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 $190 per night (USD)
VRBO
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 $190 per night (USD)
VRBO
From $192 per night (USD)
Expedia
Casa del Mastro, San Sano, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
San Sano is a charming hamlet located within the Chianti village of the same name, set in the heart of the Chianti Class ...
From $192 per night (USD)
Expedia
From $12198 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 $12198 per night (USD)
VRBO
From $283 per night (USD)
Expedia
Montelodoli Capanna, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Montelodoli Capanna is a beautifully restored former barn, now a charming holiday home for two. Set within a large natur ...
From $283 per night (USD)
Expedia
From $479 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 $479 per night (USD)
VRBO
From $166 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 $166 per night (USD)
VRBO
From $189 per night (USD)
VRBO
Farmhouse apartment in Chianti with garden and pool for 2 people
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Stone farmhouse. The apartment is carefully furnished and well-stocked. Satellite TV, Wifi, kitchen, fridge, freezer, wa ...
From $189 per night (USD)
VRBO
From $594 per night (USD)
Expedia
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 $594 per night (USD)
Expedia
From $736 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 $736 per night (USD)
VRBO
From $497 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 $497 per night (USD)
VRBO
From $364 per night (USD)
VRBO
An enchanting small villa, perfect for two, with a private pool.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Il Diaccino is a lovely small villa, perfect for two, which overlooks an extraordinary landscape of hills, vineyards and ...
From $364 per night (USD)
VRBO
From $769 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 $769 per night (USD)
VRBO
From $577 per night (USD)
VRBO
Farmhouse in Chianti
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
The "Crocino in Chianti" offers the opportunity to immerse yourself in the Italian Middle Ages. Here the border disputed ...
From $577 per night (USD)
VRBO
From $268 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>A short distance from cycling, hiking trails, and more, this family-friendly villa lets you experience it all. Gaiole ...
From $268 per night (USD)
VRBO
From $178 per night (USD)
VRBO
Gorgeous home in Gaiole in Chianti (SI)
Bedrooms:
3
Bathrooms:
5
Sleeps:
9
In Gaiole in Chianti, this independent vacation home with private pool awaits you amidst the nature of the Chianti Class ...
From $178 per night (USD)
VRBO
From $970 per night (USD)
VRBO
Awesome home in Gaiole in Chianti SI
Bedrooms:
6
Bathrooms:
7
Sleeps:
16
In the heart of the Chianti area, between Radda in Chianti, Gaiole and Panzano, there is an enchanted hamlet where you c ...
From $970 per night (USD)
VRBO
From $619 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 $619 per night (USD)
VRBO
Click For Pricing
VRBO
Il Nibbio In Gaiole in Chianti, Tuscany
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
***FROM APRIL 1ST FOR NEW BOOKINGS 2026, FREE CANCELLATION UP TO 30 DAYS BEFORE ARRIVAL*** Property for exclusive use Ho ...
Click For Pricing
VRBO
From $317 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 $317 per night (USD)
VRBO
From $772 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 to Villa LisiDor, our beautiful Tuscan farmhouse in an exceptional loca ...
From $772 per night (USD)
Expedia
From $319 per night (USD)
VRBO
Lovely home in Gaiole in Chianti
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Beautiful detached stone vacation home with private pool, whose origins date back to 1500, on the hills of Chianti Class ...
From $319 per night (USD)
VRBO
From $325 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 $325 per night (USD)
VRBO
From $197 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 $197 per night (USD)
VRBO
From $342 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 $342 per night (USD)
VRBO
From $512 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 $512 per night (USD)
VRBO
From $161 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 $161 per night (USD)
Expedia
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VRBO
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 ...
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VRBO
From $102 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 $102 per night (USD)
VRBO
From $102 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 $102 per night (USD)
VRBO
From $178 per night (USD)
Expedia
Mantegna, Galenda, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Galenda is a small, charming hamlet set on a ridge in the heart of the Chianti Classico, offering beautiful views over o ...
