Windley Key, FL

Travel Guide

A colorful building with a sign reading "Florida Keys Brewing Co." and a Santa Claus decoration.
A forest path surrounded by dense green foliage and trees.
A rocky cliff with intricate erosion patterns and a small cave entrance.
A close-up of a palm plant with long, green leaves against a rocky background.
A forest path surrounded by trees and foliage.
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

4 out of 5
84001 Overseas Hwy Islamorada FL
$272 nightly
The price is $306 total per night from Sep 2 to Sep 3
$306 total
Sep 2 - Sep 3
Total with taxes and fees
Book a stay at this beach resort in Islamorada. Enjoy free WiFi, 3 outdoor pools, and 4 restaurants. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (255 reviews)
"I’d recommend getting breakfast locally instead of the resort’s breakfast. Very friendly and helpful staff."

Reviewed on Aug 23, 2026

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

3.5 out of 5
84951 Overseas Hwy Islamorada FL
$139 nightly
The price is $156 total per night from Aug 30 to Aug 31
$156 total
Aug 30 - Aug 31
Total with taxes and fees
Book a stay at this beach motel in Islamorada. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in ...
8.2/10 Very Good! (1,015 reviews)
"Was Great! Everyone was super nice and helpful!"

Reviewed on Aug 23, 2026

Fisher Inn Resort & Marina
Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

3 out of 5
84801 Overseas Highway Islamorada FL
$141 nightly
The price is $159 total per night from Sep 7 to Sep 8
$159 total
Sep 7 - Sep 8
Total with taxes and fees
Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free parking, and a marina. Our guests praise the pool and the helpful staff in our reviews. ...
Coconut Cove Resort and Marina
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.
Islamorada Anglers Reef! “Sandbar Bungalow Villa" AMAZING! Middle row location!

Islamorada Anglers Reef! “Sandbar Bungalow Villa" AMAZING! Middle row location!

Islamorada FL
Book a stay at this beach vacation home in Islamorada. Enjoy a beach locale, a garden, and laundry facilities. Popular attractions Hog Heaven and Windley Key ...
9.8/10 Exceptional! (164 reviews)
"Beautiful layout with plenty of room. Everything worked well and we enjoyed our stay.Alex is quick to respond to messages about anything.We will be back again next year."

Reviewed on Aug 4, 2026

Islamorada Anglers Reef! “Sandbar Bungalow Villa" AMAZING! Middle row location!
Breezy Palms Resort

Breezy Palms Resort

2.5 out of 5
80015 Overseas Highway Islamorada FL
Book a stay at this beach aparthotel in Islamorada. Enjoy free WiFi, a beach locale, and a marina. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (733 reviews)
"The room was spacious and clean. We were very happy with it. They only provide maid service every 3 days, and that was simply changing sheets and towels. The only issue is the smell from the beach due to dead sea grass and other stink. It made the beach impossible to use, and often was unpleasant ..."

Reviewed on Aug 25, 2026

Breezy Palms Resort
Treasure Harbor

Treasure Harbor

3 out of 5
200 Treasure Harbor Dr Islamorada FL
Stay at this houseboat in Islamorada. Enjoy free WiFi, free parking, and premium bedding. Our guests praise the helpful staff in our reviews. Popular attractions ...
9/10 Wonderful! (172 reviews)
"Great air conditioning. Very cozy quaint get away. I would return. Great pit stop heading down to Key West."

Reviewed on Aug 23, 2026

Treasure Harbor
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.

Stay near popular Windley Key attractions

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