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 $350 per night (USD)
VRBO
Lo Scoiattolo n° 10 by Interhome
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Carefully renovated "Podere La Massa" consists of a detached house and 8 apartments. It is surrounded by olive groves, f ...
From $350 per night (USD)
VRBO
From $166 per night (USD)
Expedia
Il Ghiro n°8 by Interhome
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Carefully renovated "Podere La Massa" consists of a detached house and 8 apartments. It is surrounded by olive groves, f ...
From $166 per night (USD)
Expedia
From $493 per night (USD)
VRBO
Il Gufo n°1 by Interhome
Bedrooms:
4
Bathrooms:
7
Sleeps:
13
Carefully renovated "Podere La Massa" consists of a detached house and 8 apartments. It is surrounded by olive groves, f ...
From $493 per night (USD)
VRBO
From $79 per night (USD)
Expedia
Cerbiatto n°5A by Interhome
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Carefully renovated "Podere La Massa" consists of a detached house and 8 apartments. It is surrounded by olive groves, f ...
From $79 per night (USD)
Expedia
From $95 per night (USD)
VRBO
Pulcino n°3 by Interhome
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Carefully renovated "Podere La Massa" consists of a detached house and 8 apartments. It is surrounded by olive groves, f ...
From $95 per night (USD)
VRBO
From $140 per night (USD)
Expedia
Il Pettirosso n°7 by Interhome
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Carefully renovated "Podere La Massa" consists of a detached house and 8 apartments. It is surrounded by olive groves, f ...
From $140 per night (USD)
Expedia
Click For Pricing
VRBO
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 ...
Click For Pricing
VRBO
From $179 per night (USD)
Expedia
Dionisia, Capannole, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Capannole is a small, idyllic hamlet in the heart of the Chianti Classico, set within one of Tuscany’s most beautiful la ...
From $179 per night (USD)
Expedia
From $114 per night (USD)
VRBO
Cosy apartment in villa with A/C, WIFI, pool, TV, terrace, pets allowed and panoramic view
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Property Summary Nestled in the picturesque hamlet of Rietine, just 4 km from the centre of Gaiole in Chianti, Italy, M ...
From $114 per night (USD)
VRBO
From $114 per night (USD)
Expedia
Beautiful apartment in villa with WIFI, A/C, pool, TV, terrace, pets allowed and panoramic view
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Property Summary Nestled in the picturesque hamlet of Rietine, just 4 km from the centre of Gaiole in Chianti, Italy, M ...
From $114 per night (USD)
Expedia
From $333 per night (USD)
VRBO
Portion Farmhouse nestled in the heart of Chianti with private pool,
Bedrooms:
1
Bathrooms:
4
Sleeps:
9
Close to ecotours, mountain biking, and more, this family-friendly vacation home brings it all within reach. Gaiole i ...
From $333 per night (USD)
VRBO
From $786 per night (USD)
Expedia
Villa Radda by MMega
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
External Description Villa Radda is located in the countryside of Gaiole in Chianti. The property is accessed through ...
From $786 per night (USD)
Expedia
From $4780 per night (USD)
VRBO
Villa Gaiole - Seven Bedroom Villa, Sleeps 14
Bedrooms:
8
Bathrooms:
7
Sleeps:
14
Offering panoramic vistas over Chianti’s rolling hills and woodlands, Villa Gaiole is a serene Tuscan retreat that sleep ...
From $4780 per night (USD)
VRBO
From $166 per night (USD)
Expedia
Coccinella n°6 by Interhome
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Carefully renovated "Podere La Massa" consists of a detached house and 8 apartments. It is surrounded by olive groves, f ...
From $166 per night (USD)
Expedia
From $1734 per night (USD)
VRBO
Villa Chianti, elegant villa in Gaiole in Chianti
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Situated in a rural area, this welcoming villa brings all of Gaiole in Chianti within your reach. Jump into your car ...
From $1734 per night (USD)
VRBO
$\Villa Erbolino\ with Private Garden, Outdoor Stone Tub, and Wi-Fi$
From $2761 per night (USD)
Expedia
\"Villa Erbolino\" with Private Garden, Outdoor Stone Tub, and Wi-Fi
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Villa Erbolino is located in Gaiole in Chianti and is the perfect choice for a relaxing getaway. This two-story property ...
From $2761 per night (USD)
Expedia
From $214 per night (USD)
VRBO
Lavanda, Montebuoni, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Montebuoni is a charming hamlet in the heart of Tuscany that captures the feel of a traditional Chianti village. Once a ...
