Search Islamorada Cottage Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 8 - Aug 10
In two weeks
Aug 15 - Aug 17
In one month
Aug 29 - Aug 31
In two months
Sep 26 - Sep 28

Browse Select Islamorada Cottages

Oceanfront Private Cottage!
Guests can enjoy access to the beach and a pier from this coastal property.

Oceanfront Private Cottage!

10.0 out of 10, Exceptional, (107)
"Great location close to restaurants and everything else you may need!"
Oceanfront Private Cottage!
Mercy’s waterfront piece of paradise
Enjoy breathtaking ocean views from this beachfront balcony, surrounded by palm trees.

Mercy’s waterfront piece of paradise

Mercy’s waterfront piece of paradise
Cottage w/ Bay View FREE Kayaks, Snorkel`
Relax on the beach with lounge chairs and tables, surrounded by palm trees and a wooden pier.

Cottage w/ Bay View FREE Kayaks, Snorkel`

Cottage w/ Bay View FREE Kayaks, Snorkel`
Luxury Key Largo Home w/ Guest House & Pool!
Enjoy al fresco dining in a serene setting surrounded by lush greenery and a staircase leading to an upper level.

Luxury Key Largo Home w/ Guest House & Pool!

3.0 star property
Luxury Key Largo Home w/ Guest House & Pool!
Walk to Beach: Home 8 Mi to Key Largo!
Stroll through the charming garden, surrounded by lush plants and trees, to the inviting front entrance of this cozy home.

Walk to Beach: Home 8 Mi to Key Largo!

3.0 star property
Walk to Beach: Home 8 Mi to Key Largo!
Canal-front Florida Keys Home w/ Dock!
Enjoy a tranquil view of the marina from this balcony with seating for two.

Canal-front Florida Keys Home w/ Dock!

3.0 star property
Canal-front Florida Keys Home w/ Dock!
Half-mi to Boat Ramp: Canal-front Florida Keys Gem
House (4 Bedrooms) | Front of property

Half-mi to Boat Ramp: Canal-front Florida Keys Gem

3.0 star property
Half-mi to Boat Ramp: Canal-front Florida Keys Gem
Waterfront Gem w/ Decks, Views & More in Key Largo
Relax in this inviting outdoor seating area with a glass-top table and wicker chairs.

Waterfront Gem w/ Decks, Views & More in Key Largo

3.0 star property
Waterfront Gem w/ Decks, Views & More in Key Largo
Close to Beach: Canal-front Home in Islamorada
Relax on the balcony with a wicker sofa and enjoy the view of the surrounding neighborhood.

Close to Beach: Canal-front Home in Islamorada

3.0 star property
Close to Beach: Canal-front Home in Islamorada
Kayaking, sailing, snorkeling Free w/ Cottage
Relax on the beach with lounge chairs and tables, surrounded by palm trees and a thatched-roof structure.

Kayaking, sailing, snorkeling Free w/ Cottage

Kayaking, sailing, snorkeling Free w/ Cottage
1 Mi to Dtwn: Oceanfront Gem w/ Resort Amenities!
Relax on the beach with a view of the ocean from our lounge chairs.

1 Mi to Dtwn: Oceanfront Gem w/ Resort Amenities!

3.0 star property
1 Mi to Dtwn: Oceanfront Gem w/ Resort Amenities!
Bungalow w/ FREE Kayaks, Sailboat, Bicycle Use
Relax on the beach with lounge chairs and tables, surrounded by palm trees and a wooden pier.

Bungalow w/ FREE Kayaks, Sailboat, Bicycle Use

Bungalow w/ FREE Kayaks, Sailboat, Bicycle Use
Cottage w/ Private Yard, Free Kayaks, Boats, Etc
Relax on the beach with lounge chairs and enjoy the tranquil atmosphere near a thatched-roof structure and wooden pier.

Cottage w/ Private Yard, Free Kayaks, Boats, Etc

Cottage w/ Private Yard, Free Kayaks, Boats, Etc
Large House w/ FREE Sailboat, Kayaks, Snorkel and Fishing Gear
Relax on the beach with lounge chairs and a shaded hut, surrounded by palm trees and a wooden pier.

Large House w/ FREE Sailboat, Kayaks, Snorkel and Fishing Gear

Large House w/ FREE Sailboat, Kayaks, Snorkel and Fishing Gear
Free sailing, kayaking, water toys etc w/ Cottage
Relax on the beach with lounge chairs and a table, surrounded by palm trees and a thatched-roof structure.

Free sailing, kayaking, water toys etc w/ Cottage

Free sailing, kayaking, water toys etc w/ Cottage
Key Largo Cottages w/ Free Sailboat, Kayaks + More
Relax on the beach with lounge chairs and enjoy the tranquil atmosphere.

Key Largo Cottages w/ Free Sailboat, Kayaks + More

Key Largo Cottages w/ Free Sailboat, Kayaks + More
Cottage w/ FREE Sailboat, Kayak, Bikes & More
Relax on the beach with lounge chairs and a table, surrounded by a serene beachside setting and a wooden pier.

Cottage w/ FREE Sailboat, Kayak, Bikes & More

Cottage w/ FREE Sailboat, Kayak, Bikes & More
Cottage w/ Full Kitchen FREE sailboats and kayaks
Relax on the beach with lounge chairs and enjoy refreshments at the nearby kiosk.

Cottage w/ Full Kitchen FREE sailboats and kayaks

Cottage w/ Full Kitchen FREE sailboats and kayaks
Cosy Cottage in Islamorada with private garden & pool - 6 pers.
Relax by the pool surrounded by lush greenery and palm trees.

Cosy Cottage in Islamorada with private garden & pool - 6 pers.

Cosy Cottage in Islamorada with private garden & pool - 6 pers.
Charming Seaside Getaway with All the Comforts of Home
Relax in style on this serene patio, surrounded by lush greenery and a tranquil body of water.

Charming Seaside Getaway with All the Comforts of Home

Charming Seaside Getaway with All the Comforts of Home
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Islamorada Hotel Reviews

Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

10/10 Excellent
"Beautiful setting with nice pool as well! The staff is very friendly and helpful, especially Clancy!!"
Rebecca 1-night trip
Posted 1 day ago
Coconut Cove Resort and Marina