Book Hotels in Windley Key, FL

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Top Windley Key hotels

Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$249 nightly
The price is $280 total per night from Jan 28 to Jan 29
$280 total
Jan 28 - Jan 29
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 clean and nice. Not a 5 star resort. But nice. Breakfast was good

Reviewed on Jan 11, 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
$179 nightly
The price is $201 total per night from Jan 27 to Jan 28
$201 total
Jan 27 - Jan 28
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 ...
Great property for the price. Our first room was right next to a very noisy construction project, and smelled very strongly of cleaning liquid -- they were great about moving us to an upgraded room and we had an absolutely lovely stay other than that. If you're a strong kayaker or paddleboarder you ...

Reviewed on Jan 4, 2026

Opens in a new windowLime Tree Bay Resort
Reefhouse Resort & Marina

Reefhouse Resort & Marina

3.5 out of 5
103800 Overseas Hwy Key Largo FL
Fully refundableReserve now, pay when you stay
$309 nightly
The price is $343 total per night from Jan 14 to Jan 15
$343 total
Jan 14 - Jan 15
Total with taxes and fees
This smoke-free 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 ...
Amenities

Reviewed on Jan 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
$239 nightly
The price is $269 total per night from Jan 14 to Jan 15
$269 total
Jan 14 - Jan 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 ...
Great place to stay! The staff were wonderful! Quiet, peaceful, and enjoyable stay! Rooms were spacious and clean!

Reviewed on Jan 8, 2026

Opens in a new windowCoconut Cove Resort and Marina
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
$356 nightly
The price is $400 total per night from Jan 21 to Jan 22
$400 total
Jan 21 - Jan 22
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 wonderfull time. Everyone was very attentive and helpful.

Reviewed on Jan 11, 2026

Opens in a new windowThree Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Waterside Suites & Marina

Waterside Suites & Marina

3.5 out of 5
201 Ocean Drive Key Largo FL
Fully refundableReserve now, pay when you stay
$162 nightly
The price is $183 total per night from Jan 25 to Jan 26
$183 total
Jan 25 - Jan 26
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 ...
Friendly staff, clean rooms, not far from highway, right on canal, just need to be able to handle stairs to get to upstairs bedroom/shower

Reviewed on Jan 7, 2026

Opens in a new windowWaterside Suites & Marina
Drop Anchor

Drop Anchor

3 out of 5
84959 Overseas Highway, 222 Islamorada FL
$216 nightly
The price is $238 total per night from Jan 19 to Jan 20
$238 total
Jan 19 - Jan 20
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 staff was personable, great location, having the bicycles and kayaks were a great touch

Reviewed on Jan 1, 2026

Opens in a new windowDrop Anchor
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
$156 nightly
The price is $176 total per night from Jan 25 to Jan 26
$176 total
Jan 25 - Jan 26
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 ...
Amazing

Reviewed on Jan 7, 2026

Opens in a new windowMarina Del Mar Resort and Marina
Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

3.5 out of 5
84951 Overseas Hwy Islamorada FL
Fully refundable
$200 nightly
The price is $225 total per night from Jan 19 to Jan 20
$225 total
Jan 19 - Jan 20
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. ...
Todo ok

Reviewed on Jan 4, 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 2 days ago
Travelocity Verified Review
"The king suite with ocean view was fantastic. The resort is in good shape with plenty of space to lounge, activities and includes nice breakfast options. Also close to many bars and restaurants. "
A verified traveler stayed at Chesapeake Beach Resort
Chesapeake Beach Resort

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