A beach with white lounge chairs, a covered pavilion, and palm trees.

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Islamorada cottages

Two small, single-story buildings with a red and yellow exterior, each with a door and windows, and surrounded by greenery and trees.

1. Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,015 reviews)
"The family running the food truck and tiki hut were great. Felt like we were guests in their home."
United States
Douglas
$90 nightly
The price is $101
Nov 15 - Nov 16
Total with taxes and fees
Tropical Cottages
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 room was very clean and comfortable, my only issue was it was close to the road so all you hear is road traffic. I asked to move rooms but we weren’t able to. The breakfast was nice- homemade omelet and waffles, a selections of items to toast. The bar tender Jose was super nice and very helpful as well as maintenance man Douglas- he was super Friendly. We thought the amenities were great and we would totally stay again!"
Wendy Gail 6-night trip
Posted 14 hours ago
Chesapeake Beach Resort

Find out more about Islamorada

Islamorada Cottages information

Number of reviews
Accommodation
27 Cottages
Lowest Price
$101
Highest Price
$101

Frequently asked questions

Why book your cottage in Islamorada with Expedia?
We think that traveling 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.
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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 Center are on most travelers' itineraries. You shouldn't miss Windley Key Fossil Reef Geological State Park, Theater 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.

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