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.
Villa Casagrande Resort & SPA

Villa Casagrande Resort & SPA

$1,092
per person
Oct 23 - Oct 29
found 19 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Florence (FLR)
9.2/10 Wonderful! (402 reviews)
What a wonderful 3 night break at Villa Casagrande! My wife and I had a beautiful stay in this historic villa. There’s a little steep walk up to the pool and restaurant next to it which were perfect and where we spent most of our time relaxing and sunbathing with the view of the trees and the Tuscan mountains. The staff were incredible, so kind, quick to help and made our stay even more pleasant. We both had lovely massages and relaxed in the spa area and one evening did the historic tour and wine tasting which was exceptional. The guides and sommeliers were so knowledgeable and so lovely and the organic Chianti wines they produce are an absolute must to taste and buy. The hotel’s main restaurant was the best in Filigne (the local town) and the food was incredible. One of the nights we had a live musician who was fantastic. We had dinner twice there; mushroom tagliatelle, the lamb, the wild boar gnocchi and paccheri carbonara were to die for! It’s only 50 mins on the train to Florence which is one of our favourite cities to explore in one day and we picked this place especially because it’s only a 12 minute walk from the Filigne Valdarno station and avoids the need to hire a car. We went for the comfort room which was spacious and clean and the air con was great and important for us it had a powerful shower. We truly had a wonderful time and absolutely cannot wait to go back next year! Grazie Villa Casagrande!

Reviewed on Aug 14, 2026

LHP Certaldo Resort

LHP Certaldo Resort

$1,693
per person
Sep 18 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.2/10 Wonderful! (537 reviews)
Relais Della Rovere

Relais Della Rovere

$1,109
per person
Oct 23 - Oct 29
found 19 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Florence (FLR)
9/10 Wonderful! (260 reviews)
We stayed here with our grown up children and their baby. The hotel was clean, well-maintained and very convenient to either drive or walk to the centre. The pool was clean and well maintained with plenty of sun beds for everyone all through the day so, happily, no one felt the need to “reserve” them. Breakfast was delicious with lots of options. We also had lunch and dinner once during our stay. The food was lovely. However, one of us eats gluten-free food and, despite ordering a dish that did not list gluten as an ingredient, it did have gluten-containing decorations on it so beware of that if it would affect you. The staff replaced the dish straight away though with one that was safe to eat. We made sure that we stressed the gluten-free need after that regardless of what the menu says. Our rooms were clean and very spacious with comfortable enormous beds which the parents of the baby were very grateful for as it easily fitted all three of them with room to spare. We all had a great time and would strongly recommend it. PS take some bug spray as there are mosquitoes around

Reviewed on Aug 10, 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

LHP Certaldo Resort

$1,693
per person
Sep 18 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.2/10 Wonderful! (537 reviews)
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3 Night Beach vacations in Chianti Region

Price found within the past 48 hours. Click for updated prices.
Villa Casagrande Resort & SPA

Villa Casagrande Resort & SPA

$932
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.2/10 Wonderful! (402 reviews)
What a wonderful 3 night break at Villa Casagrande! My wife and I had a beautiful stay in this historic villa. There’s a little steep walk up to the pool and restaurant next to it which were perfect and where we spent most of our time relaxing and sunbathing with the view of the trees and the Tuscan mountains. The staff were incredible, so kind, quick to help and made our stay even more pleasant. We both had lovely massages and relaxed in the spa area and one evening did the historic tour and wine tasting which was exceptional. The guides and sommeliers were so knowledgeable and so lovely and the organic Chianti wines they produce are an absolute must to taste and buy. The hotel’s main restaurant was the best in Filigne (the local town) and the food was incredible. One of the nights we had a live musician who was fantastic. We had dinner twice there; mushroom tagliatelle, the lamb, the wild boar gnocchi and paccheri carbonara were to die for! It’s only 50 mins on the train to Florence which is one of our favourite cities to explore in one day and we picked this place especially because it’s only a 12 minute walk from the Filigne Valdarno station and avoids the need to hire a car. We went for the comfort room which was spacious and clean and the air con was great and important for us it had a powerful shower. We truly had a wonderful time and absolutely cannot wait to go back next year! Grazie Villa Casagrande!

Reviewed on Aug 14, 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

Hotel Tenuta Il Burchio

$1,195
per person
Sep 19 - Sep 22
found 11 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Florence (FLR)
8.6/10 Excellent! (206 reviews)
We stayed there for two nights , the room we had was clean and spacious . On-site parking was not great and there’s only one restaurant at the hotel but they don’t always take guests and you have to make reservation ahead and no room services. Be prepared to stay hungry or risk loosing your parking spot and drive to town . I don’t recommend going there , there are many other more convenient and accommodating places to stay .

