Gaiole in Chianti, Tuscany Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Gaiole in Chianti, Tuscany on RentalSaver.com!

Gaiole in Chianti Rentals

From $128 per night (USD)
VRBO
Tuscan apt. magnificent panorama, pure nature, relaxation, private pool, WiFi
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The 4-room apartment is ideal for families and small groups. The entrance is at ground level, two bedrooms and a bathroo ...
From $128 per night (USD)
VRBO
From $159 per night (USD)
Expedia
Chianti Holiday House, private jacuzzi up to 6 pax
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Recently renovated, is located in a scenic hillside location in a picturesque village nestled in the heart of Chianti, s ...
From $159 per night (USD)
Expedia
From $142 per night (USD)
VRBO
WINERY STAY IN THE HILLS OF CHIANTI
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Farm stay in Gaiole in Chianti with an outdoor pool This farm stay features an outdoor pool. Bathrooms include showers. ...
From $142 per night (USD)
VRBO
From $161 per night (USD)
Expedia
Casa del Mastro, San Sano, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
An authentic Chianti village, San Sano allows you to immerse yourself in the charm and character of Tuscan life. Origina ...
From $161 per night (USD)
Expedia
From $11640 per night (USD)
VRBO
Traditional Stone House in the Heart of Chianti
Bedrooms:
0
Bathrooms:
2
Sleeps:
4
Perfect for those who want to enjoy a relaxing holiday in the Chianti countryside among vineyards and woods. The place i ...
From $11640 per night (USD)
VRBO
From $307 per night (USD)
Expedia
Montelodoli Capanna, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
With an atmosphere of a private country cottage grandeur, with climbing vines trailing across the exterior walls, this s ...
From $307 per night (USD)
Expedia
From $416 per night (USD)
VRBO
Gittori, Gaiole in Chianti, Siena and Chianti
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Located just a short stroll from the historical center of Gaiole in Chianti, Gittori is a luxury villa in the heart of t ...
From $416 per night (USD)
VRBO
From $107 per night (USD)
Expedia
Tuscan apartment in an idyllic location, grandiose panorama, pool, WiFi
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The 3-room apartment guarantees an enchanting view of the rolling green hills as far as Siena from the bed. It is on the ...
From $107 per night (USD)
Expedia
From $109 per night (USD)
VRBO
Apartment in Tuscan stone house, surrounded by nature with private pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The 3-room apartment offers comfort for families or a small group. It is located at ground level, the terrace is located ...
From $109 per night (USD)
VRBO
From $138 per night (USD)
Expedia
Farmhouse apartment in Chianti with garden and pool for 2 people
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Stone farmhouse. The apartment is carefully furnished and well-stocked. Satellite TV, Wifi, kitchen, fridge, freezer, wa ...
From $138 per night (USD)
Expedia
From $128 per night (USD)
VRBO
Tuscan apartment with magnificent panorama, private pool, WLAN, pure nature, relaxation
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
<p>A short distance from birdwatching, wildlife walks, and more, this family-friendly apartment lets you experience it a ...
From $128 per night (USD)
VRBO
From $617 per night (USD)
VRBO
Sestuccia is a beautiful Tuscan villa just a short distance from Gaiole in Chianti
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Sestuccia is a beautiful Tuscan villa, located a short distance from Gaiole in Chianti and also within easy reach of Rad ...
From $617 per night (USD)
VRBO
From $328 per night (USD)
VRBO
Stunning private villa with A/C, private pool, WIFI, TV, patio, panoramic view and parking
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Independent house with private pool in the Chianti Classico, in an old hamlet of houses surrounded by vineyards, olive g ...
From $328 per night (USD)
VRBO
From $326 per night (USD)
Expedia
San Sano - Villa with private pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Independent house with private pool in the Chianti Classico, in an old hamlet of houses surrounded by vineyards, olive g ...
From $326 per night (USD)
Expedia
From $576 per night (USD)
VRBO
Farmhouse in Chianti
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
The "Crocino in Chianti" offers the opportunity to immerse yourself in the Italian Middle Ages. Here the border disputed ...