From $178 per night (USD)
Expedia
From $124 per night (USD)
VRBO
Casa Allegra, Montebuoni, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
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 $124 per night (USD)
VRBO
From $240 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 $240 per night (USD)
Expedia
From $148 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 $148 per night (USD)
VRBO
From $228 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 $228 per night (USD)
Expedia
From $364 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 $364 per night (USD)
VRBO
From $201 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 $201 per night (USD)
Expedia
From $137 per night (USD)
VRBO
Casa del Vignaiolo, 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 $137 per night (USD)
VRBO
From $598 per night (USD)
Expedia
Podere Terrena, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Podere Terrena is a charming holiday home located on a small agriturismo in a wonderfully peaceful hillside setting, sur ...
From $598 per night (USD)
Expedia
From $783 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 $783 per night (USD)
VRBO
From $307 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 $307 per night (USD)
Expedia
From $387 per night (USD)
VRBO
Casetta Kiwi, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Casetta Kiwi is a charming Chianti holiday home in the historic hamlet of Bricciano, made up of 18th-century buildings a ...
From $387 per night (USD)
VRBO
From $641 per night (USD)
Expedia
Canonica di Vertine, Gaiole in Chianti, Siena and Chianti
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Canonica di Vertine is a unique holiday home located in the picturesque medieval hamlet of Vertine. This historic buildi ...
From $641 per night (USD)
Expedia
From $221 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 $221 per night (USD)
VRBO
From $210 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 $210 per night (USD)
Expedia
From $186 per night (USD)
VRBO
Capanna di Camporata, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Capanna di Camporata is a charming Chianti holiday home, ideal for a relaxing getaway for two. This single-storey stone ...
From $186 per night (USD)
VRBO
From $285 per night (USD)
Expedia
Nicchio, Agriturismo Vinci, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Agriturismo Vinci is a small, idyllic hamlet in the heart of the Chianti Classico, comprising just five charming holiday ...
From $285 per night (USD)
Expedia
From $187 per night (USD)
VRBO
Bell´Aria, Montebuoni, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Montebuoni is a charming hamlet in the heart of Tuscany that captures the feel of a traditional Chianti village. Once a ...
From $187 per night (USD)
VRBO
From $156 per night (USD)
Expedia
Pesci, Montefiorile, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Montefiorile is a peaceful hillside hamlet in the heart of the Chianti Classico region, set within one of Tuscany’s most ...
From $156 per night (USD)
Expedia
From $159 per night (USD)
VRBO
Il Sole, 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 $159 per night (USD)
VRBO
From $537 per night (USD)
Expedia
Vecchio Frantoio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Vecchio Frantoio is a beautifully restored holiday home in Chianti with a terraced garden and a large pool. Once a histo ...
From $537 per night (USD)
Expedia
From $642 per night (USD)
VRBO
Valliole, Gaiole in Chianti, Siena and Chianti
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Valliole is a 17th-century villa in the Chianti region with breathtaking postcard-perfect views across the vineyards of ...
From $642 per night (USD)
VRBO
From $249 per night (USD)
Expedia
Trifoglio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Trifoglio is a beautifully restored stone cottage set in an authentic 18th-century hamlet in the heart of Chianti Classi ...
From $249 per night (USD)
Expedia
From $150 per night (USD)
VRBO
Santa Lucia, 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 $150 per night (USD)
VRBO
From $190 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 $190 per night (USD)
Expedia
From $168 per night (USD)
VRBO
La Chiocciola, 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 ...
From $168 per night (USD)
VRBO
From $261 per night (USD)
Expedia
Casa Isabella, 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 $261 per night (USD)
Expedia
From $228 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 $228 per night (USD)
VRBO
From $526 per night (USD)
Expedia
Torretta Barbischio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Torretta Barbischio is a characterful Chianti holiday home, ideal for a relaxing stay with family or friends. The buildi ...
From $526 per night (USD)
Expedia
From $278 per night (USD)
VRBO
Private villa in heart of the Chianti, pool and wifi
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Aia di Ama is a traditional Chianti country house offering the perfect setting for a relaxing holiday with friends or fa ...
