Raccoon Key Luxury Holidays

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Top Luxury holiday packages in Raccoon Key

Price found within the past 48 hours. Click for updated prices.
  • 26 Dec - 29 Dec

    Southernmost Beach Resort and Guesthouses + Flight

    Old Town Key West
    3 nights
    4.0 star property
    8.6/10 - Excellent (3,658 reviews)
    Return • Orlando (MCO) - Key West (EYW)
    MCO - EYW • 1 stop EYW - MCO • Direct
    £1,444
    £1,098
    per traveller
    found 1 hour ago
    Southernmost Beach Resort and Guesthouses
  • 26 Dec - 29 Dec

    The Key West Hotel + Flight

    Key West Historic District
    3 nights
    3.0 star property
    9.2/10 - Wonderful (565 reviews)
    "Clean, clean, clean. Hidden! Elite Backyard Oasis. Top Tier bar and fantastic nightly entertainment. If your traveling with anyone under 25, choose different. Will be back, no doubt!"
    Reviewed October 29, 2026
    Return • Orlando (MCO) - Key West (EYW)
    MCO - EYW • 1 stop EYW - MCO • Direct
    £1,988
    £1,320
    per traveller
    found 1 hour ago
    The Key West Hotel
  • 26 Dec - 29 Dec

    Southernmost House - Adult Exclusive + Flight

    Old Town Key West
    3 nights
    4.0 star property
    9.4/10 - Exceptional (1,004 reviews)
    "Stunning, I dont have to say anymore"
    Reviewed November 10, 2026
    Return • Orlando (MCO) - Key West (EYW)
    MCO - EYW • 1 stop EYW - MCO • Direct
    £1,822
    £1,338
    per traveller
    found 1 hour ago
    Southernmost House - Adult Exclusive
  • 26 Dec - 29 Dec

    The Marker Key West Harbor Resort + Flight

    Key West Historic District
    3 nights
    4.0 star property
    9.2/10 - Wonderful (1,049 reviews)
    Return • Orlando (MCO) - Key West (EYW)
    MCO - EYW • 1 stop EYW - MCO • Direct
    £1,649
    £1,239
    per traveller
    found 1 hour ago
    The Marker Key West Harbor Resort
  • 26 Dec - 29 Dec

    Orchid Key Inn - Adults Only + Flight

    Old Town Key West
    3 nights
    3.5 star property
    9.8/10 - Exceptional (1,006 reviews)
    "We LOVED our stay here. Small, boutique motel with a vintage feel. Right on Duvall, but you would never know it once in the motel. It was secluded and quiet with a lovely tropical feel. Loved the grounds - beautiful flowers, palms, gorgeous pool at night with candles around the tables. The staff was so helpful and friendly. Breakfast buffet is pretty good, but the areas around the pool were my favorite to sit & relax with a glass of wine from the bar. Our room was clean & comfortable. Lots of..."
    Reviewed November 8, 2026
    Return • Orlando (MCO) - Key West (EYW)
    MCO - EYW • 1 stop EYW - MCO • Direct
    £1,592
    £1,214
    per traveller
    found 1 hour ago
    Orchid Key Inn - Adults Only

What to do in Raccoon Key

Top Luxury Raccoon Key Hotels

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.

All you need to know about luxury holidays in Raccoon Key

What can I expect from a luxury Raccoon 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 Raccoon Key?

Tick the all-inclusive and 5-star filters to find the crème de la crème of Raccoon 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 Raccoon 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 Raccoon Key starting at £1,098. Prices and availability are subject to change. Additional terms may apply.

Are there luxury spa holidays in Raccoon Key?

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

You can wangle a top-notch luxury holiday in Raccoon 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 Raccoon 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 Raccoon Key with Expedia?

Nobody does luxury quite like Expedia. With so many gorgeous properties in Raccoon 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.