Castellina in Chianti Villas

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Villas in Castellina in Chianti

Spectacular Villa sleeping 12, Large private Pool, 9 km South of Florence City

Impruneta (Florence) Tuscany

Located in Impruneta, this villa is in a rural location, within a 10-minute drive of Villa Medicea di Lilliano - Malenchini and Circolo Golf Ugolino.

Pool

Hot Tub

Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano

San Gimignano SI, Italy

Located in San Gimignano, this villa is in a rural location, within a 15-minute walk of Museum San Gimignano 1300 and Casa e Torre Campatelli.

Pool

Kitchen

Villa Bartolini Baldelli - Authentic XV century villa with garden and pool

Toscana Città Metropolitana di Firenze

Located in Impruneta, this villa is within a 10-minute drive of Florence American Cemetery and Memorial and Florence Charterhouse.

Pool

Kitchen

Relais Badia a Passignano

Via Martiri di Pratale 12 Barberino Tavarnelle FI

With a stay at this villa in Barberino Tavarnelle (Tavarnelle Val di Pesa), you'll be within a 15-minute drive of Abbey of Passignano and Passignano Abbey.

Pool

Kitchen

Exclusive Estate | Personal Concierge & Heated Pool

impruneta Toscana

$1,071 nightly

$1,075 total

Nov 1 - Nov 2

Total with taxes and fees

Free Cancellation

Located in Impruneta, this villa is in a rural location, within a 15-minute drive of Circolo Golf Ugolino and Florence American Cemetery and Memorial.

Pool

Kitchen

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

San Casciano in Val di Pesa Tuscany

Located in San Casciano in Val di Pesa, this villa is in a rural location, within a 10-minute drive of Monastery of Sorelle Clarisse and Florence American Cemetery and Memorial.

Pool

Kitchen

Gorgeous view on vineyards, Stone Tuscan private Villa

Toscana Provincia di Siena

With a stay at this villa in Castelnuovo Berardenga, you'll be on a lake, within a 15-minute drive of Piazza del Campo and Terra di Seta.

Pool

Hot Tub

HISTORICAL RESIDENCE CHIANTI private swimming pool 30 km from FLORENCE

Empoli Tuscany

Located in Empoli, this villa is in a rural location, within a 10-minute drive of Chiesa di San Giovanni Battista and Civic Museum of Paleontology in Empoli.

Pool

Kitchen

Podere Il Boschetto - Luxury Estate in Siena

Siena Provincia di Siena

Located in Siena, this villa is in a rural location, within a 5-minute drive of Palasport Mens Sana and Porta Camollia.

Pool

Kitchen

La Ruota by PosarelliVillas

Duddova Tuscany

With a stay at this villa in Bucine, you'll be within a 15-minute drive of Villa a Sesta Polo Club and Berardenga Riding Centre.

Pool

Kitchen

Marvelous home just steps from the Chianti and beyond

cavriglia Tuscany

Located in Cavriglia, this villa is in a rural location, a 2-minute drive from Gianfranco Carla Fineschi Botanical Rose Garden and 6 minutes from Le Miccine.

Kitchen

Washer

Villa Costa, Stunning Villa in the heart of Tuscany.

Siena Tuscany

With a stay at this villa in Radicondoli, you'll be 7.5 mi (12.1 km) from Val di Merse and 9 mi (14.4 km) from Terre di Vini.

Pool

Kitchen

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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.