San Gusme Holiday Houses

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Our top choices for San Gusme holiday homes

A clear blue pool with a view of green hills and a distant building.

1. Casale Rosennano Apartment – Shared Garden, Wi-Fi, Medieval Setting

Rosennano

includes taxes & fees

7 Sept - 8 Sept

A building with a stone facade, a door, a window, and a patio area with chairs and a table.

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

Casetta

includes taxes & fees

20 Sept - 21 Sept

A rectangular swimming pool with a wooden deck and metal railing, surrounded by a grassy area with trees and a clear sky.

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

Castelnuovo Berardenga

Anonymous traveller

includes taxes & fees

7 Sept - 8 Sept

A modern hotel room with a flat-screen TV displaying 'NETFLIX', a jacuzzi, and a neon sign.

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

Toscana

includes taxes & fees

20 Sept - 21 Sept

A dining area with a brick archway, wooden dining table, chairs, and a chandelier.

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

Montevarchi

includes taxes & fees

7 Sept - 8 Sept

A hot tub with a mountain view, surrounded by greenery and a tall tree.

6. Le Fate Apartment – Villa Assolata

Pietraviva

includes taxes & fees

2 Oct - 3 Oct

A swimming pool with a colorful inflatable ring and a water fountain.

7. 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

13 Sept - 14 Sept

A stone building with a gated entrance, terracotta pots with flowers, and a staircase leading up to the door.

8. 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

14 Sept - 15 Sept

A swimming pool with lounge chairs, a tiled deck, and surrounding trees.

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

Bucine

includes taxes & fees

7 Sept - 8 Sept

A garden pathway leading to a stone building with a brick wall, a pergola, and a small brick structure in the background.

10. 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

12 Sept - 13 Sept

A covered patio with a wooden table and chairs, stone walls, and a view of a garden.

11. Villa 'Il Fienile Il Sole Verde' with Shared Pool and Wi-Fi

Bucine

Anonymous traveller

includes taxes & fees

20 Sept - 21 Sept

A rustic building with a brick facade, a small arched window, and a door.

12. 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

13 Sept - 14 Sept

A rustic kitchen with stone walls, a wooden ceiling, a green sofa with cushions, and a view through a large arched window.

13. Vacation Home 'La Limonaia' with Pool, Private Terrace & Wi-Fi

Monte San Savino

"My husband and I booked this place and were unable to stay due to lack of communication regarding check-in procedure. The listing states the host will make contact 3 days before which didn’t happen. We sent several messages the day of check-in and didn’t hear from the host until well after the check-in time (4pm). Given the remote location and time of day, we were worried we wouldn’t have anywhere to stay for the night so we booked a hotel in Arezzo which we were lucky to get on a holiday...

Anonymous traveller

includes taxes & fees

10 Sept - 11 Sept

A stone building with a tiled roof, a central door, and a small courtyard with a fountain.

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

Monteriggioni

includes taxes & fees

8 Sept - 9 Sept

A brick building with a garden, a metal fence, and a clear sky.

15. Casa Marisa in Castellina in Chianti

Castellina in Chianti

includes taxes & fees

8 Sept - 9 Sept

A stone building with a gravel path, outdoor seating, and greenery.

16. The Arch Among the Hills of Castellina

Topina

includes taxes & fees

1 Oct - 2 Oct

A person sitting at an outdoor table with a drink, a bowl of bread, and a glass of juice.

17. Dolce Casa 2 by Tiny Away

Rigutino

includes taxes & fees

8 Sept - 9 Sept

A dining area with a table and chairs, a sofa, and large windows with curtains.

18. 'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi

Gaiole in Chianti

includes taxes & fees

8 Sept - 9 Sept

An outdoor patio with a wooden pergola, a sofa, a table, and chairs.

19. Blue villa surrounded by greenery between Arezzo Florence and Siena

TERRANUOVA BRACCIOLINI

includes taxes & fees

1 Oct - 2 Oct

A street with outdoor seating, a building with a shop entrance, and a sign with a prohibition symbol.

20. Holiday Home 'La Casa Gialla Di Buonconvento' with Wi-Fi and Air Conditioning

Buonconvento

includes taxes & fees

23 Sept - 24 Sept

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Top San Gusme Hotel Reviews

Borgo San Felice Resort

10/10 Excellent

"An unforgettable stay in Tuscany!** Our stay at Borgo San Felice was truly incredible from beginning to end. From the moment our private driver picked us up at the train station and brought us through the beautiful Tuscan countryside to the resort, everything felt seamless and special. The property itself is absolutely breathtaking pictures truly don’t do it justice. We enjoyed dinner on the property, a wonderful couples massage, a private wine tour and tasting, and a relaxing pool day. We especially loved the live piano music in the evenings; it added such a romantic and elegant touch to the entire experience. The service was one of the highlights of our stay. A special shout-out to **Herman at the pool**, who was always attentive and completely on point with everything we needed. We also had an amazing experience at **Poggio Rosso**, where **Matia provided top-notch service** and made our Michelin-starred dinner feel even more memorable. Every detail from the beautiful grounds and peaceful atmosphere to the food, wine, spa, and exceptional hospitality—made our time here unforgettable. Borgo San Felice gave us exactly the Tuscany experience we were hoping for and more. We absolutely loved our stay and would return in a heartbeat. Highly recommend! 🇮🇹🍷✨"

Castello di Leonina Relais

10/10 Excellent

"We stayed 4 days and are so glad we stayed here. The area has a restaurant right outside with the best view where they serve lunch and dinner. They also have a bar and a pool. It’s an old castle and yet they keep it clean and pretty restored. Breakfast buffet in the morning was included for us. The bathroom comment from others might be from not understanding how to use it as you have to pump the button several times to flush. The staff was wonderful and helpful. They spoke English and some Spanish."

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San Gusme Holiday Homes information

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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for San Gusme holiday homes

1. Casale Rosennano Apartment – Shared Garden, Wi-Fi, Medieval Setting

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

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

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