From $214 per night (USD)
VRBO
From $3117 per night (USD)
Expedia
VILLA CHIANTIVERTINE
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
This historical ‘casa colonica’ with a fabulous 360° view has been recently restored and transformed in a luxury villa f ...
From $3117 per night (USD)
Expedia
From $1360 per night (USD)
VRBO
'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
2 parking spaces are available on the property. Small or medium-sized pets are allowed for an extra fee. Guests bringing ...
From $1360 per night (USD)
VRBO
From $7433 per night (USD)
Expedia
CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28
Bedrooms:
14
Bathrooms:
14
Sleeps:
28
Wonderful Resort located in the heart of Chianti Classico, only 30 minutes from Siena, the nearest large city and 15 mi ...
From $7433 per night (USD)
Expedia
From $1452 per night (USD)
VRBO
Villa With Private Pool In The Heart Of The Chianti Region
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
San Piero Terre is a south-facing stone farmhouse that has been a family holiday villa for two generations. Decorated to ...
From $1452 per night (USD)
VRBO
From $1353 per night (USD)
Expedia
Beautiful villa for 16 guests with private pool, A/C, WIFI, TV, patio and panoramic view
Bedrooms:
9
Bathrooms:
7
Sleeps:
16
La Maccinaia 14 is a lovely stone building (650 sq m) with WiFi internet, air conditioning and private pool. The proper ...
From $1353 per night (USD)
Expedia
From $998 per night (USD)
VRBO
Villa in San Vincenti with 5 bedrooms sleeps 12
Bedrooms:
7
Bathrooms:
5
Sleeps:
12
La Maccinaia is a beautiful and comfortable villa with heated salt-water system swimming pool, located in a very quiet ...
From $998 per night (USD)
VRBO
Click For Pricing
Expedia
Private and Peaceful Medieval Villa in the heart of Chianti
Bedrooms:
7
Bathrooms:
7
Sleeps:
18
Tenuta di San Giusto; a very peaceful and characteristic villa dated from the year 1000. Situated in the municipality of ...
Click For Pricing
Expedia
From $1636 per night (USD)
VRBO
Beautiful villa for 22 guests with WIFI, A/C, private pool, TV and panoramic view
Bedrooms:
10
Bathrooms:
11
Sleeps:
22
Borgo San Vincenti is located in San Vincenti, Italy and only 39 km (24 mi) from Siena in the tourist area "Siena And Su ...
From $1636 per night (USD)
VRBO
From $218 per night (USD)
Expedia
Hut with a view in the heart of the Chianti area with swimming pool and Jacuzzzi
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Delicious ex finely restored stable, inserted in an ancient farmhouse. The property is completely independent, private p ...
From $218 per night (USD)
Expedia
From $630 per night (USD)
VRBO
Lo Spicchio, Radda in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Lo Spicchio is a picture-perfect Chianti holiday home. Surrounded by olive groves and vineyards, it sits in a postcard l ...
From $630 per night (USD)
VRBO
From $464 per night (USD)
VRBO
Sun-kissed holiday home
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Holiday in the heart of Chianti Classico in Gaiole in Chianti. Authentic and charming holiday home surrounded by a garde ...
From $464 per night (USD)
VRBO
From $438 per night (USD)
VRBO
Villa Oliveta, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Villa Oliveta is a beautiful holiday home set on a hillside in the heart of the Chianti Classico region. It offers far-r ...
From $438 per night (USD)
VRBO
From $513 per night (USD)
Expedia
Villa Solatio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Villa Solatio is a former farmhouse that has been restored with great care and respect for its history. Today, this char ...
From $513 per night (USD)
Expedia
From $859 per night (USD)
VRBO
Casa Perano, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Casa Perano is a lovingly restored natural stone villa perched on a hilltop, with far-reaching views across the iconic C ...
From $859 per night (USD)
VRBO
From $193 per night (USD)
Expedia
Capanna di Citerna, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Capanna di Citerna is a beautifully restored holiday home in an exceptional location, surrounded by the vineyards of the ...
From $193 per night (USD)
Expedia
From $376 per night (USD)
VRBO
Villa Montemarcoli, a haven of peace and love in Gaiole in Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
A short distance from cycling, hiking trails, and more, this welcoming villa lets you experience it all. Jump into yo ...
From $376 per night (USD)
VRBO
From $1422 per night (USD)
Expedia
Pet friendly home in Gaiole in Chianti
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Beautiful and spacious Tuscan villa with swimming pool. Enjoy an unforgettable and relaxing vacation in this beautifu ...
