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 $372 per night
CA $372
CA $509 total
Aug 11 - Aug 12
includes taxes & fees
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
Reserve now, pay when you stay
0.85 km from city centre
The price is CA $156 per night
CA $156
CA $220 total
Jul 23 - Jul 24
includes taxes & fees
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 $204 per night
CA $204
CA $230 total
Jul 17 - Jul 18
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
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

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 $262 per night
CA $262
CA $388 total
Aug 13 - Aug 14
includes taxes & fees
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

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 $272 per night
CA $272
CA $383 total
Jul 23 - Jul 24
includes taxes & fees
Stay at this 3.5-star 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 $454 per night
CA $454
CA $587 total
Aug 11 - Aug 12
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

Hampton Inn Key Largo Manatee Bay
102400 Overseas Hwy, Key Largo, FL
Free cancellation
Reserve now, pay when you stay
25.7 km from city centre
The price is CA $162 per night
CA $162
CA $182 total
Aug 4 - Aug 5
includes taxes & fees
Book a stay at this beach hotel in Key Largo. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions John Pennekamp Coral Reef State Park and Jimmy Johnson's Big Chill are located nearby.
On private beach
Pool

Islander Resort
82100 Overseas Highway, Islamorada, FL
Free cancellation
Reserve now, pay when you stay
5.32 km from city centre
The price is CA $285 per night
CA $285
CA $413 total
Aug 11 - Aug 12
includes taxes & fees
Stay at this 4-star beach hotel in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Keys History & Discovery Center and Islamorada Brewery & Distillery 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! (125 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 $132 |
Highest Price | CA $454 |
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, Chesapeake Beach Resort, Baker's Cay Resort Key Largo, Curio Collection by Hilton, Hampton Inn Key Largo Manatee Bay, Islander Resort |
Recent Windley Key hotel reviews by fellow wanderers

Amara Cay Resort
5 out of 5
Posted 20 hours ago
Travelocity Verified Review
"Large shower. Relaxing environment. Kayaks. Ability to use resort amenities until 4 on day of checkout. Room decorated for relaxation. "
A verified traveller stayed at Amara Cay Resort
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