Windley Key Travel Guide

Tourist 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
The price is AU$488 per night from 1 Nov to 2 Nov
AU$488
1 Nov - 2 Nov
includes taxes & fees
Stay at this beach resort in Islamorada. Enjoy free Wi-Fi, 3 outdoor pools and 4 restaurants. Our guests praise the helpful staff and the clean rooms in their ...
9/10 Wonderful! (296 reviews)
"We've stayed at many places over the years . This place and the room that we had were the best . Waking up in bed to a view of the ocean can't be beat. It is situated on the most luxurious of all the keys.. can't wait to return ."

Reviewed on 19 Oct 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
The price is AU$286 per night from 22 Oct to 23 Oct
AU$286
22 Oct - 23 Oct
includes taxes & fees
Stay at this beach motel in Islamorada. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms in their reviews. ...
8.2/10 Very good! (1,010 reviews)
"We had a nice stay at Fisher Inn. The location was great, the rooms were spacious, and having two king beds was a bonus. The bathroom was on the small side, but it was clean. We also appreciated the Keurig coffee maker in the room, especially having dark roast coffee available, and there were some ..."

Reviewed on 21 Oct 2026

Fisher Inn Resort & Marina
Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

3 out of 5
84801 Overseas Highway Islamorada FL
The price is AU$239 per night from 26 Oct to 27 Oct
AU$239
26 Oct - 27 Oct
includes taxes & fees
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 their reviews. Popular ...
Coconut Cove Resort and Marina
See all 2,661 properties in Windley Key
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.
Oceanside Getaway: Beautiful Home with Boat Slip, Pool & Beach - Gated community

Oceanside Getaway: Beautiful Home with Boat Slip, Pool & Beach - Gated community

Islamorada FL
Stay at this holiday home in Islamorada. Enjoy free Wi-Fi, a garden and laundry facilities. Our guests praise the helpful staff in their reviews. Popular attractions ...
9.8/10 Exceptional! (180 reviews)
"Nice property a little tight on the parking. Pool and boat slip very nice"

Reviewed on 18 Sept 2026

Oceanside Getaway: Beautiful Home with Boat Slip, Pool & Beach - Gated community
Breezy Palms Resort

Breezy Palms Resort

2.5 out of 5
80015 Overseas Highway Islamorada FL
Stay at this beach aparthotel in Islamorada. Enjoy free Wi-Fi, a beach locale and a marina. Our guests praise the helpful staff and the clean rooms in their ...
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 Wi-Fi, free parking and premium bedding. Our guests praise the helpful staff in their reviews. Popular attractions ...
9/10 Wonderful! (179 reviews)
"The boat was very clean and included all the amenities we needed. The air conditioning worked very well. The host was extremely accommodating with our very late check-in and early departure. I would definitely recommend!"

Reviewed on 15 Oct 2026

Treasure Harbor
See all properties in Windley Key
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

A waterfall at SeaWorld, with text reading "I eat the sea" and "Marine Mammal Park, Islamorada, Florida".

Theater of the Sea

9.2/10 (921 reviews)
Swim with the dolphins and sharks and feed the crocodiles and sea turtles near the lagoon of this vast interactive park for marine mammals.
See properties

Explore a world of travel with Expedia