From $278 per night (USD)
VRBO
From $153 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 $153 per night (USD)
Expedia
From $114 per night (USD)
VRBO
Bella Vista, Montebuoni, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Montebuoni is a charming hamlet in the heart of Tuscany that captures the feel of a traditional Chianti village. Once a ...
From $114 per night (USD)
VRBO
From $295 per night (USD)
Expedia
L'Agrifoglio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
L’Agrifoglio is a charming holiday home in the heart of the Chianti Classico region, set within a peaceful historic haml ...
From $295 per night (USD)
Expedia
From $267 per night (USD)
VRBO
La Rana, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
La Rana is a welcoming Chianti holiday home on the edge of the pretty village of San Sano, ideal for a family of four or ...
From $267 per night (USD)
VRBO
From $179 per night (USD)
Expedia
Due Leoni, Montebuoni, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Montebuoni is a charming hamlet in the heart of Tuscany that captures the feel of a traditional Chianti village. Once a ...
From $179 per night (USD)
Expedia
From $148 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 $148 per night (USD)
VRBO
Click For Pricing
Expedia
Le Volte, Gaiole in Chianti, Siena and Chianti
Bedrooms:
5
Bathrooms:
3
Sleeps:
6
Le Volte is a welcoming Chianti holiday home, ideal for a relaxing stay with family or friends. Set in a small hamlet, i ...
Click For Pricing
Expedia
From $214 per night (USD)
VRBO
La Vigna, 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 $152 per night (USD)
Expedia
La Contessina, Montebuoni, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Montebuoni is a charming hamlet in the heart of Tuscany that captures the feel of a traditional Chianti village. Once a ...
From $152 per night (USD)
Expedia
From $139 per night (USD)
VRBO
Il Portico, Montefienali, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Montefienali is a small, atmospheric hamlet tucked into the rolling hills of Chianti, offering a peaceful retreat surrou ...
From $139 per night (USD)
VRBO
From $228 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 $228 per night (USD)
Expedia
From $218 per night (USD)
VRBO
L'Oliveta, 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 $218 per night (USD)
VRBO
From $210 per night (USD)
Expedia
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 $210 per night (USD)
Expedia
From $664 per night (USD)
VRBO
Il Molinaccio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Il Molinaccio is a unique holiday home in the heart of Chianti, with a rich history that stretches back to the Middle Ag ...
From $664 per night (USD)
VRBO
From $148 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 $148 per night (USD)
Expedia
From $375 per night (USD)
VRBO
Villa Riecine, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Villa Riecine is a luxurious holiday home located on the grounds of the renowned winery of the same name. Surrounded by ...
From $375 per night (USD)
VRBO
From $203 per night (USD)
Expedia
Sassolaia, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sassolaia is a Chianti holiday home in a dreamlike secluded location, surrounded by olive groves and vineyards with swee ...
From $203 per night (USD)
Expedia
From $840 per night (USD)
VRBO
Sestuccia, Gaiole in Chianti, Siena and Chianti
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Sestuccia is a beautifully renovated stone house set in the rolling hills of the Chianti Classico region. This modern vi ...
From $840 per night (USD)
VRBO
From $113 per night (USD)
Expedia
Casetta con Vista, 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 $113 per night (USD)
Expedia
From $304 per night (USD)
VRBO
Sangiovese all'Aia, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sangiovese all’Aia is a charming holiday home in Chianti, located on the grounds of Agriturismo Trappoline, where wine a ...
From $304 per night (USD)
VRBO
From $153 per night (USD)
Expedia
Ciacchieri, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Ciacchieri is a charming Chianti holiday accommodation with a private pool, ideal for couples or small families. The apa ...
From $153 per night (USD)
Expedia
From $150 per night (USD)
VRBO
Raffaello, Montefienali, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Montefienali is a small, atmospheric hamlet tucked into the rolling hills of Chianti, offering a peaceful retreat surrou ...