From $576 per night (USD)
VRBO
From $235 per night (USD)
Expedia
Casa BD in Gaiole - 150 m² apartment with a view & travel guide - sleeps 8
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
<p>Close to cycling, hiking trails, and more, this family-friendly villa brings it all within reach. Church of San Sigis ...
From $235 per night (USD)
Expedia
Click For Pricing
VRBO
Villa in Chianti with Pool & Tennis Court
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
This villa with a private swimming pool and tennis court is located in the heart of the Chianti Classico region in Tusca ...
Click For Pricing
VRBO
From $159 per night (USD)
VRBO
Gorgeous home in Gaiole in Chianti (SI)
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
In Gaiole in Chianti, this independent vacation home with private pool awaits you amidst the nature of the Chianti Class ...
From $159 per night (USD)
VRBO
From $279 per night (USD)
VRBO
Sestuccina
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Villa La Grotta is a romantic cottage with a double bedroom, kitchen, living room and bathroom. The villa is located a f ...
From $279 per night (USD)
VRBO
From $343 per night (USD)
VRBO
Lovely home in Gaiole in Chianti SI
Bedrooms:
7
Bathrooms:
8
Sleeps:
18
In the heart of the Chianti area, between Radda in Chianti, Gaiole and Panzano, there is an enchanted hamlet where you c ...
From $343 per night (USD)
VRBO
From $681 per night (USD)
VRBO
CASA VISTA - Four Bedroom Villa, Sleeps 8
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Located in a small village in the very heart of Chianti classico, you find this restored ancient house next to the churc ...
From $681 per night (USD)
VRBO
From $522 per night (USD)
Expedia
Villa Fauno A: A welcoming apartment located in a small hamlet at the foot of a castle, with Free WI-FI.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Villa Fauno A is a welcoming apartment located in a small hamlet at the foot of a castle. It sleeps four people. From Vi ...
From $522 per night (USD)
Expedia
From $522 per night (USD)
VRBO
Villa Fauno D: A welcoming apartment located in a small hamlet at the foot of a castle, with Free WI-FI.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Villa Fauno D is a welcoming apartment located in a small hamlet at the foot of a castle. It sleeps four people. From Vi ...
From $522 per night (USD)
VRBO
From $863 per night (USD)
Expedia
Secluded villa between Chianti vineyards, private pool, tennis, large garden
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Ciao from Petra & Alexa! We warmly welcome you in our unbeatable location, halfway between Siena and Florence! First of ...
From $863 per night (USD)
Expedia
From $295 per night (USD)
VRBO
Lovely home in Gaiole in Chianti
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Beautiful detached stone vacation home with private pool, whose origins date back to 1500, on the hills of Chianti Class ...
From $295 per night (USD)
VRBO
From $118 per night (USD)
Expedia
Apartment in the castle, with restaurant and swimming pool, pink
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This stunning large apartment of 80 sqm for 5 people is located in the medieval castle, near the restaurant and the rece ...
From $118 per night (USD)
Expedia
From $254 per night (USD)
VRBO
Lavanda, Castellare in Chianti, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Castellare in Chianti's cottages and apartments are nestled in the woods in the uplands of Gaiole in Chianti 8 Km from t ...
From $254 per night (USD)
VRBO
From $134 per night (USD)
Expedia
Villa Mimosa , San Regolo in Brolio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
San Regolo in Brolio is a lovely modern hamlet of villas, located on the edge of the village of San Regolo. It’s within ...
From $134 per night (USD)
Expedia
From $240 per night (USD)
VRBO
Rosmarino, Castellare in Chianti, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Castellare in Chianti's cottages and apartments are nestled in the woods in the uplands of Gaiole in Chianti 8 Km from t ...
From $240 per night (USD)
VRBO
From $335 per night (USD)
Expedia
Sestuccina, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sestuccina is a stylish holiday home in the heart of Chianti Classico, ideal for a couple seeking a romantic retreat, bu ...
From $335 per night (USD)
Expedia
From $213 per night (USD)
VRBO
Peperoncino, Castellare in Chianti, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Castellare in Chianti's cottages and apartments are nestled in the woods in the uplands of Gaiole in Chianti 8 Km from t ...
From $213 per night (USD)
VRBO
From $170 per night (USD)
Expedia
Casa del Vignaiolo, San Sano, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
An authentic Chianti village, San Sano allows you to immerse yourself in the charm and character of Tuscan life. Origina ...
