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
$225 nightly
The price is $254 total per night from Dec 15 to Dec 16
$254 total
Dec 15 - Dec 16
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 ...
Great place
Reviewed on Nov 28, 2025
Lime Tree Bay Resort
68500 Overseas Hwy Long Key FL
Fully refundableReserve now, pay when you stay
$171 nightly
The price is $193 total per night from Dec 18 to Dec 19
$193 total
Dec 18 - Dec 19
Total with taxes and fees
This resort features a private beach, 3 outdoor pools, and a restaurant. Business travelers can take advantage of the free WiFi in public areas. Enjoy the outdoor ...
Extremely good service. Staff was really good.
Reviewed on Dec 8, 2025
Reefhouse Resort & Marina
103800 Overseas Hwy Key Largo FL
$269 nightly
The price is $298 total per night from Dec 14 to Dec 15
$298 total
Dec 14 - Dec 15
Total with taxes and fees
This smoke-free 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 ...
Staff was amazing and food was excellent
Reviewed on Dec 2, 2025
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$271 nightly
The price is $304 total per night from Dec 17 to Dec 18
$304 total
Dec 17 - Dec 18
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 ...
Beautiful room, stunning views
Reviewed on Nov 19, 2025
Coconut Cove Resort and Marina
84801 Overseas Highway Islamorada FL
$155 nightly
The price is $175 total per night from Dec 17 to Dec 18
$175 total
Dec 17 - Dec 18
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 ...
Great place to stay! Clean, great location and great customer service. Very easy to check in, front desk was so sweet! Highly recommended!!! Had a great experience overall
Reviewed on Dec 5, 2025
Waterside Suites & Marina
201 Ocean Drive Key Largo FL
Fully refundableReserve now, pay when you stay
$157 nightly
The price is $177 total per night from Dec 21 to Dec 22
$177 total
Dec 21 - Dec 22
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 ...
Love the area
Reviewed on Dec 8, 2025
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$245 nightly
The price is $276 total per night from Dec 18 to Dec 19
$276 total
Dec 18 - Dec 19
Total with taxes and fees
A private beach and a restaurant are featured at this resort. If you want to take your pet along, this pet-friendly property offers everything you'll need for ...
Great location right on the ocean
Reviewed on Dec 5, 2025
Drop Anchor
84959 Overseas Highway, 222 Islamorada FL
$166 nightly
The price is $183 total per night from Dec 15 to Dec 16
$183 total
Dec 15 - Dec 16
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 ...
Had a wonderful stay at Drop Anchor! Very adorable and super clean. Loved the amenities and the hotel staff were amazing!
Reviewed on Dec 7, 2025
Fisher Inn Resort & Marina
84951 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$158 nightly
The price is $178 total per night from Dec 18 to Dec 19
$178 total
Dec 18 - Dec 19
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. ...
The hotel was great for a quick one-stop stopover. The room was very nice and comfortable (a bit unexpected given the exterior of the property).
Reviewed on Dec 3, 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
Waterside Suites & Marina
5 out of 5
Posted 2 days ago
Travelocity Verified Review
"Love the area "
A verified traveler stayed at Waterside Suites & Marina
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