Gaiole in Chianti Villas

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Villas in Gaiole in Chianti

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

Authentic Private Tuscan Villa for 12 people in Greve: the Heart of Chianti

Greve in Chianti (Firenze) Toscana

Located in Greve in Chianti, this villa is in a rural location, within a 15-minute drive of Piazza Matteotti and Verrazzano Castle.

Pool

Hot Tub

CASA PILAR villa with pool and jacuzzi for exclusive use in chianti.-20% 12_21/5

Strada In Chianti Città Metropolitana di Firenze

Located in Greve in Chianti, this villa is in a rural location, a 5-minute drive from Circolo Golf Ugolino and 10 minutes from Villa Medicea di Lilliano - Malenchini.

Pool

Hot Tub

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

La Ruota - Village house rental in Duddova, Chianti

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

Secluded Villa, private heated Pool, Wi-fi and TV. Secure Payment

Civitella di val di chiana Province of Arezzo

Located in Civitella in Val di Chiana, this villa is in a rural location, within a 10-minute drive of Sienese Gate and Civitella Longobard Castle.

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

Wonderful private villa for 4 guests with pool, A/C, WIFI, TV and terrace

Asciano Tuscany

Located in Asciano, this villa is within a 5-minute drive of Crete Senesi and Museo Cassioli.

Kitchen

Washer

"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

Villa with private pool on 25 acres in the heart of Chianti, close to Siena

Pievasciata Tuscany

Located in Castelnuovo Berardenga, this villa is in a rural location, within a 15-minute drive of Chianti Sculpture Park and Borgo Scopeto e Caparzo Srl.

Pool

Kitchen

Villa in Montalcino, exclusive for you, stunning view!!!

Montalcino Provincia di Siena

Located in Montalcino, this villa is in a rural location, within a 10-minute drive of Museo del Tartufo and San Giovanni d'Asso Station.

Pool

Kitchen

Exclusive comfort for a small group- Countryside Tuscan Villa near Florence

Bagno a Ripoli, San Bartolomeo A Quarate Tuscany

Located in Bagno a Ripoli, this villa is in a rural location, within a 15-minute drive of Ruffino - Tenuta di Poggio Casciano and Villa Medicea di Lilliano - Malenchini.

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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.