Book Cheap Hotels in Windley Key
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Most frequently booked Windley Key hotels

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy Islamorada FL
Free cancellation
Reserve now, pay when you stay
1.98 km from city centre
The price is CA $379 per night
CA $379
CA $529 total
Jul 7 - Jul 8
includes taxes & fees
Book a stay at this beach resort in Islamorada. Enjoy free WiFi, 3 outdoor pools, and 4 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Windley Key Fossil Reef Geological State Park and History of Diving Museum are located nearby.
On private beach
Pool

Fisher Inn Resort & Marina
84951 Overseas Hwy Islamorada FL
Free cancellation
Reserve now, pay when you stay
0.87 km from city centre
The price is CA $200 per night
CA $200
CA $271 total
Jun 15 - Jun 16
includes taxes & fees
Book a stay at this beach motel in Islamorada. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Windley Key Fossil Reef Geological State Park and Rain Barrel Village are located nearby.
On private beach
Pool

Coconut Cove Resort and Marina
84801 Overseas Highway Islamorada FL
1.08 km from city centre
The price is CA $250 per night
CA $250
CA $282 total
Jun 15 - Jun 16
includes taxes & fees
Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free parking, and a marina. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Windley Key Fossil Reef Geological State Park and History of Diving Museum are located nearby.
Pool
Breakfast included

Drop Anchor
84959 Overseas Highway, 222 Islamorada FL
0.7 km from city centre
The price is CA $158 per night
CA $158
CA $227 total
Jun 16 - Jun 17
includes taxes & fees
Stay at this hotel in Islamorada. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Windley Key Fossil Reef Geological State Park and Rain Barrel Village are located nearby.
Pool
Pet-friendly

Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Free cancellation
Reserve now, pay when you stay
5.91 km from city centre
The price is CA $284 per night
CA $284
CA $422 total
Jul 8 - Jul 9
includes taxes & fees
Book a stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Florida Keys Brewing Co. and MoradaWay Arts & Cultural District are located nearby.
On private beach
Pool

Reefhouse Resort & Marina
103800 Overseas Hwy Key Largo FL
Free cancellation
Reserve now, pay when you stay
28.41 km from city centre
The price is CA $278 per night
CA $278
CA $369 total
Jun 21 - Jun 22
includes taxes & fees
Book a stay at this luxury hotel in Key Largo. Enjoy free parking, a full-service spa, and 3 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions John Pennekamp Coral Reef State Park and Jimmy Johnson's Big Chill are located nearby.
On private beach
Pool

Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Free cancellation
Reserve now, pay when you stay
2.93 km from city centre
The price is CA $249 per night
CA $249
CA $358 total
Jun 18 - Jun 19
includes taxes & fees
Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. Popular attractions History of Diving Museum and Windley Key Fossil Reef Geological State Park are located nearby.
On private beach
Pool

Baker's Cay Resort Key Largo, Curio Collection by Hilton
97000 Overseas Hwy Key Largo FL
Free cancellation
Reserve now, pay when you stay
17.38 km from city centre
The price is CA $343 per night
CA $343
CA $464 total
Jun 30 - Jul 1
includes taxes & fees
Book a stay at this beach resort in Key Largo. Enjoy 2 outdoor pools, 2 restaurants, and a private beach. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Jimmy Johnson's Big Chill and John Pennekamp Coral Reef State Park are located nearby.
On private beach
Pool

Waterside Suites & Marina
201 Ocean Drive Key Largo FL
Free cancellation
Reserve now, pay when you stay
22.44 km from city centre
The price is CA $186 per night
CA $186
CA $249 total
Jun 28 - Jun 29
includes taxes & fees
Stay at this hotel in Key Largo. Enjoy free WiFi, a marina, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Jimmy Johnson's Big Chill and John Pennekamp Coral Reef State Park are located nearby.
Pool
Pet-friendly
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.
Top hotels in Windley Key for Extended Stay

Island Bay Resort
92530 OVERSEAS HIGHWAY Tavernier FL
The price is CA $372 per night from Jul 1 to Jul 2
CA $372
CA $419 total
Jul 1 - Jul 2
includes taxes & fees
10/10 Exceptional! (170 reviews)
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.
Windley Key hotels essential information
Accommodation | 2,714 hotels |
|---|---|
Lowest Price | CA $227 |
Highest Price | CA $2,864 |
Popular hotels | Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort, Fisher Inn Resort & Marina, Coconut Cove Resort and Marina, Drop Anchor, Cheeca Lodge & Spa, Reefhouse Resort & Marina, Chesapeake Beach Resort, Baker's Cay Resort Key Largo, Curio Collection by Hilton, Waterside Suites & Marina |
Recent Windley Key hotel reviews by fellow wanderers

Baker's Cay Resort Key Largo, Curio Collection by Hilton
5 out of 5
Posted 1 hour ago
Travelocity Verified Review
"Bakers Cay was beautiful everything was clean and the amenities were awesome it is perfect for kids to or a romantic getaway beautiful!"
A verified traveller stayed at Baker's Cay Resort Key Largo, Curio Collection by Hilton
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