From $1422 per night (USD)
Expedia
From $1029 per night (USD)
VRBO
Casale San Vincenti, Gaiole in Chianti, Siena and Chianti
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
Casale San Vincenti is a stylishly restored natural stone villa nestled on a hill in a small hamlet, offering sweeping ...
From $1029 per night (USD)
VRBO
From $706 per night (USD)
Expedia
Chianti Villa with pool far reaching views towards the sunset in woods&vineyards
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
Restored from the ruin of a typical Tuscan farmhouse this Podere sits high on a hilltop at 600 meter above sea-level (wh ...
From $706 per night (USD)
Expedia
From $1460 per night (USD)
VRBO
San Marcellino, Gaiole in Chianti, Siena and Chianti
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Immerse yourself in the world of wine at this villa in the grounds of Rocca di Montegrossi, one of the finest wineries i ...
From $1460 per night (USD)
VRBO
From $767 per night (USD)
Expedia
Casa Boccaccio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Casa Boccaccio is a spacious, design-led apartment nestled in a small historic hamlet within a former medieval castle co ...
From $767 per night (USD)
Expedia
From $15145 per night (USD)
VRBO
Villa Vigneto Estate
Bedrooms:
22
Bathrooms:
27
Sleeps:
60
Featured as the villa in Gino's Italian Escape, ITV Series aired in November 2019. Read more here Burrowed in the hea ...
From $15145 per night (USD)
VRBO
From $2452 per night (USD)
Expedia
Borgo Merlo - Nine Bedroom Villa, Sleeps 22
Bedrooms:
9
Bathrooms:
9
Sleeps:
22
You will find Borgo Merlo in the verdant Chianti hills in the heart of Tuscany. The accommodation here comprises three n ...
From $2452 per night (USD)
Expedia
From $160 per night (USD)
VRBO
La Luna, Montefiorile, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Montefiorile is a peaceful hillside hamlet in the heart of the Chianti Classico region, set within one of Tuscany’s most ...
From $160 per night (USD)
VRBO
From $1496 per night (USD)
Expedia
Casa all'Erta, villa with private pool
Bedrooms:
7
Bathrooms:
7
Sleeps:
14
Close to horse riding, this family-friendly villa brings it all within reach. With convenient onsite parking, you'll ...
From $1496 per night (USD)
Expedia
From $1994 per night (USD)
VRBO
Borgo San Polino, villa with private pool
Bedrooms:
9
Bathrooms:
9
Sleeps:
22
Located in Gaiole in Chianti, this welcoming villa brings it all within your reach. Jump into your car and make short ...
From $1994 per night (USD)
VRBO
From $4840 per night (USD)
VRBO
Luxury Tuscany Hillside Villa With Heated Pool Close to Chianti Towns and Siena
Bedrooms:
7
Bathrooms:
7
Sleeps:
14
Perfectly positioned on a hill with 360-degree views of the verdant Chianti countryside, Le Pratola is the perfect luxur ...
From $4840 per night (USD)
VRBO
From $574 per night (USD)
VRBO
Riecine Capanna 4, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Riecine Capanna 4 is a luxurious holiday home set on the renowned Riecine wine estate, ideal for two couples or a small ...
From $574 per night (USD)
VRBO
From $286 per night (USD)
Expedia
Pastore, Montefiorile, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Montefiorile is a peaceful hillside hamlet in the heart of the Chianti Classico region, set within one of Tuscany’s most ...
From $286 per night (USD)
Expedia
From $514 per night (USD)
VRBO
Apartment 'Reggioli- Appartamento Del Cestaio' with Mountain View, Shared Garden and Balcony
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
We offer you a chance for rural adventure in a wild and isolated setting unparalleled in Tuscany. You are invited to sha ...
From $514 per night (USD)
VRBO
From $372 per night (USD)
Expedia
Apartment 'Reggioli- Appartamento Erborista' with Mountain View, Shared Garden and Wi-Fi
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
We offer you a chance for rural adventure in a wild and isolated setting unparalleled in Tuscany. You are invited to sha ...
From $372 per night (USD)
Expedia
From $401 per night (USD)
VRBO
Apartment 'Reggioli- Appartamento Falegname' with Mountain View, Shared Garden and Balcony
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
We offer you a chance for rural adventure in a wild and isolated setting unparalleled in Tuscany. You are invited to sha ...
