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

Filter

Popular Areas

From $115 per night (USD)
VRBO
Bella Vista, Montebuoni, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Once a wine and olive oil producing estate, Montebuoni's original stone buildings have been restored into cottages and a ...
From $115 per night (USD)
VRBO
From $255 per night (USD)
Expedia
Pinturicchio, 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 $255 per night (USD)
Expedia
From $270 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 $270 per night (USD)
VRBO
From $142 per night (USD)
Expedia
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 $142 per night (USD)
Expedia
From $217 per night (USD)
VRBO
La Vigna, Montebuoni, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Once a wine and olive oil producing estate, Montebuoni's original stone buildings have been restored into cottages and a ...
From $217 per night (USD)
VRBO
From $140 per night (USD)
Expedia
Il Portico, Montefienali, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
In the upland of the Chianti vineyards and forests on an ancient Roman road, the 13th century Montefienali resort sits o ...
From $140 per night (USD)
Expedia
From $204 per night (USD)
VRBO
Villa Giacinto, San Regolo in Brolio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
San Regolo in Brolio is a lovely modern hamlet of villas, located on the edge of the village of San Regolo. It’s within ...
From $204 per night (USD)
VRBO
From $407 per night (USD)
Expedia
La Capannina, 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 $407 per night (USD)
Expedia
From $770 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 $770 per night (USD)
VRBO
From $308 per night (USD)
Expedia
Sangiovese, Vignale, Castelnuovo Berardenga, Siena and Chianti
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Set on a Chianti hillside, Vignale is a beautifully restored collection of original farm buildings, thoughtfully transfo ...
From $308 per night (USD)
Expedia
From $142 per night (USD)
VRBO
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 $142 per night (USD)
VRBO
From $362 per night (USD)
Expedia
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 $362 per night (USD)
Expedia
From $183 per night (USD)
VRBO
Casa Dante, San Donato in Perano, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Perched on vines San Donato in Perano dates back to a medieval castle. The resort is restored into six individually owne ...
From $183 per night (USD)
VRBO
From $275 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 $275 per night (USD)
Expedia
From $105 per night (USD)
VRBO
Casa Barbara, Montebuoni, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Once a wine and olive oil producing estate, Montebuoni's original stone buildings have been restored into cottages and a ...
From $105 per night (USD)
VRBO
From $178 per night (USD)
Expedia
La Casanova, Radda in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
This charming single-storey stone cottage clings to a south-facing hillside, offering fabulous views of the surrounding ...
From $178 per night (USD)
Expedia
From $133 per night (USD)
VRBO
Casetta con Vista, Montebuoni, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Once a wine and olive oil producing estate, Montebuoni's original stone buildings have been restored into cottages and a ...
From $133 per night (USD)
VRBO
From $314 per night (USD)
Expedia
Il Boschetto, Radda in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Il Boschetto is a charming Chianti holiday home with beautiful views over olive groves, vineyards and the rolling Tuscan ...
From $314 per night (USD)
Expedia
From $184 per night (USD)
VRBO
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 $184 per night (USD)
VRBO
From $153 per night (USD)
Expedia
Raffaello, Montefienali, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
In the upland of the Chianti vineyards and forests on an ancient Roman road, the 13th century Montefienali resort sits o ...
From $153 per night (USD)
Expedia
From $447 per night (USD)
VRBO
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 $447 per night (USD)
VRBO
From $156 per night (USD)
Expedia
Scorpione, Montefiorile, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
A Chianti Classico hillside resort, Montefiorile's cottages are nestled on a south bank with magnificent views across ro ...
From $156 per night (USD)
Expedia
From $242 per night (USD)
VRBO
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 $242 per night (USD)
VRBO
From $204 per night (USD)
Expedia
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 $204 per night (USD)
Expedia
From $201 per night (USD)
VRBO
Malvasia, 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 $201 per night (USD)
VRBO
From $188 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 $188 per night (USD)
Expedia
From $392 per night (USD)
VRBO
Casa Zaccardi, Pretaccione, Castelnuovo Berardenga, Siena and Chianti
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Once the home of travelling priests 1000 years ago, Pretaccione has been sympathetically restored into individually owne ...
From $392 per night (USD)
VRBO
From $238 per night (USD)
Expedia
Pergola, 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 $238 per night (USD)
Expedia
From $375 per night (USD)
VRBO
Poggio della Villa, Radda in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Poggio della Villa is a beautiful Chianti holiday home just two kilometres from the centre of Radda, offering everything ...
