

Private Cottage On Bayfront Estate With Heated Pool, Deep Dockage, Kayaks And More

cottage, Islamorada, Village of Islands
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.
Cottage With Dock Space - Islamorada, FL
10 1 review

Cottage With Dock Space

cottage, Islamorada, 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.
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.

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 ∙ 1 Bedroom ∙ 4 Guests - Islamorada, FL
No reviews

Cottage ∙ 1 Bedroom ∙ 4 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.

Cottage ∙ 1 Bedroom ∙ 4 Guests - Islamorada, FL
No reviews

Cottage ∙ 1 Bedroom ∙ 4 Guests

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.

Islamorada Bungalow 2 Bed & Pool - Islamorada, FL
9.9 104 reviews

Islamorada Bungalow 2 Bed & Pool

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.

Cottage ∙ 1 Bedroom ∙ 4 Guests - Islamorada, FL
No reviews

Cottage ∙ 1 Bedroom ∙ 4 Guests

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.

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
©2026 cozycozy.com