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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Cottages in Islamorada and around

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`
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!
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!
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!
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!
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
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
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
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
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
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
Bayside view Cottage , Free kayaks and sailboat
Relax on the beach with a pier stretching into the calm waters, surrounded by moored boats and a shaded area.

Bayside view Cottage , Free kayaks and sailboat

Bayside view Cottage , Free kayaks and sailboat
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
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.
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
"The hotel is very well located. It was a very comfortable place and Jeff was very nice and made great omelettes in the morning"
Juan Andres 2-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.