From $375 per night (USD)
VRBO
From $298 per night (USD)
Expedia
Mastro 3, San Sano, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
An authentic Chianti village, San Sano allows you to immerse yourself in the charm and character of Tuscan life. Origina ...
From $298 per night (USD)
Expedia
Click For Pricing
VRBO
BOSSI CASTLE App. Geranium
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Castle of Bossi is located in the southern part of the Chianti Classico in the municipality of Castelnuovo Berardeng ...
Click For Pricing
VRBO
Click For Pricing
Expedia
CASTLE OF BOSSI Ginestra Apartment
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Castello di Bossi is located in the southern part of the Chianti Classico in the municipality of Castelnuovo Berarde ...
Click For Pricing
Expedia
$Apartment \Pieve\ - Chianti as you've always dreamed of it$
From $209 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 $209 per night (USD)
VRBO
From $151 per night (USD)
VRBO
BELLAVISTA (Castle of Bossi) Colombaia
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Bellavista is a beautiful tuscan house, divided into 8 apartments, located in the domaine of Castello di Bossi, in the ...
From $151 per night (USD)
VRBO
From $279 per night (USD)
VRBO
BELLAVISTA (Castle of Bossi) San Polo
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Bellavista is a beautiful tuscan house, divided into 8 apartments, located in the domaine of Castello di Bossi, in the s ...
From $279 per night (USD)
VRBO
From $235 per night (USD)
VRBO
BELLAVISTA (Castle of Bossi) San Giusto
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Bellavista is a beautiful tuscan house, divided into 8 apartments, located in the domaine of Castello di Bossi, in the s ...
From $235 per night (USD)
VRBO
From $235 per night (USD)
VRBO
BELLAVISTA (Castello di Bossi) SAN PAOLO apartment
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Bellavista is a beautiful tuscan house, divided into 8 apartments, located in the domaine of Castello di Bossi, in the s ...
From $235 per night (USD)
VRBO
From $127 per night (USD)
Expedia
Antico Borgo di Montefienali - Apartment il Portico
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Borgo di Montefienali is a medieval hamlet , dating back to the 13th Century , was once a resting place along the ancien ...
From $127 per night (USD)
Expedia
Click For Pricing
VRBO
Antico Borgo Montefienali - Apartment La Chiocciola
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Borgo di Montefienali is a medieval hamlet , dating back to the 13th Century , was once a resting place along the ancien ...
Click For Pricing
VRBO
From $223 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 $223 per night (USD)
Expedia
From $1528 per night (USD)
VRBO
Gated Private Estate🏡 San Felice Adjacent 🌈Classic Views, 🍇Vineyards
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Private residence of an American owner, made available to guests certain periods from May through October. A gated and p ...
From $1528 per night (USD)
VRBO
From $150 per night (USD)
Expedia
La Farfalla n°5 by Interhome
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Carefully renovated "Podere La Massa" consists of a detached house and 8 apartments. It is surrounded by olive groves, f ...
From $150 per night (USD)
Expedia
From $530 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 $530 per night (USD)
VRBO
From $235 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 $235 per night (USD)
Expedia
From $676 per night (USD)
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 ...
From $676 per night (USD)
VRBO
From $116 per night (USD)
Expedia
Tribolina by Interhome
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Manor house "Tribolina", 550 m a.s.l.. 2 houses in the residence. 3 km from the centre of Cavriglia, 12 km from the cent ...
From $116 per night (USD)
Expedia
From $159 per night (USD)
VRBO
La Colomba n°4 by Interhome
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Carefully renovated "Podere La Massa" consists of a detached house and 8 apartments. It is surrounded by olive groves, f ...
From $159 per night (USD)
VRBO
From $338 per night (USD)
Expedia
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 $338 per night (USD)
Expedia
From $149 per night (USD)
VRBO
Il Ghiro n°8 by Interhome
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Carefully renovated "Podere La Massa" consists of a detached house and 8 apartments. It is surrounded by olive groves, f ...
From $149 per night (USD)
VRBO
From $116 per night (USD)
Expedia
Prestigious detached villa with fireplace recently renovated.
