Book Hotels in Windley Key, FL

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Jul 24 - Jul 26
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Top Windley Key hotels

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 16 to Aug 17
$201 total
Aug 16 - Aug 17
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 ...
"This is our 2nd stay and we will be back! Small resort, not over crowded. Beautiful views & very relaxing!"

Reviewed on Jul 21, 2026

Opens in a new windowLime Tree Bay Resort
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
$226 nightly
The price is $254 total per night from Aug 2 to Aug 3
$254 total
Aug 2 - Aug 3
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. ...
"Food choices all where great!"

Reviewed on Jul 21, 2026

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

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 ...
"Wonderful resort and friendly staff!"

Reviewed on Jul 21, 2026

Opens in a new windowThree Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Drop Anchor

Drop Anchor

3 out of 5
84959 Overseas Highway, 222 Islamorada FL
$160 nightly
The price is $176 total per night from Jul 22 to Jul 23
$176 total
Jul 22 - Jul 23
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 ...
"We really enjoyed the laid back vibe, matched with the amenities and the location. We had a great stay!"

Reviewed on Jul 21, 2026

Opens in a new windowDrop Anchor
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
$168 nightly
The price is $189 total per night from Aug 9 to Aug 10
$189 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
Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

3 out of 5
84801 Overseas Highway Islamorada FL
$189 nightly
The price is $213 total per night from Jul 22 to Jul 23
$213 total
Jul 22 - Jul 23
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 ...
Opens in a new windowCoconut Cove Resort and 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
$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. ...
Opens in a new windowBaker's Cay Resort Key Largo, Curio Collection by Hilton
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
$226 nightly
The price is $254 total per night from Aug 19 to Aug 20
$254 total
Aug 19 - Aug 20
Total with taxes and fees
A private beach, 2 restaurants, and an outdoor pool are all featured at this resort. If you want to take your pet along, this pet-friendly property offers everything ...
Opens in a new windowAmara Cay Resort
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$198 nightly
The price is $223 total per night from Aug 17 to Aug 18
$223 total
Aug 17 - Aug 18
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
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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

Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
Posted 4 hours ago
Travelocity Verified Review
"Food choices all where great!"
A verified traveler stayed at Cheeca Lodge & Spa
Cheeca Lodge & Spa

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