Name: Beautiful house on Chianti hilltop with exceptional views.
Rating: 10

Top Beach vacation packages in Chianti Region

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

Villa Casagrande Resort & SPA

$1,547

per person

Jun 23 - Jun 28

found 4 hours ago

Roundtrip non-stop flight included

San Francisco (SFO) to Florence (FLR)

9.2/10 Wonderful! (385 reviews)

L’ambiance est exceptionnelle, le service est chaleureux et prévenant, et le restaurant est aussi excellent. Je recommande chaleureusement.

Reviewed on Apr 20, 2026

LHP Certaldo Resort

$1,713

per person

Jul 22 - Jul 28

found 1 day ago

Roundtrip flight included

San Juan (SJU) to Florence (FLR)

9.2/10 Wonderful! (530 reviews)

The staff were excellent, especially Carim.

Reviewed on May 10, 2026

Relais Della Rovere

$1,820

per person

Jun 24 - Jun 30

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to Florence (FLR)

9/10 Wonderful! (246 reviews)

We had a delightful stay. The staff was incredibly friendly and helpful, especially Jessica! The building and grounds are amazing. Our room was spacious, clean, quiet and comfortable. Dinner at restaurant onsite was also very good. While out of town a ways we enjoyed the 40 walk and climb up to the old walled city.

Reviewed on May 12, 2026

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5* Beach vacations in Chianti Region

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

LHP Certaldo Resort

$1,713

per person

Jul 22 - Jul 28

found 1 day ago

Roundtrip flight included

San Juan (SJU) to Florence (FLR)

9.2/10 Wonderful! (530 reviews)

The staff were excellent, especially Carim.

Reviewed on May 10, 2026

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4 Night Beach vacations in Chianti Region

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

Hotel Tenuta Il Burchio

$499

per person

Jul 16 - Jul 20

found 22 hours ago

Roundtrip non-stop flight included

Frankfurt (FRA) to Florence (FLR)

8.8/10 Excellent! (203 reviews)

An old-style Tuscan country estate with a peaceful atmosphere, attentive service, excellent breakfast.The surroundings are serene and picturesque， perfect for a quiet escape from the city. However, the room next door had poor sound insulation on the night I stayed, which slightly affected my sleep quality. The room and facilities are a bit dated, so travelers who prefer a more modern style may want to confirm their room type in advance.

Reviewed on Oct 29, 2025

LHP Certaldo Resort

$1,278

per person

Aug 8 - Aug 11

found 16 hours ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Florence (FLR)

9.2/10 Wonderful! (530 reviews)

The staff were excellent, especially Carim.

Reviewed on May 10, 2026

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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 $499. Prices and availability are subject to change. Additional terms may apply.

When should I book a Chianti Region beach holiday?

For a bustling beach break, book in . For a less crowded coast, is the time to turn up.

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.)

Top Beach Chianti Region Hotels

Villa Casagrande Resort & SPA

Via del Puglia, 61 Figline e Incisa Valdarno FI

44 min drive from Antinori nel Chianti Classico

Book a stay at this spa hotel in Figline e Incisa Valdarno. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Soffena Abbey and Museum ...

9.2/10 Wonderful! (388 reviews)

"L’ambiance est exceptionnelle, le service est chaleureux et prévenant, et le restaurant est aussi excellent. Je recommande chaleureusement."

Reviewed on Apr 20, 2026

UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

Ruffoli Toscana

25 min drive from Antinori nel Chianti Classico

Book a stay at this family-friendly farm stay in Greve in Chianti. Enjoy free WiFi, a garden, and patios. Popular attractions Querciabella and Savignola Winery ...

9.4/10 Exceptional! (21 reviews)

"This is truly a unique and special property providing incredible value . One of the most beautiful views in a spectacular setting hidden away in the Tuscan hills above Panzano. A perfect location for day trips to vinyards, restaurants and the Chianti area. Our apartment was extremely well appointed ..."

Reviewed on Jul 6, 2025

Beautiful house on Chianti hilltop with exceptional views.

Siena Tuscany

34 min drive from Antinori nel Chianti Classico

Book a stay at this family-friendly farm stay in Castellina in Chianti. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Lilliano Estate ...

10/10 Exceptional! (73 reviews)

"House was clean and comfortable and the place was even better than the pictures online. Stunning views and a great location to explore the many beautiful towns in the area."

Reviewed on Apr 3, 2026

See all 4,810 properties in Chianti Region

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.