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 $523 per night
CA $523
CA $684 total
includes taxes & fees
1 Apr - 2 Apr
Stay at this 3.5-star 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
0.85 km from city centre
The price is CA $321 per night
CA $321
CA $408 total
includes taxes & fees
2 Apr - 3 Apr
Stay at this 3.5-star 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 $400 per night
CA $400
CA $449 total
includes taxes & fees
26 Mar - 27 Mar
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 $370 per night
CA $370
CA $467 total
includes taxes & fees
26 Mar - 27 Mar
Stay at this 3-star 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

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 $249 per night
CA $249
CA $321 total
includes taxes & fees
27 Mar - 28 Mar
Stay at this 3.5-star 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

Baker's Cay Resort Key Largo, Curio Collection by Hilton
97000 Overseas Hwy, Key Largo, FL
17.38 km from city centre
The price is CA $523 per night
CA $523
CA $667 total
includes taxes & fees
2 Apr - 3 Apr
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

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 $341 per night
CA $341
CA $465 total
includes taxes & fees
9 Apr - 10 Apr
Book a stay at this beach hotel in Islamorada. Enjoy 2 outdoor pools, a private beach, and a 24-hour front desk. 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

Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Free cancellation
Reserve now, pay when you stay
5.91 km from city centre
The price is CA $732 per night
CA $732
CA $920 total
includes taxes & fees
9 Apr - 10 Apr
Stay at this 5-star 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 Matecumbe United Methodist Church and Florida Keys Brewing Co. 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 $428 per night
CA $428
CA $539 total
includes taxes & fees
1 Apr - 2 Apr
Stay at this 3.5-star beach hotel in Key Largo. Enjoy free parking, a full-service spa, and 3 restaurants. Our guests praise the pool and the bar in our reviews. Popular attractions John Pennekamp Coral Reef State Park and Jimmy Johnson's Big Chill are located nearby.
On private beach
Pool
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, Key Largo, Tavernier, FL
9.8/10 Exceptional! (111 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 | 2,731 hotels |
---|---|
Lowest Price | CA $249 |
Highest Price | CA $732 |
Popular hotels | Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort, Fisher Inn Resort & Marina, Coconut Cove Resort and Marina, Drop Anchor, Waterside Suites & Marina, Baker's Cay Resort Key Largo, Curio Collection by Hilton, Chesapeake Beach Resort, Cheeca Lodge & Spa, Reefhouse Resort & Marina |
Recent Windley Key hotel reviews by fellow wanderers

Chesapeake Beach Resort
5 out of 5
Posted 2 days ago
Travelocity Verified Review
"Very clean, very beautiful. Sea on the back side love it. "
A verified traveller stayed at Chesapeake Beach Resort
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