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 $112 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 $112 per night (USD)
VRBO
From $132 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 $132 per night (USD)
Expedia
From $126 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 $126 per night (USD)
VRBO
From $164 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 $164 per night (USD)
Expedia
From $10375 per night (USD)
VRBO
Traditional Stone House in the Heart of Chianti
Bedrooms:
2
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 $10375 per night (USD)
VRBO
From $249 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 $249 per night (USD)
Expedia
From $422 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 $422 per night (USD)
VRBO
From $1783 per night (USD)
Expedia
Podere Campi, Gaiole in Chianti, Siena and Chianti
Bedrooms:
5
Bathrooms:
6
Sleeps:
10
Podere Campi is one of the most unique villas in Tuscany that we offer. A medieval priests house and originally a strate ...
From $1783 per night (USD)
Expedia
From $95 per night (USD)
VRBO
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 $95 per night (USD)
VRBO
From $97 per night (USD)
Expedia
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 $97 per night (USD)
Expedia
From $131 per night (USD)
VRBO
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 $131 per night (USD)
VRBO
From $116 per night (USD)
Expedia
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 $116 per night (USD)
Expedia
From $550 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 $550 per night (USD)
VRBO
$Wonderful private villa with private pool, WIFI, A\/C, TV, patio, panoramic view and parking$
From $299 per night (USD)
Expedia
Wonderful private villa with private pool, WIFI, A\/C, 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 $299 per night (USD)
Expedia
From $303 per night (USD)
VRBO
San Sano - Holiday Country Villa with swimming pool in Chianti, Tuscany
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 $303 per night (USD)
VRBO
From $685 per night (USD)
Expedia
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 $685 per night (USD)
Expedia
From $196 per night (USD)
VRBO
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. Gaiole in Chianti S ...
From $196 per night (USD)
VRBO
From $834 per night (USD)
Expedia
Belvilla by OYO Villa Petra
Bedrooms:
6
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 ...
From $834 per night (USD)
Expedia
From $161 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 $161 per night (USD)
VRBO
From $323 per night (USD)
VRBO
8 bedroom accommodation 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 $323 per night (USD)
VRBO
From $661 per night (USD)
VRBO
CASA VISTA - Four Bedroom private Villa
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 $661 per night (USD)
VRBO
From $231 per night (USD)
Expedia
Beautiful apartment with shared pool in a typical historic village in Chianti.
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Beautiful apartment with shared pool in a typical historic village in Chianti. Galenda is located between the towns of ...
From $231 per night (USD)
Expedia
From $249 per night (USD)
VRBO
Sestuccina
Bedrooms:
2
Bathrooms:
3
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 $249 per night (USD)
VRBO
From $466 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 $466 per night (USD)
Expedia
From $466 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 $466 per night (USD)
VRBO
From $153 per night (USD)
Expedia
Detached house in heart of Chianti Classico,pool,quiet panoramic position,WLAN
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
The house is located on the outskirts of the historic hamlet Starda (12th century). Century). The CASA La Quercia is lo ...
From $153 per night (USD)
Expedia
From $672 per night (USD)
VRBO
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 $672 per night (USD)
VRBO
From $269 per night (USD)
Expedia
4 bedroom accommodation 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 $269 per night (USD)
Expedia
From $105 per night (USD)
VRBO
Apartment in the castle, with restaurant and swimming pool, pink
Bedrooms:
2
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 $105 per night (USD)
VRBO
From $226 per night (USD)
Expedia
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 $226 per night (USD)
Expedia
From $119 per night (USD)
VRBO
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 $119 per night (USD)
VRBO
From $214 per night (USD)
Expedia
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 $214 per night (USD)
Expedia
From $299 per night (USD)
VRBO
Sestuccina, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This romantic contemporary hideaway garners top marks from those who’ve discovered it – including, not surprisingly, a h ...
From $299 per night (USD)
VRBO
From $190 per night (USD)
Expedia
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 $190 per night (USD)
Expedia
From $158 per night (USD)
VRBO
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 $158 per night (USD)
VRBO
From $519 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 $519 per night (USD)
Expedia
From $726 per night (USD)
VRBO
Borratella, Gaiole in Chianti, Siena and Chianti
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
A luxurious old stone villa set among acres of vines in the heart of Chianti, Borratella is a fabulous holiday home for ...
