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Sep 18 - Sep 20
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Top Windley Key hotels

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
$186 nightly
The price is $209 total per night from Sep 29 to Sep 30
$209 total
Sep 29 - Sep 30
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. ...
"Clean and comfortable rooms, but I did get a dated feel, but certainly served our purpose. The property supplied EVERYTHING needed to enjoy your stay. I didn’t have dinner there, but their breakfast was elevated and delish. The Adult pool we used had an exercise instructor, a spa and was crystal ..."

Reviewed on Sep 14, 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
$190 nightly
The price is $214 total per night from Oct 14 to Oct 15
$214 total
Oct 14 - Oct 15
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 ...
"/"

Reviewed on Sep 13, 2026

Opens in a new windowChesapeake Beach Resort
Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

3 out of 5
84801 Overseas Highway Islamorada FL
$149 nightly
The price is $168 total per night from Sep 16 to Sep 17
$168 total
Sep 16 - Sep 17
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 ...
"This was a beautiful place to stay. The scenery was just absolutely breathtaking. Loved the bedroom and amenities. Staff were all sweet and treated you like family. I will definitely be going back!"

Reviewed on Sep 13, 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
$132 nightly
The price is $149 total per night from Oct 15 to Oct 16
$149 total
Oct 15 - Oct 16
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 ...
"1"

Reviewed on Sep 14, 2026

Opens in a new windowWaterside Suites & Marina
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
$286 nightly
The price is $322 total per night from Sep 28 to Sep 29
$322 total
Sep 28 - Sep 29
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. ...
"The hotel is very lovely and cozy, the entire staff is very friendly, and the areas and rooms are very clean; I recommend it."

Reviewed on Sep 13, 2026

Opens in a new windowBaker's Cay Resort Key Largo, Curio Collection by Hilton
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
$248 nightly
The price is $279 total per night from Sep 27 to Sep 28
$279 total
Sep 27 - Sep 28
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 ...
Opens in a new windowThree Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
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
$147 nightly
The price is $166 total per night from Sep 21 to Sep 22
$166 total
Sep 21 - Sep 22
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. ...
Opens in a new windowFisher Inn Resort & Marina
Drop Anchor

Drop Anchor

3 out of 5
84959 Overseas Highway, 222 Islamorada FL
$155 nightly
The price is $171 total per night from Sep 16 to Sep 17
$171 total
Sep 16 - Sep 17
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 ...
Opens in a new windowDrop Anchor
Reefhouse Resort & Marina

Reefhouse Resort & Marina

4.5 out of 5
103800 Overseas Hwy Key Largo FL
Fully refundableReserve now, pay when you stay
$259 nightly
The price is $286 total per night from Sep 16 to Sep 17
$286 total
Sep 16 - Sep 17
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 ...
Opens in a new windowReefhouse 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

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection

4 out of 5
Posted 13 hours ago
Travelocity Verified Review
"Lovely hotel. Very expensive just to buy drinks though but good location."
A verified traveler stayed at Playa Largo Resort & Spa, Autograph Collection
Playa Largo Resort & Spa, Autograph Collection

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