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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
$439 nightly
The price is $489 total per night from Mar 8 to Mar 9
$489 total
Mar 8 - Mar 9
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 ...
Wonderful location, beautiful view of the sunset. Staff was friendly and helpful. Great restaurants, live music! Two bedroom suite with sitting area, dining area, full kitchen and balcony overlooking the beach and the pool was perfect setting for our girls weekend.

Reviewed on Mar 4, 2026

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
$389 nightly
The price is $438 total per night from Mar 6 to Mar 7
$438 total
Mar 6 - Mar 7
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 ...
Property right on the water. very clean. florida old time feel. the beach has sand up until the edge of the water, then coral like most places. very nice pool. expansive grounds. room is nice, not large but clean, whatever you want. note: ask for top floor. you can hear everyone walking above you. ...

Reviewed on Mar 3, 2026

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
$524 nightly
The price is $590 total per night from Mar 12 to Mar 13
$590 total
Mar 12 - Mar 13
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. ...
This Resort is unbelievable from the rooms to the beach, walking & biking trails, golf course 27 acres of lush property. Lots of shops & restaurants nearby including Bass Pro Shop, small artists shops & brewery within walking/biking distance.

Reviewed on Feb 25, 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
$409 nightly
The price is $460 total per night from Mar 22 to Mar 23
$460 total
Mar 22 - Mar 23
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 ...
Beautiful ocean view from our room staff was very helpful very clean room

Reviewed on Mar 4, 2026

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
$319 nightly
The price is $359 total per night from Mar 9 to Mar 10
$359 total
Mar 9 - Mar 10
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 ...
We loved the view from our room. Pool area was great ! It was so convenient to have the tiki bar/ restaurant so close to the property.Food was excellent ! Staff was great !

Reviewed on Mar 2, 2026

Opens in a new windowLime Tree Bay 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
$475 nightly
The price is $534 total per night from Mar 23 to Mar 24
$534 total
Mar 23 - Mar 24
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 ...
We had a fantastic stay at Three Waters Resort and Marina. The ocean view room with terrace (Atlantic Shores) was beautiful, and being just steps from the beach and pools made it incredibly easy to relax and enjoy every moment. The included amenities: paddle boards, kayaks, bikes, etc. made it easy ...

Reviewed on Mar 3, 2026

Opens in a new windowThree Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Drop Anchor

Drop Anchor

3 out of 5
84959 Overseas Highway, 222 Islamorada FL
$248 nightly
The price is $275 total per night from Mar 11 to Mar 12
$275 total
Mar 11 - Mar 12
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 unit was older but clean. The facility was well maintained. The issue was the noise. The folks in the adjacent unit began arguing loudly around 8:00 pm. There was a lot of bagging on the walls that could be felt in our bed. Chairs were scooted across the floor with a loud screeching sound. The ...

Reviewed on Mar 2, 2026

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
$285 nightly
The price is $321 total per night from Mar 8 to Mar 9
$321 total
Mar 8 - Mar 9
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. ...
Pool heater on back order. Above ground pool. Otherwise great place.

Reviewed on Mar 4, 2026

Opens in a new windowFisher Inn Resort & Marina
Marina Del Mar Resort and Marina

Marina Del Mar Resort and Marina

2 out of 5
527 Caribbean Drive Key Largo FL
Fully refundableReserve now, pay when you stay
$221 nightly
The price is $249 total per night from Mar 11 to Mar 12
$249 total
Mar 11 - Mar 12
Total with taxes and fees
A marina, 2 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Enjoy the gym and perks like free self parking and free WiFi. You'll ...
The room was in need of repair. It was very rundown but the property was at the marina and the views were just beautiful. The staff was very pleasant. We had a wonderful stay despite the condition of the room

Reviewed on Mar 4, 2026

Opens in a new windowMarina Del Mar 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

Waterside Suites & Marina

Waterside Suites & Marina

5 out of 5
Posted 2 days ago
Travelocity Verified Review
"Great area. Room very clean and comfortable. Could use laundry in the room. "
A verified traveler stayed at Waterside Suites & Marina
Waterside Suites & Marina

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