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 $499 per night
CA $499
CA $652 total
Mar 4 - Mar 5
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
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 $445 per night
CA $445
CA $501 total
Mar 24 - Mar 25
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 $257 per night
CA $257
CA $338 total
Feb 25 - Feb 26
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

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 $477 per night
CA $477
CA $592 total
Feb 23 - Feb 24
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

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 $425 per night
CA $425
CA $556 total
Mar 24 - Mar 25
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 $497 per night
CA $497
CA $660 total
Mar 4 - Mar 5
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

Lime Tree Bay Resort
68500 Overseas Hwy Long Key FL
26.68 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 $259 per night
CA $259
CA $330 total
Mar 1 - Mar 2
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
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! (150 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 $330 |
Highest Price | CA $3,464 |
Popular hotels | Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort, Fisher Inn Resort & Marina, Coconut Cove Resort and Marina, Drop Anchor, Reefhouse Resort & Marina, Chesapeake Beach Resort, Cheeca Lodge & Spa, Lime Tree Bay Resort, Marina Del Mar Resort and Marina |
Recent Windley Key hotel reviews by fellow wanderers

Marina Del Mar Resort and Marina
5 out of 5
Posted 21 hours ago
Travelocity Verified Review
"The room was clean and tidy. Breakfast was good. Staff were helpful and two restaurants were right next door. The location right on the marina was nice too,"
A verified traveller stayed at Marina Del Mar Resort and Marina
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