From $726 per night (USD)
VRBO
From $282 per night (USD)
Expedia
La Fontanella, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Set on a slight rise, with extensive views of undulating vineyards, Fontanella has a relaxed feel inside and out. At the ...
From $282 per night (USD)
Expedia
From $246 per night (USD)
VRBO
Casetta Kiwi, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
The secluded lavender-edged pool of Casetta Kiwi is sun-drenched all day long. At 18 meters in length, this is a serious ...
From $246 per night (USD)
VRBO
From $657 per night (USD)
Expedia
Canonica di Vertine, Gaiole in Chianti, Siena and Chianti
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
One for history lovers. Canonica di Vertine is an extraordinary property with a deep history, as one would expect from i ...
From $657 per night (USD)
Expedia
From $209 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 $209 per night (USD)
VRBO
From $169 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 $169 per night (USD)
Expedia
From $148 per night (USD)
VRBO
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 $148 per night (USD)
VRBO
From $166 per night (USD)
Expedia
Capanna di Camporata, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This typical Chianti cottage is ideal for a couple who are looking for a romantic and peaceful hideaway, yet it is also ...
From $166 per night (USD)
Expedia
From $254 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 $254 per night (USD)
VRBO
From $252 per night (USD)
Expedia
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 $252 per night (USD)
Expedia
From $144 per night (USD)
VRBO
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 $144 per night (USD)
VRBO
From $154 per night (USD)
Expedia
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 $154 per night (USD)
Expedia
From $572 per night (USD)
VRBO
Vecchio Frantoio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Vecchio Frantoio is a beautifully restored two-storey stone-built villa in the hamlet of Casanuova di Ama, surrounded by ...
From $572 per night (USD)
VRBO
From $563 per night (USD)
Expedia
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 $563 per night (USD)
Expedia
From $222 per night (USD)
VRBO
Trifoglio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Wish list: a restored stone barn, deep in the heart of Chianti, surrounded by castles and quaint villages. If this chime ...
From $222 per night (USD)
VRBO
From $425 per night (USD)
Expedia
Il Trebbio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
If your Chianti villa wish-list includes a hill, a view, a private pool and a property oozing with atmosphere, you'll lo ...
From $425 per night (USD)
Expedia
From $120 per night (USD)
VRBO
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 $120 per night (USD)
VRBO
From $182 per night (USD)
Expedia
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 $182 per night (USD)
Expedia
From $158 per night (USD)
VRBO
La Chiocciola, Montefienali, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Deep in the upland forests of the Chianti on an ancient Roman road, the 13th century Montefienali resort sits on a ridge ...
From $158 per night (USD)
VRBO
From $227 per night (USD)
Expedia
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 $227 per night (USD)
Expedia
From $214 per night (USD)
VRBO
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 $214 per night (USD)
VRBO
From $521 per night (USD)
Expedia
Torretta Barbischio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Set in a tiny hamlet with an excellent local restaurant a short distance from Gaiole, one of Chianti’s most popular hill ...
From $521 per night (USD)
Expedia
From $239 per night (USD)
VRBO
Private villa in heart of the Chianti, pool and wifi
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Set in the heart of Chianti Classico, Aia di Ama provides a tranquil rural retreat amid vineyards and olive groves that ...
From $239 per night (USD)
VRBO
From $148 per night (USD)
Expedia
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 $148 per night (USD)
Expedia
From $130 per night (USD)
VRBO
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 $130 per night (USD)
VRBO
From $470 per night (USD)
Expedia
Le Volte, Gaiole in Chianti, Siena and Chianti
Bedrooms:
5
Bathrooms:
3
Sleeps:
6
What a delicious villa! It’s no surprise that Le Volte, set in a hamlet in the heart of Chianti’s hills, gets a very hig ...
From $470 per night (USD)
Expedia
From $188 per night (USD)
VRBO
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 $188 per night (USD)
VRBO
From $154 per night (USD)
Expedia
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 $154 per night (USD)
Expedia
From $127 per night (USD)
VRBO
Il Portico, Montefienali, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Deep in the upland forests of the Chianti on an ancient Roman road, the 13th century Montefienali resort sits on a ridge ...
From $127 per night (USD)
VRBO
From $214 per night (USD)
Expedia
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 $214 per night (USD)
Expedia
From $191 per night (USD)
VRBO
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 $191 per night (USD)
VRBO
From $534 per night (USD)
Expedia
Camporatina, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
The ideal holiday home for mixed groups or families, Camporatina is an attractive property – both inside and out – and i ...
