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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!
Step out onto the deck and enjoy the serene surroundings.

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!
Enjoy meals in this kitchen with a central island and dining area.

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 cooking in this well-equipped kitchen with a central island, ample counter space, and stainless steel appliances.

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
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
Waterfront Gem w/ Decks, Views & More in Key Largo
Enjoy cooking in this well-equipped kitchen with a central island and oven.

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
Enjoy a tranquil beach experience with a picturesque pier and calm waters.

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 by the serene pool surrounded by palm trees and natural rock formations.

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.
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Top Islamorada Hotel Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Its not to close or to far"
Donis 1-night trip
Posted 1 day ago
Chesapeake Beach 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.