Book Hotels in Windley Key, FL
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Top Windley Key hotels
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$185 nightly
The price is $208 total per night from Oct 18 to Oct 19
$208 total
Oct 18 - Oct 19
Total with taxes and fees
A private beach, a marina, and 2 outdoor pools are all featured at this smoke-free hotel. Enjoy a day at the beach kayaking, or relax with sun loungers. Unwind ...
"Everything about the Chesapeake resort is perfect ,had the most incredible time ,will definitely return !!!"
Reviewed on Sep 17, 2026
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$264 nightly
The price is $297 total per night from Sep 23 to Sep 24
$297 total
Sep 23 - Sep 24
Total with taxes and fees
This Art Deco resort features a private beach, a marina, and 4 restaurants. Enjoy a day at the beach snorkeling, or relax with sun loungers. Families will appreciate ...
"We had an excellent stay at Three Waters Resort in Islamorada. Everything about the property was great from start to finish. Our room was very clean, comfortable, and well maintained, and the entire resort was beautiful and inviting. One of the things we really enjoyed was all of the included amenities. ..."
Reviewed on Sep 15, 2026
Coconut Cove Resort and Marina
84801 Overseas Highway Islamorada FL
$149 nightly
The price is $168 total per night from Sep 20 to Sep 21
$168 total
Sep 20 - Sep 21
Total with taxes and fees
A marina and an outdoor pool are featured at this hotel. Families will appreciate the children's pool and barbecue grills. Enjoy the gym and free perks like ...
"The location and property was well kept. Very nice pool and the room was very clean and worth the price. The welcoming was the best part, Crystal has a great attitude and very helpful with our questions both on property and in the town. We will come back"
Reviewed on Sep 16, 2026
Waterside Suites & Marina
201 Ocean Drive Key Largo FL
Fully refundableReserve now, pay when you stay
$132 nightly
The price is $149 total per night from Oct 18 to Oct 19
$149 total
Oct 18 - Oct 19
Total with taxes and fees
A marina and an outdoor pool are featured at this smoke-free hotel. WiFi in public areas is free. A terrace, a picnic area, and luggage storage are also on ...
"1"
Reviewed on Sep 14, 2026
Drop Anchor
84959 Overseas Highway, 222 Islamorada FL
$167 nightly
The price is $183 total per night from Sep 23 to Sep 24
$183 total
Sep 23 - Sep 24
Total with taxes and fees
An outdoor pool, free self parking, and barbecue grills are featured at this hotel. WiFi in public areas is free. A business center, a garden, and a picnic area ...
"Great resort. Staff were helpful and the location is amazing"
Reviewed on Sep 15, 2026
Fisher Inn Resort & Marina
84951 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $156 total per night from Sep 21 to Sep 22
$156 total
Sep 21 - Sep 22
Total with taxes and fees
A private beach and an outdoor pool are featured at this Art Deco motel. Spend a day at the beach snorkeling, or relax with sun loungers and beach umbrellas. ...
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
$186 nightly
The price is $209 total per night from Sep 29 to Sep 30
$209 total
Sep 29 - Sep 30
Total with taxes and fees
This luxury resort features a private beach, a golf course, and a full-service spa. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. ...
Reefhouse Resort & Marina
103800 Overseas Hwy Key Largo FL
Fully refundableReserve now, pay when you stay
$259 nightly
The price is $286 total per night from Sep 20 to Sep 21
$286 total
Sep 20 - Sep 21
Total with taxes and fees
This luxury hotel features a private beach, a full-service spa, and a marina. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Family-friendly ...
Baker's Cay Resort Key Largo, Curio Collection by Hilton
97000 Overseas Hwy Key Largo FL
Fully refundableReserve now, pay when you stay
$286 nightly
The price is $322 total per night from Sep 28 to Sep 29
$322 total
Sep 28 - Sep 29
Total with taxes and fees
A private beach, 2 restaurants, and 2 outdoor pools are all featured at this resort. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. ...
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.
Hotels in Windley Key with star-rating
Check Windley Key Hotels by Star Rating
5 Star Hotels
2 properties
Recent Windley Key hotel reviews by fellow wanderers
Chesapeake Beach Resort
5 out of 5
Posted 2 hours ago
Travelocity Verified Review
"Everything about the Chesapeake resort is perfect ,had the most incredible time ,will definitely return !!!"
A verified traveler stayed at Chesapeake Beach Resort
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