Book Hotels in Windley Key, FL

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Jun 19 - Jun 21
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Top Windley Key hotels

Reefhouse Resort & Marina

Reefhouse Resort & Marina

4.5 out of 5
103800 Overseas Hwy Key Largo FL
Fully refundableReserve now, pay when you stay
$239 nightly
The price is $264 total per night from Jun 21 to Jun 22
$264 total
Jun 21 - Jun 22
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 ...
"The place was Excellent! I love the views and the services. ❤️🫶 100% I book this hotel again."

Reviewed on Jun 11, 2026

Opens in a new windowReefhouse Resort & 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
$266 nightly
The price is $299 total per night from Jun 15 to Jun 16
$299 total
Jun 15 - Jun 16
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. ...
"Property and room are beautiful, up to date and well-maintained. Secluded and calm as well. In-house dining was 6.5/10, concierge attitude was subpar and room service the first night was not good, second room service took an hour and a half ."

Reviewed on Jun 13, 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
$230 nightly
The price is $258 total per night from Jun 18 to Jun 19
$258 total
Jun 18 - Jun 19
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 ...
"Everyone was friendly and room was nice."

Reviewed on Jun 13, 2026

Opens in a new windowChesapeake Beach Resort
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
$336 nightly
The price is $378 total per night from Jul 7 to Jul 8
$378 total
Jul 7 - Jul 8
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 loved our stay at the Three waters resort. Room was very clean, and the whole property was beautiful. we loved that house keeping came every day. We did wish some stuff stayed open a bit longer, a lot of the staff was so nice but there was a few that just seemed rude. Good and drinks are a little ..."

Reviewed on Jun 13, 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
$179 nightly
The price is $201 total per night from Jun 15 to Jun 16
$201 total
Jun 15 - Jun 16
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 ...
"The property was very beautiful and the staff was great. They have an ice machine on site and a large pool area. The tiki bar is a great spot in the evening to sit and have a drink"

Reviewed on May 25, 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
$157 nightly
The price is $176 total per night from Jun 16 to Jun 17
$176 total
Jun 16 - Jun 17
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 ...
"Super clean. Very quiet"

Reviewed on Jun 10, 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
$295 nightly
The price is $331 total per night from Jun 30 to Jul 1
$331 total
Jun 30 - Jul 1
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. ...
"Bakers Cay was beautiful everything was clean and the amenities were awesome it is perfect for kids to or a romantic getaway beautiful!"

Reviewed on Jun 14, 2026

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
$188 nightly
The price is $212 total per night from Jun 15 to Jun 16
$212 total
Jun 15 - Jun 16
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. ...
"The property was nice and seemed well maintained. We came down with a 19 ft boat and the parking was very minimum. There wasn’t actual trailer parking like they advertise on the website. There was only the car parking lot where you can also park your boat or trailer."

Reviewed on Jun 14, 2026

Opens in a new windowFisher Inn Resort & Marina
Drop Anchor

Drop Anchor

3 out of 5
84959 Overseas Highway, 222 Islamorada FL
$160 nightly
The price is $176 total per night from Jun 15 to Jun 16
$176 total
Jun 15 - Jun 16
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
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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

Islander Resort

Islander Resort

5 out of 5
Posted 1 hour ago
Travelocity Verified Review
"The property and room were clean. The staff were helpful. There were lots of activities to keep us busy. My only complaint was when I purchased on e drink from the bar there was an automatic 20% tip on the bill. If you’re going to automatically charge me just raise the price of the drink and pay your employees a fair wage."
A verified traveler stayed at Islander Resort
Islander Resort

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