Book Cheap Hotels in Windley Key
Save an extra 10% or more on select hotels with Member Discounts
Access exclusive hotel deals, only with the Travelocity app
Check hotel availability in Windley Key
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 $400 per night
CA $400
CA $542 total
Jan 21 - Jan 22
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
0.87 km from city centre
The price is CA $237 per night
CA $237
CA $312 total
Jan 19 - Jan 20
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 $361 per night
CA $361
CA $406 total
Jan 18 - Jan 19
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 $218 per night
CA $218
CA $294 total
Jan 19 - Jan 20
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 $244 per night
CA $244
CA $353 total
Jan 29 - Jan 30
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
26.68 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

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 $201 per night
CA $201
CA $266 total
Jan 21 - Jan 22
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

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 $164 per night
CA $164
CA $224 total
Jan 18 - Jan 19
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

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 $374 per night
CA $374
CA $523 total
Jan 29 - Jan 30
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
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! (144 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 | 2,763 hotels |
|---|---|
Lowest Price | CA $224 |
Highest Price | CA $3,517 |
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, Waterside Suites & Marina, Marina Del Mar Resort and Marina, Cheeca Lodge & Spa |
Recent Windley Key hotel reviews by fellow wanderers

Waterside Suites & Marina
5 out of 5
Posted 1 day ago
Travelocity Verified Review
"Very quiet and clean! Staff were very friendly and accommodating! Close to great restaurants and dive shops."
A verified traveller stayed at Waterside Suites & Marina
Hotels near…
Areas of Windley Key
Most popular
Hotels
- Motels Cumberland
- Hotels with a Pool in North Bay
- Hotels with Waterslides in Fargo
- Cottages Fenelon Falls
- Farmstay Upstate New York
- Cabins Saskatchewan
- B&B Point Edward
- Pet Friendly Hotels in Northern Ontario
- Best Western Plus Executive Inn
- Hotels in International Drive District
- Kid Friendly Hotels in St. Albert
- All Inclusive Resorts & Hotels in St. Croix Island
- Hotels in Santa María Huatulco
- HiltonHotels Hotels in Port Elgin
Flights
- Air Canada Paris (CDG) to Montreal (YUL) flights
- Montreal to Nanaimo (YUL - YCD)
- Flights to Petawawa
- JetBlue Airways Boston (BOS) to Orlando (MCO) flights
- Air Canada Toronto (YYZ) to Lagos (LOS) flights
- Air Canada Goffs (YHZ) to Newark (EWR) flights
- Edmonton to Kalispell (YEG - FCA)
- WestJet Toronto (YYZ) to Nashville (BNA) flights
- Flights from Winnipeg to Osoyoos
- Flights to Yellowstone National Park
- Avianca Toronto (YYZ) to Lima (LIM) flights











