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

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From $760 per night (USD)
VRBO
Case Domine, Radda in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Case Domine is a lovingly restored Tuscan holiday home nestled among the vineyards of the Chianti Classico. The buildin ...
From $760 per night (USD)
VRBO
From $1686 per night (USD)
Expedia
Beautiful villa for 22 guests with WIFI, A/C, private pool, TV and panoramic view
Bedrooms:
10
Bathrooms:
11
Sleeps:
22
Conveniently located in San Vincenti, Italy in the tourist area "Siena And Surroundings" and only 39 km (24 mi) from Sie ...
From $1686 per night (USD)
Expedia
From $182 per night (USD)
VRBO
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 $182 per night (USD)
VRBO
From $771 per night (USD)
Expedia
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 $771 per night (USD)
Expedia
From $282 per night (USD)
VRBO
A paradise of cypress and olive trees
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Close to cycling, hiking trails, and more, this smoke-free vacation home brings it all within reach. Jump into your c ...
From $282 per night (USD)
VRBO
From $437 per night (USD)
Expedia
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 $437 per night (USD)
Expedia
From $167 per night (USD)
VRBO
Apartment in Radda with Garden
Bedrooms:
4
Bathrooms:
2
Sleeps:
6
This 2-bedroom farmhouse in Radda in Chianti is ideal for a small family with kids. Located in Tuscany, Italy, it can ho ...
From $167 per night (USD)
VRBO
From $1104 per night (USD)
Expedia
BEAUTIFUL VILLA with private Pool in the heart of Chianti
Bedrooms:
6
Bathrooms:
7
Sleeps:
14
Located in Castelnuovo Berardenga, this welcoming villa brings it all within your reach. With convenient onsite parki ...
From $1104 per night (USD)
Expedia
From $628 per night (USD)
VRBO
Villa Fauno F: A welcoming cottage located in a small hamlet at the foot of a castle, with Free WI-FI.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Villa Fauno F is a welcoming cottage located in a small hamlet at the foot of a castle. It sleeps four people. From Vill ...
From $628 per night (USD)
VRBO
From $5354 per night (USD)
VRBO
Chianti villa rental
Bedrooms:
6
Bathrooms:
5
Sleeps:
11
Summary: Villa Castiglioni is a stunning Chianti villa rental. It is situated in the Chianti region in Tuscany, an area ...
From $5354 per night (USD)
VRBO
From $443 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 $443 per night (USD)
VRBO
From $902 per night (USD)
Expedia
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 $902 per night (USD)
Expedia
From $218 per night (USD)
VRBO
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 $218 per night (USD)
VRBO
From $353 per night (USD)
Expedia
Villa Montemarcoli, a haven of peace and love in Gaiole in Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Close to cycling, hiking trails, and more, this welcoming villa brings it all within reach. Jump into your car and ma ...
From $353 per night (USD)
Expedia
From $580 per night (USD)
VRBO
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 $580 per night (USD)
VRBO
From $436 per night (USD)
Expedia
Cielo di Radda, Radda in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Cielo di Radda is a stylish villa in the heart of the Chianti Classico, just a few minutes’ walk from the charming town ...
From $436 per night (USD)
Expedia
From $1047 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 $1047 per night (USD)
VRBO
From $134 per night (USD)
Expedia
Chiantishire Lovely Cottage with Garden & Parking!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Located in Castelnuovo Berardenga, this welcoming apartment brings it all within your reach. There's convenient onsit ...
From $134 per night (USD)
Expedia
From $250 per night (USD)
VRBO
Poggio Vitignano Charming Cottage W/Pool & Parking
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Located in Castelnuovo Berardenga, this welcoming apartment brings it all within your reach. With convenient onsite p ...
From $250 per night (USD)
VRBO
From $566 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 $566 per night (USD)
Expedia
From $660 per night (USD)
VRBO
Villa Poggiarello, Castelnuovo Berardenga, Siena and Chianti
Bedrooms:
5
Bathrooms:
7
Sleeps:
10
Villa Poggiarello is a tastefully restored Tuscan farmhouse in a beautiful panoramic setting, surrounded by well-kept ga ...
