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 $142 per night (USD)
VRBO
Apartment 'Casale Rosennano - Loggia' with Shared Garden & Wi-Fi
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Located in the medieval village of Rosennano, the apartment 'Casale Rosennano - Loggia' is part of a characteristic farm ...
From $142 per night (USD)
VRBO
$\La Casina delle Fate\ a pretty little house in Tuscany$
From $92 per night (USD)
VRBO
\"La Casina delle Fate\" a pretty little house in Tuscany
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
The CASINA DELLE FATE is a 5 km from the "heart" of Chianti classico - It will take 45 minutes (35 km) from Siena, 60 mi ...
From $92 per night (USD)
VRBO
From $129 per night (USD)
VRBO
Podere II Colto - Located In A Beautiful Forested Area In Chianti Region heart
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The house was built in 1891 and has a square floor plan. When you enter you find an old stone pavement. From here you se ...
From $129 per night (USD)
VRBO
From $115 per night (USD)
Expedia
Apartment Casale Rosennano - Scuderie with Shared Garden & Wi-Fi
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Located in the medieval village of Rosennano, the apartment Casale Rosennano - Scuderie is part of a characteristic farm ...
From $115 per night (USD)
Expedia
From $116 per night (USD)
VRBO
Apartment Casale Rosennano - Tinaia with Shared Garden & Wi-Fi
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Located in the medieval village of Rosennano, the apartment Casale Rosennano - Tinaia is part of a characteristic farmho ...
From $116 per night (USD)
VRBO
From $149 per night (USD)
Expedia
Apartment Casale Rosennano - Padronale with Shared Garden & Wi-Fi
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Located in the medieval village of Rosennano, the apartment Casale Rosennano - Padronale is part of a characteristic far ...
From $149 per night (USD)
Expedia
From $129 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 $129 per night (USD)
VRBO
From $160 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 $160 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 $158 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 $158 per night (USD)
Expedia
From $11702 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 $11702 per night (USD)
VRBO
From $305 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 $305 per night (USD)
Expedia
From $418 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 $418 per night (USD)
VRBO
From $108 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 $108 per night (USD)
Expedia
From $110 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 $110 per night (USD)
VRBO
From $170 per night (USD)
VRBO
An enchanting cottage for a perfect vacation
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Leccino is one of three houses that are part of Podere Pornanino, a 36-hectare organic farm producing extra virgin olive ...
From $170 per night (USD)
VRBO
From $948 per night (USD)
VRBO
Villa il Roseto In Gaiole in Chianti, Tuscany
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Property for exclusive use Stonework Villa in typical Tuscan style, 250 sq. m., with 4 double bedrooms and 4 bathrooms, ...
From $948 per night (USD)
VRBO
From $229 per night (USD)
VRBO
Best Location. Heart of Tuscany; Still offering 2023 pricing!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
We continue to provide an oustanding location and beautiful home at reasonable rates. This is a perfect location for a ...
From $229 per night (USD)
VRBO
From $145 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 $145 per night (USD)
VRBO
From $129 per night (USD)
Expedia
Tuscan apartment with magnificent panorama, private pool, WLAN, pure nature, relaxation
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
A short distance from birdwatching, wildlife walks, and more, this family-friendly apartment lets you experience it a ...
From $129 per night (USD)
Expedia
From $467 per night (USD)
VRBO
Villa on Chianti hill in heart of Tuscany, super-large pool, 14 ha plot
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Restored from the ruin of a typical Tuscan farmhouse this Podere sits high on a hilltop at 600 meter above sea-level (wh ...
From $467 per night (USD)
VRBO
From $2722 per night (USD)
Expedia
Villa Le Cantine di Cerreto, a magnificent villa for rent in the Sienese countryside, with an in...
Bedrooms:
8
Bathrooms:
8
Sleeps:
14
Villa Cerreto is owned by a renowned Florentine family belonging to the fashion industry and dates back to the 1700’s. T ...
