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
20 Jun - 22 Jun
In two weeks
27 Jun - 29 Jun
In one month
11 Jul - 13 Jul
In two months
8 Aug - 10 Aug

Featured Cottages in Islamorada

Canal-front Florida Keys Home w/ Dock!
Interior

Canal-front Florida Keys Home w/ Dock!

3.0 star property
Canal-front Florida Keys Home w/ Dock!
Luxury Key Largo Home w/ Guest House & Pool!
Interior

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!
Interior

Walk to Beach: Home 8 Mi to Key Largo!

3.0 star property
Walk to Beach: Home 8 Mi to Key Largo!
Half-mi to Boat Ramp: Canal-front Florida Keys Gem
Interior

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

3.0 star property
Half-mi to Boat Ramp: Canal-front Florida Keys Gem
Close to Beach: Canal-front Home in Islamorada
Interior

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!
Interior

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

3.0 star property
1 Mi to Dtwn: Oceanfront Gem w/ Resort Amenities!
Waterfront Gem w/ Decks, Views & More in Key Largo
Interior

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

3.0 star property
Waterfront Gem w/ Decks, Views & More in Key Largo
Lush Tropical Plantings In A Gated Compound Located Directly On The Florida Bay 1 Bedroom Cottage by RedAwning
Property grounds

Lush Tropical Plantings In A Gated Compound Located Directly On The Florida Bay 1 Bedroom Cottage by RedAwning

3.0 star property
Lush Tropical Plantings In A Gated Compound Located Directly On The Florida Bay 1 Bedroom Cottage by RedAwning
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

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.