From $170 per night (USD)
Expedia
From $290 per night (USD)
VRBO
Casetta Kiwi, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Casetta Kiwi is a charming Chianti holiday home in the historic hamlet of Bricciano, made up of 18th-century buildings a ...
From $290 per night (USD)
VRBO
From $771 per night (USD)
Expedia
Canonica di Vertine, Gaiole in Chianti, Siena and Chianti
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Canonica di Vertine is a unique holiday home located in the picturesque medieval hamlet of Vertine. This historic buildi ...
From $771 per night (USD)
Expedia
From $234 per night (USD)
VRBO
Basilico, Castellare in Chianti, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Castellare in Chianti's cottages and apartments are nestled in the woods in the uplands of Gaiole in Chianti 8 Km from t ...
From $234 per night (USD)
VRBO
From $190 per night (USD)
Expedia
Villa Rosabella, San Regolo in Brolio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
San Regolo in Brolio is a lovely modern hamlet of villas, located on the edge of the village of San Regolo. It’s within ...
From $190 per night (USD)
Expedia
From $159 per night (USD)
Expedia
Vinaio, Montefiorile, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
A Chianti Classico hillside resort, Montefiorile's cottages are nestled on a south bank with magnificent views across ro ...
From $159 per night (USD)
Expedia
From $186 per night (USD)
Expedia
Capanna di Camporata, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Capanna di Camporata is a charming Chianti holiday home, ideal for a relaxing getaway for two. This single-storey stone ...
From $186 per night (USD)
Expedia
From $285 per night (USD)
VRBO
Nicchio, Agriturismo Vinci, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Surrounded by the rolling Chianti hills covered with vineyards and olive groves, this property is wonderfully positioned ...
From $285 per night (USD)
VRBO
From $523 per night (USD)
Expedia
Podere Terrena, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Guests of this attractive stone villa in the heart of Chianti, which is made even more beautiful by climbing roses and p ...
From $523 per night (USD)
Expedia
From $1240 per night (USD)
VRBO
Borratella, Gaiole in Chianti, Siena and Chianti
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Borratella is a spacious Chianti holiday home, ideal for a large family or a group of friends. This house offers total p ...
From $1240 per night (USD)
VRBO
From $302 per night (USD)
Expedia
La Fontanella, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
La Fontanella is a traditional stone farmhouse located on the edge of the charming village of San Sano. Surrounded by vi ...
From $302 per night (USD)
Expedia
From $255 per night (USD)
VRBO
Mantegna, Galenda, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
A Chianti Classico hamlet resort, Galenda's cottages lay on a ridge with magnificent views across rolling hills draped w ...
From $255 per night (USD)
VRBO
From $152 per night (USD)
Expedia
Pesci, Montefiorile, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
A Chianti Classico hillside resort, Montefiorile's cottages are nestled on a south bank with magnificent views across ro ...
From $152 per night (USD)
Expedia
From $170 per night (USD)
VRBO
Il Sole, Montefiorile, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
A Chianti Classico hillside resort, Montefiorile's cottages are nestled on a south bank with magnificent views across ro ...
From $170 per night (USD)
VRBO
From $527 per night (USD)
Expedia
Vecchio Frantoio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Vecchio Frantoio is a beautifully restored holiday home in Chianti with a terraced garden and a large pool. Once a histo ...
From $527 per night (USD)
Expedia
From $632 per night (USD)
VRBO
Valliole, Gaiole in Chianti, Siena and Chianti
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
This sprawling 17th-century villa occupies a dreamy position in the heart of rolling Chianti country with views across o ...
From $632 per night (USD)
VRBO
From $249 per night (USD)
Expedia
Trifoglio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Trifoglio is a beautifully restored stone cottage set in an authentic 18th-century hamlet in the heart of Chianti Classi ...
From $249 per night (USD)
Expedia
From $446 per night (USD)
VRBO
Il Trebbio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Il Trebbio is a charming holiday home in Chianti, peacefully located on a hill with panoramic views over vineyards and t ...
From $446 per night (USD)
VRBO
From $135 per night (USD)
Expedia
Il Balcone, Borgo Gaiole, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Borgo Gaiole is a large hamlet with 40 villas, all overlooking the Chianti town of Gaiole. It's a short walk into the pr ...
