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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
$319 nightly
The price is $354 total per night from May 3 to May 4
$354 total
May 3 - May 4
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 beach was very nice.

Reviewed on Apr 29, 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 3 to May 4
$261 total
May 3 - May 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 ...
Very good location the rooms are Amazing

Reviewed on Apr 30, 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. ...
👍

Reviewed on Apr 29, 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
$289 nightly
The price is $325 total per night from May 18 to May 19
$325 total
May 18 - May 19
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 place rents out full time rooms the furniture is terrible the place is falling apart

Reviewed on Apr 29, 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 27 to May 28
$164 total
May 27 - May 28
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 ...
Fine but not special. Room was overall clean, except for small stains on the sheets and a very strong deodorizer smell in the carpet. Pool was nice but small and cluttered around it. Air conditioning was wonderful! Staff had a call on speakerphone the entire check in time. To be fair the manager ...

Reviewed on Apr 29, 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 May 3 to May 4
$232 total
May 3 - May 4
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
Fully refundableReserve now, pay when you stay
$384 nightly
The price is $432 total per night from May 19 to May 20
$432 total
May 19 - May 20
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. ...
Nice stay. Staff was very friendly and helpful

Reviewed on Apr 29, 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 May 3 to May 4
$223 total
May 3 - May 4
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

Bayside Inn Key Largo

Bayside Inn Key Largo

5 out of 5
Posted 4 hours ago
Travelocity Verified Review
"This little gem was paradise. It might not be the biggest resort around but it had everything you needed. The waterfront area had ample lounges and adirondack deck chairs to allow you to take in the beauty of Buttonwood sound. The rooms are equipped with microwaves, refrigerators, and Keurig machines.. The office has a wonderful coffee maker that grinds and brews your coffee. I have the best cappuccinos every morning. We took advantage of the complementary bicycles and paddle boards. It was our first time in Key largo but the next time, we need a place to relax, this is definitely the place."
A verified traveler stayed at Bayside Inn Key Largo
Bayside Inn Key Largo

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