Bedrooms:
0
Bathrooms:
2
Sleeps:
4
Independent house in an ancient village of the '900, located 10 km from the center of Siena (15 minutes by car). Just r ...
From $116 per night (USD)
Expedia
From $472 per night (USD)
VRBO
Il Gufo n°1 by Interhome
Bedrooms:
4
Bathrooms:
7
Sleeps:
16
Carefully renovated "Podere La Massa" consists of a detached house and 8 apartments. It is surrounded by olive groves, f ...
From $472 per night (USD)
VRBO
From $74 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 $74 per night (USD)
Expedia
From $81 per night (USD)
VRBO
Pulcino n°3 by Interhome
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Carefully renovated "Podere La Massa" consists of a detached house and 8 apartments. It is surrounded by olive groves, f ...
From $81 per night (USD)
VRBO
From $132 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 $132 per night (USD)
Expedia
From $357 per night (USD)
VRBO
Wonderful private villa with private pool, WIFI, A/C, TV, patio, pets allowed and panoramic view
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Property Summary Villa del Poggio is a rustic single-family house located in the peaceful countryside just 2 km from the ...
From $357 per night (USD)
VRBO
From $126 per night (USD)
Expedia
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 ...
From $126 per night (USD)
Expedia
Click For Pricing
VRBO
Villa 'Castello di Monteluco a Lecchi' with Hill View, Pool & Wi-Fi
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The villa Castello di Monteluco a Lecchi in Gaiole in Chianti is the ideal accommodation for a relaxing holiday with a m ...
Click For Pricing
VRBO
From $235 per night (USD)
Expedia
BELLAVISTA (Castle of Bossi) San Sano
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Bellavista is a beautiful tuscan house, divided into 8 apartments, located in the domaine of Castello di Bossi, in the s ...
From $235 per night (USD)
Expedia
From $220 per night (USD)
VRBO
Dionisia, Capannole, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Nestled between vine covered hills, Capannole is a peaceful hamlet of eleven private houses which date back to 1400. A f ...
From $220 per night (USD)
VRBO
From $147 per night (USD)
Expedia
Nice apartment in villa with WIFI, A/C, pool, TV, terrace, pets allowed and panoramic view
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Property Summary The Montechioccioli 3-family house is a cosy and rustic vacation rental surrounded by vineyards in the ...
From $147 per night (USD)
Expedia
From $157 per night (USD)
VRBO
Lovely apartment in villa for 6 guests with WIFI, pool, TV, terrace, pets allowed and panoramic ...
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Property Summary The Montechioccioli 3-family house is a cosy and rustic vacation rental surrounded by vineyards in the ...
From $157 per night (USD)
VRBO
From $132 per night (USD)
Expedia
Lovely apartment in villa for 6 guests with pool, WIFI, TV, terrace, pets allowed and panoramic ...
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Property Summary The Montechioccioli 3-family house is a cosy and rustic vacation rental surrounded by vineyards in the ...
From $132 per night (USD)
Expedia
From $533 per night (USD)
VRBO
Beautiful apartment in villa with private pool, WIFI, TV, terrace, pets allowed and panoramic view
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
Property Summary The Montechioccioli 3-family house is a cosy and rustic vacation rental surrounded by vineyards in the ...
From $533 per night (USD)
VRBO
From $217 per night (USD)
VRBO
Holiday house Pievasciata for 1 - 4 persons with 2 bedrooms - Holiday home
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
ED Refnr. 2025493 Welcome to our several hundred year old farmhouse in picturesque Tuscan style, a place that has retai ...
From $217 per night (USD)
VRBO
From $288 per night (USD)
VRBO
Portion Farmhouse nestled in the heart of Chianti with private pool,
Bedrooms:
1
Bathrooms:
4
Sleeps:
9
A short distance from ecotours, mountain biking, and more, this family-friendly vacation home lets you experience it ...
From $288 per night (USD)
VRBO
From $4043 per night (USD)
VRBO
Tuscan Villa Near Florence | Vineyard Views | Pool
Bedrooms:
7
Bathrooms:
5
Sleeps:
10
Villa Vertine is a 16th-Century Tuscan villa tucked into the heart of Chianti's hillside vineyards and olive groves. It' ...
From $4043 per night (USD)
VRBO
From $164 per night (USD)
VRBO
Holiday apartment Gaiole in Chianti for 1 - 4 persons with 2 bedrooms - Holiday apartment in one or
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
ED Refnr. 2763085 Quietly situated holiday residence with a shared pool and its own hand-weaving enterprise on site ...
