Windley Key, Islamorada hotel rooms at the Hersha Hospitality

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Check prices for these dates

Tonight
Aug 22 - Aug 23
Tomorrow
Aug 23 - Aug 24
This weekend
Aug 22 - Aug 24
Next weekend
Aug 29 - Aug 31

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

Islander Resort
Exterior

Islander Resort

4.0 star property
9.2 out of 10, Wonderful, (1001)
"The resort is perfect!!"
The price is ₩268,664
₩396,700 total
includes taxes & fees
Sep 10 - Sep 11
Islander Resort
Islander Bayside Villas and Boatslips
Restaurant

Islander Bayside Villas and Boatslips

3.5 star property
8.8 out of 10, Excellent, (380)
"The villas were nice and relaxing but the association with the islander resort made to stay great. "
The price is ₩266,984
₩394,809 total
includes taxes & fees
Sep 22 - Sep 23
Islander Bayside Villas and Boatslips
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 Windley Key Hotel Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Morning breakfast was great. Staff was very attentive and pleasant. Room view was amazing. Very convenient for a person in our party that is disabled. "
James 2-night trip
Posted 1 day ago
Chesapeake Beach Resort