Gaiole in Chianti Villas

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Villas in Gaiole in Chianti

Artisti del Cavallo Tourism

VIA DI SINALUNGA 65 Foiano della Chiana AR

$84 nightly

$95 total

Dec 8 - Dec 9

Total with taxes and fees

With a stay at Artisti del Cavallo Tourism in Foiano della Chiana, you'll be in the suburbs, just steps from Val di Chiana and a 3-minute drive from Chiesa-Museo della Fraternità di Santa Maria.

Pet friendly

Parking included

Il Poggio dell'Eremita

Sinalunga Tuscany

$162 nightly

$165 total

Dec 8 - Dec 9

Total with taxes and fees

Located in Sinalunga, this villa is in the mountains, a 1-minute drive from Val di Chiana and 7 minutes from Torre Il Cassero.

Kitchen

Free WiFi

Holiday Villa With Swimming Pool In Arezzo.

Castel Focognano Toscana

With a stay at this villa in Castel Focognano, you'll be in the mountains, and 7.6 mi (12.3 km) from ExpArt and 8 mi (12.9 km) from Santa Maria of Sasso Sanctuary.

Pool

Hot Tub

Villa with concierge service & heated pool at 20 minute from Florence center

impruneta Toscana

$1,557 nightly

$1,562 total

Jan 5 - Jan 6, 2026

Total with taxes and fees

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

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

- Top Location - Villa in San Gimignano, Top View, 4 DBL En-Suite, Pool, A. C, WiFi

San Gimignano Toscana

Located in San Gimignano, this villa is in a rural location, within a 10-minute drive of Sant'Agostino Church and Rocca of Montestaffoli.

Pool

Kitchen

Charming Tuscan Villa Near Siena/ Capitivating Private Setting / Lrg Heated Pool

Castelnuovo Berardenga Tuscany

With a stay at this villa in Castelnuovo Berardenga, you'll be 4.7 mi (7.6 km) from Villa a Sesta Polo Club and 5.1 mi (8.1 km) from Felsina.

Pool

Kitchen

San Gimignano - Panoramic garden and beautiful pool!

San Gimignano Toscana

Located in San Gimignano, this villa is in a rural location, within a 10-minute drive of Sant'Agostino Church and Rocca of Montestaffoli.

Pool

Kitchen

Villa Salivolpe - on top of a Chianti hill - Private swimming pool

Santa Cristina in Salivolpe Tuscany

Located in San Casciano in Val di Pesa, this villa is in a rural location, within a 15-minute drive of Antinori nel Chianti Classico and Monastary of Sorelle Clarisse.

Pool

Hot Tub

Luxury Villa Basilio Chianti

Località Vegi 16 Castellina in Chianti SI

With a stay at this villa in Castellina in Chianti, you'll be within a 15-minute drive of Casa Vinicola Luigi Cecchi and City Hall Castellina In Chianti.

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

Hot Tub

Charming Villa Torre in Chianti, 8 ensuite bedrooms, pool, Florence, Wi-Fi, 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 Monastary of Sorelle Clarisse and Florence American Cemetery and Memorial.

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.