From $660 per night (USD)
VRBO
From $484 per night (USD)
Expedia
Casa Momi - One Bedroom Villa, Sleeps 2
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This romantic home in the Chianti Classico countryside offers stunning views of rolling hills, forests, and vineyards an ...
From $484 per night (USD)
Expedia
From $2078 per night (USD)
VRBO
Terra di Siena 12, Emma Villas
Bedrooms:
7
Bathrooms:
6
Sleeps:
12
The rate includes: - Utilities: electricity - water - gas for kitchen use and hot water - weekly linen, initial and fina ...
From $2078 per night (USD)
VRBO
From $1602 per night (USD)
Expedia
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 $1602 per night (USD)
Expedia
From $849 per night (USD)
VRBO
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 $849 per night (USD)
VRBO
From $290 per night (USD)
Expedia
La Porcilaia, Pretaccione, Castelnuovo Berardenga, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Once the home of travelling priests 1000 years ago, Pretaccione has been sympathetically restored into individually owne ...
From $290 per night (USD)
Expedia
From $398 per night (USD)
VRBO
Casa Il Caggio, Italien
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Close to cycling, hiking trails, and more, this smoke-free vacation home brings it all within reach. Jump into your c ...
From $398 per night (USD)
VRBO
From $236 per night (USD)
Expedia
Casa Marina, Radda in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Casa Marina is a charming three-storey holiday home located in the historic center of Radda, one of the most beautiful t ...
From $236 per night (USD)
Expedia
From $12464 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 heart ...
From $12464 per night (USD)
VRBO
From $2482 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 $2482 per night (USD)
Expedia
From $164 per night (USD)
VRBO
La Luna, 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 $164 per night (USD)
VRBO
From $1339 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 $1339 per night (USD)
Expedia
From $2023 per night (USD)
VRBO
Borgo San Polino, villa with private pool
Bedrooms:
9
Bathrooms:
9
Sleeps:
20
Located in Gaiole in Chianti, this welcoming villa brings it all within your reach. Jump into your car and make short ...
From $2023 per night (USD)
VRBO
From $203 per night (USD)
Expedia
Holiday Home 'Beretone' with Mountain View, Wi-Fi and Air Conditioning
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Overlooking the mountain, the holiday home "Beretone" in Radda in Chianti impresses guests with its fantastic views. The ...
From $203 per night (USD)
Expedia
From $427 per night (USD)
VRBO
La Serra Vitignano-Stunning Villa W/Swimming Pool!
Bedrooms:
4
Bathrooms:
4
Sleeps:
6
Located in Castelnuovo Berardenga, this welcoming villa brings it all within your reach. You'll easily make the 18-mi ...
From $427 per night (USD)
VRBO
From $527 per night (USD)
Expedia
Mulino nel Chianti 10, Emma Villas
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
The rate includes: - Utilities: electricity, water, gas for kitchen use. - weekly linen, initial and final cleaning - Ze ...
From $527 per night (USD)
Expedia
From $329 per night (USD)
VRBO
Apartment 'Villa Sofia Spa' with Private Whirlpool, Wi-Fi and Air Conditioning
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The holiday apartment "Villa Sofia Spa" is located in Gaiole in Chianti and is perfect for an unforgettable holiday with ...
From $329 per night (USD)
VRBO
From $356 per night (USD)
Expedia
Villa 'Country house Sofia Villas' with Private Pool, Wi-Fi and Air Conditioning
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The villa "Country house Sofia Villas" is located in Gaiole in Chianti and is the ideal accommodation for a relaxing get ...
From $356 per night (USD)
Expedia
From $4521 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 $4521 per night (USD)
VRBO
From $552 per night (USD)
Expedia
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 $552 per night (USD)
Expedia
From $289 per night (USD)
VRBO
Pastore, Montefiorile, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
A Chianti Classico hillside resort, Montefiorile's cottages are nestled on a south bank with magnificent views across ro ...
