Chianti Region Kid friendly Vacations

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Top Kid friendly vacation packages in Chianti Region

Price found within the past 48 hours. Click for updated prices.
Hotel Borgo San Luigi

Hotel Borgo San Luigi

$359
per person
Nov 6 - Nov 9
found 3 hours ago
Roundtrip flight included
London (LHR) to Florence (FLR)
9.2/10 Wonderful! (438 reviews)
Had an incredible stay here! It was so beautiful and peaceful, the staff was also amazing and super helpful.

Reviewed on Sep 7, 2026

Hotel Borgo di Cortefreda Relais

Hotel Borgo di Cortefreda Relais

Tavarnelle Val di Pesa
$1,463
per person
Oct 11 - Oct 15
found 6 hours ago
Roundtrip non-stop flight included
Kansas City (MKC) to Florence (FLR)
9.4/10 Exceptional! (520 reviews)
Relais Della Rovere

Relais Della Rovere

$1,281
per person
Oct 24 - Oct 29
found 23 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Florence (FLR)
9/10 Wonderful! (263 reviews)
Perfect.

Reviewed on Sep 9, 2026

Villa Scacciapensieri Boutique Hotel

Villa Scacciapensieri Boutique Hotel

Scacciapensieri
$2,035
per person
Oct 12 - Oct 17
found 1 day ago
Roundtrip flight included
Louisville (SDF) to Florence (FLR)
9.2/10 Wonderful! (457 reviews)
The staff were very friendly and helpful. The bar service is the best.

Reviewed on Sep 8, 2026

Villa Lecchi Hotel Wellness

Villa Lecchi Hotel Wellness

$1,758
per person
Oct 19 - Oct 23
found 22 hours ago
Roundtrip non-stop flight included
Norfolk (ORF) to Florence (FLR)
9.4/10 Exceptional! (87 reviews)
Beautiful place, beautiful and amazing people starting with the owners, and then Mateo, Sarah, Georgia and Claudia. We didn’t want to leave they were amazing treat us like family.

Reviewed on Aug 19, 2026

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3 Night Kid friendly vacations in Chianti Region

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

Palagina la Dimora

$358
per person
Nov 6 - Nov 9
found 3 hours ago
Roundtrip flight included
London (LHR) to Florence (FLR)
9/10 Wonderful! (355 reviews)
Wonderful Tuscany escape. Charming villa with spectacular views and amazing restaurant overlooking vineyards. Tecla at reception and the rest of the staff made the stay so special. Can’t wait to return!

Reviewed on Sep 9, 2026

Hotel Borgo San Luigi

Hotel Borgo San Luigi

$359
per person
Nov 6 - Nov 9
found 3 hours ago
Roundtrip flight included
London (LHR) to Florence (FLR)
9.2/10 Wonderful! (438 reviews)
Had an incredible stay here! It was so beautiful and peaceful, the staff was also amazing and super helpful.

Reviewed on Sep 7, 2026

Hotel Borgo di Cortefreda Relais

Hotel Borgo di Cortefreda Relais

Tavarnelle Val di Pesa
$976
per person
Oct 17 - Oct 19
found 18 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.4/10 Exceptional! (520 reviews)
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4 Night Kid friendly vacations in Chianti Region

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

Hotel Bellavista Impruneta

$302
per person
Oct 21 - Oct 25
found 23 hours ago
Roundtrip flight included
London (LON) to Florence (FLR)
9.2/10 Wonderful! (127 reviews)
Premesso che non avevo letto bene i servizi garantiti in camera, quando mi sono trovato senza frigo, che mi sarebbe venuto comodo per conservare l'insulina, ci sono rimasto male, però la signorina che era di turno fino alle 22.30 è stata oltre misura cortese risolvendomi il problema in altra maniera. Ho apprezzato. La colazione mi è parsa costosa per quella che era il suo costo e con poche proposte per gli intolleranti al lattosio quale sono io. Non c'è ascensore, ma una scala ripida per raggiungere la reception dalla porta d'ingresso e per persone oltre una certa potrebbe essere disagevole. Comunque il giudizio finale è buono per qualità del servizio del personale della reception funzionalità del bagno ed il prezzo della stanza. Impruneta comunque per la sua bellezza vale anche qualche sacrificio. D'altronde l'hotel non è proprio giovane.

Reviewed on Jul 24, 2026

Hotel Borgo di Cortefreda Relais

Hotel Borgo di Cortefreda Relais

Tavarnelle Val di Pesa
$1,343
per person
Oct 18 - Oct 21
found 1 day ago
Roundtrip flight included
Miami (MIA) to Florence (FLR)
9.4/10 Exceptional! (520 reviews)
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FAQs: family vacation packages in Chianti Region

How can I find the best family vacation packages in Chianti Region?

For fam-tastic vacation packages in Chianti Region, check the family-friendly filter and add child-charming amenities, like water parks and pools. Read reviews written by other broods to be sure your chosen stay packs plenty of rest and play.

