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Chianti Region Beach Vacations

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Top Beach vacation packages in Chianti Region

Price found within the past 48 hours. Click for updated prices.
  • 2 restaurants; breakfast, lunch, and dinner served
    Sep 27 - Oct 3

    Villa Casagrande Resort & SPA + Flight

    Figline e Incisa Valdarno
    5 nights
    4.0 star property
    9.2/10 - Wonderful (398 reviews)
    "If you are thinking of staying anywhere else in toscana…DON’T! This was the most amazing stay. We extended our stay because it was so beautiful and full of history. The amenities are also wonderful!"
    Reviewed June 14, 2026
    Roundtrip • Miami (MIA) - Florence (FLR)
    MIA - FLR • 1 stop FLR - MIA • 1 stop
    $1,346
    $1,246
    per traveler
    found 2 days ago
    Villa Casagrande Resort & SPA
  • Front of property
    Sep 30 - Oct 5

    LHP Certaldo Resort + Flight

    Certaldo
    4 nights
    5.0 star property
    9.2/10 - Wonderful (536 reviews)
    "Lovely hotel with contemporary design just off the main train station in Certaldo. Clearly clean and well-maintained. The pool itself is tiny but useful enough for breaking up the summer heat in Tuscany."
    Reviewed July 12, 2026
    Roundtrip • Boston (BOS) - Florence (FLR)
    BOS - FLR • 1 stop FLR - BOS • 1 stop
    $1,773
    $1,493
    per traveler
    found 2 hours ago
    LHP Certaldo Resort

Discover the most popular places to visit in Chianti Region

A spiral staircase with a person standing on it.

Antinori nel Chianti Classico

9.4/10 (16 reviews)
You can enjoy a tasting or tour at Antinori nel Chianti Classico during your travels to Bargino. Check out the churches and wineries in this walkable area.

What to do in Chianti Region

City Sightseeing Florence Hop-on Hop-off

City Sightseeing Florence Hop-on Hop-off Bus Tour

$33
per adult
76% of travelers recommend
City Sightseeing Florence Hop-on Hop-off Bus Tour
See all activities in Chianti Region

Top Beach Chianti Region Hotels

Terrace/patio

Canaiolo holiday home with mini-pool in the center of Greve in Chianti

Canaiolo holiday home with mini-pool in the center of Greve in Chianti
4.2 mi from Chianti Region
10.0 out of 10, Exceptional, (2 reviews)
"This was such a perfect spot - we stayed for 9 nights and it allowed us to to make a number of day trips to towns like Florence, Montrfioralle, Cinque Terre and San Gimignano while enjoying everything Greve has to offer on days in between.We stayed with our two kids, and loved the outdoor area. We can’t wait to return.Hosts were fantastic, unit was comfortable and clean - couldn’t ask for anything more.Thank you for having us!"
$392 nightly
The price is $397
Aug 15 - Aug 16
Total with taxes and fees
Canaiolo holiday home with mini-pool in the center of Greve in Chianti
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.
See all properties in Chianti Region

Find your perfect Chianti Region beach vacation

How do I book the best Chianti Region beach vacation packages?

Life’s a beach when you dive into our brilliant Chianti Region beach vacation deals. Chuck a check in the filter boxes to find ocean views, pools, and resorts just a short saunter from the sizzling sands.

How can I find cheap beach vacations in Chianti Region?

A rental steps from the shore creates an amazingly affordable Chianti Region beach vacation. Seaside sojourns during low season start from $1,246. Prices and availability are subject to change. Additional terms may apply.

How can I book the best family beach vacations in Chianti Region?

With a flick of a finger, the family-friendly filter brings you the best breaks on offer for the whole brood. Look out for kids’ clubs, waterparks, and other incredible extras for a vacay the little ones will love.

How do I find a Chianti Region beachfront vacation?

Check the beachfront filter and, bam, the best available oceanside resorts will appear before your eyes. Along with the incredible view, when you book a beachfront resort, you can get from the lapping waves to your patio lounger in a matter of moments.

Can I book a package including a Chianti Region vacation beach house rental?

Hit up the vacation rental filter to book your dream beach house. Once you’ve selected the most alluring abode, add your flights and car rental for the perfect package deal.

Can I find Chianti Region beach vacation deals?

Sort your search results by deals to delight in amazing Chianti Region beach vacation offers. If you want more pizzazz for your pennies, travel outside the high season or stay a little further from the shoreline.

Can I book a Chianti Region beach trip with free cancellation and/or flexible dates?

Just like the Chianti Region tides, plans change. Filter by payment option to find trips with free cancellation. Buy now, pay later options are also available for full-on flexibility.

Why should I book my Chianti Region beach vacation with Expedia?

Relax long before you see the shore with simple search, fantastic filters, and more great deals than there are grains of sand in Chianti Region. (OK, maybe not that last part.)