Book Hotels in Windley Key, FL

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Nov 6 - Nov 8
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Top Windley Key hotels

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
$272 nightly
The price is $306 total per night from Nov 29 to Nov 30
$306 total
Nov 29 - Nov 30
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 must have been there on the off season, we were there October 36 through 30, only one restaurant was open and the water taxi didn't run,we had 2 drinks at the pool our bill was $42.00 that was with out the tip, 😭, the resort frees were $65.00 a day for what I don't know, there was nothing there, ..."

Reviewed on Oct 30, 2026

Opens in a new windowThree Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

3 out of 5
84801 Overseas Highway Islamorada FL
$169 nightly
The price is $190 total per night from Nov 1 to Nov 2
$190 total
Nov 1 - Nov 2
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 ...
"Temp RV staff was great. Beautiful property, a little old school. This place is great, but not for Rich snobs."

Reviewed on Oct 31, 2026

Opens in a new windowCoconut Cove Resort and Marina
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
$178 nightly
The price is $200 total per night from Nov 1 to Nov 2
$200 total
Nov 1 - Nov 2
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 were disappointed in a few things, one being the comfort- the couch in our room was so uncomfortable we couldn’t sit for long at all- it was also dirty with stains- fir the cost if the room, spending some money on a new, comfortable couch with washable cushion covers wouldn’t be too much to ask- ..."

Reviewed on Oct 28, 2026

Opens in a new windowFisher Inn Resort & Marina
Drop Anchor

Drop Anchor

3 out of 5
84959 Overseas Highway, 222 Islamorada FL
$215 nightly
The price is $237 total per night from Nov 1 to Nov 2
$237 total
Nov 1 - Nov 2
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
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
$232 nightly
The price is $261 total per night from Dec 1 to Dec 2
$261 total
Dec 1 - Dec 2
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. ...
Opens in a new windowCheeca Lodge & Spa
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 Nov 1 to Nov 2
$286 total
Nov 1 - Nov 2
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
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$186 nightly
The price is $209 total per night from Nov 2 to Nov 3
$209 total
Nov 2 - Nov 3
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 ...
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
Fully refundableReserve now, pay when you stay
$182 nightly
The price is $204 total per night from Nov 3 to Nov 4
$204 total
Nov 3 - Nov 4
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 ...
Opens in a new windowLime Tree Bay Resort
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
$294 nightly
The price is $331 total per night from Nov 10 to Nov 11
$331 total
Nov 10 - Nov 11
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. ...
Opens in a new windowBaker's Cay Resort Key Largo, Curio Collection by Hilton
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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

The Pelican Key Largo Cottages

The Pelican Key Largo Cottages

5 out of 5
Posted 1 hour ago
Travelocity Verified Review
"Beautiful property and location. Cute little cottages."
A verified traveler stayed at The Pelican Key Largo Cottages
The Pelican Key Largo Cottages

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