Vacation rentals in Monteguidi

La Casetta

“La Casetta”, is a new restored enchanting apartment immersed in the splendid Tuscan countryside, only 2 kms from the medieval village of Casole d'Elsa in Siena province. Situated in a old farm complex with private entrance, large private garden, and access to the communal swimming pool. Furnished with utmost care down to the finest detail. Ideal for a relaxing, regenerative week with family or friends, emerged in an uncontaminated natural landscape. Possibility of excursions on foot and by bicycle in an evocative natural setting of lush forests and gentle hills of rare beauty. One can enjoy local dishes of the wonderful Tuscan tradition in many of the nearby restaurants or organize splendid home-cooked meals with the barbecue in the garden. Ideally situated for visits the many nearby towns and cities rich in art and beauty: 30 mins to Siena, 1 hour to Florence ,30 mins to San Gimignano and Volterra, 45 mins to the Chianti area. La Casetta is the ideal place to regenerate your body and mind. (We are the same owners of “La Senesina" apartment near Siena check out our rating on the web! Our 5 stars ratings are your warranty for a great stunning vacation)

Family · Location · Condition

Exclusive Tuscan Villa with private pool

Amazing exclusive authentic big villa, real Tuscan style, air condition. 15 guests. 6 double bedrooms and 1 triple rooms. Bright dining room, fully equipped kitchen. Private pool (15x7mt). The area is really quiet and super relaxing. You will enjoy a stunning view over the characteristic tuscan countryside. About 15 minutes drive from San Gimignano, the most famous medieval village just between Florence and Siena. Wifi, private parking area!! The best place for trekking and outdoor sport lovers!

Family · Location · Kitchen

Podere Vergianoni immerso nelChianti con piscina

Podere Vergianoni è un antica proprietà del 1600 a gestione familiare situato nelle splendide colline del Chianti in Toscana con la possibilità di organizzare navetta privata e esperienze locali direttamente con la nostra famiglia . L'appartamento è disponibile per 2 adulti con possibilità aggiunta divano letto per 2 bambini sotto i 12 anni . Nel grande cortile esterno troverete una piscina a sale con area relax su terrazza panoramica con vista su castello e vigneti con tramonti unici.

Value · Family · Parking

Dimora San Donato - Apt.1985

Dimora San Donato, located in the historic centre of Casole d'Elsa, combines refinement and elegance. The interiors, spacious with great attention to detail, offer a perfect blend between tradition and modernity. The location allows guests to immerse themselves in the daily life of the village, surrounded by a breathtaking landscape of rolling hills and centuries old cypresses. The Dimora represents a journey into the heart of Tuscany, where history, culture and natural beauty come together.

Location · Family · Laundry

Tuscan Hilltop Retreat | Views, Charm, Fireplace

Imagine waking up to rolling Tuscan hills, stepping onto your private terrace with a cup of coffee, and realizing you have nowhere else to be. No crowds, no tour buses—just church bells, the fragrance of home‑cooked food, and the peaceful rhythm of an authentic hilltop village. This 14th‑century stone duplex in Radicondoli sits at the heart of a real working village—not a tourist set piece—and puts you within easy reach of Siena, Florence, San Gimignano, and the Chianti wine region.

Location · Family · Comfort

Casa al Gianni - Il Fienile di Simignano

Trasformato da un antico fienile, questo rifugio lussuoso offre 5 camere, 4 bagni, grande cucina attrezzata, ampio living, un ampio giardino privato con parcheggio, hot tub, patio con divani, BBQ, fire pit e cucina esterna. Ideale per chi cerca un'esperienza unica, unisce fascino rustico a comfort moderni. Perfetto per famiglie o gruppi, promette serate magiche sotto le stelle, tra relax nell'hot tub e cene all'aperto. Una fuga memorabile vi aspetta in questo angolo di paradiso!

Location · Value · Condition

Podere Tignano, 4-bedroom villa in the Chianti!

Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.

Value · Location · Checkout

Romantic Villa with private pool - "Il Pollaio"

Il Pollaio is a traditional, charming Tuscan stone house with a warm, relaxed atmosphere, surrounded by the peace and quiet of the countryside. With air conditioning, a private pool nestled in the greenery and a fully fenced property. Extra services on request: private chef and housekeeping every other day. Ideally located, yet secluded and private. Ample parking. PLEASE NOTE: Read the details under “Show more” in “Other things to note”

Location · Family · Amenities

Charming Tuscan Villa with pool

Podere Casalino is a traditional Tuscan farmhouse with a stand alone guest-suite. It sleeps up to six in the 3 bedrooms of the main house plus up to 2 guests in the separate guest-suite. Nestled on a panoramic hill and located just 3.8 km from Volterra, Podere Casalino is easily accessible via a paved road and has private parking onsite. The property was completely restored and preserved 25 years ago and updated again in 2025.

Location · Family · Outdoor spaces

Green Dome @ The Land Before Time Retreats

Nestled among Tuscan olive groves between Volterra and San Gimignano, The Land Before Time – Quad & Saddle Retreats offers 4 Green Domes with private jacuzzi, en-suite bathroom, air conditioning and Wi-Fi. Enjoy breakfast each morning in the Cupola Lounge with stunning views. During your stay, experience horseback rides through scenic trails, quad tours to discover hidden Tuscany, or simply relax under the starry sky.

Value · Family · View

Il Frantoio - Charming Loft in the old town

This elegant and spacious Loft “Il Frantoio”, with a living area of 160 m², is located in the old town of the medieval village Radicondoli. The open space kitchen and livingroom area is designed to give a high comfort and reminds us the ancient function of this bluilding that was the oil mill of the comunity. The Loft was recently completly restored with a high focus on comfort and best quality materials.

Location · Value · Pets

Panoramic villa & private pool-VacaVilla Exclusive

Property for exclusive use Stone farmhouse of 250 m2, with exclusive swimming pool, completely independent and able to accommodate 9 people in 4 double bedrooms, 1 single sofa bed and 3 bathrooms. The property has a large garden with private swimming pool, loggia equipped for outdoor dining, barbecue, WI-FI internet connection, satellite TV, air conditioning, heating and parking.

Location · Family · Hospitality