From $135 per night (USD)
Expedia
From $204 per night (USD)
VRBO
Sesamo, Castellare in Chianti, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Castellare in Chianti's cottages and apartments are nestled in the woods in the uplands of Gaiole in Chianti 8 Km from t ...
From $204 per night (USD)
VRBO
From $179 per night (USD)
Expedia
La Chiocciola, Montefienali, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
In the upland of the Chianti vineyards and forests on an ancient Roman road, the 13th century Montefienali resort sits o ...
From $179 per night (USD)
Expedia
From $289 per night (USD)
VRBO
Casa Isabella, San Sano, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
An authentic Chianti village, San Sano allows you to immerse yourself in the charm and character of Tuscan life. Origina ...
From $289 per night (USD)
VRBO
From $240 per night (USD)
Expedia
Salvia, Castellare in Chianti, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Castellare in Chianti's cottages and apartments are nestled in the woods in the uplands of Gaiole in Chianti 8 Km from t ...
From $240 per night (USD)
Expedia
From $527 per night (USD)
VRBO
Torretta Barbischio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Torretta Barbischio is a characterful Chianti holiday home, ideal for a relaxing stay with family or friends. The buildi ...
From $527 per night (USD)
VRBO
From $268 per night (USD)
Expedia
Private villa in heart of the Chianti, pool and wifi
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Aia di Ama is a traditional Chianti country house offering the perfect setting for a relaxing holiday with friends or fa ...
From $268 per night (USD)
Expedia
From $166 per night (USD)
VRBO
Origano, Castellare in Chianti, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Castellare in Chianti's cottages and apartments are nestled in the woods in the uplands of Gaiole in Chianti 8 Km from t ...
From $166 per night (USD)
VRBO
From $134 per night (USD)
Expedia
Villa Violetto, San Regolo in Brolio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
San Regolo in Brolio is a lovely modern hamlet of villas, located on the edge of the village of San Regolo. It’s within ...
From $134 per night (USD)
Expedia
From $527 per night (USD)
VRBO
Le Volte, Gaiole in Chianti, Siena and Chianti
Bedrooms:
5
Bathrooms:
3
Sleeps:
6
Le Volte is a welcoming Chianti holiday home, ideal for a relaxing stay with family or friends. Set in a small hamlet, i ...
From $527 per night (USD)
VRBO
From $219 per night (USD)
Expedia
La Vigna, Montebuoni, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Once a wine and olive oil producing estate, Montebuoni's original stone buildings have been restored into cottages and a ...
From $219 per night (USD)
Expedia
From $194 per night (USD)
VRBO
Mietitore, Montefiorile, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
A Chianti Classico hillside resort, Montefiorile's cottages are nestled on a south bank with magnificent views across ro ...
From $194 per night (USD)
VRBO
From $146 per night (USD)
Expedia
Il Portico, Montefienali, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
In the upland of the Chianti vineyards and forests on an ancient Roman road, the 13th century Montefienali resort sits o ...
From $146 per night (USD)
Expedia
From $240 per night (USD)
VRBO
Vaniglia, Castellare in Chianti, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Castellare in Chianti's cottages and apartments are nestled in the woods in the uplands of Gaiole in Chianti 8 Km from t ...
From $240 per night (USD)
VRBO
From $242 per night (USD)
Expedia
L'Oliveta, Montebuoni, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Once a wine and olive oil producing estate, Montebuoni's original stone buildings have been restored into cottages and a ...
From $242 per night (USD)
Expedia
From $190 per night (USD)
VRBO
Villa Giacinto, San Regolo in Brolio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
San Regolo in Brolio is a lovely modern hamlet of villas, located on the edge of the village of San Regolo. It’s within ...
From $190 per night (USD)
VRBO
From $902 per night (USD)
Expedia
Il Molinaccio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Il Molinaccio is a unique holiday home in the heart of Chianti, with a rich history that stretches back to the Middle Ag ...
From $902 per night (USD)
Expedia
From $803 per night (USD)
VRBO
Villa San Michele, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Villa San Michele enjoys a wonderfully private location on a Chianti hilltop and was once the residence of wealthy lando ...