From $289 per night (USD)
VRBO
From $597 per night (USD)
Expedia
Country House / Farm House in Siena with 4 bedrooms sleeps 9
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
In the heart of Sienese Chianti,surrounded by vineyards is this detached house with private pool, private and fenced out ...
From $597 per night (USD)
Expedia
From $680 per night (USD)
VRBO
Stunning private villa with private pool, WIFI, A/C, TV, patio, pets allowed and panoramic view
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Holiday home Casa Di Luca Country Home - Castelnuovo Berardenga is a nice stone building (160 sq m) that includes air c ...
From $680 per night (USD)
VRBO
From $423 per night (USD)
Expedia
Cosy private home in Medieval Village, with large terrace, pool and garden
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
OVERVIEW The house situated on the outskirts of the medieval hamlet of Montebenichi is the perfect place to relax & exp ...
From $423 per night (USD)
Expedia
From $1426 per night (USD)
VRBO
Family friendly Chianti Villa with private pool.
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Immerse yourself in the authentic Tuscan way of living in this spacious, comfortable and family friendly villa with larg ...
From $1426 per night (USD)
VRBO
From $319 per night (USD)
Expedia
San Sano - San Sano ,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 $319 per night (USD)
Expedia
From $1872 per night (USD)
VRBO
Scandelaia 12, Emma Villas
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
The rate includes: - Utilities: electricity/heating, water, gas for kitchen use - weekly linen, initial and final cleani ...
From $1872 per night (USD)
VRBO
From $203 per night (USD)
Expedia
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 $203 per night (USD)
Expedia
From $257 per night (USD)
VRBO
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 $257 per night (USD)
VRBO
From $161 per night (USD)
Expedia
Apartment 'Reggioli- Appartamento Falegname' with Mountain View, Shared Garden and Balcony
Bedrooms:
1
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 $161 per night (USD)
Expedia
From $224 per night (USD)
VRBO
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 $224 per night (USD)
VRBO
From $683 per night (USD)
Expedia
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 $683 per night (USD)
Expedia
From $114 per night (USD)
VRBO
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 $114 per night (USD)
VRBO
From $136 per night (USD)
Expedia
Casa Vecchia, Montebuoni, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Once a wine and olive oil producing estate, Montebuoni's original stone buildings have been restored into cottages and a ...
From $136 per night (USD)
Expedia
From $1148 per night (USD)
VRBO
Villa Barbischio - Gaiole In Chianti ,Tuscany
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Beautiful independent villa with private pool situated in the heart of the Chianti region, a short distance away from th ...
From $1148 per night (USD)
VRBO
From $3222 per night (USD)
Expedia
Villa in Radda In Chianti with 6 bedrooms sleeps 12
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
Villa Pianoro is a charming, panoramic villa in the rolling hills of Radda in Chianti which looks out over vineyards and ...
From $3222 per night (USD)
Expedia
From $199 per night (USD)
VRBO
Villa Nova - Villa a Sesta ,Tuscany
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Beautiful country house situated in the heart of the renowned Chianti Classico region, approx. 20 km from Siena away. Th ...
From $199 per night (USD)
VRBO
From $1307 per night (USD)
Expedia
Belvilla by OYO Villa Petra Sei
Bedrooms:
6
Bathrooms:
4
Sleeps:
6
This villa with a private swimming pool and tennis court is located in the heart of the Chianti Classico region in Tusca ...
From $1307 per night (USD)
Expedia
From $490 per night (USD)
VRBO
Holiday Home 'Vertine Countryside' with Private Terrace, Wi-Fi and Air Conditioning
Bedrooms:
2
Bathrooms:
5
Sleeps:
9
Located in Gaiole in Chianti, the holiday home Vertine Countryside has everything you need for a relaxing holiday. The 2 ...