From $164 per night (USD)
VRBO
From $315 per night (USD)
VRBO
Holiday apartment Gaiole in Chianti for 2 - 9 persons with 4 bedrooms - Twin house
Bedrooms:
4
Bathrooms:
4
Sleeps:
9
ED Refnr. 2762603 Borgo del Trebbio with 4 independent apartments overlooking the woods and in a quiet location. A deli ...
From $315 per night (USD)
VRBO
From $189 per night (USD)
VRBO
Holiday house Gaiole in Chianti for 1 - 2 persons with 1 bedroom - Holiday house
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
ED Refnr. 2769546 Quietly situated holiday residence with a shared pool and its own hand-weaving enterprise on site ...
From $189 per night (USD)
VRBO
Click For Pricing
Expedia
MONTELUCCI CHIANTI, GAIOLE IN CHIANTI - HOLIDAY HOUSE 8/10 BEDS
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
MONTELUCCI CHIANTI .............. WHEREVER THE NATURE RESTS ................. PRISTINE NATURE FARM Montelucci, FROM THE ...
Click For Pricing
Expedia
From $753 per night (USD)
VRBO
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 $753 per night (USD)
VRBO
From $5281 per night (USD)
Expedia
16th-Century Chianti Farmhouse by Cuvee | Vineyard & Pool
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
WHY IT'S SPECIAL- Tucked in the vineyards in the heart of Chianti Classico, the restored farmhouse is a magical and lux ...
From $5281 per night (USD)
Expedia
Click For Pricing
VRBO
Villa Gaiole - Seven Bedroom Villa, Sleeps 14
Bedrooms:
8
Bathrooms:
7
Sleeps:
14
Offering panoramic vistas over Chianti’s hills and woodlands, Villa Gaiole is a serene escape in the Tuscan countryside ...
Click For Pricing
VRBO
From $149 per night (USD)
Expedia
Coccinella n°6 by Interhome
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Carefully renovated "Podere La Massa" consists of a detached house and 8 apartments. It is surrounded by olive groves, f ...
From $149 per night (USD)
Expedia
From $1780 per night (USD)
VRBO
Villa Chianti, elegant villa in Gaiole in Chianti
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Located in a rural area, this welcoming villa lets you experience it all in Gaiole in Chianti. Jump into your car and ...
From $1780 per night (USD)
VRBO
From $240 per night (USD)
Expedia
LA RONDINAIA. CHARMING HOUSE WITH GARDEN AND POOL. AMAZING VIEW
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
LA RONDINAIA apartment was obtained by restoring an ancient cellar where wine was left to age in large oak vats. Beneat ...
From $240 per night (USD)
Expedia
$\Villa Erbolino\ with Private Garden, Outdoor Stone Bathtub & Wi-Fi$
From $1008 per night (USD)
VRBO
\"Villa Erbolino\" with Private Garden, Outdoor Stone Bathtub & Wi-Fi
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
The Villa Erbolino is located in Gaiole in Chianti and is the ideal accommodation for a relaxing getaway. The 2-storey ...
From $1008 per night (USD)
VRBO
From $4273 per night (USD)
VRBO
Villa Pianvecchio by Fantasia Villas
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
Pianvecchio is a charming, panoramic villa in the rolling hills of Radda in Chianti which looks out over vineyards and o ...
From $4273 per night (USD)
VRBO
From $4365 per night (USD)
VRBO
Villa Castiglioni by Fantasia Villas
Bedrooms:
6
Bathrooms:
4
Sleeps:
10
Castiglioni is a charming, panoramic villa in the rolling hills of Radda in Chianti which looks out over vineyards and o ...
From $4365 per night (USD)
VRBO
From $122 per night (USD)
VRBO
Apartment Cortona
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Farm stay in Montevarchi with an outdoor pool This farm stay features an outdoor pool and a garden. Guest accommodation ...
From $122 per night (USD)
VRBO
From $881 per night (USD)
VRBO
Podere Villole All Apartments Package Welcome to the heart of Tuscany.
Bedrooms:
5
Bathrooms:
6
Sleeps:
14
Farm stay in Montevarchi with an outdoor pool Along with an outdoor pool, this farm stay has laundry facilities and a ga ...