From $150 per night (USD)
VRBO
From $443 per night (USD)
Expedia
Le Cerreta, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Le Cerreta is a traditional Tuscan stone villa in a secluded setting, offering breathtaking panoramic views, an elegant ...
From $443 per night (USD)
Expedia
From $156 per night (USD)
VRBO
Scorpione, Montefiorile, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Montefiorile is a peaceful hillside hamlet in the heart of the Chianti Classico region, set within one of Tuscany’s most ...
From $156 per night (USD)
VRBO
From $228 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 $228 per night (USD)
Expedia
From $210 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 $210 per night (USD)
VRBO
From $383 per night (USD)
Expedia
Casa Virginia, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Casa Virginia is a welcoming Chianti holiday home, ideal for a relaxing break with family or a small group of friends. S ...
From $383 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
Montebuoni is a charming hamlet in the heart of Tuscany that captures the feel of a traditional Chianti village. Once a ...
From $167 per night (USD)
VRBO
From $173 per night (USD)
Expedia
Timo, Castellare in Chianti, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Castellare in Chianti's cottages and apartments are nestled in the woods in the uplands of Gaiole in Chianti 8 Km from t ...
From $173 per night (USD)
Expedia
From $137 per night (USD)
VRBO
Bacco, Montefiorile, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Montefiorile is a peaceful hillside hamlet in the heart of the Chianti Classico region, set within one of Tuscany’s most ...
From $137 per night (USD)
VRBO
From $215 per night (USD)
Expedia
Pergola, Montebuoni, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
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 $215 per night (USD)
Expedia
$Apartment \Pieve\ - Chianti as you've always dreamed of it$
From $249 per night (USD)
VRBO
Apartment \"Pieve\" - Chianti as you've always dreamed of it
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The 70 m² apartment with private garden, for pleasant outdoor breakfasts or relaxing al fresco dinners on summer evening ...
From $249 per night (USD)
VRBO
From $14501 per night (USD)
VRBO
Antico Borgo di Montefienali - Apartment il Portico
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Borgo di Montefienali is a medieval hamlet , dating back to the 13th Century , was once a resting place along the ancien ...
From $14501 per night (USD)
VRBO
From $15350 per night (USD)
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 ...
From $15350 per night (USD)
VRBO
From $243 per night (USD)
Expedia
Podere Lucignano Secondo - La Mangiatoia
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
In the very heart of the charming Tuscan countryside, among the smooth hills of Sienese Chianti and the fragrance of its ...
From $243 per night (USD)
Expedia
From $166 per night (USD)
VRBO
La Farfalla n°5 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)
VRBO
From $774 per night (USD)
Expedia
VILLA GAIA - Five Bedroom Villa, Sleeps 10
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
A typical Chianti Villa in Tuscany, once a a 15th century mill, located in the countryside, just 15 minutes from Siena, ...
From $774 per night (USD)
Expedia
From $596 per night (USD)
VRBO
Podere Lucignano Secondo - La Villa
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
In the very heart of the charming Tuscan countryside, among the smooth hills of Sienese Chianti and the fragrance of its ...
From $596 per night (USD)
VRBO
From $297 per night (USD)
Expedia
Podere Lucignano Secondo - Le Logge
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
In the very heart of the charming Tuscan countryside, among the smooth hills of Sienese Chianti and the fragrance of its ...
From $297 per night (USD)
Expedia
Click For Pricing
VRBO
Mulinaccio di Badia, Gaiole in Chianti, Siena and Chianti
Bedrooms:
6
Bathrooms:
5
Sleeps:
8
Mulinaccio di Badia is a charming holiday home set in the gentle hills of the Chianti Classico, surrounded by vineyards ...
Click For Pricing
VRBO
From $175 per night (USD)
Expedia
La Colomba n°4 by Interhome
Bedrooms:
2
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 $175 per night (USD)
Expedia

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Gaiole in Chianti Rentals

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Results: 214 Rentals