From $401 per night (USD)
VRBO
From $226 per night (USD)
Expedia
Campo al Sole, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Campo al Sole is a perfectly private retreat for two, quietly set in the rolling hills of the Chianti Classico. This tra ...
From $226 per night (USD)
Expedia
From $6761 per night (USD)
VRBO
Casa Faraona, villa with private pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Imagine the perfect Chianti villa - a secluded house with a private pool and fabulous 180-degree views. That's just what ...
From $6761 per night (USD)
VRBO
From $131 per night (USD)
Expedia
Holiday Home 'L'arco Della Fonte' with Private Terrace, Wi-Fi and Air Conditioning
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The holiday home L'arco della Fonte is located in Gaiole in Chianti and is the ideal accommodation for a relaxing getawa ...
From $131 per night (USD)
Expedia
From $93 per night (USD)
VRBO
Casa Vecchia, Montebuoni, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Montebuoni is a charming hamlet in the heart of Tuscany that captures the feel of a traditional Chianti village. Once a ...
From $93 per night (USD)
VRBO
From $2767 per night (USD)
Expedia
Villa Biancofiore: A characteristic and welcoming three-story ancient tuscan country house situated in the heart of the Tuscan countryside, with Free WI-FI.
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Villa Biancofiore is a characteristic and welcoming three-story ancient tuscan country house situated in the heart of th ...
From $2767 per night (USD)
Expedia
From $427 per night (USD)
VRBO
Dependance with private garden and swimming pool in Chianti Classico area.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Splendid annex completely renovated and independent within the La Corte del Chianti structure. The annex has a beautiful ...
From $427 per night (USD)
VRBO
From $306 per night (USD)
Expedia
'La Casa Di Emma' Apartment with Wi-Fi and Air Conditioning
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
La Casa di Emma is a welcoming apartment located in the heart of Chianti, in an authentic Tuscan village surrounded by v ...
From $306 per night (USD)
Expedia
From $152 per night (USD)
VRBO
Caravaggio, Galenda, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Galenda is a small, charming hamlet set on a ridge in the heart of the Chianti Classico, offering beautiful views over o ...
From $152 per night (USD)
VRBO
From $361 per night (USD)
Expedia
Villa Vinsantaia, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
2
Villa Vinsantaia, located on the edge of the charming village of San Sano, offers an authentic and tranquil escape in th ...
From $361 per night (USD)
Expedia
From $125 per night (USD)
VRBO
Chiara House In Galenda, Pool Wifi
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Portion of a farmhouse with swimming pool (approx. 72 m2) for shared use with 3 other units in Galenda, in the heart of ...
From $125 per night (USD)
VRBO
From $135 per night (USD)
Expedia
Stunning villa with pool, WIFI, TV, terrace and panoramic view, close to Greve In Chianti
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Chiara House In Galenda, Chianti, Pool And Nature is a beautiful holiday home (90 sq m) with WiFi internet. The propert ...
From $135 per night (USD)
Expedia
From $439 per night (USD)
VRBO
Casanova di Bricciano, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Set on the grounds of a family-run organic winery, this stone-built villa offers a harmonious blend of Tuscan charm and ...
From $439 per night (USD)
VRBO
From $344 per night (USD)
Expedia
Casa di Amici, San Sano, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
San Sano is a charming hamlet located within the Chianti village of the same name, set in the heart of the Chianti Class ...
From $344 per night (USD)
Expedia
From $169 per night (USD)
VRBO
Il Cinghiale by Interhome
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Montefienali 15 km from Gaiole in Chianti: Historical holiday village "Montefienali", 600 m a.s.l., from the 13rd centur ...
From $169 per night (USD)
VRBO
From $104 per night (USD)
Expedia
Montechioccioli by Interhome
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Cosy, rustic 3-family house "Montechioccioli", surrounded by vineyards. 3 apartments in the property. In the hamlet Riet ...
From $104 per night (USD)
Expedia
From $1331 per night (USD)
VRBO
Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Guests of this lovely stone villa in the heart of Chianti, made even more beautiful by climbing roses and plenty of plan ...
From $1331 per night (USD)
VRBO
From $187 per night (USD)
Expedia
Lovely apartment for 6 guests with pool, A/C, WIFI, TV, patio, pets allowed and panoramic view
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Property Summary Nestled in the rolling hills of Tuscany, Italy, the historic hamlet of Montefienali offers an extraord ...
From $187 per night (USD)
Expedia
From $390 per night (USD)
VRBO
Casa Luce, San Donato in Perano, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
San Donato in Perano is set within the historic landscape of the Chianti Classico and has origins dating back to the med ...