From $2722 per night (USD)
Expedia
From $314 per night (USD)
VRBO
L'Angolino In Radda in Chianti, Tuscany
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Property for exclusive use Beautiful stone farmhouse, completely independent, 120 sq. m., holding up to 6 persons with t ...
From $314 per night (USD)
VRBO
From $620 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 $620 per night (USD)
VRBO
From $819 per night (USD)
VRBO
Le Diacce: Beautiful Old Farmhouse with Breathtaking Countryside View
Bedrooms:
6
Bathrooms:
5
Sleeps:
12
What we offer is a beautiful and spacious old stone house in the heart of the unspoiled Chianti countryside. It has been ...
From $819 per night (USD)
VRBO
From $165 per night (USD)
Expedia
Adorable house in charming Chianti hamlet btwn Siena, Arezzo and Florence
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Casa Secciano is located strategically between these 3 artistic cities allowing for easy access to tourist sites, but at ...
From $165 per night (USD)
Expedia
From $184 per night (USD)
VRBO
Villa Nova - Apartment with swimming pool
Bedrooms:
2
Bathrooms:
1
Sleeps:
5
Beautiful country house situated in the heart of the renowned Chianti Classico region, approx. 20 km from Siena away. Th ...
From $184 per night (USD)
VRBO
From $359 per night (USD)
VRBO
Il Colombaio In Gaiole in Chianti, Tuscany
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Property for exclusive use Ancient tower dating back to the 1600s with an apartment in a separate farmhouse, hosting a t ...
From $359 per night (USD)
VRBO
From $243 per night (USD)
VRBO
LA LOGGIA. HOUSE WITH STUNNING VIEW ABOVE THE CHIANTI REGION AND PANORAMIC POOL
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
LA LOGGIA House, renovated in 2015, is a large independent apartment, ideal to be rented by those who love nature, tranq ...
From $243 per night (USD)
VRBO
From $765 per night (USD)
VRBO
Castello di Cacchiano In Gaiole in Chianti, Tuscany
Bedrooms:
4
Bathrooms:
4
Sleeps:
7
Property for exclusive use Il Bindaccio is an independent part of the castle with private swimming pool and Jacuzzi, hol ...
From $765 per night (USD)
VRBO
From $343 per night (USD)
VRBO
Wonderful private villa with private pool, A/C, 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 $343 per night (USD)
VRBO
From $342 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 $342 per night (USD)
Expedia
From $284 per night (USD)
VRBO
An enchanting small villa, perfect for two, with an unparalleled view.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Il Diaccino is an enchanting small villa, perfect for two, with a magnificent view. It overlooks an extraordinary landsc ...
From $284 per night (USD)
VRBO
From $789 per night (USD)
VRBO
Beautiful historic Villa; sleeps max 13. 5 Bedrooms 5 Bathrooms, Private Pool
Bedrooms:
5
Bathrooms:
5
Sleeps:
13
* Beautifully restored Tuscan villa with 12th century origins. For maximum 13 people * Set in 5 acres of park, surrounde ...
From $789 per night (USD)
VRBO
From $257 per night (USD)
VRBO
LA TORRE, AN EAGLE NEST ABOVE THE TUSCANY LANDSCAPE
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Casa La Torre is located in an ancient palace overlooking the small hamlet of Rosennano. Its renovation was completed in ...
From $257 per night (USD)
VRBO
From $579 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 $579 per night (USD)
Expedia
From $243 per night (USD)
VRBO
Casa BD in Gaiole - 150 m² apartment with a view & travel guide - sleeps 8
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Close to cycling, hiking trails, and more, this family-friendly villa brings it all within reach. Church of San Sigis ...
From $243 per night (USD)
VRBO
From $223 per night (USD)
Expedia
Chianti View, Garden for your small Family, Pool & Jacuzzi
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Villa Marioli is a farmhouse complex in the heart of Tuscany: a unique terrace overlooking the Chianti countryside. The ...
