Book Hotels in Windley Key, FL

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Top Windley Key hotels

Reefhouse Resort & Marina

Reefhouse Resort & Marina

3.5 out of 5
103800 Overseas Hwy, Key Largo, FL
Fully refundableReserve now, pay when you stay
$259 nightly
The price is $286 total per night from Oct 26 to Oct 27
$286 total
Oct 26 - Oct 27
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

Reviewed on Oct 19, 2025

Opens in a new windowReefhouse Resort & Marina
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
$161 nightly
The price is $182 total per night from Oct 29 to Oct 30
$182 total
Oct 29 - Oct 30
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 ...
Everyone was so nice and helpful at this resort!!! I had such an amazing time and would definitely recommend to any family & friends!!!

Reviewed on Oct 20, 2025

Opens in a new windowChesapeake Beach Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
$199 nightly
The price is $224 total per night from Oct 26 to Oct 27
$224 total
Oct 26 - Oct 27
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. ...
Nice room with everything you need.

Reviewed on Oct 20, 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
$262 nightly
The price is $295 total per night from Nov 2 to Nov 3
$295 total
Nov 2 - Nov 3
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 ...
View was beautiful. Parking lot clean. The staff could use more training on guest interaction. Drink prices way to high.

Reviewed on Oct 18, 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
Fully refundableReserve now, pay when you stay
$186 nightly
The price is $210 total per night from Oct 29 to Oct 30
$210 total
Oct 29 - Oct 30
Total with taxes and fees
A private beach, 2 restaurants, and an outdoor pool are all featured at this resort. If you want to take your pet along, this pet-friendly property offers everything ...
This was our second stay there and will definitely go back. The location is great and there is plenty of well-maintained beach area to enjoy. The room was large, clean and updated. However, the view from the room left a lot to be desired. We booked a standard room so we didn't have expectations one ...

Reviewed on Oct 14, 2025

Opens in a new windowAmara Cay Resort
Drop Anchor

Drop Anchor

3 out of 5
84959 Overseas Highway, 222, Islamorada, FL
$149 nightly
The price is $163 total per night from Oct 26 to Oct 27
$163 total
Oct 26 - Oct 27
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

Reviewed on Oct 22, 2025

Opens in a new windowDrop Anchor
Baker's Cay Resort Key Largo, Curio Collection by Hilton

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

4 out of 5
97000 Overseas Hwy, Key Largo, FL
Fully refundableReserve now, pay when you stay
$339 nightly
The price is $381 total per night from Nov 2 to Nov 3
$381 total
Nov 2 - Nov 3
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. ...
We had the absolute best fall break vacation here and will most definitely be back

Reviewed on Oct 19, 2025

Opens in a new windowBaker's Cay Resort Key Largo, Curio Collection by Hilton
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
$138 nightly
The price is $155 total per night from Oct 26 to Oct 27
$155 total
Oct 26 - Oct 27
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. ...
It was great

Reviewed on Oct 19, 2025

Opens in a new windowFisher Inn Resort & Marina
Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

3 out of 5
84801 Overseas Highway, Islamorada, FL
$149 nightly
The price is $168 total per night from Oct 26 to Oct 27
$168 total
Oct 26 - Oct 27
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 pool was my favorite part, love that it was 24 hours and it was gorgeous!

Reviewed on Oct 21, 2025

Opens in a new windowCoconut Cove Resort and 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

Drop Anchor

Drop Anchor

5 out of 5
Posted 3 days ago
Travelocity Verified Review
"Great"
A verified traveler stayed at Drop Anchor
Drop Anchor

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