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Most frequently booked Windley Key hotels

Drop Anchor

Drop Anchor

3.0 out of 5.0 84959 Overseas Highway, 222, Islamorada, FL
(12 Reviews)
An outdoor pool, free self parking, and free newspapers are featured at this hotel. WiFi in public areas is free. A garden, a picnic area, and barbecue grills are also on offer.
Pelican Cove Resort & Marina

Pelican Cove Resort & Marina

3.0 out of 5.0 84457 Overseas Highway, Islamorada, FL
(13 Reviews)
This smoke-free hotel features a private beach, a marina, and a restaurant. Dine at the beachfront restaurant and relax with sun loungers. Enjoy the outdoor pool and unwind at the poolside bar and bar/lounge.
Postcard Inn Beach Resort & Marina

Postcard Inn Beach Resort & Marina

3.0 out of 5.0 84001 Overseas Hwy, Islamorada, FL
(30 Reviews)
This Art Deco resort features a private beach, a marina, and 3 restaurants. Dine at the beachfront restaurant and relax with sun loungers. Enjoy the 2 outdoor pools, and relax with drinks at the beach bar and poolside bar.

Cheap Hotels in Windley Key

Pack your bags—it’s time to embark on a getaway. Whether you’re craving a solo retreat or promising your family a vacation to remember, book one of the best hotels in Windley Key. These hotels are located within easy access of the city’s hottest attractions and entertainment, so you won’t miss a beat while you’re in town. Spend the days exploring the local landmarks and the evenings getting to know the nightlife. After exploring the city from top to bottom, rest up at a hotel that speaks to you. Find the perfect place that matches your trip’s vibe, from a trendy boutique to family-friendly accommodations.

Allow us here at Travelocity to pair you with up Windley Key hotels that suit your vacation preferences. Discover places with convenient on-site restaurants, around-the-clock service, and pools where your kids can make a splash. Some hotels may boast fitness rooms and spa services, while others feature game rooms and Wi-Fi access. To top it all off, you’ll score cheap hotels in Windley Key that let you spend more on your activities and less on your lodging. Book and bundle your flight and hotel deals together today and save up to $537. It’s time to explore a new city, and break out of your routine.

Recent Windley Key hotel reviews by fellow wanderers

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.