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Jul 31 - Aug 2
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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
$259 nightly
The price is $286 total per night from Aug 2 to Aug 3
$286 total
Aug 2 - Aug 3
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 ...
"From the moment we arrived to the moment we left it was a wonderful experience"

Reviewed on Jul 30, 2026

Opens in a new windowReefhouse Resort & Marina
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 Aug 10 to Aug 11
$306 total
Aug 10 - Aug 11
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 ...
"Room suite was spacious better than just a regular room kind of small. Microwave would of been nice to re heat left overs. Cove is best for adults looking to have a chil vibe without kids. Beaches i thought could of been raked daily since there not that big. Restaurants on site were nice Lil pricey ..."

Reviewed on Jul 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
$149 nightly
The price is $168 total per night from Aug 30 to Aug 31
$168 total
Aug 30 - Aug 31
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 ...
"Amazing staff! Clancy is great! This place is so cute family oriented and friendly! I cant wait to stay here again!"

Reviewed on Jul 23, 2026

Opens in a new windowCoconut Cove Resort and Marina
Drop Anchor

Drop Anchor

3 out of 5
84959 Overseas Highway, 222 Islamorada FL
$142 nightly
The price is $155 total per night from Aug 3 to Aug 4
$155 total
Aug 3 - Aug 4
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 hotel it’s nice but they don’t have beach . Not beach … they just have pool."

Reviewed on Jul 31, 2026

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
$302 nightly
The price is $340 total per night from Aug 17 to Aug 18
$340 total
Aug 17 - Aug 18
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. ...
"Great new suites. Great beach"

Reviewed on Jul 31, 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
$158 nightly
The price is $178 total per night from Aug 9 to Aug 10
$178 total
Aug 9 - Aug 10
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
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
$207 nightly
The price is $233 total per night from Aug 10 to Aug 11
$233 total
Aug 10 - Aug 11
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
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
$179 nightly
The price is $201 total per night from Aug 3 to Aug 4
$201 total
Aug 3 - Aug 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
Waterside Suites & Marina

Waterside Suites & Marina

3.5 out of 5
201 Ocean Drive Key Largo FL
Fully refundableReserve now, pay when you stay
$137 nightly
The price is $154 total per night from Aug 24 to Aug 25
$154 total
Aug 24 - Aug 25
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 ...
Opens in a new windowWaterside Suites & 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 hours ago
Travelocity Verified Review
"Great experience!"
A verified traveler stayed at Chesapeake Beach Resort
Chesapeake Beach Resort

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