Raccoon Key Romantic Vacations

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Top Romantic vacation packages in Raccoon Key

Price found within the past 48 hours. Click for updated prices.
  • Jan 14 - Jan 18

    Ibis Bay Beach Resort + Flight

    Northside Resort
    4 nights
    2.5 star property
    8.2/10 - Very good (2,426 reviews)
    Roundtrip • Boston (BOS) - Key West (EYW)
    BOS - FLL • Nonstop MIA - BOS • 1 stop
    $1,216
    $913
    per traveler
    found 2 days ago
    Ibis Bay Beach Resort
  • Jan 14 - Jan 18

    The Gardens Hotel + Flight

    Old Town Key West
    4 nights
    4.0 star property
    9.8/10 - Exceptional (1,001 reviews)
    "Wonderful location, great room, cozy property. Check in and out was very easy. Would definitely stay here again the next time Im in Key West"
    Reviewed November 8, 2026
    Roundtrip • Boston (BOS) - Key West (EYW)
    BOS - FLL • Nonstop MIA - BOS • 1 stop
    $2,878
    $2,036
    per traveler
    found 2 days ago
    The Gardens Hotel
  • Jan 14 - Jan 18

    Southernmost Beach Resort and Guesthouses + Flight

    Old Town Key West
    4 nights
    4.0 star property
    8.6/10 - Excellent (3,657 reviews)
    Roundtrip • Boston (BOS) - Key West (EYW)
    BOS - FLL • Nonstop MIA - BOS • 1 stop
    $2,316
    $1,661
    per traveler
    found 2 days ago
    Southernmost Beach Resort and Guesthouses
  • Jan 14 - Jan 18

    Blue Flamingo Resort Key West + Flight

    New Town
    4 nights
    4.0 star property
    8.6/10 - Excellent (2,787 reviews)
    "All staff extremely helpful and easy to talk too. Would recommend blue flamingo to everyone"
    Reviewed November 10, 2026
    Roundtrip • Boston (BOS) - Key West (EYW)
    BOS - FLL • Nonstop MIA - BOS • 1 stop
    $1,476
    $1,075
    per traveler
    found 2 days ago
    Blue Flamingo Resort Key West
  • Jan 14 - Jan 18

    The Perry Hotel & Marina Key West + Flight

    Stock Island
    4 nights
    4.0 star property
    9.4/10 - Exceptional (1,318 reviews)
    Roundtrip • Boston (BOS) - Key West (EYW)
    BOS - FLL • Nonstop MIA - BOS • 1 stop
    $1,543
    $1,132
    per traveler
    found 2 days ago
    The Perry Hotel & Marina Key West

What to do in Raccoon Key

Top Romantic 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.

How to find a romantic Raccoon Key vacation

How can I find the best Raccoon Key vacation packages for couples?

To win over the love of your life, first choose where and when you want to bring the romance. Now flirt with the filters to add ocean views, spa, pools, and anything else that gets your heart racing.

How can I find cheap Raccoon Key romantic packages for two?

For dollar-friendly delights, sort your search results by price or deals. You can also filter by budget to find romantic retreats at prices you’ll love. For an affordable and alluring adventure, try self-catering.

How can I plan a great romantic trip to Raccoon Key?

Find what fills you with joy and dive right in, whether you thrill in a little adventure or lust for long lazy days by the pool, handcrafted cocktails in hand. Fire cupid’s arrow at our filters and build your dream trip for two.

How much is a trip for two to Raccoon Key?

Put a price on love with stunning deals for duos starting at just $913. Prices and availability are subject to change. Additional terms may apply.

Can I book Raccoon Key spa packages for couples?

Check the filter box for a seductive stay at a spa. Sort your results by price, deals, rating, and more to guarantee the perfect match.

How can I book romantic weekend getaway packages in Raccoon Key?

To book a loved-up break in Raccoon Key, enter your travel dates and sort by price, deals, rating—whatever matters most to you and your partner. Now, you can add some adult-only amenities, like a hot tub or full-service spa for total R, R, & R (that’s romance, rest, and recuperation).

Can I book a romantic trip to Raccoon Key with free cancellation and/or flexible dates?

The course of true love should always run smooth, but we get that there are hiccups. So, filter by payment option to search for romantic stays with free cancellation and buy now, pay later options.

Why should I book my Raccoon Key romantic holiday with Expedia?

If you’ve only got eyes for excellent escapes, book your loved-up break with Expedia. Fling the filters to find accommodation you’ll adore. And what’s more attractive than ATOL protection?