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
$259 nightly
The price is $286 total per night from Oct 19 to Oct 20
$286 total
Oct 19 - Oct 20
Total with taxes and fees
This smoke-free 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 ...
"Staff were very kind and helpful."
Reviewed on Oct 10, 2025

Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
$172 nightly
The price is $194 total per night from Oct 22 to Oct 23
$194 total
Oct 22 - Oct 23
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 ...
"The pools where very clean and very comfy, the place is keep very clean. Thank you."
Reviewed on Oct 13, 2025

Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
$199 nightly
The price is $224 total per night from Oct 26 to Oct 27
$224 total
Oct 26 - Oct 27
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. ...
"Wonderful resort. Would stay again. Dinner was amazing."
Reviewed on Oct 15, 2025

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
$245 nightly
The price is $276 total per night from Oct 26 to Oct 27
$276 total
Oct 26 - Oct 27
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 ...
"Went for our anniversary..will be back."
Reviewed on Oct 15, 2025

Waterside Suites & Marina
201 Ocean Drive, Key Largo, FL
Fully refundableReserve now, pay when you stay
$131 nightly
The price is $148 total per night from Oct 29 to Oct 30
$148 total
Oct 29 - Oct 30
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 ...
Love it
"Absolutely loved the hotel. The room was amazing. Great view of the boat cancel"
Reviewed on Oct 11, 2025

Drop Anchor
84959 Overseas Highway, 222, Islamorada, FL
$130 nightly
The price is $142 total per night from Oct 21 to Oct 22
$142 total
Oct 21 - Oct 22
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 ...
"Clean, comfortable room, friendly staff. Grounds clean and properly taken care of. Would stay here again."
Reviewed on Oct 1, 2025

Baker's Cay Resort Key Largo, Curio Collection by Hilton
97000 Overseas Hwy, Key Largo, FL
Fully refundableReserve now, pay when you stay
$354 nightly
The price is $398 total per night from Oct 26 to Oct 27
$398 total
Oct 26 - Oct 27
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. ...
"Excellent hotel"
Reviewed on Oct 14, 2025

Fisher Inn Resort & Marina
84951 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
$136 nightly
The price is $153 total per night from Oct 27 to Oct 28
$153 total
Oct 27 - Oct 28
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 really enjoyed our stay here. Great staff. Room was quite large with fridge, sink, and small stove. Very comfortable and clean. We used their kayak (they have 1) and paddleboard, also borrowed their bikes for an afternoon ride. Great pool. Breakfast was bagels, muffins, toast, and cereal; exactly ..."
Reviewed on Oct 14, 2025

Coconut Cove Resort and Marina
84801 Overseas Highway, Islamorada, FL
$155 nightly
The price is $175 total per night from Oct 29 to Oct 30
$175 total
Oct 29 - Oct 30
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 ...
"What a true florida gem. Real old Florida"
Reviewed on Oct 11, 2025
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
3 properties
Recent Windley Key hotel reviews by fellow wanderers

Cheeca Lodge & Spa
5 out of 5
Posted 3 days ago
Travelocity Verified Review
"Wonderful resort. Would stay again. Dinner was amazing. "
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