Reviewed on Jun 21, 2026

Relais Della Rovere

Relais Della Rovere

$1,606
per person
Sep 29 - Oct 2
found 16 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Florence (FLR)
9/10 Wonderful! (260 reviews)
We stayed here with our grown up children and their baby. The hotel was clean, well-maintained and very convenient to either drive or walk to the centre. The pool was clean and well maintained with plenty of sun beds for everyone all through the day so, happily, no one felt the need to “reserve” them. Breakfast was delicious with lots of options. We also had lunch and dinner once during our stay. The food was lovely. However, one of us eats gluten-free food and, despite ordering a dish that did not list gluten as an ingredient, it did have gluten-containing decorations on it so beware of that if it would affect you. The staff replaced the dish straight away though with one that was safe to eat. We made sure that we stressed the gluten-free need after that regardless of what the menu says. Our rooms were clean and very spacious with comfortable enormous beds which the parents of the baby were very grateful for as it easily fitted all three of them with room to spare. We all had a great time and would strongly recommend it. PS take some bug spray as there are mosquitoes around

Reviewed on Aug 10, 2026

Villa Casagrande Resort & SPA

Villa Casagrande Resort & SPA

$1,562
per person
Sep 29 - Oct 2
found 16 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Florence (FLR)
9.2/10 Wonderful! (402 reviews)
What a wonderful 3 night break at Villa Casagrande! My wife and I had a beautiful stay in this historic villa. There’s a little steep walk up to the pool and restaurant next to it which were perfect and where we spent most of our time relaxing and sunbathing with the view of the trees and the Tuscan mountains. The staff were incredible, so kind, quick to help and made our stay even more pleasant. We both had lovely massages and relaxed in the spa area and one evening did the historic tour and wine tasting which was exceptional. The guides and sommeliers were so knowledgeable and so lovely and the organic Chianti wines they produce are an absolute must to taste and buy. The hotel’s main restaurant was the best in Filigne (the local town) and the food was incredible. One of the nights we had a live musician who was fantastic. We had dinner twice there; mushroom tagliatelle, the lamb, the wild boar gnocchi and paccheri carbonara were to die for! It’s only 50 mins on the train to Florence which is one of our favourite cities to explore in one day and we picked this place especially because it’s only a 12 minute walk from the Filigne Valdarno station and avoids the need to hire a car. We went for the comfort room which was spacious and clean and the air con was great and important for us it had a powerful shower. We truly had a wonderful time and absolutely cannot wait to go back next year! Grazie Villa Casagrande!

Reviewed on Aug 14, 2026

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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 $932. 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

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! (404 reviews)
"What a wonderful 3 night break at Villa Casagrande! My wife and I had a beautiful stay in this historic villa. There’s a little steep walk up to the pool and restaurant next to it which were perfect and where we spent most of our time relaxing and sunbathing with the view of the trees and the Tuscan ..."

Reviewed on Aug 14, 2026

Villa Casagrande Resort & SPA
LHP Certaldo Resort

LHP Certaldo Resort

via del Molino, 74 Certaldo FI
  • 27 min drive from Antinori nel Chianti Classico
Book a stay at this luxury hotel in Certaldo. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular ...
LHP Certaldo Resort
CHIANTI VINEYARDS OLIVE GROVES FOOD TASTINGS SCENIC VIEWS

CHIANTI VINEYARDS OLIVE GROVES FOOD TASTINGS SCENIC VIEWS

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 laundry facilities. Popular attractions Querciabella and Savignola ...
9.2/10 Wonderful! (30 reviews)
"Such a lovely property with a view that never quits. The pool is so refreshing and did I mention the view? Great place for a small group with the ability to expand to additional rooms on the property with notice. We will definitely be going back!"

Reviewed on Jul 1, 2026

CHIANTI VINEYARDS OLIVE GROVES FOOD TASTINGS SCENIC VIEWS
See all 4,900 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.

Things to do

City Sightseeing Florence Hop-on Hop-off

City Sightseeing Florence Hop-on Hop-off Bus Tour

$28
per adult
76% of travellers recommend
City Sightseeing Florence Hop-on Hop-off Bus Tour
Uffizi & Accademia Timed Entry: Small Group Duomo Walking Tour

Uffizi & Accademia Timed Entry: Small Group Duomo Walking Tour

$56
per adult
96% of travellers recommend
Uffizi & Accademia Timed Entry: Small Group Duomo Walking Tour
Siena: Cathedral Complex Pass with Audio Guide

Siena: Cathedral Complex Pass with Audio Guide (OPA SI PASS)

$21
per adult
Siena: Cathedral Complex Pass with Audio Guide (OPA SI PASS)
See all activities in Chianti Region

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.