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A coastal landscape with a sandy beach, clear turquoise waters, and a network of small islands.

Keewaydin Island Luxury Holidays

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Top Luxury holiday packages in Keewaydin Island

Price found within the past 48 hours. Click for updated prices.
  • Lobby
    21 Sept - 25 Sept

    Trianon Bonita Bay + Flight

    Bonita Bay
    4 nights
    3.5 star property
    9.2/10 - Wonderful (1,780 reviews)
    Return • London (LON) - Fort Myers (RSW)
    LHR - MIA • Direct MIA - LHR • 1 stop
    £838
    £775
    per traveller
    found 1 day ago
    Trianon Bonita Bay
  • In-room safe, blackout curtains, iron/ironing board, cots/infant beds
    21 Sept - 25 Sept

    Casa Ybel Resort + Flight

    Mid Island
    4 nights
    2.5 star property
    8.8/10 - Excellent (397 reviews)
    "Disappointed to learn that this resort charges for chairs on the beach. Having a kitchen was a selling point for us, as we don’t like to eat out every meal on vacation. Unfortunately, there were very few utensils, cookware and storage pieces within. The paper products were extremely cheap for a resort of this type. We had trouble with one TV in the bedroom and front desk was not concerned about helping us with this. They referred us to call back the next day. We did see an employee doing..."
    Reviewed August 1, 2026
    Return • London (LON) - Fort Myers (RSW)
    LHR - MIA • Direct MIA - LHR • 1 stop
    £1,187
    £977
    per traveller
    found 1 day ago
    Casa Ybel Resort
  • Lobby
    21 Sept - 25 Sept

    Innovation Hotel + Flight

    Naples
    4 nights
    4.0 star property
    9.8/10 - Exceptional (632 reviews)
    "Un excelente lugar limpio tranquilo y cómodo lo único malo es q no tiene piscina y aveces es necesario para un lugar como ese"
    Reviewed August 2, 2026
    Return • London (LON) - Fort Myers (RSW)
    LHR - MIA • Direct MIA - LHR • 1 stop
    £1,197
    £1,021
    per traveller
    found 1 day ago
    Innovation Hotel
  • 2 outdoor pools, pool cabanas (surcharge), pool umbrellas
    21 Sept - 25 Sept

    The Perry Hotel Naples + Flight

    Naples
    4 nights
    4.5 star property
    9.6/10 - Exceptional (993 reviews)
    "Bartenders were great."
    Reviewed August 3, 2026
    Return • London (LON) - Fort Myers (RSW)
    LHR - MIA • Direct MIA - LHR • 1 stop
    £925
    £790
    per traveller
    found 1 day ago
    The Perry Hotel Naples
  • 3 restaurants; breakfast, lunch, dinner and brunch served
    21 Sept - 25 Sept

    Lani Kai Beachfront Resort + Flight

    Fort Myers Beach
    4 nights
    3.5 star property
    8.8/10 - Excellent (1,852 reviews)
    "Although we had an ocean front view, it was almost impossible to sit on our balcony and enjoy it due to the massive amount of cigarette smoking that goes on there. We also had to request three times to have our room cleaned once and have fresh towels for the week that we were staying there. The setup of the beach chairs and umbrellas less than 6 inches apart, meant that I was forced to endure every person‘s conversation sitting on either side of me ….not really my ideal situation when I’m trying..."
    Reviewed August 3, 2026
    Return • London (LON) - Fort Myers (RSW)
    LHR - MIA • Direct MIA - LHR • 1 stop
    £931
    £857
    per traveller
    found 1 day ago
    Lani Kai Beachfront Resort

All you need to know about luxury holidays in Keewaydin Island

What can I expect from a luxury Keewaydin Island 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 Keewaydin Island?

Tick the all-inclusive and 5-star filters to find the crème de la crème of Keewaydin Island 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 Keewaydin Island?

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 Keewaydin Island starting at £775. Prices and availability are subject to change. Additional terms may apply.

Are there luxury spa holidays in Keewaydin Island?

For sunset massages on the shoreline and view-filled saunas, use our spa filter to find your ideal Keewaydin Island 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 Keewaydin Island?

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 Keewaydin Island?

You can wangle a top-notch luxury holiday in Keewaydin Island 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 Keewaydin Island 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 Keewaydin Island with Expedia?

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