Book Hotels in Windley Key, FL

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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
$259 nightly
The price is $286 total per night from Oct 19 to Oct 20
$286 total
Oct 19 - Oct 20
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 ...
"Staff were very kind and helpful."

Reviewed on Oct 10, 2025

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
$172 nightly
The price is $194 total per night from Oct 22 to Oct 23
$194 total
Oct 22 - Oct 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 ...
"The pools where very clean and very comfy, the place is keep very clean. Thank you."

Reviewed on Oct 13, 2025

Opens in a new windowChesapeake Beach Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
$199 nightly
The price is $224 total per night from Oct 26 to Oct 27
$224 total
Oct 26 - Oct 27
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. ...
"Wonderful resort. Would stay again. Dinner was amazing."

Reviewed on Oct 15, 2025

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

3.5 out of 5
84001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
$245 nightly
The price is $276 total per night from Oct 26 to Oct 27
$276 total
Oct 26 - Oct 27
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 ...
"Went for our anniversary..will be back."

Reviewed on Oct 15, 2025

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
$131 nightly
The price is $148 total per night from Oct 29 to Oct 30
$148 total
Oct 29 - Oct 30
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 ...
Love it
"Absolutely loved the hotel. The room was amazing. Great view of the boat cancel"

Reviewed on Oct 11, 2025

Opens in a new windowWaterside Suites & Marina
Drop Anchor

Drop Anchor

3 out of 5
84959 Overseas Highway, 222, Islamorada, FL
$130 nightly
The price is $142 total per night from Oct 21 to Oct 22
$142 total
Oct 21 - Oct 22
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 ...
"Clean, comfortable room, friendly staff. Grounds clean and properly taken care of. Would stay here again."

Reviewed on Oct 1, 2025

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
$354 nightly
The price is $398 total per night from Oct 26 to Oct 27
$398 total
Oct 26 - Oct 27
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. ...
"Excellent hotel"

Reviewed on Oct 14, 2025

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
$136 nightly
The price is $153 total per night from Oct 27 to Oct 28
$153 total
Oct 27 - Oct 28
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. ...
"We really enjoyed our stay here. Great staff. Room was quite large with fridge, sink, and small stove. Very comfortable and clean. We used their kayak (they have 1) and paddleboard, also borrowed their bikes for an afternoon ride. Great pool. Breakfast was bagels, muffins, toast, and cereal; exactly ..."

Reviewed on Oct 14, 2025

Opens in a new windowFisher Inn Resort & Marina
Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

3 out of 5
84801 Overseas Highway, Islamorada, FL
$155 nightly
The price is $175 total per night from Oct 29 to Oct 30
$175 total
Oct 29 - Oct 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 ...
"What a true florida gem. Real old Florida"

Reviewed on Oct 11, 2025

Opens in a new windowCoconut Cove 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.

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