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Our top choices for Windley Key hotels
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio ResortIslamorada
9.0 out of 10, Wonderful, (115)
Discover a waterfront escape at this Art Deco resort with 3 outdoor pools and 4 restaurants including Latin American cuisine. Kayak, snorkel, or unwind on the private beach while enjoying stunning ocean views and nearby marine attractions.
"Beautiful place to stay"
Jonathan
The price is NZ$539
includes taxes & fees
17 Dec - 18 Dec
8.8 out of 10, Excellent, (1000)
This waterfront hotel offers an outdoor pool, complimentary kayaking, and free bike rentals to explore nearby attractions. Located near Windley Key Fossil Reef Geological State Park, guests appreciate the clean rooms and exceptional staff service.
"Had a wonderful stay at Drop Anchor! Very adorable and super clean. Loved the amenities and the hotel staff were amazing! "
Laura
The price is NZ$222
includes taxes & fees
17 Dec - 18 Dec
9.0 out of 10, Wonderful, (150)
Overlooks Florida Bay with a stunning outdoor pool and private beach area. This hotel offers complimentary breakfast and parking, plus convenient access to diving spots and Windley Key Fossil Reef Geological State Park.
"Great place to stay! Clean, great location and great customer service. Very easy to check in, front desk was so sweet! Highly recommended!!! Had a great experience overall"
Elaysi
The price is NZ$263
includes taxes & fees
16 Dec - 17 Dec
8.2 out of 10, Very good, (1003)
Wake to ocean views at this Florida Keys retreat offering free breakfast and water activities. Enjoy kayaking, snorkelling, or cycling with complimentary equipment. Just minutes from Windley Key Fossil Reef and Rain Barrel Village, with helpful staff to enhance your stay.
"Great location, room was spotless and perfectly met my needs. I plan to return next year."
M
The price is NZ$276
includes taxes & fees
18 Dec - 19 Dec
9.4 out of 10, Exceptional, (9)
Located in Islamorada, this waterside hotel offers an outdoor pool and 2 bars/lounges for tropical drinks. The Ocean View Pub serves lunch and dinner, while free WiFi and parking add value to your Keys adventure.
"Awesome place to stay, restaurant and bar attached, outside bar and dining area overlooking the bay. Pool also very nice. "
Rick
The price is NZ$305
includes taxes & fees
18 Dec - 19 Dec
9.4 out of 10, Exceptional, (717)
Waterfront escape with a private beach, marina, and complimentary kayaks and bikes. The outdoor pool provides refreshing relaxation after exploring nearby Mangrove Marina. Rooms include convenient refrigerators and microwaves for extended stays.
"The room was very clean. The staff was nice. The property was very safe and quiet."
ROBERT
The price is NZ$413
includes taxes & fees
5 Jan - 6 Jan 2026
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.
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Venture to sights like Windley Key Fossil Reef Geological State Park as you discover the local area in Windley Key.
Top Windley Key Hotel Reviews
More cheap accommodation in Windley Key
The Pelican Key Largo Cottages
99340 Overseas Highway Key Largo FL
The price is NZ$236 per night from 16 Dec to 17 Dec
NZ$236
16 Dec - 17 Dec
includes taxes & fees
8.8/10 Excellent! (1,005 reviews)
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