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
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug
In one month
22 Aug - 24 Aug
In two months
19 Sept - 21 Sept

Featured Cottages in Islamorada

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
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
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!
Waterfront Home w/ Private Hot Tub in Tavernier!
Interior

Waterfront Home w/ Private Hot Tub in Tavernier!

3.0 star property
Waterfront Home w/ Private Hot Tub in Tavernier!
Lanai, Pool & Patios: Waterfront Home in Tavernier
Interior

Lanai, Pool & Patios: Waterfront Home in Tavernier

3.0 star property
Lanai, Pool & Patios: Waterfront Home in Tavernier
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

Pines & Palms Resort

Pines & Palms Resort

10/10 Excellent
"Everything at Pine and Palms was perfect! Great location!!! Ate at Square Grouper for dinner. Ride our bikes there. "
Ilene 1-night trip
Posted 1 day ago
Pines & Palms Resort

Frequently asked questions

Why book your cottage in Islamorada with Expedia?
We think that travelling should be a walk in the park, so if you're on the lookout for cottages in Islamorada at the perfect price, Expedia has got you covered. Stick to the budget and select a low-cost option far from the rush of the city, or book a luxury cottage to spoil your loved ones.
How can I find cheap cottages in Islamorada?
Expedia is here to help you locate cheap cottages in Islamorada. To discover your special stay in a matter of clicks, try out our convenient filter tool to refine your search results by star rating, amenities and budget.
What is there to do in Islamorada near my cottage?
Whatever you're interested in, Islamorada has a whole lot to capture your imagination. Florida Keys Brewing Co., History of Diving Museum and Bud n' Mary's Dive Centre are on most travellers' itineraries. You shouldn't miss Windley Key Fossil Reef Geological State Park, Theatre of the Sea and Anne's Beach either. With Expedia's Islamorada hotel deals, you can discover more wonderful attractions like these with the money you save.