How can I book family-friendly vacations in Chianti Region on a budget?

For family- and wallet-friendly trips, filter your search results by budget. You can also sort by price. When bringing the whole brigade on a budget, consider staying in low season or outside the city or. To save more coin, accommodation with a kitchen can be your friend—a bowl of pasta at home is always cheaper than feeding the team at a restaurant.

What does a family trip to Chianti Region cost?

You could book your amazing family trip to Chianti Region just $302. But with so many brilliant breaks on offer, there’s something for every wallet. Prices and availability are subject to change. Additional terms may apply.

Can I book an all-inclusive Chianti Region family vacation package?

Check the all-inclusive filter for an all-you-could-ever-wish-for family vacay. Click more of your favorite filters for even more extravagance. Perhaps an ocean view, spa, or hot tub. Maybe a water park, epic kids club, or activities galore.

How can I plan a fun family vacation in Chianti Region?

Search for stays with kid-satisfying extras, like water parks, and teenage-friendly free Wi-Fi, so they can post about all their vacation adventures for all their buddies back home. Book up local attractions, excursions, and experiences—and they might even put their phone down for a few minutes.

How can I find Chianti Region family vacation deals?

Delightful deals often dwell outside high season, so move your travel dates around for top deals. You can also book up a little away from the major Chianti Region landmarks to save cash. Whenever you wish to travel, sort your search results by deals for the most brilliant bargains.

Can I book a Chianti Region family vacation package with free cancellation and/or flexible dates?

Free cancellation makes for a hassle-free family vacation. Filter by payment option to find fully flexible trips, including buy now, pay later options.

Why should I book my Chianti Region family trip with Expedia?

You can easily find fun for all the family with the super-handy filters. It’s easy to build your dream kid-friendly vacation in just a few clicks. And you can bundle your accommodation, airfare, and car rental in just a few more.

Top Kid friendly Chianti Region Hotels

VILLA IRIS LUXURY SAN GIMIGNANO, 6 EN-SUITE BEDROOMS, SWIMMING POOL, SPA, SAUNA.

VILLA IRIS LUXURY SAN GIMIGNANO, 6 EN-SUITE BEDROOMS, SWIMMING POOL, SPA, SAUNA.

San Gimignano
  • 29 min drive from Antinori nel Chianti Classico
Book a stay at this family-friendly villa in San Gimignano. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Fonti Medievali and Archaeological ...
10/10 Exceptional! (122 reviews)

Families like: Private pool, kitchen, playground, game room

Travelers say...
"My family of 10, 2 grandparents, two adult children and their spouses plus 4 teenagers spent a wonderful week at that the Villa Iris. The house is lovely and has air conditioning. The 6 bedrooms with 6 bathrooms were great to have. Every day we went went to a different hill town, explored them and ..."

Reviewed on Jul 25, 2026

VILLA IRIS LUXURY SAN GIMIGNANO, 6 EN-SUITE BEDROOMS, SWIMMING POOL, SPA, SAUNA.
Querceto di Castellina

Querceto di Castellina

Località Querceto 9 Castellina in Chianti SI
  • 24 min drive from Antinori nel Chianti Classico
Stay at this country house in Castellina in Chianti. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Il Molino di Grace Winery and Pieve ...
9.4/10 Exceptional! (43 reviews)
"First of all, the property is in a beautiful location with amazing views and a very peaceful, quiet atmosphere. It has so much potential! The swimming pool is absolutely beautiful, with an incredible view—it really feels like a dream pool. Castellina, the charming old town nearby, was also one of ..."

Reviewed on Aug 30, 2026

Querceto di Castellina
Hu Norcenni Girasole Village

Hu Norcenni Girasole Village

Via Norcenni 7 Figline e Incisa Valdarno FI
  • 40 min drive from Antinori nel Chianti Classico
Book a stay at this family-friendly campground in Figline e Incisa Valdarno. Enjoy free parking, 7 outdoor pools, and 3 restaurants. Popular attractions Fashion ...
8.6/10 Excellent! (331 reviews)

Families like: Outdoor pools, free waterpark access, kids club, playground

Travelers say...
"Amazing venue , lots of kids entertainment. Lots of facilities- shops restaurants. Splash parks were brilliant. Highly recommended."

Reviewed on Sep 3, 2026

Hu Norcenni Girasole Village
See all 4,925 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

$29
per adult
76% of travellers recommend
City Sightseeing Florence Hop-on Hop-off Bus Tour
Florence: Pasta Cooking Class with Unlimited Wine

Florence: Pasta Cooking Class with Unlimited Wine

$19
per adult
94% of travellers recommend
Florence: Pasta Cooking Class with Unlimited Wine
Michaelangelo's David

Accademia timed-entry Ticket with Instant Delivery & Priority Access

$45
per adult
94% of travellers recommend
Accademia timed-entry Ticket with Instant Delivery & Priority Access
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.