From $223 per night (USD)
Expedia
From $222 per night (USD)
VRBO
Romantic with Chianti Panorama, Pool & Jacuzzi
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Villa Marioli is a farmhouse complex in the heart of Tuscany: a unique terrace overlooking the Chianti countryside. The ...
From $222 per night (USD)
VRBO
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Expedia
Chianti for Four with view, Pool & Jacuzzi
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Villa Marioli is a farmhouse complex in the heart of Tuscany: a unique terrace overlooking the Chianti countryside. The ...
Click For Pricing
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 $160 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 $160 per night (USD)
VRBO
From $225 per night (USD)
VRBO
Nest in Chianti with Pool, Jacuzzi and View
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Villa Marioli is a farmhouse complex in the heart of Tuscany: a unique terrace overlooking the Chianti countryside. The ...
From $225 per night (USD)
VRBO
From $252 per night (USD)
Expedia
Under the Chianti Sun. View, Pool & Jacuzzi for your Family
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Villa Marioli is a farmhouse complex in the heart of Tuscany: a unique terrace overlooking the Chianti countryside. The ...
From $252 per night (USD)
Expedia
From $222 per night (USD)
VRBO
Typical, Charming with Chianti View, Pool & Jacuzzi
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Villa Marioli is a farmhouse complex in the heart of Tuscany: a unique terrace overlooking the Chianti countryside. The ...
From $222 per night (USD)
VRBO
From $330 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 $330 per night (USD)
VRBO
From $685 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 $685 per night (USD)
VRBO
From $234 per night (USD)
VRBO
Il Nibbio In Gaiole in Chianti, Tuscany
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Property for exclusive use Holiday home made from a ancient medieval fortress in stone, 140 sq. m., holding up to 5 pers ...
From $234 per night (USD)
VRBO
From $187 per night (USD)
VRBO
Townhouse Casa Gorizia - Authentic Tuscany
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Set in a medieval hamlet amongst the Tuscan Hills, Montebenichi feels a world away and yet is close to some of Tuscany's ...
From $187 per night (USD)
VRBO
From $281 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 $281 per night (USD)
VRBO
$Apartment \Oak\ - the Chianti as you've always dreamed of$
From $139 per night (USD)
VRBO
Apartment \"Oak\" - the Chianti as you've always dreamed of
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
ur little gem of 55 sqm with private entrance and outdoor area for breakfasts and dinners to 'open and pleasant evening ...
From $139 per night (USD)
VRBO
From $1606 per night (USD)
Expedia
Villa Siena 10, Emma Villas
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
The price includes: - Utilities water - gas for kitchen use and hot water - wireless internet connection - weekly linen, ...
From $1606 per night (USD)
Expedia
From $132 per night (USD)
VRBO
In the heart of Chianti: view over the valley, relaxation & art, wine & sun
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Val delle Corti is a small winery in Radda in Chianti. The ‘Capanna’, an old, tastefully restored natural stone hay bar ...
From $132 per night (USD)
VRBO
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Expedia
Appartamento per 5 nel Chianti Classico con Piscina Vicino a Siena
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Close to ecotours, birdwatching, and more, this pet-friendly apartment brings it all within reach. Jump into your car ...
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Expedia
Click For Pricing
VRBO
Appartamento per 4 nel Chianti Classico con Piscina Vicino a Siena
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
A short distance from ecotours, birdwatching, and more, this pet-friendly apartment lets you experience it all. Jump ...
Click For Pricing
VRBO
From $1197 per night (USD)
VRBO
Villa Giusterna - Ancient villa in the Tuscan hills
Bedrooms:
9
Bathrooms:
8
Sleeps:
16
Located in a rural area, this welcoming villa lets you experience it all in Bucine. With convenient onsite parking, y ...
From $1197 per night (USD)
VRBO
From $595 per night (USD)
VRBO
JUNIPER APARTMENT IN THE TUSCAN HILLS
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Located in a rural area, this welcoming apartment lets you experience it all in Bucine. With convenient onsite parkin ...
