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.
Villa Pitiana

Villa Pitiana

$1,051
per person
Oct 12 - Oct 18
found 19 hours ago
Roundtrip flight included
New York (JFK) to Florence (FLR)
8.6/10 Excellent! (153 reviews)
Hotel Borgo di Cortefreda Relais

Hotel Borgo di Cortefreda Relais

$1,383
per person
Oct 12 - Oct 18
found 19 hours ago
Roundtrip flight included
New York (JFK) to Florence (FLR)
9.4/10 Exceptional! (509 reviews)
This hotel is advertised and presented as more of a high class property than it actually is and the majority of the staff is not attentive or helpful. We are a family of 4 and were looking for a room in Tuscany that could provide us with space, the advertised room for 4 is not actually meant for 4, it was a standard room, with a king and two rollaway beds. Did they all fit, yes. Should they all have been put in there and advertised as a room for 4, absolutely not! Maybe if you have two little ones, but not two pre-teens or older. That was our first disappointment. The hotel is not staffed well, they have two bars, but only one is open at a time so the staff can cover both and the indoor bar was never really staffed, if we wanted to get a drink we had to ask the front desk to call someone. Multiple times during our stay we were waiting for service, an employee looked at us, didn't acknowledge us, went off to do or help someone else. We tip and are a polite family, so it's not like we were rude to any of the staff. After being told the pool menu was available until 7:30, we planned to get food upon our return. We went to order at 6:45 and were told it was closed, so we had to pay $10 extra for room service to get the same food. Everything is very dated, the spa wasn't really a spa or easily accessible so we weren't able to use that either. I will say the food was good and the outdoor space was nice, but ultimately we were VERY disappointed and I would not recommend this hotel.

Reviewed on Aug 6, 2026

Relais Della Rovere

Relais Della Rovere

$1,526
per person
Sep 27 - Oct 3
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Florence (FLR)
9/10 Wonderful! (258 reviews)
I planned my proposal here and I can’t say enough about all the staff who helped me make it an amazing moment that we will never forget. The hotel is beautiful and a must visit for anyone looking to experience the real Tuscany.

Reviewed on Aug 5, 2026

Villa Lecchi Hotel Wellness

Villa Lecchi Hotel Wellness

$1,251
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.4/10 Exceptional! (85 reviews)
Villa Scacciapensieri Boutique Hotel

Villa Scacciapensieri Boutique Hotel

Scacciapensieri
$1,839
per person
Sep 14 - Sep 19
found 10 hours ago
Roundtrip flight included
San Francisco (SFO) to Florence (FLR)
9.2/10 Wonderful! (448 reviews)
Very enjoyable stay

Reviewed on Aug 2, 2026

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3 Night Kid friendly vacations in Chianti Region

Price found within the past 48 hours. Click for updated prices.
Hotel Borgo di Cortefreda Relais

Hotel Borgo di Cortefreda Relais

$922
per person
Oct 4 - Oct 7
found 12 hours ago
Roundtrip flight included
New York (NYC) to Florence (FLR)
9.4/10 Exceptional! (509 reviews)
This hotel is advertised and presented as more of a high class property than it actually is and the majority of the staff is not attentive or helpful. We are a family of 4 and were looking for a room in Tuscany that could provide us with space, the advertised room for 4 is not actually meant for 4, it was a standard room, with a king and two rollaway beds. Did they all fit, yes. Should they all have been put in there and advertised as a room for 4, absolutely not! Maybe if you have two little ones, but not two pre-teens or older. That was our first disappointment. The hotel is not staffed well, they have two bars, but only one is open at a time so the staff can cover both and the indoor bar was never really staffed, if we wanted to get a drink we had to ask the front desk to call someone. Multiple times during our stay we were waiting for service, an employee looked at us, didn't acknowledge us, went off to do or help someone else. We tip and are a polite family, so it's not like we were rude to any of the staff. After being told the pool menu was available until 7:30, we planned to get food upon our return. We went to order at 6:45 and were told it was closed, so we had to pay $10 extra for room service to get the same food. Everything is very dated, the spa wasn't really a spa or easily accessible so we weren't able to use that either. I will say the food was good and the outdoor space was nice, but ultimately we were VERY disappointed and I would not recommend this hotel.

Reviewed on Aug 6, 2026

Villa Scacciapensieri Boutique Hotel

Villa Scacciapensieri Boutique Hotel

Scacciapensieri
$926
per person
Oct 4 - Oct 7
found 12 hours ago
Roundtrip flight included
New York (NYC) to Florence (FLR)
9.2/10 Wonderful! (448 reviews)
Very enjoyable stay

Reviewed on Aug 2, 2026

Hotel Borgo San Luigi

Hotel Borgo San Luigi

$1,177
per person
Oct 25 - Oct 27
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Florence (FLR)
9.2/10 Wonderful! (431 reviews)
Beautiful hotel and helpful staff Excellent food and amenities

Reviewed on Aug 4, 2026

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4 Night Kid friendly vacations in Chianti Region

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

Villa Pitiana

$1,044
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
8.6/10 Excellent! (153 reviews)
Hotel Borgo di Cortefreda Relais

Hotel Borgo di Cortefreda Relais

$1,056
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.4/10 Exceptional! (509 reviews)
This hotel is advertised and presented as more of a high class property than it actually is and the majority of the staff is not attentive or helpful. We are a family of 4 and were looking for a room in Tuscany that could provide us with space, the advertised room for 4 is not actually meant for 4, it was a standard room, with a king and two rollaway beds. Did they all fit, yes. Should they all have been put in there and advertised as a room for 4, absolutely not! Maybe if you have two little ones, but not two pre-teens or older. That was our first disappointment. The hotel is not staffed well, they have two bars, but only one is open at a time so the staff can cover both and the indoor bar was never really staffed, if we wanted to get a drink we had to ask the front desk to call someone. Multiple times during our stay we were waiting for service, an employee looked at us, didn't acknowledge us, went off to do or help someone else. We tip and are a polite family, so it's not like we were rude to any of the staff. After being told the pool menu was available until 7:30, we planned to get food upon our return. We went to order at 6:45 and were told it was closed, so we had to pay $10 extra for room service to get the same food. Everything is very dated, the spa wasn't really a spa or easily accessible so we weren't able to use that either. I will say the food was good and the outdoor space was nice, but ultimately we were VERY disappointed and I would not recommend this hotel.

Reviewed on Aug 6, 2026

Villa Lecchi Hotel Wellness

Villa Lecchi Hotel Wellness

$1,251
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.4/10 Exceptional! (85 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 $922. 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! (41 reviews)
"Beautiful property and location, great staff will definitely return"

Reviewed on Oct 11, 2025

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 Museum ...
8.6/10 Excellent! (329 reviews)

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

Travelers say...
"Two large pool sites. Helpful staff. Lots of entertainment. Restaurant options and a well stocked reasonably priced food market."

Reviewed on Aug 7, 2026

Hu Norcenni Girasole Village
See all 4,888 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
The Best of Tuscany in One Day Sightseeing Tour

The Best of Tuscany Tour: Siena, San Gimignano, Pisa and Lunch at a Winery

$82
per adult
98% of travellers recommend
The Best of Tuscany Tour: Siena, San Gimignano, Pisa and Lunch at a Winery
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.