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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
$339 nightly
The price is $376 total per night from Apr 30 to May 1
$376 total
Apr 30 - May 1
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 ...
Clean room, friendly staff, ocean front. Very nice

Reviewed on Apr 27, 2026

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
$232 nightly
The price is $261 total per night from May 10 to May 11
$261 total
May 10 - May 11
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 ...
We loved our stay, the staff was very friendly specially the 2 gentlemen that were in the breakfast. The hotel was very well maintained and peaceful. Our room was excellent the only complain I have is the A/C hitting our bed directly. But other than that I would stay here again.

Reviewed on Apr 29, 2026

Opens in a new windowChesapeake Beach Resort
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
$312 nightly
The price is $351 total per night from May 14 to May 15
$351 total
May 14 - May 15
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 had an ocean front room in the new wing and can honestly say it was lovely. The staff were great, the hotel facilities were lovely and food and drinks all good.

Reviewed on Apr 28, 2026

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

4 out of 5
84001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$322 nightly
The price is $362 total per night from May 25 to May 26
$362 total
May 25 - May 26
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 ...
Clean updated room, great view and balcony! Loved the property and amenities.

Reviewed on Apr 25, 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 Apr 30 to May 1
$201 total
Apr 30 - May 1
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 ...
Amazing place, peaceful sunrise was gorgeous. Coconut trees were everywhere. White sand raked neatly! Well kept and tons of wildlife. Fishing dock with cleaning area. Separate area with amazing built grilling area. Pool with waterfall can be used all night. We had a whirlpool tub and continental ...

Reviewed on Apr 26, 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
$146 nightly
The price is $164 total per night from May 20 to May 21
$164 total
May 20 - May 21
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 ...
Nope didn’t stay! Absolutely horrible. Nothing around, basically drive through trailer park to get there. Then no refund either after coming from North Dakota. The whole establishment was lie online. Good from far, far from good!

Reviewed on Apr 28, 2026

Opens in a new windowWaterside Suites & Marina
Drop Anchor

Drop Anchor

3 out of 5
84959 Overseas Highway, 222 Islamorada FL
$210 nightly
The price is $232 total per night from Apr 30 to May 1
$232 total
Apr 30 - May 1
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 ...
Our room was comfortable and clean. The grounds and pool were really nice. The entire staff were awesome. It was really cool having the kayaks on the property. We had a great stay.

Reviewed on Apr 26, 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
$384 nightly
The price is $432 total per night from May 5 to May 6
$432 total
May 5 - May 6
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. ...
Room was great! Didn't like the fact you could order food at their restaurant and take tour leftovers back but no way to warm them up unless you went to the front desk. Pool and hot tub were filthy with cups and fruit over the weekend and not cleaned til check out time Tuesday morning of course. ...

Reviewed on Apr 28, 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
$198 nightly
The price is $223 total per night from Apr 30 to May 1
$223 total
Apr 30 - May 1
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. ...
Great place but needs new beds to noisy bother neighbor plus definitely needs a blender for making drinks 🍸

Reviewed on Apr 29, 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.

Recent Windley Key hotel reviews by fellow wanderers

Chesapeake Beach Resort

Chesapeake Beach Resort

5 out of 5
Posted 6 hours ago
Travelocity Verified Review
"We loved our stay, the staff was very friendly specially the 2 gentlemen that were in the breakfast. The hotel was very well maintained and peaceful. Our room was excellent the only complain I have is the A/C hitting our bed directly. But other than that I would stay here again."
A verified traveler stayed at Chesapeake Beach Resort
Chesapeake Beach Resort

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