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Top Windley Key hotels

Reefhouse Resort & Marina

Reefhouse Resort & Marina

4.5 out of 5
103800 Overseas Hwy Key Largo FL
Fully refundableReserve now, pay when you stay
$239 nightly
The price is $264 total per night from Jun 21 to Jun 22
$264 total
Jun 21 - Jun 22
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 ...
"The place was Excellent! I love the views and the services. ❤️🫶 100% I book this hotel again."

Reviewed on Jun 11, 2026

Opens in a new windowReefhouse Resort & 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
$283 nightly
The price is $318 total per night from Jul 6 to Jul 7
$318 total
Jul 6 - Jul 7
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. ...
"5 star"

Reviewed on Jun 13, 2026

Opens in a new windowCheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$230 nightly
The price is $258 total per night from Jun 14 to Jun 15
$258 total
Jun 14 - Jun 15
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 ...
"This place was great! Very private, great amenities, staff, location, and accessible! Has everything you need for intimate location Oceanview is stellar, you can walk right into the ocean and relax with provided chairs, umbrellas, and towels. They have breakfast included with all breakfast types ..."

Reviewed on Jun 12, 2026

Opens in a new windowChesapeake Beach Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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

4 out of 5
84001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$336 nightly
The price is $378 total per night from Jul 7 to Jul 8
$378 total
Jul 7 - Jul 8
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 ...
"Nice! I thoroughly enjoyed the experience. enjoyed it."

Reviewed on Jun 13, 2026

Opens in a new windowThree Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

3 out of 5
84801 Overseas Highway Islamorada FL
$179 nightly
The price is $201 total per night from Jun 14 to Jun 15
$201 total
Jun 14 - Jun 15
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 property was very beautiful and the staff was great. They have an ice machine on site and a large pool area. The tiki bar is a great spot in the evening to sit and have a drink"

Reviewed on May 25, 2026

Opens in a new windowCoconut Cove Resort and Marina
Waterside Suites & Marina

Waterside Suites & Marina

3.5 out of 5
201 Ocean Drive Key Largo FL
Fully refundableReserve now, pay when you stay
$155 nightly
The price is $175 total per night from Jun 14 to Jun 15
$175 total
Jun 14 - Jun 15
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 ...
"Super clean. Very quiet"

Reviewed on Jun 10, 2026

Opens in a new windowWaterside Suites & Marina
Drop Anchor

Drop Anchor

3 out of 5
84959 Overseas Highway, 222 Islamorada FL
$160 nightly
The price is $176 total per night from Jun 15 to Jun 16
$176 total
Jun 15 - Jun 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 ...
"Great stay for boaters! right on the water and easy to launch. The rooms were clean and had the essentials. The staff was super friendly and helpful."

Reviewed on Jun 10, 2026

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
$296 nightly
The price is $333 total per night from Jun 30 to Jul 1
$333 total
Jun 30 - Jul 1
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. ...
"Overall great. Some of the staff can be more friendly"

Reviewed on Jun 12, 2026

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
$188 nightly
The price is $212 total per night from Jun 15 to Jun 16
$212 total
Jun 15 - Jun 16
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. ...
"We had a wonderful stay! The staff were friendly and welcoming. Our room was clean, spacious, and very comfortable, with everything we needed for a relaxing visit. The hotel amenities were excellent and really added to the overall experience. We would definitely stay here again and highly recommend ..."

Reviewed on Jun 9, 2026

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.

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