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 $359 per night
CA $359
CA $495 total
May 25 - May 26
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 $230 per night
CA $230
CA $304 total
Apr 30 - May 1
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 $245 per night
CA $245
CA $276 total
Apr 30 - May 1
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 $238 per night
CA $238
CA $316 total
May 7 - May 8
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

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 $252 per night
CA $252
CA $360 total
May 28 - May 29
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

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 $341 per night
CA $341
CA $484 total
May 14 - May 15
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

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 $457 per night
CA $457
CA $589 total
May 5 - May 6
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 John Pennekamp Coral Reef State Park and Bluefin Rock Harbor Marina 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 $172 per night
CA $172
CA $232 total
May 12 - May 13
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 John Pennekamp Coral Reef State Park and Jacob's Aquatic Center are located nearby.
Pool
Pet-friendly

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 $407 per night
CA $407
CA $513 total
May 6 - May 7
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 Caribbean Club Bar 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 Tavernier FL
The price is CA $482 per night from Apr 30 to May 1
CA $482
CA $542 total
Apr 30 - May 1
includes taxes & fees
10/10 Exceptional! (164 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 | 2,741 hotels |
|---|---|
Lowest Price | CA $192 |
Highest Price | CA $3,455 |
Popular hotels | Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort, Fisher Inn Resort & Marina, Coconut Cove Resort and Marina, Drop Anchor, Chesapeake Beach Resort, Cheeca Lodge & Spa, Baker's Cay Resort Key Largo, Curio Collection by Hilton, Waterside Suites & Marina, Reefhouse Resort & Marina |
Recent Windley Key hotel reviews by fellow wanderers

Bayside Inn Key Largo
4 out of 5
Posted 1 hour ago
Travelocity Verified Review
"Air conditioning worked well. Shower pressure was great. We had a great time "
A verified traveller stayed at Bayside Inn Key Largo
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