Raccoon Key Luxury Vacations

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Top Luxury vacation packages in Raccoon Key

Price found within the past 48 hours. Click for updated prices.

Parrot Key Hotel & Villas

Northside Resort

$1,095

per person

Nov 23 - Nov 27

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (1,464 reviews)

I liked the place, the waterfront building allowed us to see a beautiful sunset. The amenities were okay, I just stayed a day and the restaurant was closed.

Reviewed on Sep 7, 2026

The Gardens Hotel

Old Town Key West

Save 100% on your flight

$1,806

per person

Nov 21 - Nov 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.8/10 Exceptional! (1,003 reviews)

Absolutely beautiful place to spend our week! Everyone was kind and went out of their way to accommodate us!! Our room was beautiful and so comfortable. The only drawback to our cottage was the fact that there was black mold in the beautiful walkin shower and burnt out light bulbs. Disappointing for such a wonderful place! We made great friends and promise to be back next year!! One final note to ALL the hardworking staff...thank you all! Everyone worked hard to make things comfortable and amazing!! Our room was cleaned everyday by the sweetest team of gals. Breakfast was made and served every morning by the sweetest people! The Gardens Hotel has..hands down..the best team working there!!! Thank you to all!!

Reviewed on Sep 6, 2026

Lighthouse Suites Collection

Old Town Key West

Save 100% on your flight

$1,737

per person

Nov 21 - Nov 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

No reviews

The Perry Hotel & Marina Key West

$1,108

per person

Nov 21 - Nov 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,328 reviews)

We loved that Matt's Stockyard cooked our Fresh Lobsters !

Reviewed on Sep 6, 2026

The Marker Key West Harbor Resort

Key West Historic District

$1,525

per person

Nov 21 - Nov 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (1,003 reviews)

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3 Night Luxury vacations in Raccoon Key

Price found within the past 48 hours. Click for updated prices.

Lighthouse Suites Collection

Old Town Key West

$1,148

per person

Nov 20 - Nov 23

found 2 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

No reviews

The Gardens Hotel

Old Town Key West

$1,455

per person

Nov 12 - Nov 15

found 8 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.8/10 Exceptional! (1,003 reviews)

Reviewed on Sep 6, 2026

Southernmost House - Adult Exclusive

Old Town Key West

$1,913

per person

Nov 26 - Nov 29

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,001 reviews)

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4 Night Luxury vacations in Raccoon Key

Price found within the past 48 hours. Click for updated prices.

Hyatt Vacation Club at Windward Pointe, Key West

Save 100% on your flight

$1,166

per person

Nov 17 - Nov 21

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,254 reviews)

It’s ok, over price near airport noise was load in the afternoon

Reviewed on Sep 7, 2026

The Key West Hotel

Key West Historic District

Save 100% on your flight

$1,688

per person

Nov 23 - Nov 27

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (562 reviews)

Great place to stay - highly recommend.

Reviewed on Aug 20, 2026

Hyatt Vacation Club at Sunset Harbor, Key West

Old Town Key West

Save 100% on your flight

$1,181

per person

Nov 17 - Nov 21

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

8.6/10 Excellent! (415 reviews)

Room was great for long stays and families. A little outdated but the location was amazing! Easy walk to Mallory square and Duval street. Only complaint is a rooster waking us at 5 am but that’s Key West!

Reviewed on Sep 6, 2026

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What can I expect from a luxury Raccoon Key vacation?

Luxury means the very finest of the things you enjoy most. Indulge your every waking moment—and restful night—with a luxury Raccoon Key vacation. Sip handcrafted cocktails by an infinity pool, sink into bliss at a full-service spa with a massage cabana on the beach, and chat, cheers, and laugh through exquisite breakfasts, lunches, and dinners with spectacular views. 

How can I find all-inclusive luxury vacation packages in Raccoon Key?

By refining your filters, the most opulent all-inclusive vacation packages will appear before your eyes. Check the 5* filter to find truly sensational stays. You barely need to lift a finger. 

Can I book a cheap Raccoon Key luxury vacation?

Affordable luxury is only ever a few clicks away. Enter your travel dates and sort the grandiose getaways on offer by price to see the most fiscally friendly retreats first. Filter by budget, too, to find your perfect balance of luxury. Right now, luxury vacations start at $1,095. Prices and availability are subject to change. Additional terms may apply.

How can I book a luxury family vacation in Raccoon Key?

Tailor your luxury family escape by checking the filters that set the whole family’s hearts a-flutter. Whether that’s wet and wild water parks, heavenly hot tubs, or the kid-quieting magic of free Wi-Fi. 

Can I book a package in Raccoon Key with a luxury vacation home?

A private paradise is true luxury! Filter by property type for houses, villas, and apartments. For an amazingly affordable all-in-one luxury experience, book your accommodation, airfare, and car rental as a package.   

How can I find the best luxury vacation deals in Raccoon Key?

Find absolute delight in the dropdown! Simply sort your tempting search results by deals to find that lean-budget luxury. For a budget conscious stay, consider booking a stay away from big cities or outside the peak months.

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

Freedom and flexibility are the greatest luxuries of all. Get both when you filter by payment option and book a trip with free cancellation or on a buy now, pay later plan. 

Why should I book my luxury trip to Raccoon Key with Expedia?

A luxurious trip follows a stress-free booking experience. Find, build, and book the most glorious of getaways in seconds—with ATOL protection for added peace of mind.