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 $419 per night
CA $419
CA $563 total
Jan 20 - Jan 21
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
0.85 km from city centre
The price is CA $222 per night
CA $222
CA $295 total
Jan 11 - Jan 12
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 $295 per night
CA $295
CA $332 total
Jan 7 - Jan 8
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 $220 per night
CA $220
CA $296 total
Jan 7 - Jan 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 $240 per night
CA $240
CA $348 total
Jan 14 - Jan 15
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

Lime Tree Bay Resort
68500 Overseas Hwy Long Key FL
26.77 km from city centre
Book a stay at this beach resort in Long Key. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Long Key State Park and Fiesta Key are located nearby.
On private beach
Pool

Marina Del Mar Resort and Marina
527 Caribbean Drive Key Largo FL
Free cancellation
Reserve now, pay when you stay
22.19 km from city centre
The price is CA $160 per night
CA $160
CA $219 total
Jan 13 - Jan 14
includes taxes & fees
Stay at this hotel in Key Largo. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the breakfast and the pool in our reviews. Popular attractions John Pennekamp Coral Reef State Park and Jacob's Aquatic Center are located nearby.
Pool
Hot tub

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 $203 per night
CA $203
CA $268 total
Jan 6 - Jan 7
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 $369 per night
CA $369
CA $471 total
Jan 6 - Jan 7
includes taxes & fees
Book a stay at this beach 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
9.8/10 Exceptional! (142 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 | 2,762 hotels |
|---|---|
Lowest Price | CA $219 |
Highest Price | CA $3,477 |
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, Lime Tree Bay Resort, Marina Del Mar Resort and Marina, Waterside Suites & Marina, Reefhouse Resort & Marina |
Recent Windley Key hotel reviews by fellow wanderers

Chesapeake Beach Resort
5 out of 5
Posted 13 hours ago
Travelocity Verified Review
"One of the most beautiful hotel I have ever stayed. It's on the pricey side, but worth staying it. We loved everything about it. "
A verified traveller stayed at Chesapeake Beach Resort
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