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 $273 per night
CA $273
CA $400 total
Dec 17 - Dec 18
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 $117 per night
CA $117
CA $178 total
Dec 18 - Dec 19
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 $180 per night
CA $180
CA $203 total
Dec 3 - Dec 4
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 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 $175 per night
CA $175
CA $276 total
Dec 3 - Dec 4
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
Free cancellation
Reserve now, pay when you stay
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

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 $254 per night
CA $254
CA $381 total
Dec 17 - Dec 18
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 $321 per night
CA $321
CA $417 total
Dec 14 - Dec 15
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

Amara Cay Resort
80001 Overseas Hwy Islamorada FL
8.79 km from city centre
The price is CA $260 per night
CA $260
CA $386 total
Dec 11 - Dec 12
includes taxes & fees
Book a stay at this beach resort in Islamorada. Enjoy 2 restaurants, a private beach, and 3 bars/lounges. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Bud n' Mary's Dive Center and Hurricane Monument 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 $356 per night from Dec 4 to Dec 5
CA $356
CA $400 total
Dec 4 - Dec 5
includes taxes & fees
9.8/10 Exceptional! (139 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 | 2,786 hotels |
|---|---|
Lowest Price | CA $178 |
Highest Price | CA $3,545 |
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, Cheeca Lodge & Spa, Reefhouse Resort & Marina, Amara Cay Resort |
Recent Windley Key hotel reviews by fellow wanderers

Lime Tree Bay Resort
5 out of 5
Posted 2 days ago
Travelocity Verified Review
"Beautiful scenery and clean comfy rooms! Great staff.
"
A verified traveller stayed at Lime Tree Bay Resort
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