From $595 per night (USD)
VRBO
From $597 per night (USD)
VRBO
OAK APARTMENT IN THE TUSCAN HILLS
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Situated in a rural area, this welcoming apartment brings all of Bucine within your reach. Jump into your car and mak ...
From $597 per night (USD)
VRBO
From $597 per night (USD)
VRBO
JAY APARTMENT IN THE TUSCAN HILLS
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Situated in a rural area, this welcoming apartment brings all of Bucine within your reach. Jump into your car and mak ...
From $597 per night (USD)
VRBO
From $222 per night (USD)
VRBO
Apartment in an idyllic holiday complex in the middle of the winery T6
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Three-room apartment for 6 people: ground floor or first floor, living room with double sofa bed, kitchenette, one doubl ...
From $222 per night (USD)
VRBO
From $417 per night (USD)
VRBO
Traumblick in die Toskana vom Ferienhaus mit Pool auf Hügel zw. Siena u. Florenz
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Close to hiking trails, mountain biking, and more, this family-friendly vacation home brings it all within reach. Jum ...
From $417 per night (USD)
VRBO
From $525 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 $525 per night (USD)
Expedia
From $525 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 $525 per night (USD)
VRBO
From $2620 per night (USD)
VRBO
Luxury Villa in Radda Chianti,heatable Pool,Aircon,SPA room,gym room,sleep 10
Bedrooms:
7
Bathrooms:
6
Sleeps:
12
This charming wine estate with panoramic views is located on the hills at just 1.5 km from Radda in Chianti, a lovely me ...
From $2620 per night (USD)
VRBO
From $166 per night (USD)
VRBO
Traumblick in die Toskana vom Landhaus mit Pool auf Hügel zw. Siena u. Florenz
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Located in a rural area, this welcoming cottage lets you experience it all in Castelnuovo Berardenga. Jump into your ...
From $166 per night (USD)
VRBO
From $4211 per night (USD)
Expedia
Private Villa with hot tub, sauna, private pool, A/C, WIFI, TV, patio, close to Greve In Chianti
Bedrooms:
7
Bathrooms:
5
Sleeps:
11
Villa Castiglioni is a lovely holiday home with WiFi internet, air conditioning and private pool. The property can acc ...
From $4211 per night (USD)
Expedia
Click For Pricing
VRBO
House Ciaccheri Holidays in Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The house is located in the heart of the Chianti Classico area within the town of Gaiole in Chianti, the town square is ...
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VRBO
From $867 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 $867 per night (USD)
Expedia
From $400 per night (USD)
VRBO
Beautiful home in Moncioni
Bedrooms:
6
Bathrooms:
5
Sleeps:
12
In a unique panoramic position, between the Arno Valley and Chianti, this villa is situated on its own hill, surrounded ...
From $400 per night (USD)
VRBO
From $270 per night (USD)
Expedia
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 $270 per night (USD)
Expedia
From $268 per night (USD)
VRBO
BELLAVISTA San Piero
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Bellavista is a beautiful tuscan house, divided into 8 apartments, located in the domaine of Castello di Bossi, in the s ...
From $268 per night (USD)
VRBO
From $367 per night (USD)
VRBO
Eremo Chiostro In Gaiole in Chianti, Tuscany
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
The charm of the ancient Eremo nel Chianti will capture your soul all the while you stay there and it will cling to your ...
From $367 per night (USD)
VRBO
From $238 per night (USD)
VRBO
Eremo Fattore In Gaiole in Chianti, Tuscany
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
The charm of the ancient Eremo nel Chianti will capture your soul all the while you stay there and it will cling to your ...
From $238 per night (USD)
VRBO
From $399 per night (USD)
VRBO
Eremo Magnolia In Gaiole in Chianti, Tuscany
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
The charm of the ancient Eremo nel Chianti will capture your soul all the while you stay there and it will cling to your ...
From $399 per night (USD)
VRBO
From $399 per night (USD)
VRBO
Eremo Granaio In Gaiole in Chianti, Tuscany
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
The charm of the ancient Eremo nel Chianti will capture your soul all the while you stay there and it will cling to your ...
