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 $664 per night
CA $664
CA $843 total
includes taxes & fees
4 Mar - 5 Mar
Stay at this 3.5-star 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
0.85 km from city centre
The price is CA $344 per night
CA $344
CA $434 total
includes taxes & fees
4 Mar - 5 Mar
Stay at this 3.5-star 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 $288 per night
CA $288
CA $324 total
includes taxes & fees
4 Mar - 5 Mar
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 $612 per night
CA $612
CA $740 total
includes taxes & fees
11 Mar - 12 Mar
Stay at this 3-star 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

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 $302 per night
CA $302
CA $340 total
includes taxes & fees
1 Apr - 2 Apr
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 Jimmy Johnson's Big Chill and John Pennekamp Coral Reef State Park are located nearby.
Pool
Hot tub

Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Free cancellation
Reserve now, pay when you stay
5.91 km from city centre
The price is CA $657 per night
CA $657
CA $837 total
includes taxes & fees
1 Apr - 2 Apr
Stay at this 5-star 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 Matecumbe United Methodist Church and Florida Keys Brewing Co. 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 $505 per night
CA $505
CA $626 total
includes taxes & fees
4 Mar - 5 Mar
Stay at this 3.5-star beach hotel in Key Largo. Enjoy free parking, a full-service spa, and 3 restaurants. Our guests praise the pool and the bar in our reviews. Popular attractions John Pennekamp Coral Reef State Park and Jimmy Johnson's Big Chill are located nearby.
On private beach
Pool

Bayside Inn Key Largo
99490 Overseas Hwy, Key Largo, FL
Free cancellation
Reserve now, pay when you stay
21.72 km from city centre
The price is CA $321 per night
CA $321
CA $397 total
includes taxes & fees
9 Mar - 10 Mar
Stay at this 3-star beach hotel in Key Largo. Enjoy free WiFi, a private beach, and a 24-hour fitness center. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Jimmy Johnson's Big Chill and John Pennekamp Coral Reef State Park are located nearby.

Baker's Cay Resort Key Largo, Curio Collection by Hilton
97000 Overseas Hwy, Key Largo, FL
Free cancellation
Reserve now, pay when you stay
17.38 km from city centre
The price is CA $622 per night
CA $622
CA $779 total
includes taxes & fees
4 Mar - 5 Mar
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
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 | 2,753 hotels |
---|---|
Lowest Price | CA $288 |
Highest Price | CA $664 |
Popular hotels | Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort, Fisher Inn Resort & Marina, Coconut Cove Resort and Marina, Drop Anchor, Marina Del Mar Resort and Marina, Cheeca Lodge & Spa, Reefhouse Resort & Marina, Bayside Inn Key Largo, Baker's Cay Resort Key Largo, Curio Collection by Hilton |
Recent Windley Key hotel reviews by fellow wanderers

Chesapeake Beach Resort
5 out of 5
Posted 2 days ago
Travelocity Verified Review
"Excellent location for family trip or fishing. Clean friendly hotel lovely custom made free breakfast by Mr Chris. Also pet friendly"
A verified traveller stayed at Chesapeake Beach Resort
Hotels near…
Areas of Windley Key
Most popular
Hotels
Hotels with smoking rooms in TimminsSuper 8 by Wyndham St-JeromeKid Friendly Hotels in LunenburgCottages Belle RiverHotels in Turner ValleyHotels in International DriveCabins Beaver MinesWaterpark Hotels and Resorts in DetroitCasino Resorts & Hotels in WindsorHotel Wedding Venues in KitchenerQuattro Hotel & Conference Centre, Ascend Hotel CollectionExtended Stay Hotels Honolulu
Flights
Flights from Halifax to Pigeon ForgeFlair Airlines Toronto (YYZ) to Saskatoon (YXE) flightsToronto to Comox (YYZ - YQQ)Alaska Airlines Bellingham (BLI) to Mazatlán (MZT) flightsFlights to Miramar BeachAir India Delhi (DEL) to Vancouver (YVR) flightsWestJet Hamilton (YHM) to Windsor (YQG) flightsDelta Toronto (YYZ) to New York (JFK) flightsAir Canada Edmonton (YEG) to Narita (NRT) flightsDelta Toronto (YYZ) to Sao Paulo (GRU) flights