From $803 per night (USD)
VRBO
From $134 per night (USD)
Expedia
Villa Fiorella, San Regolo in Brolio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
San Regolo in Brolio is a lovely modern hamlet of villas, located on the edge of the village of San Regolo. It’s within ...
From $134 per night (USD)
Expedia
From $359 per night (USD)
VRBO
Villa Riecine, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
An exquisite combination of modern and rustic styles, set on a wine-producing country estate, Riecine is a thoroughly co ...
From $359 per night (USD)
VRBO
From $241 per night (USD)
Expedia
Casa Dante, San Donato in Perano, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Perched on vines San Donato in Perano dates back to a medieval castle. The resort is restored into six individually owne ...
From $241 per night (USD)
Expedia
From $272 per night (USD)
VRBO
Sassolaia, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Close to two of the Chianti’s most renowned and beautiful towns, and with views across the olive groves and vineyards, a ...
From $272 per night (USD)
VRBO
From $793 per night (USD)
Expedia
Sestuccia, Gaiole in Chianti, Siena and Chianti
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Sestuccia is a beautifully renovated stone house set in the rolling hills of the Chianti Classico region. This modern vi ...
From $793 per night (USD)
Expedia
From $296 per night (USD)
VRBO
L'Agrifoglio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
L’Agrifoglio is a charming holiday home in the heart of the Chianti Classico region, set within a peaceful historic haml ...
From $296 per night (USD)
VRBO
From $263 per night (USD)
Expedia
La Rana, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Perfect for small groups of friends or a family of four who favour both privacy and proximity to local village life, thi ...
From $263 per night (USD)
Expedia
From $179 per night (USD)
VRBO
Ciacchieri, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Ciacchieri is a charming Chianti holiday accommodation with a private pool, ideal for couples or small families. The apa ...
From $179 per night (USD)
VRBO
From $179 per night (USD)
Expedia
Raffaello, Montefienali, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
In the upland of the Chianti vineyards and forests on an ancient Roman road, the 13th century Montefienali resort sits o ...
From $179 per night (USD)
Expedia
From $423 per night (USD)
VRBO
Le Cerreta, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Le Cerreta is a traditional Tuscan stone villa in a secluded setting, offering breathtaking panoramic views, an elegant ...
From $423 per night (USD)
VRBO
From $158 per night (USD)
Expedia
Scorpione, Montefiorile, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
A Chianti Classico hillside resort, Montefiorile's cottages are nestled on a south bank with magnificent views across ro ...
From $158 per night (USD)
Expedia
From $240 per night (USD)
VRBO
Maggiorana, Castellare in Chianti, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Castellare in Chianti's cottages and apartments are nestled in the woods in the uplands of Gaiole in Chianti 8 Km from t ...
From $240 per night (USD)
VRBO
From $190 per night (USD)
Expedia
Villa Girasole , San Regolo in Brolio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
San Regolo in Brolio is a lovely modern hamlet of villas, located on the edge of the village of San Regolo. It’s within ...
From $190 per night (USD)
Expedia
From $412 per night (USD)
VRBO
Casa Virginia, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Casa Virginia is a welcoming Chianti holiday home, ideal for a relaxing break with family or a small group of friends. S ...
From $412 per night (USD)
VRBO
From $177 per night (USD)
Expedia
La Taverna, Montebuoni, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Once a wine and olive oil producing estate, Montebuoni's original stone buildings have been restored into cottages and a ...
From $177 per night (USD)
Expedia
From $262 per night (USD)
VRBO
Sangiovese all'Aia, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sangiovese all’Aia is a charming holiday home in Chianti, located on the grounds of Agriturismo Trappoline, where wine a ...
From $262 per night (USD)
VRBO
From $186 per night (USD)
Expedia
Timo, Castellare in Chianti, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Castellare in Chianti's cottages and apartments are nestled in the woods in the uplands of Gaiole in Chianti 8 Km from t ...
From $186 per night (USD)
Expedia
From $159 per night (USD)
VRBO
Bacco, Montefiorile, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
A Chianti Classico hillside resort, Montefiorile's cottages are nestled on a south bank with magnificent views across ro ...