From $534 per night (USD)
Expedia
From $169 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 $169 per night (USD)
VRBO
From $681 per night (USD)
Expedia
Il Molinaccio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
With origins dating back to the early Middle Ages, Il Molinaccio was initially built as a defence watchtower and has sin ...
From $681 per night (USD)
Expedia
From $659 per night (USD)
VRBO
Villa San Michele, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
It’s no surprise to discover that the wealthy landowners who once ruled over much of this area chose this villa as their ...
From $659 per night (USD)
VRBO
From $119 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 $119 per night (USD)
Expedia
From $320 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 $320 per night (USD)
VRBO
From $215 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 $215 per night (USD)
Expedia
From $243 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 $243 per night (USD)
VRBO
From $707 per night (USD)
Expedia
Sestuccia, Gaiole in Chianti, Siena and Chianti
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Visit in the heat of the summer and you will be living outdoors at Sestuccia – and doing so in great style. The main vil ...
From $707 per night (USD)
Expedia
From $325 per night (USD)
VRBO
L'Agrifoglio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Something of a Tardis, this renovated cottage in Bricciano, a hamlet of 18th-century farmhouses in the heart of the Chia ...
From $325 per night (USD)
VRBO
From $234 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 $234 per night (USD)
Expedia
From $258 per night (USD)
VRBO
Sangiovese all'Aia, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sangiovese all'Aia is a delightful villa and a fine choice if you are a family of four or a couple seeking just a little ...
From $258 per night (USD)
VRBO
From $134 per night (USD)
Expedia
Ciacchieri, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
You will feel a real part of Tuscan life in Ciacchieri, a cheerfully decorated apartment in Gaiole, a small town at the ...
From $134 per night (USD)
Expedia
From $154 per night (USD)
VRBO
Raffaello, Montefienali, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Deep in the upland forests of the Chianti on an ancient Roman road, the 13th century Montefienali resort sits on a ridge ...
From $154 per night (USD)
VRBO
From $377 per night (USD)
Expedia
Le Cerreta, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Set atop a sunlit Chianti hill near the beautiful town of Gaiole, Le Cerreta is an exceptional private hideaway. It’s sh ...
From $377 per night (USD)
Expedia
From $136 per night (USD)
VRBO
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 $136 per night (USD)
VRBO
From $214 per night (USD)
Expedia
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 $214 per night (USD)
Expedia
From $169 per night (USD)
VRBO
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 $169 per night (USD)
VRBO
From $375 per night (USD)
Expedia
Casa Virginia, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
You will love Casa Virginia’s openness: set on a gentle slope above a vineyard, with a backdrop of olive trees, pines an ...
From $375 per night (USD)
Expedia
From $167 per night (USD)
VRBO
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 $167 per night (USD)
VRBO
From $245 per night (USD)
Expedia
Podere Filazzi, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Immersed in a deep green valley with rolling hills and gorgeous views, Podere Filazzi is a country villa with charming d ...
From $245 per night (USD)
Expedia
From $166 per night (USD)
VRBO
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 $166 per night (USD)
VRBO
From $159 per night (USD)
Expedia
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)
Expedia
From $220 per night (USD)
VRBO
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 $220 per night (USD)
VRBO
From $112 per night (USD)
Expedia
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 $112 per night (USD)
Expedia
Click For Pricing
VRBO
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
VRBO
From $802 per night (USD)
Expedia
VILLA GAIA - Five Bedroom Villa, Sleeps 10
Bedrooms:
4
Bathrooms:
6
Sleeps:
10
A typical Chianti Villa in Tuscany, once a a 15th century mill, located in the countryside, just 15 minutes from Siena, ...
From $802 per night (USD)
Expedia
From $1108 per night (USD)
VRBO
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 $1108 per night (USD)
VRBO
From $512 per night (USD)
Expedia
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 $512 per night (USD)
Expedia
From $157 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 $157 per night (USD)
VRBO
From $136 per night (USD)
Expedia
Beautiful apartment in villa with 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 $136 per night (USD)
Expedia
From $137 per night (USD)
VRBO
Lovely apartment in villa with WIFI, pool, 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 $137 per night (USD)
VRBO
From $128 per night (USD)
Expedia
Cosy 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 $128 per night (USD)
Expedia

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