From $399 per night (USD)
VRBO
From $1240 per night (USD)
VRBO
Villa Eracle: A bright and elegant three-story villa surrounded by vineyards and olive groves.
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Villa Eracle is a bright and elegant three-story villa surrounded by vineyards and olive groves. It sleeps eight people. ...
From $1240 per night (USD)
VRBO
From $3334 per night (USD)
VRBO
Radda in Chianti 5 bedroom luxury villa rental, heated pool, wine estate
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
Perched atop the undulating hills of Radda in Chianti, Villa Pancho is a picturesque, panoramic home with views of olive ...
From $3334 per night (USD)
VRBO
From $136 per night (USD)
Expedia
Studio in Chianti Villa in heart of Tuscany, super-large pool, 14 ha property
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Restored from the ruin of a typical Tuscan farmhouse, Podere Scopeto sits high on a hilltop at 600 meter above sea-level ...
From $136 per night (USD)
Expedia
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VRBO
Villa rental in Pianella near Siena - Pianella vacation villa
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
In the heart of the Chianti Classico region, this hillside estate offers a tranquil and classic Tuscan experience. Par ...
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VRBO
From $119 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 $119 per night (USD)
Expedia
From $105 per night (USD)
VRBO
Taglialegna apartment in Montefiorile
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Taglialegna is a spacious, comfortable and well-equipped cottage. It is ideal for a couple who wants to spend time toget ...
From $105 per night (USD)
VRBO
From $91 per night (USD)
VRBO
Apartment in an idyllic holiday complex in the middle of the B2 winery
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Two-room apartment for 2 people: ground floor or first floor, living room, kitchenette, double room, bathroom with showe ...
From $91 per night (USD)
VRBO
From $119 per night (USD)
VRBO
Spacious cottage in the heart of Chianti with wonderful views
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Vinaio is a spacious cottage located on the ground floor inside the pretty village of Montefiorile. It is ideal as a bas ...
From $119 per night (USD)
VRBO
From $128 per night (USD)
VRBO
Comfortable cottage in the heart of Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Reaper cottage is a private home with all modern comforts; it is located on the side of the large central house of B ...
From $128 per night (USD)
VRBO
From $262 per night (USD)
VRBO
Villa Sofia Jacuzzi® Spa
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Villa is on two floors with independent entrance, exclusive Wellness Center with Jacuzzi® for 3 people, sauna and ch ...
From $262 per night (USD)
VRBO
From $250 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 $250 per night (USD)
Expedia
From $149 per night (USD)
VRBO
Casa Allegra, 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 $149 per night (USD)
VRBO
From $255 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 $255 per night (USD)
Expedia
From $135 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 $135 per night (USD)
VRBO
From $241 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 $241 per night (USD)
Expedia
From $337 per night (USD)
VRBO
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 $337 per night (USD)
VRBO
From $214 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 $214 per night (USD)
Expedia
From $164 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 $164 per night (USD)
VRBO
From $262 per night (USD)
Expedia
Terrazza Alta, Borgo Gaiole, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
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 $262 per night (USD)
Expedia
From $406 per night (USD)
VRBO
La Casa di Radda, Radda in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
A sleek and charming bungalow in the town of Radda in Chianti, La Casa di Radda is a lovely getaway for 5 people. It’s a ...
From $406 per night (USD)
VRBO
From $525 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 $525 per night (USD)
Expedia
From $1230 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 $1230 per night (USD)
VRBO
From $303 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 $303 per night (USD)
Expedia
From $194 per night (USD)
VRBO
I Cipressi, Vignale, Castelnuovo Berardenga, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Set on a Chianti hillside, Vignale is a beautifully restored collection of original farm buildings, thoughtfully transfo ...
From $194 per night (USD)
VRBO
From $291 per night (USD)
Expedia
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 $291 per night (USD)
Expedia

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Results: 381 Rentals