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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

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
Guests can enjoy a refreshing swim in the pool surrounded by a residential building.

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!
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
House (4 Bedrooms) | 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
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 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!
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 and socialize in this outdoor patio area with cushioned seating and a round table.

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.
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Top Islamorada Hotel Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"We have been coming here for 5 years and the place gets better and better. Every year we come they have added new amenities. The beach and pools are amazing and the location makes it easy to go anywhere in the Keys quickly. If you are looking for a great resort for a great price in this area it is a GREAT option!"
Michael 4-night trip
Posted 15 hours ago
Chesapeake Beach Resort

Frequently asked questions

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.