Book Hotels in Windley Key, FL
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Top Windley Key hotels
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. ...
"Clean and comfortable rooms, but I did get a dated feel, but certainly served our purpose. The property supplied EVERYTHING needed to enjoy your stay. I didn’t have dinner there, but their breakfast was elevated and delish. The Adult pool we used had an exercise instructor, a spa and was crystal ..."
Reviewed on Sep 14, 2026
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$192 nightly
The price is $215 total per night from Oct 12 to Oct 13
$215 total
Oct 12 - Oct 13
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 ...
"/"
Reviewed on Sep 13, 2026
Coconut Cove Resort and Marina
84801 Overseas Highway Islamorada FL
$149 nightly
The price is $168 total per night from Sep 16 to Sep 17
$168 total
Sep 16 - Sep 17
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 ...
"Staff was friendly and helpful. Clean place. Great pool and ocean views"
Reviewed on Sep 15, 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 15 to Oct 16
$149 total
Oct 15 - Oct 16
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
$155 nightly
The price is $171 total per night from Sep 16 to Sep 17
$171 total
Sep 16 - Sep 17
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
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$248 nightly
The price is $279 total per night from Sep 27 to Sep 28
$279 total
Sep 27 - Sep 28
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 ...
Fisher Inn Resort & Marina
84951 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$147 nightly
The price is $166 total per night from Sep 21 to Sep 22
$166 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. ...
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 16 to Sep 17
$286 total
Sep 16 - Sep 17
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
Coconut Cove Resort and Marina
4 out of 5
Posted 1 hour ago
Travelocity Verified Review
"Staff was friendly and helpful. Clean place. Great pool and ocean views"
A verified traveler stayed at Coconut Cove Resort and Marina
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