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Windley Key Luxury Holidays

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    • Top Luxury holiday packages in Windley Key

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    Discover the most popular places to visit in Windley Key

    Windley Key Fossil Reef Geological State Park

    Rating: 8.8/10 (184 reviews)

    Explore the fossilized reef of a former quarry in this island park, as you learn about the history and ecology from the interpretive trails.

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    Hog Heaven

    After visiting Hog Heaven, make a plan to see the other sights and activities in Islamorada. Discover the beautiful sunsets in this relaxing area or enjoy its fishing spots.

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    Top Luxury Windley Key Hotels

    Coconut Cove Resort and Marina

    A clear blue pool surrounded by palm trees and a thatched-roof structure, with a view of the ocean in the background.
    • Address: 84801 Overseas Highway, Islamorada, FL, 33036, US
    • Location: 0.7 mi from Windley Key
    • Star rating: 3/5
    • Guest rating: 9/10 (Wonderful, 309 reviews)
    • Price: £143, includes taxes & fees, 15 Nov - 16 Nov, for Top Luxury Windley Key Hotels
    • Review: "This is my second time staying here. It's a laid-back, extremely quiet place, so if you're looking for the party vibe, definitely not for you. The "beach" is really no more than a mangrove swamp, but that's typical of the Keys. For beaches, look elsewhere in Florida. The pool makes up for it, though. It is absolutely beautiful, with a waterfall and a chiller, so the water is always cool and refreshing even at the height of summer. And best of all: the pool is open 24 hours! This place is super...

    Drop Anchor

    A beach with palm trees, a thatched-roof hut, and beach chairs.
    • Address: 84959 Overseas Highway, 222, Islamorada, FL, 33036, US
    • Location: 0.4 mi from Windley Key
    • Star rating: 3/5
    • Guest rating: 8.6/10 (Excellent, 1000 reviews)
    • Price: £134, includes taxes & fees, 24 Nov - 25 Nov, for Top Luxury Windley Key Hotels
    • Review: They were amazing! Amenities were great fun! Will definitely be back!

    Fisher Inn Resort & Marina

    A beachfront hotel with a pool, beach chairs, and a view of the ocean at sunset.
    • Address: 84951 Overseas Hwy, Islamorada, FL, 33036, US
    • Location: 0.5 mi from Windley Key
    • Star rating: 3.5/5
    • Guest rating: 8.2/10 (Very good, 1002 reviews)
    • Price: £139, includes taxes & fees, 29 Nov - 30 Nov, for Top Luxury Windley Key Hotels
    • Review: A+

    The Ocean View Inn & Pub

    A bedroom with a large bed, a sliding glass door to a balcony, a wooden cabinet, and a kitchen area with a microwave.
    • Address: 84500 Overseas Hwy, Islamorada, FL, 33036, US
    • Location: 0.8 mi from Windley Key
    • Star rating: 2/5
    • Guest rating: 9.2/10 (Wonderful, 35 reviews)
    • Price: £158, includes taxes & fees, 16 Nov - 17 Nov, for Top Luxury Windley Key Hotels
    • Review: Centrally located to the things we wanted to do. We loved the bar/restaurant that was attached. There was live music both nights we stayed! It was a great amenity while sitting by the pool. The staff were very friendly and helpful. The only downfall was the AC didn’t circulate very well, so bring a fan! Other than that we loved it! Would definitely return.

    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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    All you need to know about luxury holidays in Windley Key

    What can I expect from a luxury Windley Key holiday?

    Luxury on holiday is all about relaxing and feeling good. Whether you choose a sumptuous spa, Michelin-starred restaurant or super-king bed is your call. Use our amenities filters to find the things that tick all your boxes.

    How can I find all-inclusive luxury holidays in Windley Key?

    Tick the all-inclusive and 5-star filters to find the crème de la crème of Windley Key holidays. With everything included in the package price, you can drink and dine to your heart’s content, without worrying about that bill at the end.

    Can I book a cheap luxury holiday to Windley Key?

    A luxury holiday doesn’t have to break the bank. Travel out of peak season, choose a hotel or resort a little way out or go for a last-minute getaway and you’ll find some cracking deals. Sort by price to find luxury holidays to Windley Key starting at £921. Prices and availability are subject to change. Additional terms may apply.

    Are there luxury spa holidays in Windley Key?

    For sunset massages on the shoreline and view-filled saunas, use our spa filter to find your ideal Windley Key spa hotel. Book a whole weekend soaking away your stresses, or hop into the spa after the beach, some golf or a local advent-ahhhh.

    What should I look for when booking a luxury family holiday in Windley Key?

    Luxury isn’t just for adults. Those little touches designed for little people make a family holiday genuinely stress free … which is the greatest luxury of all. Look for spacious suites, pools toddlers can splash in, and breakfast buffets with waffles, pancakes and Nutella galore.

    Can I book luxury last-minute holidays to Windley Key?

    You can wangle a top-notch luxury holiday in Windley Key for a fraction of the normal price by booking last minute. Just enter your dates and see what’s available – if you’re flexible ... even better!

    Can I book a luxury holiday in Windley Key with free cancellation and/or flexible dates?

    If you’re splashing out on a luxury holiday, make sure your money is safe by booking with free cancellation. Just use the fully refundable filter and make sure you read all the terms and conditions.

    Why should I book my luxury travel to Windley Key with Expedia?

    Nobody does luxury quite like Expedia. With so many gorgeous properties in Windley Key to choose from, as well as access to first-class flight deals and hire cars with horsepower, there’s no better place to book.

    Explore a world of travel with Expedia