Book Hotels in Windley Key, FL

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Top Windley Key hotels

Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$167 nightly
The price is $188 total per night from Dec 3 to Dec 4
$188 total
Dec 3 - Dec 4
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

Opens in a new windowChesapeake Beach Resort
Lime Tree Bay Resort

Lime Tree Bay Resort

3.5 out of 5
68500 Overseas Hwy Long Key FL
Fully refundableReserve now, pay when you stay
$179 nightly
The price is $201 total per night from Dec 3 to Dec 4
$201 total
Dec 3 - Dec 4
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 ...
The room was well appointed and super clean. We loved the little beach.

Reviewed on Nov 26, 2025

Opens in a new windowLime Tree Bay Resort
Reefhouse Resort & Marina

Reefhouse Resort & Marina

3.5 out of 5
103800 Overseas Hwy Key Largo FL
Fully refundableReserve now, pay when you stay
$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 ...
Great location and service.

Reviewed on Nov 26, 2025

Opens in a new windowReefhouse Resort & Marina
Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

3 out of 5
84801 Overseas Highway Islamorada FL
$140 nightly
The price is $158 total per night from Dec 3 to Dec 4
$158 total
Dec 3 - Dec 4
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 ...
Clean room attention is excellent

Reviewed on Nov 27, 2025

Opens in a new windowCoconut Cove Resort and Marina
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
$240 nightly
The price is $271 total per night from Dec 17 to Dec 18
$271 total
Dec 17 - Dec 18
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. ...
We stayed in the newest section of the Cheeca Lodge. It is so incredibly nice! We had other family staying in the lagoon area. We enjoyed all the activities on the property as well. My nephew especially loved the par3 golf course. I really loved the staff at Cheeca Lodge too. Shelia, Amber and David ...

Reviewed on Nov 26, 2025

Opens in a new windowCheeca Lodge & Spa
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

3.5 out of 5
84001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$254 nightly
The price is $285 total per night from Dec 17 to Dec 18
$285 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

Opens in a new windowThree Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
$207 nightly
The price is $233 total per night from Dec 4 to Dec 5
$233 total
Dec 4 - Dec 5
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 ...
Loved the resort

Reviewed on Nov 21, 2025

Opens in a new windowAmara Cay Resort
Drop Anchor

Drop Anchor

3 out of 5
84959 Overseas Highway, 222 Islamorada FL
$130 nightly
The price is $142 total per night from Dec 4 to Dec 5
$142 total
Dec 4 - Dec 5
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 ...
The staff was very nice. Thanks

Reviewed on Nov 24, 2025

Opens in a new windowDrop Anchor
Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

3.5 out of 5
84951 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $127 total per night from Dec 18 to Dec 19
$127 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. ...
Recomendado el hotel tiene varios juegos que hacer con los ninos ademas puedes montar kayaks bicicleta.

Reviewed on Nov 30, 2025

Opens in a new windowFisher Inn Resort & Marina
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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.

Recent Windley Key hotel reviews by fellow wanderers

Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton

5 out of 5
Posted 1 day ago
Travelocity Verified Review
"Lovely resort with dr"
A verified traveler stayed at Baker's Cay Resort Key Largo, Curio Collection by Hilton
Baker's Cay Resort Key Largo, Curio Collection by Hilton

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