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Photo by Sydney Thompson
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Lovers Key Romantic Vacations

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    Save up to $2,000 when you book a flight and hotel together*
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Top Romantic vacation packages in Lovers Key

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

    Manasota Key Resort + Flight

    Manasota Key
    3 nights
    2.5 star property
    9.4/10 - Exceptional (306 reviews)
    Roundtrip Boston (BOS) - Fort Myers (RSW)
    BOS - RSWNonstop RSW - BOSNonstop
    Save 100% on your flight
    $915
    $613
    per traveler
    found 2 days ago
    Manasota Key Resort
  • Sep 6 - Sep 12

    LaPlaya Beach & Golf Resort - A Noble House Resort + Flight

    Vanderbilt Beach
    6 nights
    4.5 star property
    9.0/10 - Wonderful (1,008 reviews)
    Roundtrip Boston (BOS) - Fort Myers (RSW)
    BOS - RSWNonstop RSW - BOS1 stop
    Save 100% on your flight
    $1,923
    $1,135
    per traveler
    found 2 days ago
    LaPlaya Beach & Golf Resort - A Noble House Resort
  • Oct 19 - Oct 25

    The Perry Hotel Naples + Flight

    Naples
    6 nights
    4.5 star property
    9.6/10 - Exceptional (988 reviews)
    "Good 👍"
    Reviewed August 2, 2026
    Roundtrip Boston (BOS) - Fort Myers (RSW)
    BOS - RSWNonstop RSW - BOSNonstop
    Save 100% on your flight
    $1,460
    $928
    per traveler
    found 2 days ago
    The Perry Hotel Naples
  • Oct 15 - Oct 20

    Tween Waters Island Resort & Spa + Flight

    Captiva
    5 nights
    3.0 star property
    8.6/10 - Excellent (1,003 reviews)
    "It took more than two hours to check in after check point of 4:00 pm - We supposed to get a call to confirm that the room was ready, a call that never happened. There has been a lot of rain so it did not help to have a clear view of the whole property. Restaurants are of good quality and the staff was very nice."
    Reviewed August 1, 2026
    Roundtrip Boston (BOS) - Fort Myers (RSW)
    BOS - RSWNonstop RSW - BOSNonstop
    Save 100% on your flight
    $1,326
    $860
    per traveler
    found 1 day ago
    Tween Waters Island Resort & Spa
  • Oct 18 - Oct 24

    Casa Ybel Resort + Flight

    Mid Island
    6 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
    Roundtrip Boston (BOS) - Fort Myers (RSW)
    BOS - MIANonstop MIA - BOSNonstop
    Save 100% on your flight
    $1,444
    $964
    per traveler
    found 1 day ago
    Casa Ybel Resort

What to do in Lovers Key

Top Romantic Lovers 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 Lovers Key vacation

How can I find the best Lovers 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 Lovers 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 Lovers 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 Lovers Key?

Put a price on love with stunning deals for duos starting at just $613. Prices and availability are subject to change. Additional terms may apply.

Can I book Lovers 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 Lovers Key?

To book a loved-up break in Lovers 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 Lovers 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 Lovers 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?