Gaiole in Chianti Holiday Houses

A stone castle with battlements overlooking a lush valley with vineyards.

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Our top choices for Gaiole in Chianti holiday homes

1. Chianti Summer Vacation Home with Pool, Garden, and Wi-Fi

Gaiole in Chianti

includes taxes & fees

11 Aug - 12 Aug

2. Farmhouse in Chianti

gaiole in chianti

"This location provided our blended family an authentic experience in a small village on top of a mountain in Chianti. The house is surrounded by olive groves and wine grapes. The pool was great and the village, literally less than a city block up the road. Folks are incredibly friendly and helpful. Two of the rooms had their own bathrooms and the other two share a bathroom. There is a common kitchen for cooking and eating. We cooked most nights and ate on the outside terrace. Allesandra is a...

Lara W.

includes taxes & fees

1 Sept - 2 Sept

3. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

Ruffoli

"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 and beautifully decorated. Spacious and varied outdoor sitting areas and patios with a very nice pool area. Our hostess Babette was extremely accomodating and informative which added to our overall...

James

includes taxes & fees

11 Aug - 12 Aug

4. Villa with large garden in the Chianti hills

Siena

Julie H.

includes taxes & fees

1 Sept - 2 Sept

5. Holiday Home 'Poggio Loccano' with Private Garden and Balcony

Montevarchi

includes taxes & fees

11 Aug - 12 Aug

6. Love Nest Siena: Romantic Suite with SPA & Jacuzzi

Toscana

includes taxes & fees

19 Aug - 20 Aug

7. Chianti Craft House Badia a Passignano

Barberino Tavarnelle

Oscar O.

includes taxes & fees

14 Aug - 15 Aug

8. Casa Marisa in Castellina in Chianti

Castellina in Chianti

includes taxes & fees

8 Sept - 9 Sept

9. Peaceful corner with garden between Chianti and Crete, very close to Old Town

Casetta

includes taxes & fees

3 Sept - 4 Sept

10. Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi

Castelnuovo Berardenga

Anonymous traveller

includes taxes & fees

17 Aug - 18 Aug

11. Apartment Casale Rosennano - Riserva with Shared Garden & Wi-Fi

Rosennano

includes taxes & fees

8 Sept - 9 Sept

12. Little cozy house

Loro Ciuffenna

includes taxes & fees

12 Aug - 13 Aug

13. Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi

Bucine

"Upon arrival Guido had everything prepared for us. A bottle of his amazing wine that he makes along with 2 wine glasses we’re waiting on the farmhouse table. The home had 2 very comfortable bedrooms and a bathroom along with a living room and kitchen. Front porch overlooks the stunning Tuscany fields. The swimming pool was refreshing and everything was beyond perfect. This location was everything and more. The hosts were so helpful. I will come back her again..make sure to take time for the...

Marianne H.

includes taxes & fees

8 Sept - 9 Sept

14. Cozy Tuscan-style apartment Suitable for families. Pets allowed

Toscana

"This refurbished cottage is a hidden gem, surrounded by fruit trees on a hillside facing Siena. You’ll need a car — it s about a 5-minute drive on a steep, narrow, winding road to get to the stores by the freeway. The cottage was bigger than we were expecting, with a small but well-equipped kitchen. The host turned on the AC in anticipation of our arrival. There are two bedrooms on the main floor with AC, and a fourth bed in a loft."

Shanti R.

includes taxes & fees

17 Aug - 18 Aug

15. The Arch Among the Hills of Castellina

Topina

includes taxes & fees

8 Sept - 9 Sept

16. Exclusive Stone Tower.

Casciano

Ryan C.

includes taxes & fees

14 Aug - 15 Aug

17. House with views of the Chianti

impruneta

Chase B.

includes taxes & fees

29 Aug - 30 Aug

18. Vana Hills House - Three Bedroom House, Sleeps 8

Monteriggioni

includes taxes & fees

31 Aug - 1 Sept

19. Villa 'La Stalla Il Sole Verde' with Shared Pool, Wi-Fi, Pets Allowed

Bucine

includes taxes & fees

27 Aug - 28 Aug

20. Casa Vacanze Le Case

San Gimignano

Jackie

includes taxes & fees

28 Aug - 29 Aug

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Top Gaiole in Chianti Hotel Reviews

Hotel Mulino di Firenze, WorldHotels Crafted

10/10 Excellent

"Great hotel, around 20 mins drive from Florence so not too far but bear in mind if you’re driving there is a restricted zone. The property is an old mill from the 1300s with a beautiful view over the River Arno. Staff was very friendly and breakfast was very nice - although it’s certainly nothing particularly exceptional, just an ok buffet spread with the usual. The rooms are nice but a little dated (however it’s a really really old building, so some might find this part of the charm). Overall would go back and recommend."

"Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C

10/10 Excellent

"Our family of 18 stayed at the Villa this July (2026) and could not have been more pleased with everything associated with our stay. Jacopo and Beatrice truly are first class hosts. They helped us book 3 vehicles that were dropped off and picked up directly at the Villa which was a great time saver. They also provided a grocery shopping service so that we had drinks and snacks at the villa when we arrived.The meal service was truly fantastic! We opted for the Welcome dinner and the Florentine BBQ, both of which were great. We visited a lot of places while in Italy but the family dinners at sunset were among our favorites.The Villa was beautiful and spacious. The grandkids really enjoyed the open spaces and the pool. The views from the back deck of the surrounding Tuscan countryside were also very special. We even got to see hot air balloons on a few occasions. The relative close proximity to Firenze was also clutch for day trips on high-speed trains. There is a good reason why this Villa won the VRBO Vacation Rental of the Year. You simply cannot go wrong here. I am very thankful for the memories that will last a lifetime and role this villa and the hosts played in making that happen!"

Borgo Scopeto Wine & Country Relais

10/10 Excellent

"We spent a wonderful week at Borgo Scopeto and thoroughly enjoyed every minute. It has everything you'd hope for from a luxury Tuscan retreat: beautiful historic buildings, immaculately kept grounds, and a peaceful atmosphere full of character. The staff were warm, attentive and genuinely welcoming without ever feeling intrusive, and the food was consistently excellent. One of the biggest advantages is its location. Siena is only a short drive away - you can even see the city's campanile while having breakfast - so it was easy to combine days by the pool with exploring one of Tuscany's most beautiful cities (and, inevitably, a bit of shopping to keep our teenage daughter happy). A fantastic place to stay, and one we'd happily recommend."

Find out more about Gaiole in Chianti

Gaiole in Chianti Holiday Homes information

Number of reviews	128
Accommodation	1353 Holiday Homes
Lowest Price	NZ$173
Highest Price	NZ$1,682

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Change your mind

Treat yourself

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Check prices for these dates

Our top choices for Gaiole in Chianti holiday homes

1. Chianti Summer Vacation Home with Pool, Garden, and Wi-Fi

2. Farmhouse in Chianti

3. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

4. Villa with large garden in the Chianti hills

5. Holiday Home 'Poggio Loccano' with Private Garden and Balcony

6. Love Nest Siena: Romantic Suite with SPA & Jacuzzi

7. Chianti Craft House Badia a Passignano

8. Casa Marisa in Castellina in Chianti

9. Peaceful corner with garden between Chianti and Crete, very close to Old Town

10. Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi

11. Apartment Casale Rosennano - Riserva with Shared Garden & Wi-Fi

12. Little cozy house

13. Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi

14. Cozy Tuscan-style apartment Suitable for families. Pets allowed

15. The Arch Among the Hills of Castellina

16. Exclusive Stone Tower.

17. House with views of the Chianti

18. Vana Hills House - Three Bedroom House, Sleeps 8

19. Villa 'La Stalla Il Sole Verde' with Shared Pool, Wi-Fi, Pets Allowed

20. Casa Vacanze Le Case

Find holiday rentals that suit your style

Top Gaiole in Chianti Hotel Reviews

Hotel Mulino di Firenze, WorldHotels Crafted

Hotel Athena

Italiana Hotels Florence

"Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C

Borgo Scopeto Wine & Country Relais

Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Tornano Wine Resort

La Certosa di Pontignano

Hu Firenze Camping In Town

Find out more about Gaiole in Chianti

Gaiole in Chianti Holiday Homes information

Explore a world of travel with Expedia

Holiday Homes in Gaiole in Chianti

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Gaiole in Chianti holiday homes

1. Chianti Summer Vacation Home with Pool, Garden, and Wi-Fi

2. Farmhouse in Chianti

3. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

4. Villa with large garden in the Chianti hills

5. Holiday Home 'Poggio Loccano' with Private Garden and Balcony

6. Love Nest Siena: Romantic Suite with SPA & Jacuzzi

7. Chianti Craft House Badia a Passignano

8. Casa Marisa in Castellina in Chianti

9. Peaceful corner with garden between Chianti and Crete, very close to Old Town

10. Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi

11. Apartment Casale Rosennano - Riserva with Shared Garden & Wi-Fi

12. Little cozy house

13. Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi

14. Cozy Tuscan-style apartment Suitable for families. Pets allowed

15. The Arch Among the Hills of Castellina

16. Exclusive Stone Tower.

17. House with views of the Chianti

18. Vana Hills House - Three Bedroom House, Sleeps 8

19. Villa 'La Stalla Il Sole Verde' with Shared Pool, Wi-Fi, Pets Allowed

20. Casa Vacanze Le Case

Find holiday rentals that suit your style

Top Gaiole in Chianti Hotel Reviews

Hotel Mulino di Firenze, WorldHotels Crafted

Find out more about Gaiole in Chianti

Gaiole in Chianti Holiday Homes information

Explore a world of travel with Expedia