Find all hotels by Hersha Hospitality in Windley Key, FL from $207

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Compare rooms and suites by Hersha Hospitality in Windley Key with rates, reviews, and availability. Most hotels are fully refundable.

Islander Resort
3 outdoor pools, cabanas (surcharge), pool umbrellas
Islander Resort
4.0 star property
9.0 out of 10, Wonderful, 1,010 reviews
"One of the best locations in Islamorada on the ocean with the huge beach and a walk anc road to great restaurants. Excellent, recently remodeled rooms."
The price is $207
$288 total
includes taxes & fees
Jun 23 - Jun 24
Islander Resort
Islander Bayside Villas and Boatslips
Outdoor pool, pool umbrellas, sun loungers
Islander Bayside Villas and Boatslips
3.5 star property
9.0 out of 10, Wonderful, 338 reviews
"Clean and close to everything "
The price is $239
$324 total
includes taxes & fees
Jun 16 - Jun 17
Islander Bayside Villas and Boatslips
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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.

Hersha Hospitality Windley Key Hotel Guide

Some globe-trotters choose hotels based on location, but others book by name. And thanks to Expedia you don’t have to pick. It is why we offer such an expansive range of Hersha Hospitality hotels in Windley Key, Islamorada. Known for well-appointed rooms and friendly, personalized service, each of the top Hersha Hospitality Windley Key hotels guarantees an unparalleled level of comfort and quality.

You’ll find best-in-class amenities like clean rooms and quiet atmospheres, and some Windley Key Hersha Hospitality locations may even offer extra little benefits and discounts for frequent travelers.

Recent reviews of Windley Key hotels
Expedia verified reviews

Islander Resort

Islander Resort

5/5 Excellent
"One of the best locations in Islamorada on the ocean with the huge beach and a walk anc road to great restaurants. Excellent, recently remodeled rooms."
A verified traveler stayed at Islander Resort
Posted 9 hours ago
Islander Resort