Radicondoli Villas

A snow-covered landscape with rolling hills and distant mountains under a clear sky.

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Our top choices for Radicondoli villas

A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

1. Villa Montecastello

Monteriggioni

Alvaro

HK$1,484 total

includes taxes & fees

3 Oct - 4 Oct

A gazebo with a thatched roof overlooking a scenic landscape.

2. Villa Gelsomino a Casa Conti di Sotto-Toscana mare piscine/spa- idromassaggio

Toscana

Giulia O.

HK$3,318 total

includes taxes & fees

16 Oct - 17 Oct

A stone exterior wall, a glass door entrance, and a brick pathway leading to a staircase.

3. Villa Duomo Mare – Entire House with Garden & Terrace, Walk to Center

Massa Marittima

HK$4,409 total

includes taxes & fees

13 Oct - 14 Oct

A brick building with a gravel courtyard, a staircase, and potted plants.

4. GuestHost - Porta Romana Elegant House with Private Parking!

Siena

Kathleen M.

HK$2,798 total

includes taxes & fees

5 Oct - 6 Oct

A two-story building with a garden, a gazebo, and a statue.

5. Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills

Gambassi Terme

HK$38,336 total

includes taxes & fees

4 Oct - 5 Oct

A stone building with a large glass door, a wooden deck, and a stone wall.

6. Villa "Arnilù" with Private Pool & Wi-Fi

San Gimignano

HK$47,205 total

includes taxes & fees

5 Oct - 6 Oct

A landscaped garden with a central fountain, a pool, and a small building with a tiled roof.

7. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32

Siena

Ron M.

HK$62,352 total

includes taxes & fees

2 Oct - 3 Oct

A covered outdoor area with a pool, wicker furniture, and a view of the countryside.

8. Villa Podere Cafaggio with Private Pool, Terrace, and Air Conditioning

Monteverdi Marittimo

HK$23,650 total

includes taxes & fees

13 Oct - 14 Oct

An outdoor dining area with a table and chairs, overlooking a historic town with a prominent tower and buildings.

9. Villa Mami: A Tuscan Retreat of Elegance and Charm

Toscana

HK$24,297 total

includes taxes & fees

18 Oct - 19 Oct

A villa with a swimming pool, surrounded by lush greenery and hills.

10. Villa Belvedere with Private Pool and Volterra Views

Gambassi Terme

HK$9,317 total

includes taxes & fees

2 Oct - 3 Oct

A stone building with balconies, a gravel path, and a tree.

11. Villa "Bouganville - Colleberto" with Sea View, Private Terrace & Wi-Fi

Follonica

Anonymous traveller

HK$3,144 total

includes taxes & fees

7 Oct - 8 Oct

A clear pool with lounge chairs, a wooden deck, and a view of hills in the background.

12. Villa 'La Vigna' with Private Pool, Wi-Fi and Air Conditioning

Gavorrano

HK$26,884 total

includes taxes & fees

13 Oct - 14 Oct

A table with a red and white checkered tablecloth, a hanging light fixture, and a view of green hills and trees.

13. Villa 'Casa Alta Esclusiva' with private pool, private terrace and Wi-Fi

Murlo

"Our stay at this property was absolutely excellent! The home was spotless, beautifully decorated, and even more spacious than the photos showed. Every amenity listed was fully functional, and the brand new swimming pool was amazing. The location was perfect— isolated peaceful and quiet, yet just a short drive from the Buonconvento .The host was wonderful to work with. Communication was lightning-fast, and the check-in and checkout instructions were crystal clear. They truly went above and beyond...

martina p.

A two-story house with a stone facade, a tiled roof, and a well-maintained lawn.

14. Pet-Friendly Finca Lucente with Mountain View, Pool, Garden & Wi-Fi

Roccastrada GR

HK$11,843 total

includes taxes & fees

2 Oct - 3 Oct

A covered balcony with a brick railing, a bench, and a view of lush greenery.

15. Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany

Certaldo - Firenze

Kelly C.

HK$5,182 total

includes taxes & fees

2 Oct - 3 Oct

A covered outdoor patio with a wooden table and chairs, a vase of flowers, and a view of the countryside.

16. Villa Capanna: A Window onto Tuscany

Vico dʼArbia

HK$15,229 total

includes taxes & fees

17 Oct - 18 Oct

A rustic stone building with a tower, covered walkways, and a grassy courtyard.

17. Villa Torre Among the Hills of Siena

Vico dʼArbia

HK$15,851 total

includes taxes & fees

1 Nov - 2 Nov

A pool with a view of rolling hills and a distant tower.

18. Villa Tosca

Peccioli

A stone building with a swimming pool, wooden deck, and a tall tree.

19. Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

Radda in Chianti

Amber M.

HK$14,249 total

includes taxes & fees

1 Nov - 2 Nov

A person in a swimming pool with a view of a vineyard and hills.

20. "A Casa di Franca Villa con piscina"

Gambassi Terme

"Pros: La estancia en la casa fue muy bonita. Estaba cerca de Florencia, Siena, Sant Gimigano, etc. Viajamos toda la familia y los propietarios fueron muy acogedores. La piscina es un sitio perfecto para relajarse y bañarse después de ver la Toscana. Nuestros hijos y sobrinos jugaron porque tenían de todo. La casa muy equipada y limpia con televisión en todas las habitaciones. Los propietarios además nos ayudaron con un pequeño contratiempo que tuvimos. Nos sentimos como en casa, muchas...

Anonymous traveller

HK$16,506 total

includes taxes & fees

19 Oct - 20 Oct

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Top Radicondoli Hotel Reviews

Borgo Scopeto Wine & Country Relais

10/10 Excellent

"A peaceful luxurious stay with amazing amenities, 6 star service & and amazing dinner restaurant."

Castiglion del Bosco, A Rosewood Hotel

10/10 Excellent

"Castiglion del Bosco is truly exquisite, the perfect way to experience Tuscany in luxury while still feeling completely surrounded by nature. The property is impeccable, from the beautiful gardens and grounds to the elegant rooms. Everything feels authentically Italian, refined and incredibly well maintained. The service is exceptional and very personalized. The staff genuinely goes out of their way to make you feel welcome. General Manager Nicola Migheli even greeted us personally upon arrival, which was a lovely touch. We also saw him regularly walking the property with his team, and it was clear how hands-on he is with every detail. One thing to know is that getting in and out requires about 40 minutes on a bumpy dirt road. It wasn’t terrible, but worth mentioning if you plan to explore frequently. That said, this is a hotel you don’t need to leave. It’s a beautiful place to slow down, relax and enjoy Tuscany in a truly special setting. We absolutely loved our stay!"

Fattoria di Vegi

10/10 Excellent

"Booked this as a last minute decision to shorten our time in Milan (and fine a place close to Florence on our way to Montepulciano) We only stayed one night, but wish it had been longer. If you are looking for informal luxury, you will find it at this idyllic Tuscan Estate. They are still expanding their amenities to include a gym, tennis court, and Spa (planned for a 2027 open) what they DO offer is a quiet, thoughtful experience. The room was perfection and the restaurant on the property - delicious. There were a few artists there taking advantage of the atelier, or painting on the property. The estate is located an hour’s drive outside of Florence and is well worth the trip if you are looking for a place to relax. We hope to return with more time to enjoy it."

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