From $390 per night (USD)
VRBO
From $1087 per night (USD)
Expedia
Exclusive private villa with private pool
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
Agrivilla Montelucci (from the Latin “Mons Luci”, sacred forest for the ancient Romans) is a wonderful stone farmhouse, ...
From $1087 per night (USD)
Expedia
From $435 per night (USD)
VRBO
Livio House, a garden with a view
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Located in Gaiole in Chianti, this welcoming apartment brings it all within your reach. Jump into your car and make s ...
From $435 per night (USD)
VRBO
From $341 per night (USD)
Expedia
Casa dei Mandorli, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Perched high in the scenic Ama hills, Casa dei Mandorli offers a peaceful retreat for a couple, with sweeping views over ...
From $341 per night (USD)
Expedia
From $762 per night (USD)
VRBO
Podere Terrena 10, Gaiole in Chianti, Siena and Chianti
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Podere Terrena 10 is a charming holiday home on a small agriturismo in a peaceful hillside setting, surrounded by forest ...
From $762 per night (USD)
VRBO
From $192 per night (USD)
Expedia
Casuccia di Ama, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Casuccia di Ama is a charming holiday home located in the heart of Chianti, perfect for two guests. Combining traditiona ...
From $192 per night (USD)
Expedia
From $756 per night (USD)
VRBO
Casa Faraona, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Casa Faraona is located in the heart of the Chianti Classico and is a spacious holiday home, ideal for a relaxing holida ...
From $756 per night (USD)
VRBO
From $1394 per night (USD)
Expedia
Casolare di Rietine, Gaiole in Chianti, Siena and Chianti
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Casolare di Rietine is a beautifully furnished Chianti holiday home with sweeping views over vineyards, olive groves and ...
From $1394 per night (USD)
Expedia
From $1008 per night (USD)
VRBO
Dimora del Chianti, stunning Tuscan stone villa surrounded by vineyards in the heart of Chianti
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Set among rolling vineyards and olive groves, this restored stone villa offers complete privacy in one of the most iconi ...
From $1008 per night (USD)
VRBO
From $190 per night (USD)
Expedia
Tuscan Escape with pool and vineyard view - Gaiole in Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Located in Gaiole in Chianti, this welcoming vacation home lets you experience it all. Jump into your car and make sh ...
From $190 per night (USD)
Expedia
From $167 per night (USD)
VRBO
Beautiful apartment in villa for 2 guests with WIFI, A/C, pool, TV and pets allowed
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Property Summary Nestled at 460 metres above sea level in the heart of the Tuscan countryside, Resort "San Regolo" is a ...
From $167 per night (USD)
VRBO
From $236 per night (USD)
Expedia
Cosy apartment in villa for 4 guests with pool, A/C, WIFI, TV and pets allowed
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Property Summary Nestled at 460 metres above sea level in the heart of the Tuscan countryside, Resort "San Regolo" is a ...
From $236 per night (USD)
Expedia
From $151 per night (USD)
VRBO
San Regolo by Interhome
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Resort "San Regolo", 460 m a.s.l.. 6 houses in the resort. In the hamlet San Regolo 10 km from the centre of Gaiole in C ...
From $151 per night (USD)
VRBO
From $213 per night (USD)
Expedia
San Regolo by Interhome
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Resort "San Regolo", 460 m a.s.l.. 6 houses in the resort. In the hamlet San Regolo 10 km from the centre of Gaiole in C ...
From $213 per night (USD)
Expedia
From $993 per night (USD)
VRBO
Tenuta Altaluce, Gaiole in Chianti, Siena and Chianti
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Tenuta Altaluce is a beautifully restored Tuscan farmhouse estate, offering complete privacy and tranquillity in the hea ...
From $993 per night (USD)
VRBO
From $113 per night (USD)
Expedia
GuestHost - Comfy Apt near the Castle of Brolio
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Located in Gaiole in Chianti, this welcoming apartment lets you experience it all. Jump into your car and make short ...
From $113 per night (USD)
Expedia
From $4779 per night (USD)
VRBO
Villa Gallonero: A spacious age-old farm house surrounded by the greenery, with Free WI-FI.
Bedrooms:
12
Bathrooms:
15
Sleeps:
30
Villa Gallonero is a spacious age-old farm house surrounded by the greenery. It sleeps 30 people. From Villa Gallonero y ...
