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Check prices for these dates

In two weeks
12 Sept - 14 Sept
In one month
26 Sept - 28 Sept
In two months
24 Oct - 26 Oct
In three months
21 Nov - 23 Nov

Featured Cottages in Islamorada

Our top choices for Islamorada cottages

Oceanfront Private Cottage!
Exterior

Oceanfront Private Cottage!

10.0 out of 10, Exceptional, (108)
"Great location close to restaurants and everything else you may need!"
Oceanfront Private Cottage!
Mercy’s waterfront piece of paradise
Outdoor pool

Mercy’s waterfront piece of paradise

Mercy’s waterfront piece of paradise
Cottage w/ Bay View FREE Kayaks, Snorkel`
Marina

Cottage w/ Bay View FREE Kayaks, Snorkel`

Cottage w/ Bay View FREE Kayaks, Snorkel`
Canal-front Florida Keys Home w/ Dock!
House (2 Bedrooms) | 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!
House (3 Bedrooms) | Interior

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
Interior

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

3.0 star property
Waterfront Gem w/ Decks, Views & More in Key Largo
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!
Close to Beach: Canal-front Home in Islamorada
House (4 Bedrooms) | Interior

Close to Beach: Canal-front Home in Islamorada

3.0 star property
Close to Beach: Canal-front Home in Islamorada
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
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!
Cottage w/ FREE Sailboat, Kayak, Bikes & More
Marina

Cottage w/ FREE Sailboat, Kayak, Bikes & More

Cottage w/ FREE Sailboat, Kayak, Bikes & More
Bungalow w/ FREE Kayaks, Sailboat, Bicycle Use
Marina

Bungalow w/ FREE Kayaks, Sailboat, Bicycle Use

Bungalow w/ FREE Kayaks, Sailboat, Bicycle Use
Kayaking, sailing, snorkeling Free w/ Cottage
Marina

Kayaking, sailing, snorkeling Free w/ Cottage

Kayaking, sailing, snorkeling Free w/ Cottage
Cottage w/ Full Kitchen FREE sailboats and kayaks
Marina

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
Marina

Large House w/ FREE Sailboat, Kayaks, Snorkel and Fishing Gear

Large House w/ FREE Sailboat, Kayaks, Snorkel and Fishing Gear
Key Largo Cottages w/ Free Sailboat, Kayaks + More
Marina

Key Largo Cottages w/ Free Sailboat, Kayaks + More

Key Largo Cottages w/ Free Sailboat, Kayaks + More
Cottage w/ Private Yard, Free Kayaks, Boats, Etc
Marina

Cottage w/ Private Yard, Free Kayaks, Boats, Etc

Cottage w/ Private Yard, Free Kayaks, Boats, Etc
Free sailing, kayaking, water toys etc w/ Cottage
Marina

Free sailing, kayaking, water toys etc w/ Cottage

Free sailing, kayaking, water toys etc w/ Cottage
Bayside view Cottage , Free kayaks and sailboat
Marina

Bayside view Cottage , Free kayaks and sailboat

Bayside view Cottage , Free kayaks and sailboat
Waterfront Cottage at Tavernier, Florida Keys
Marina

Waterfront Cottage at Tavernier, Florida Keys

10.0 out of 10, Exceptional, (3)
"My wife and I had a wonderful stay here during the month of March escaping the cold from the Northeast. The house was immaculate and decorated very nicely inside. The kitchen and bathrooms were well stocked with essentials items. The neighborhood was very peaceful and quiet and the neighbors were very friendly. The house backs up to a canal/waterway from which we could watch the graceful pelicans gliding by from the very large back deck which is where we spent a lot of our time. Rene was a...
Waterfront Cottage at Tavernier, Florida Keys
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

Find out more about Islamorada

Find out more about Islamorada

Islamorada Cottages information

Number of reviews
Accommodation
30 Cottages
Lowest Price
Highest Price

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Frequently asked questions

What is there to do in Islamorada near my cottage?
There are tons of superb things to sink your teeth into in Islamorada. Don't miss renowned attractions like Theatre of the Sea, Annes Beach and Windley Key Fossil Reef Geological State Park. Florida Keys Brewing Co., Sunset Drive Beach and Indian Key Historic State Park are other must-do's.