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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
$389 nightly
The price is $433 total per night from Mar 4 to Mar 5
$433 total
Mar 4 - Mar 5
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 ...
Nice property. Clean and comfortable rooms, nice pool and beach area. Enjoyed many great restaurants in the area.

Reviewed on Mar 2, 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
$366 nightly
The price is $412 total per night from Mar 29 to Mar 30
$412 total
Mar 29 - Mar 30
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 ...
It was wonderful

Reviewed on Mar 2, 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
$596 nightly
The price is $671 total per night from Mar 4 to Mar 5
$671 total
Mar 4 - Mar 5
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
$404 nightly
The price is $455 total per night from Mar 4 to Mar 5
$455 total
Mar 4 - Mar 5
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 were promised an ocean view room but it was near the highway with no view.

Reviewed on Mar 2, 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
$309 nightly
The price is $348 total per night from Mar 4 to Mar 5
$348 total
Mar 4 - Mar 5
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

3.5 out of 5
84001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$478 nightly
The price is $538 total per night from Mar 5 to Mar 6
$538 total
Mar 5 - Mar 6
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 ...
i paid over 7 thousand dollars for 2 rooms for 4 nights..800 a night to get a view of a parking lot. i am a gold member of Marriott. The room was so small, no latch on door and the drawers were broken. HIGHLY DISAPPOINTED

Reviewed on Mar 2, 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
$250 nightly
The price is $276 total per night from Mar 5 to Mar 6
$276 total
Mar 5 - Mar 6
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
$321 nightly
The price is $361 total per night from Mar 12 to Mar 13
$361 total
Mar 12 - Mar 13
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 location. Room was clean and updated. Enjoyed the balcony.

Reviewed on Mar 1, 2026

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

Marina Del Mar Resort and Marina

2.5 out of 5
527 Caribbean Drive Key Largo FL
Fully refundableReserve now, pay when you stay
$219 nightly
The price is $247 total per night from Mar 9 to Mar 10
$247 total
Mar 9 - Mar 10
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 ...
Rooms are really run down. Staff is good, furniture and closet doors totally need replacement. Bathroom old and uninviting. Priced high for the condition of the building. Elevator got a facelift but not the rest.

Reviewed on Mar 1, 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

Bayside Inn Key Largo

Bayside Inn Key Largo

1 out of 5
Posted 12 hours ago
Travelocity Verified Review
"Room was covered in bleach when we arrive and the floor were sticky and popping up. The smell of mildew and mold were so potent we ended up getting sick after two nights and had to leave before our check out date due to our symptoms. Told the girl at the front desk and she said a manger would call, never got a call yet. "
A verified traveler stayed at Bayside Inn Key Largo
Bayside Inn Key Largo

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