From $4779 per night (USD)
VRBO
Click For Pricing
Expedia
Il Fienile, Montefienali, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Montefienali is a small, atmospheric hamlet tucked into the rolling hills of Chianti, offering a peaceful retreat surrou ...
Click For Pricing
Expedia
From $190 per night (USD)
VRBO
GuestHost - Pool Apartment with Garden
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Splendid 70 sqm apartment in Monti, a hamlet of Gaiole in Chianti, for 2 people, located on the ground floor of a 3-stor ...
From $190 per night (USD)
VRBO
From $642 per night (USD)
Expedia
Villa la Pecine by MMega
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
External Description Villa la Pecine, an ancient mill on the Pecine stream from which it takes its name, stands in a su ...
From $642 per night (USD)
Expedia
From $157 per night (USD)
VRBO
Cosy apartment for 2 people with WIFI and TV
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Property Summary Nestled in the heart of Gaiole in Chianti, one of Tuscany's most charming medieval villages, this eleg ...
From $157 per night (USD)
VRBO
Click For Pricing
Expedia
Le Granchiaie, Gaiole in Chianti, Siena and Chianti
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Le Granchiaie is a spacious and tastefully decorated apartment, perfect for a relaxing holiday with family or friends. S ...
Click For Pricing
Expedia
From $380 per night (USD)
VRBO
Villa Altho, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Nestled in an idyllic hamlet, Villa Altho is a holiday home offering the perfect setting for relaxing holidays in Tuscan ...
From $380 per night (USD)
VRBO
From $383 per night (USD)
Expedia
La Fornace di Tremoleto - Villa with exclusive pool in Chianti
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
La Fornace di Tremoleto is a historic residence that was once the ancient furnace of the famous Castello di Brolio. The ...
From $383 per night (USD)
Expedia
From $366 per night (USD)
VRBO
Villa Il Masseto, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Villa Il Masseto is a traditional Tuscan villa, peacefully located on the edge of Gaiole in Chianti, bordered by forest ...
From $366 per night (USD)
VRBO
From $251 per night (USD)
VRBO
Cozy apartment with terrace and pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Set in the beautiful Tuscan countryside in the heart of the famous wine district of Chianti Classico, you find this newl ...
From $251 per night (USD)
VRBO
From $882 per night (USD)
VRBO
Villa Liberty in The Centre - No Ztl
Bedrooms:
6
Bathrooms:
9
Sleeps:
13
Experience Luxury and Elegance in this Liberty Style Villa near Siena's Historic Center! Step into a world of sophistica ...
From $882 per night (USD)
VRBO
From $306 per night (USD)
Expedia
Elegant modern apartment in the heart of Chianti, ideal for exclusive relaxation
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Located in Gaiole in Chianti, this welcoming apartment brings it all within your reach. Thanks to the convenient onsi ...
From $306 per night (USD)
Expedia
From $277 per night (USD)
VRBO
Casa Barbara Cozy house in hamlet of 1600s
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Located in Gaiole in Chianti, this welcoming apartment lets you experience it all. With convenient onsite parking, yo ...
From $277 per night (USD)
VRBO
From $241 per night (USD)
Expedia
Panorama House, conubbio between panorama and peace
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Located in Gaiole in Chianti, this 1-bedroom, 1-bathroom apartment lets you experience it all. Fans of nature and the ...
From $241 per night (USD)
Expedia
From $236 per night (USD)
VRBO
Montefienali La Loggia House Relaxation in a Medieval Chianti Village 3 Terraces
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
🏡 Your Exclusive Retreat in Chianti: "La Loggia" in Montefienali Escape the Routine: "La Loggia", Your Home in the Med ...
From $236 per night (USD)
VRBO
From $142 per night (USD)
Expedia
Gaiole Apartament by Interhome
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
2-family house. In the centre of Gaiole in Chianti 10 km from the centre of Radda in Chianti, 22 km from the centre of C ...
From $142 per night (USD)
Expedia
From $257 per night (USD)
VRBO
Charming 160 square meters apartment, perfect for six people, located on the first floor of a recently renovated medieval convent (no elevator).The property is located in Monti, a hamlet of Gaiole in Chianti: the area is extremely quiet and surrounded by
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
GuestHost - Chianti Charming Apartment with Pool
From $257 per night (USD)
VRBO
From $466 per night (USD)
Expedia
Adine 63, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Adine 63 is a spacious and welcoming holiday villa in the Chianti Classico area, set in a peaceful rural location surrou ...
From $466 per night (USD)
Expedia

Search Your Destination Now!

Gaiole in Chianti Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 214 Rentals