From $881 per night (USD)
VRBO
From $206 per night (USD)
VRBO
Apartment Siena
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Close to cross-country skiing, ecotours, and more, this pet-friendly vacation home brings it all within reach. With c ...
From $206 per night (USD)
VRBO
From $255 per night (USD)
VRBO
Chianti Sunshine with Pool and View
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 ...
From $255 per night (USD)
VRBO
From $366 per night (USD)
Expedia
'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
The holiday home 'Chianti Summer' is located in Gaiole in Chianti and is the ideal accommodation for a relaxing getaway. ...
From $366 per night (USD)
Expedia
From $7104 per night (USD)
VRBO
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 $7104 per night (USD)
VRBO
From $154 per night (USD)
VRBO
Holiday apartment Vagliagli for 1 - 4 persons with 1 bedroom - Farmhouse
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
ED Refnr. 2899841 Castle in the Chianti, near Siena, nice location, quiet These holiday apartments in Tuscany are part ...
From $154 per night (USD)
VRBO
Click For Pricing
VRBO
Hilltop Apartment for two
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Located in a rural area, this welcoming apartment lets you experience it all in Cavriglia. Jump into your car and mak ...
Click For Pricing
VRBO
From $3940 per night (USD)
Expedia
Luxury Villa in Tuscany for 10 People
Bedrooms:
7
Bathrooms:
5
Sleeps:
10
Every season is perfect for a trip to Chianti, that hilly area of Tuscany world famous for its picturesque landscapes an ...
From $3940 per night (USD)
Expedia
Click For Pricing
VRBO
Villino Ersilia, the charm of Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Located in Castelnuovo Berardenga, this welcoming vacation home brings it all within your reach. With convenient onsi ...
Click For Pricing
VRBO
From $115 per night (USD)
VRBO
Holiday apartment Vagliagli for 1 - 3 persons with 1 bedroom - Farmhouse
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
ED Refnr. 2899865 Castle in the Chianti, near Siena, nice location, quiet These holiday apartments in Tuscany are part ...
From $115 per night (USD)
VRBO
From $83 per night (USD)
VRBO
Holiday apartment Vagliagli for 1 - 2 persons with 1 bedroom - Farmhouse
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
ED Refnr. 2899842 Castle in the Chianti, near Siena, nice location, quiet These holiday apartments in Tuscany are part ...
From $83 per night (USD)
VRBO
From $204 per night (USD)
Expedia
Beautiful private villa with A/C, pool, WIFI, TV, patio and panoramic view, close to Siena
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Conveniently located 710 m (2323 ft) from Villa A Sesta, Italy in the tourist area "Siena And Surroundings" and only 22 ...
From $204 per night (USD)
Expedia
Click For Pricing
VRBO
ALTIDO Apartment with Garden & Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Book this one-of-a-kind house in the quiet village of Piannella and have a truly peaceful Tuscan holiday. Start your day ...
Click For Pricing
VRBO
From $243 per night (USD)
Expedia
SPLENDID! 3BR, SWIMMING POOL, GARDEN
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Located in Gaiole in Chianti, this 3-bedroom, 1-bathroom apartment lets you experience it all. Fans of nature and the ...
From $243 per night (USD)
Expedia
From $228 per night (USD)
VRBO
Holiday apartment Gaiole in Chianti for 2 - 4 persons with 2 bedrooms - Holiday house
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
ED Refnr. 2757894 Borgo del Trebbio with 4 independent apartments overlooking the woods and in a quiet location. A deli ...
From $228 per night (USD)
VRBO
From $1082 per night (USD)
Expedia
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 $1082 per night (USD)
Expedia
From $1345 per night (USD)
VRBO
Villa in San Vincenti with 7 bedrooms sleeps 16
Bedrooms:
9
Bathrooms:
7
Sleeps:
16
La Maccinaia is a beautiful and comfortable villa and dependance with a private heated, salt-water system swimming pool, ...
From $1345 per night (USD)
VRBO
From $2012 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
Holiday rental La Maccinaia 14 is a lovely stone building (650 sq m) that includes private pool, air conditioning and W ...
From $2012 per night (USD)
Expedia
From $1037 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 $1037 per night (USD)
VRBO
From $2936 per night (USD)
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 ...
From $2936 per night (USD)
Expedia

Search Your Destination Now!

Gaiole in Chianti Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 324 Rentals