From $159 per night (USD)
VRBO
From $247 per night (USD)
Expedia
Mastro 3, San Sano, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
An authentic Chianti village, San Sano allows you to immerse yourself in the charm and character of Tuscan life. Origina ...
From $247 per night (USD)
Expedia
From $126 per night (USD)
VRBO
Antico Borgo di Montefienali - Apartment il Portico
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Borgo di Montefienali is a medieval hamlet , dating back to the 13th Century , was once a resting place along the ancien ...
From $126 per night (USD)
VRBO
Click For Pricing
Expedia
Antico Borgo Montefienali - Apartment La Chiocciola
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Borgo di Montefienali is a medieval hamlet , dating back to the 13th Century , was once a resting place along the ancien ...
Click For Pricing
Expedia
From $1103 per night (USD)
VRBO
VILLA GAIA - Five Bedroom Villa, Sleeps 10
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
A typical Chianti Villa in Tuscany, once a a 15th century mill, located in the countryside, just 15 minutes from Siena, ...
From $1103 per night (USD)
VRBO
From $1237 per night (USD)
Expedia
Villa Agresto, Gaiole in Chianti, Siena and Chianti
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
Agresto sits on its own private hilltop, decorated with vineyards manicured by the Ricasoli estate. With 360-degree surr ...
From $1237 per night (USD)
Expedia
From $671 per night (USD)
VRBO
Mulinaccio di Badia, Gaiole in Chianti, Siena and Chianti
Bedrooms:
6
Bathrooms:
5
Sleeps:
8
Could there be a more apt setting for a Chianti wine region villa than on the sloping vines of a famous wine estate? Mul ...
From $671 per night (USD)
VRBO
From $125 per night (USD)
Expedia
Apartment in the castle, with restaurant and swimming pool, Ginestra
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Nice and comfortable apartment for 4 persons (70sqm), in the hamlet near the castle, about 200 meters from the swimming ...
From $125 per night (USD)
Expedia
From $176 per night (USD)
VRBO
Dionisia, Capannole, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Nestled between vine covered hills, Capannole is a peaceful hamlet of eleven private houses which date back to 1400. A f ...
From $176 per night (USD)
VRBO
From $165 per night (USD)
Expedia
Nice apartment in villa with A/C, WIFI, pool, TV, terrace, pets allowed, panoramic view and park...
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Property Summary The Montechioccioli 3-family house is a cosy and rustic vacation rental surrounded by vineyards in the ...
From $165 per night (USD)
Expedia
From $194 per night (USD)
VRBO
Beautiful apartment in villa with pool, WIFI, TV, terrace, pets allowed, panoramic view and park...
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Property Summary The Montechioccioli 3-family house is a cosy and rustic vacation rental surrounded by vineyards in the ...
From $194 per night (USD)
VRBO
From $149 per night (USD)
Expedia
Lovely apartment in villa with pool, WIFI, TV, terrace, pets allowed, panoramic view and parking
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Property Summary The Montechioccioli 3-family house is a cosy and rustic vacation rental surrounded by vineyards in the ...
From $149 per night (USD)
Expedia
From $440 per night (USD)
VRBO
Nice apartment in villa with private pool, WIFI, TV, terrace, pets allowed, panoramic view, parking
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
Property Summary The Montechioccioli 3-family house is a cosy and rustic vacation rental surrounded by vineyards in the ...
From $440 per night (USD)
VRBO
From $285 per night (USD)
Expedia
Portion Farmhouse nestled in the heart of Chianti with private pool,
Bedrooms:
1
Bathrooms:
4
Sleeps:
9
<p>A short distance from ecotours, mountain biking, and more, this family-friendly vacation home lets you experience it ...
From $285 per night (USD)
Expedia
Click For Pricing
VRBO
MONTELUCCI CHIANTI, GAIOLE IN CHIANTI - HOLIDAY HOUSE 8/10 BEDS
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
MONTELUCCI CHIANTI .............. WHEREVER THE NATURE RESTS ................. PRISTINE NATURE FARM Montelucci, FROM THE ...
Click For Pricing
VRBO
From $747 per night (USD)
Expedia
Villa Radda by MMega
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
External Description Villa Radda is located in the countryside of Gaiole in Chianti. The property is accessed through ...
From $747 per night (USD)
Expedia

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