A crowded beach with people sunbathing and swimming.

Southwest Florida Romantic Holidays

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Top Romantic holiday packages in Southwest Florida

Price found within the past 48 hours. Click for updated prices.
  • 28 Dec - 30 Dec

    Bayfront Inn Fifth Avenue + Flight

    Redevelopment Area
    2 nights
    3.5 star property
    8.8/10 - Excellent (2,003 reviews)
    "A great little hidden gem. The location was excellent, lots of shopping and restaurants within walking distance plus a onsite bar and restaurant that was great with live music. I will definitely be staying here everytime I go to Naples. The only downside was having to pay for parking at the hotel...who charges you for parking at the place you're paying to stay at? Other than that this is a great place with a nice atmosphere and excellent employees."
    Reviewed November 8, 2026
    Return • Manchester (MAN) - Fort Myers (RSW)
    MAN - RSW • 2 stops RSW - MAN • 2 stops
    £1,613
    £1,564
    per traveller
    found 1 day ago
    Bayfront Inn Fifth Avenue
  • 28 Dec - 30 Dec

    Hyatt House Naples/5th Avenue + Flight

    Old Naples
    2 nights
    3.5 star property
    9.2/10 - Wonderful (2,181 reviews)
    "Una buena manera de estar cerca de los atractivos principales"
    Reviewed November 9, 2026
    Return • Manchester (MAN) - Fort Myers (RSW)
    MAN - RSW • 2 stops RSW - MAN • 2 stops
    £1,818
    £1,742
    per traveller
    found 1 day ago
    Hyatt House Naples/5th Avenue
  • 28 Dec - 30 Dec

    Naples Bay Resort & Marina + Flight

    Oyster Bay
    2 nights
    4.0 star property
    9.4/10 - Exceptional (1,004 reviews)
    Return • Manchester (MAN) - Fort Myers (RSW)
    MAN - RSW • 2 stops RSW - MAN • 2 stops
    £1,824
    £1,756
    per traveller
    found 1 day ago
    Naples Bay Resort & Marina
  • 28 Dec - 30 Dec

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

    Vanderbilt Beach
    2 nights
    4.5 star property
    9.0/10 - Wonderful (1,001 reviews)
    "Overall, worth the stay. The place could use some updates."
    Reviewed November 5, 2026
    Return • Manchester (MAN) - Fort Myers (RSW)
    MAN - RSW • 2 stops RSW - MAN • 2 stops
    £2,292
    £2,209
    per traveller
    found 1 day ago
    LaPlaya Beach & Golf Resort - A Noble House Resort
  • 28 Dec - 30 Dec

    Inn on Fifth + Flight

    Old Naples
    2 nights
    4.0 star property
    9.4/10 - Exceptional (1,005 reviews)
    Return • Manchester (MAN) - Fort Myers (RSW)
    MAN - RSW • 2 stops RSW - MAN • 2 stops
    £1,958
    £1,902
    per traveller
    found 1 day ago
    Inn on Fifth

Discover the most popular places to visit in Southwest Florida

What to do in Southwest Florida

Top Romantic Southwest Florida 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 Southwest Florida holiday

How can I find the best Southwest Florida vacation packages for couples?

Use our easy-to-use holiday search tools to plan your most-romantic getaway to Southwest Florida. Choose a hotel suite with an on-trend bathtub with a big view. Choose a stylish hire car with the top down to woo your heart. Choose candlelit cocktails on the shoreline, a horse ride by moonlight or a dolled-up night at the casino.

Can I book cheap Southwest Florida romantic holidays for two?

Get wallet-friendly away-from-it-all romantic accommodation at Expedia, so you have more kitty to spend on romantic activities. We have cheap romantic holidays to Southwest Florida that start from £1,564. Prices and availability are subject to change. Additional terms may apply.

What should I think about when booking a Southwest Florida romantic getaway?

The most romantic holidays are about building memories, about dancing and dining and keeping the spark alive. These are moments to level up the luxury – use the star filter to find the best of the best, maybe even tick the business-class flights filter to make the journey part of the adventure.

What should I look for in a luxury romantic holiday to Southwest Florida?

Spoil yourselves with a few luxuries on your romantic trip away. You can use our filters to add that extra touch of romance to your holiday: glamorous spas, divine private dining, exquisite room service.

Can I book a romantic hot-tub holiday in Southwest Florida?

What’s more romantic than a hot tub under the stars, together? Add a glass of fizz, a gorgeous view and Cupid’s arrow and you’re good. To find accommodation with bubbles, use our dedicated hot-tub filter.

How can I find romantic holidays for couples in Southwest Florida that are all inclusive?

Enjoying an all-inclusive holiday means you can really indulge your appetites together – with the promise of no awkward arguments about splitting the bill. Simply use our all-inclusive filter to see what romantic options are available.

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

Even the best laid plans fall through sometimes. Make sure you’re not caught out – using our filters to find free cancellation accommodation. Just make sure you check the all-important small print.

Why should I book my Southwest Florida romantic holiday with Expedia?

At Expedia, we know the not-so-secret ingredients to the perfect romantic holiday. Our handy filters help you search a huge range of options and book a holiday that gets your hearts racing.