Book Hotels in Windley Key, FL
Cabins, apartments, houseboats! We offer comfortable & private vacation rentals
Save an extra 10% or more on select hotels with Member Discounts
Access exclusive hotel deals, only with the Travelocity app
Check prices for these dates
Top Windley Key hotels

Reefhouse Resort & Marina
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

Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
$283 nightly
The price is $318 total per night from Jul 6 to Jul 7
$318 total
Jul 6 - Jul 7
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. ...
"5 star"
Reviewed on Jun 13, 2026

Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$230 nightly
The price is $258 total per night from Jun 14 to Jun 15
$258 total
Jun 14 - Jun 15
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 ...
"This place was great! Very private, great amenities, staff, location, and accessible! Has everything you need for intimate location Oceanview is stellar, you can walk right into the ocean and relax with provided chairs, umbrellas, and towels. They have breakfast included with all breakfast types ..."
Reviewed on Jun 12, 2026

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
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 ...
"Nice! I thoroughly enjoyed the experience. enjoyed it."
Reviewed on Jun 13, 2026

Coconut Cove Resort and Marina
84801 Overseas Highway Islamorada FL
$179 nightly
The price is $201 total per night from Jun 14 to Jun 15
$201 total
Jun 14 - Jun 15
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

Waterside Suites & Marina
201 Ocean Drive Key Largo FL
Fully refundableReserve now, pay when you stay
$155 nightly
The price is $175 total per night from Jun 14 to Jun 15
$175 total
Jun 14 - Jun 15
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

Drop Anchor
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 ...
"Great stay for boaters! right on the water and easy to launch. The rooms were clean and had the essentials. The staff was super friendly and helpful."
Reviewed on Jun 10, 2026

Baker's Cay Resort Key Largo, Curio Collection by Hilton
97000 Overseas Hwy Key Largo FL
Fully refundableReserve now, pay when you stay
$296 nightly
The price is $333 total per night from Jun 30 to Jul 1
$333 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. ...
"Overall great. Some of the staff can be more friendly"
Reviewed on Jun 12, 2026

Fisher Inn Resort & Marina
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. ...
"We had a wonderful stay! The staff were friendly and welcoming. Our room was clean, spacious, and very comfortable, with everything we needed for a relaxing visit. The hotel amenities were excellent and really added to the overall experience. We would definitely stay here again and highly recommend ..."
Reviewed on Jun 9, 2026
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.
Hotels in Windley Key with star-rating
Check Windley Key Hotels by Star Rating

5 Star Hotels
2 properties
Recent Windley Key hotel reviews by fellow wanderers

Cheeca Lodge & Spa
5 out of 5
Posted 2 hours ago
Travelocity Verified Review
"5 star"
A verified traveler stayed at Cheeca Lodge & Spa
Explore More Ways to Travel with Travelocity
- Hotels near Bud n' Mary's Dive Center
- Matecumbe Hotels
- Hotels near Pigeon Key
- Lower Matecumbe Beach Hotels
- Lower Matecumbe Key Hotels
- Hotels near Jacob's Aquatic Center
- Hotels near Florida Keys Brewing Co.
- Hotels near Harry Harris Park
- Key Largo Hotels
- Wynken Blynken and Nod Hotels
- Hotels with Pools in Venetian Shores
- Venetian Shores Hotels
- Hotels near Matecumbe United Methodist Church
- Buccaneer Point Hotels
- Hotels near Windley Key Fossil Reef Geological State Park
- Layton Hotels
- Long Key Hotels
- Hotels near Anne's Beach
- Hotels near Baker's Cay Resort Beach
- 4 Star Hotels in Islamorada
- 5 Star Hotels in Islamorada
- Apartments in Islamorada
- B&B in Islamorada
- Condo Resorts in Islamorada
- Condos in Islamorada
- Cottages in Islamorada
- Extended Stay Hotels in Islamorada
- Guest Houses in Islamorada
- Adults Only Resorts & in Islamorada
- All Inclusive Resorts & in Islamorada
- Beach Resorts & in Islamorada
- Boutique Hotels in Islamorada
- Cheap Hotels in Islamorada
- Kid Friendly Hotels in Islamorada
- Gay Friendly Hotels in Islamorada
- Golf Resorts & in Islamorada
- Hilton Hotels in Islamorada
- Historic Hotels in Islamorada
- Hotels with Pools in Islamorada
- Hotels with Bar in Islamorada
- Hotels with Free Breakfast in Islamorada
- Hotels with Free Parking in Islamorada
- Hotels with Hot Tubs in Islamorada
- Hotels with smoking rooms in Islamorada
- Luxury Hotels in Islamorada
- Oceanfront Hotels in Islamorada
- Pet Friendly Hotels in Islamorada
- Romantic Getaways & Hotels in Islamorada
- Spa Resorts & in Islamorada
- Wyndham Hotels in Islamorada
- Islamorada Hotels
- Houseboats in Islamorada
- Lodges in Islamorada
- Motels in Islamorada
- Vacation Homes in Islamorada
- Rv Parks in Islamorada
- Resorts in Islamorada
- Villas in Islamorada
- Key Largo Village Hotels
- Hotels near Sunset Drive Beach
- Hotels near Founders Park
- Lignumvitae Key Botanical State Park Hotels
- Hotels near Jimmy Johnson's Big Chill
- Hotels near Bluefin Rock Harbor Marina
- Hotels near Fiesta Key
- Key Largo Park Hotels
- Hotels near Florida Keys Dive Center
- 3 Star Hotels in Plantation Key
- 5 Star Hotels in Plantation Key
- Chalets in Plantation Key
- Guest Houses in Plantation Key
- Holiday Park Resorts in Plantation Key
- Aimbridge Hospitality Hotels in Plantation Key
- Beach Resorts & in Plantation Key
- Cheap Hotels in Plantation Key
- Hersha Hospitality Hotels in Plantation Key
- Hotels with Pools in Plantation Key
- Hotels with Free Parking in Plantation Key
- Hotels with Kitchenettes in Plantation Key
- Hotels with smoking rooms in Plantation Key
- Plantation Key Hotels
- Houseboats in Plantation Key
- Tavernier Hotels
- Beach Hotels in Islamorada
- Resorts in Islamorada
- Pet-friendly Hotels in Islamorada
- Houseboats in Islamorada
- Hotels in Islamorada
- Luxury Hotels in Islamorada
- Flights to Islamorada
- Islamorada vacations
- Oceanfront Hotels in Islamorada
- Cottages in Islamorada
- Cheap Hotels in Islamorada
- Motels in Islamorada
- Islamorada vacation rentals
- Hotels in Plantation Key
- Visit Founders Park