From $490 per night (USD)
VRBO
From $330 per night (USD)
Expedia
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 $330 per night (USD)
Expedia
From $137 per night (USD)
VRBO
Apartment 'La Casa Di Emma' with Wi-Fi and Air Conditioning
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The holiday apartment La Casa Di Emma with step-free access and interior is located in Gaiole in Chianti and is the idea ...
From $137 per night (USD)
VRBO
From $154 per night (USD)
Expedia
Caravaggio, Galenda, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
A Chianti Classico hamlet resort, Galenda's cottages lay on a ridge with magnificent views across rolling hills draped w ...
From $154 per night (USD)
Expedia
From $2255 per night (USD)
VRBO
Villa Radda Comfortable holiday residence
Bedrooms:
2
Bathrooms:
6
Sleeps:
12
Beautiful villa with swimming pool, located in the countryside of Gaiole in Chianti. Layout: These costs are mandatory ...
From $2255 per night (USD)
VRBO
From $234 per night (USD)
Expedia
Il Giardino, Pretaccione, Castelnuovo Berardenga, Siena and Chianti
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Once the home of travelling priests 1000 years ago, Pretaccione has been sympathetically restored into individually owne ...
From $234 per night (USD)
Expedia
From $365 per night (USD)
VRBO
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 $365 per night (USD)
VRBO
From $1267 per night (USD)
VRBO
Silenzio Magico - Silenzio Magico with pool, dog allowed and garden
Bedrooms:
6
Bathrooms:
8
Sleeps:
16
Just a short distance from cycling, this pet-friendly vacation home lets you experience it all. Jump into your car an ...
From $1267 per night (USD)
VRBO
From $176 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 $176 per night (USD)
VRBO
From $869 per night (USD)
Expedia
Wonderful private villa for 12 people with WIFI, private pool, A/C and TV
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Conveniently located in Gaiole In Chianti, Italy in the tourist area "Siena And Surroundings" and only 29 km (18 mi) fro ...
From $869 per night (USD)
Expedia
From $1926 per night (USD)
VRBO
Exclusive villa in Chianti W/ View & Privacy Pool
Bedrooms:
7
Bathrooms:
9
Sleeps:
16
Located in Gaiole in Chianti, this 9-bedroom, 7-bathroom villa lets you experience it all. Fans of nature and the out ...
From $1926 per night (USD)
VRBO
Click For Pricing
Expedia
Cottage Dolcevista 4+2, Emma Villas
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This rate includes: -Utilities: electricity - water - gas for kitchen use and hot water - weekly linen, initial and fina ...
Click For Pricing
Expedia
From $201 per night (USD)
VRBO
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 located 13 km (8 mi) from Gaiole In Chianti, Italy and only 24 km ( ...
From $201 per night (USD)
VRBO
From $406 per night (USD)
Expedia
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 $406 per night (USD)
Expedia
From $348 per night (USD)
VRBO
Casa di Amici, 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 $348 per night (USD)
VRBO
From $148 per night (USD)
Expedia
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 $148 per night (USD)
Expedia
From $114 per night (USD)
VRBO
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 $114 per night (USD)
VRBO
Click For Pricing
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 ...
Click For Pricing
Expedia
From $136 per night (USD)
VRBO
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 $136 per night (USD)
VRBO
From $303 per night (USD)
Expedia
Villa del Poggio by Interhome
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Very beautiful, cosy, rustic single-family house "Villa del Poggio", surrounded by trees and vineyards. 2 km from the ce ...
From $303 per night (USD)
Expedia
From $790 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 $790 per night (USD)
VRBO
Click For Pricing
Expedia
Fabulous Villa in the Tuscan Chianti
Bedrooms:
1
Bathrooms:
6
Sleeps:
12
Nestled in Cavriglia, this 6-bedroom, 1.5-bathroom villa brings it all within your reach. Fans of nature and the outd ...
Click For Pricing
Expedia
From $172 per night (USD)
VRBO
Beautiful apartment for 6 people with A/C, pool, WIFI, TV, patio, pets allowed and panoramic view
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Property Summary Montefienali is a historical holiday village located 15 km from Gaiole in Chianti, Italy, nestled in th ...
