Book Hotels in Windley Key, FL
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Top Windley Key hotels
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
$237 nightly
The price is $266 total per night from Aug 19 to Aug 20
$266 total
Aug 19 - Aug 20
Total includes 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 ...
Great, but eat off property
"Property and service were great. Food was not great. Very difficult to find options for a picky eater. Had to DoorDash Wendy’s several times."
Reviewed on Jul 2, 2025
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
$317 nightly
The price is $357 total per night from Aug 21 to Aug 22
$357 total
Aug 21 - Aug 22
Total includes 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. ...
"Stayed here for one night. Unfortunately the weather wasn’t great so we didn’t get to experience the pool areas and such. We walked around the grounds at night in the rain and it was still breath taking. Would love to stay longer the next time I am back in the area."
Reviewed on Jul 20, 2025
Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
$183 nightly
The price is $206 total per night from Aug 12 to Aug 13
$206 total
Aug 12 - Aug 13
Total includes 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 ...
"Great view! Sweet ppl that work there!"
Reviewed on Jul 19, 2025
Islander Resort
82100 Overseas Highway, Islamorada, FL
Fully refundableReserve now, pay when you stay
$268 nightly
The price is $302 total per night from Aug 11 to Aug 12
$302 total
Aug 11 - Aug 12
Total includes taxes and fees
A private beach, 3 restaurants, and 2 outdoor pools are all featured at this hotel. Enjoy beachfront dining and relax with beach cabanas and sun loungers. Families ...
"Perfect gateaway with my husband! THANKS EXPEDIA FOR A GREAT PRICE in a wonderful place! we enjoyed it every minute. WE will back soon!"
Reviewed on Jul 19, 2025
Drop Anchor
84959 Overseas Highway, 222, Islamorada, FL
$171 nightly
The price is $188 total per night from Jul 23 to Jul 24
$188 total
Jul 23 - Jul 24
Total includes 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 ...
"This was our second stay in a month. Great location, beautiful property on the water. We love it here and cant wait to go back."
Reviewed on Jul 18, 2025
Baker's Cay Resort Key Largo, Curio Collection by Hilton
97000 Overseas Hwy, Key Largo, FL
$364 nightly
The price is $409 total per night from Aug 14 to Aug 15
$409 total
Aug 14 - Aug 15
Total includes 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. ...
"Beautiful property"
Reviewed on Jul 21, 2025
Hampton Inn Key Largo Manatee Bay
102400 Overseas Hwy, Key Largo, FL
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $133 total per night from Aug 17 to Aug 18
$133 total
Aug 17 - Aug 18
Total includes taxes and fees
A private beach and an outdoor pool are featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi ...
Great hotel but housekeeping needs to step it up
"Saw a palmetto roach outside our doorway and housekeeping never showed up."
Reviewed on Jul 20, 2025
Fisher Inn Resort & Marina
84951 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $161 total per night from Jul 23 to Jul 24
$161 total
Jul 23 - Jul 24
Total includes 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. ...
"Spacious rooms. Beautiful view"
Reviewed on Jul 21, 2025
Coconut Cove Resort and Marina
84801 Overseas Highway, Islamorada, FL
$149 nightly
The price is $168 total per night from Jul 23 to Jul 24
$168 total
Jul 23 - Jul 24
Total includes 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 ...
"Nice place great pool"
Reviewed on Jul 20, 2025
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
3 properties
Recent Windley Key hotel reviews by fellow wanderers
Baker's Cay Resort Key Largo, Curio Collection by Hilton
5 out of 5
Posted 4 hours ago
Travelocity Verified Review
"Beautiful property "
A verified traveler stayed at Baker's Cay Resort Key Largo, Curio Collection by Hilton
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An Attraction
- Hotels near Windley Key Fossil Reef Geological State Park
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