From $172 per night (USD)
VRBO
From $193 per night (USD)
Expedia
Chianti House
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Located in Gaiole in Chianti, this 3-bedroom, 2-bathroom apartment lets you experience it all. Fans of nature and the ...
From $193 per night (USD)
Expedia
From $395 per night (USD)
VRBO
Casa Luce, San Donato in Perano, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Perched on vines San Donato in Perano dates back to a medieval castle. The resort is restored into six individually owne ...
From $395 per night (USD)
VRBO
From $743 per night (USD)
Expedia
Montelucci Chianti - Agrivilla with 14 beds with private pool
Bedrooms:
6
Bathrooms:
7
Sleeps:
14
Agrivilla Montelucci (from the Latin “Mons Luci”, sacred forest for the ancient Romans) is a wonderful stone farmhouse, ...
From $743 per night (USD)
Expedia
From $397 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 $397 per night (USD)
VRBO
From $176 per night (USD)
Expedia
Cosy apartment for 4 people with A/C, pool, WIFI, TV, terrace and panoramic view, close to Siena
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Comfortable country house in the hills of the renowned Chianti Classico area, about 20 km from Siena. The interiors are ...
From $176 per night (USD)
Expedia
From $142 per night (USD)
VRBO
Apartment in an idyllic holiday complex in the middle of the winery B3
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Two-room apartment for 3 people: ground floor or first floor, living room with single sofa bed, kitchenette, double room ...
From $142 per night (USD)
VRBO
From $192 per night (USD)
Expedia
Apartment in an idyllic holiday complex in the middle of the winery B4
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Two-room apartment for 4 people: ground floor or first floor, living room with double sofa bed, kitchenette, double room ...
From $192 per night (USD)
Expedia
From $2466 per night (USD)
VRBO
Villa in Gaiole In Chianti with 7 bedrooms sleeps 14
Bedrooms:
8
Bathrooms:
7
Sleeps:
14
Villa Il Pratello, Tuscany "A beautifully restored 400-year-old private villa – perfectly located to explore the region ...
From $2466 per night (USD)
VRBO
From $352 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 $352 per night (USD)
Expedia
From $597 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 $597 per night (USD)
VRBO
From $167 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 $167 per night (USD)
Expedia
From $764 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 $764 per night (USD)
VRBO
From $151 per night (USD)
Expedia
Apartment in the heart of Chianti
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Located in Gaiole in Chianti, this welcoming apartment lets you experience it all. Thanks to the convenient onsite pa ...
From $151 per night (USD)
Expedia
From $1731 per night (USD)
VRBO
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 $1731 per night (USD)
VRBO
From $122 per night (USD)
Expedia
Apartment 'Tuscan Style , Shared Pool' with Shared Pool, Private Garden and Wi-Fi
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Located in Gaiole In Chianti, the holiday apartment Tuscan Style , Shared Pool has everything you need for a comfortable ...
From $122 per night (USD)
Expedia
Click For Pricing
VRBO
Podere Vittoria Apartment
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Located in Castelnuovo Berardenga, this 3-bedroom, 3-bathroom apartment lets you experience it all. Fans of nature an ...
Click For Pricing
VRBO
From $153 per night (USD)
Expedia
Beautiful apartment in villa for 2 people with pool, WIFI, A/C, TV and pets allowed
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Property Summary Villa San Regolo is a stunning vacation rental located in the picturesque hamlet of San Regolo, just 10 ...
From $153 per night (USD)
Expedia
From $217 per night (USD)
VRBO
Lovely apartment in villa for 4 people with A/C, WIFI, pool, TV and pets allowed
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Property Summary Villa San Regolo is a stunning vacation rental located in the picturesque hamlet of San Regolo, just 10 ...
From $217 per night (USD)
VRBO
From $133 per night (USD)
Expedia
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 $133 per night (USD)
Expedia

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Gaiole in Chianti Rentals

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Results: 324 Rentals