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 $130 per night (USD)
VRBO
Tuscan apt. magnificent panorama, pure nature, relaxation, private pool, WiFi
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The 4-room apartment is ideal for families and small groups. The entrance is at ground level, two bedrooms and a bathroo ...
From $130 per night (USD)
VRBO
From $167 per night (USD)
Expedia
Chianti Holiday House, private jacuzzi up to 6 pax
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Recently renovated, is located in a scenic hillside location in a picturesque village nestled in the heart of Chianti, s ...
From $167 per night (USD)
Expedia
From $110 per night (USD)
VRBO
Apartment in Tuscan stone house, surrounded by nature with private pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The 3-room apartment offers comfort for families or a small group. It is located at ground level, the terrace is located ...
From $110 per night (USD)
VRBO
From $138 per night (USD)
Expedia
Farmhouse apartment in Chianti with garden and pool for 2 people
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Stone farmhouse. The apartment is carefully furnished and well-stocked. Satellite TV, Wifi, kitchen, fridge, freezer, wa ...
From $138 per night (USD)
Expedia
From $658 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 $658 per night (USD)
VRBO
From $336 per night (USD)
Expedia
Wonderful private villa for 8 guests with A/C, WIFI, private pool, TV, patio and panoramic view
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 $336 per night (USD)
Expedia
From $216 per night (USD)
VRBO
Casa BD in Gaiole - 150 m² apartment with a view & travel guide - sleeps 8
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Close to cycling, hiking trails, and more, this family-friendly villa brings it all within reach. Gaiole in Chianti S ...
From $216 per night (USD)
VRBO
From $288 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 $288 per night (USD)
VRBO
From $660 per night (USD)
VRBO
Secluded villa between Chianti vineyards, private pool, tennis, large garden
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Ciao from Petra & Alexa! We warmly welcome you in our unbeatable location, halfway between Siena and Florence! First of ...
From $660 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 $127 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 $127 per night (USD)
VRBO
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Expedia
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
Expedia
From $147 per night (USD)
VRBO
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)
VRBO
From $157 per night (USD)
Expedia
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)
Expedia
From $132 per night (USD)
VRBO
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)
VRBO
From $533 per night (USD)
Expedia
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)
Expedia
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
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 $5281 per night (USD)
VRBO
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)
VRBO
From $7104 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 $7104 per night (USD)
Expedia
From $330 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 $330 per night (USD)
VRBO
From $137 per night (USD)
Expedia
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)
Expedia
From $869 per night (USD)
VRBO
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)
VRBO
From $201 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 located 13 km (8 mi) from Gaiole In Chianti, Italy and only 24 km ( ...
From $201 per night (USD)
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 $1486 per night (USD)
VRBO
Fattoria Valtellina by Boutique | Tuscany
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Summary: A serene and sophisticated four-bedroom retreat nestled in the rolling hills of Chianti, this restored stone vi ...
From $1486 per night (USD)
VRBO
From $519 per night (USD)
VRBO
Historic farmhouse in San Donato in Perano, Gaiole in Chianti, with shared pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Historic farmhouse dating back to the year 1000, between Gaiole in Chianti and Radda in Chianti with shared swimming poo ...
From $519 per night (USD)
VRBO
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 $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 $164 per night (USD)
Expedia
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)
Expedia
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)
Expedia
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)
Expedia
From $235 per night (USD)
VRBO
Il Nibbio In Gaiole in Chianti, Tuscany
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Property for exclusive use Holiday home made from a ancient medieval fortress in stone, 140 sq. m., holding up to 5 pers ...
From $235 per night (USD)
VRBO
From $285 per night (USD)
VRBO
An enchanting small villa, perfect for two, with an unparalleled view.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Il Diaccino is an enchanting small villa, perfect for two, with a magnificent view. It overlooks an extraordinary landsc ...
From $285 per night (USD)
VRBO
From $669 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 $669 per night (USD)
VRBO
From $822 per night (USD)
VRBO
Le Diacce: Beautiful Old Farmhouse with Breathtaking Countryside View
Bedrooms:
6
Bathrooms:
5
Sleeps:
12
What we offer is a beautiful and spacious old stone house in the heart of the unspoiled Chianti countryside. It has been ...
From $822 per night (USD)
VRBO
From $473 per night (USD)
VRBO
Villa on Chianti hill in heart of Tuscany, super-large pool, 14 ha plot
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Restored from the ruin of a typical Tuscan farmhouse this Podere sits high on a hilltop at 600 meter above sea-level (wh ...
From $473 per night (USD)
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 $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 $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 $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 $1686 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
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)
VRBO
From $289 per night (USD)
Expedia
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)
Expedia
From $1602 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 $1602 per night (USD)
VRBO
From $12464 per night (USD)
Expedia
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)
Expedia
From $2482 per night (USD)
VRBO
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)
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 $186 per night (USD)
Expedia
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 $186 per night (USD)
Expedia
From $743 per night (USD)
VRBO
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)
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 $566 per night (USD)
VRBO
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)
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
$\Villa Erbolino\ with Private Garden, Outdoor Stone Bathtub & Wi-Fi$
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 $257 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 $257 per night (USD)
Expedia
From $161 per night (USD)
VRBO
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)
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 $490 per night (USD)
Expedia
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)
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 $138 per night (USD)
Expedia
Lovely apartment for 2 people with WIFI and TV
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Property Summary This charming 2-family house is situated in the heart of Gaiole In Chianti, Italy, offering an ideal v ...
From $138 per night (USD)
Expedia
From $232 per night (USD)
VRBO
Il Fienile, Montefienali, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
In the upland of the Chianti vineyards and forests on an ancient Roman road, the 13th century Montefienali resort sits o ...
From $232 per night (USD)
VRBO
From $182 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 $182 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 $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 $472 per night (USD)
Expedia
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)
Expedia
From $74 per night (USD)
VRBO
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)
VRBO
From $81 per night (USD)
Expedia
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)
Expedia
From $132 per night (USD)
VRBO
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)
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 $238 per night (USD)
VRBO
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)
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
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 $2023 per night (USD)
Expedia
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)
Expedia
From $314 per night (USD)
VRBO
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)
VRBO
From $235 per night (USD)
Expedia
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)
Expedia
From $240 per night (USD)
VRBO
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)
VRBO
From $357 per night (USD)
Expedia
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)
Expedia
From $116 per night (USD)
VRBO
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)
VRBO
From $279 per night (USD)
Expedia
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)
Expedia
From $269 per night (USD)
VRBO
BELLAVISTA San Piero
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Bellavista is a beautiful tuscan house, divided into 8 apartments, located in the domaine of Castello di Bossi, in the s ...
From $269 per night (USD)
VRBO
From $433 per night (USD)
Expedia
Traumblick in die Toskana vom Ferienhaus mit Pool auf Hügel zw. Siena u. Florenz
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Close to hiking trails, mountain biking, and more, this family-friendly vacation home brings it all within reach. Jum ...
From $433 per night (USD)
Expedia
From $185 per night (USD)
VRBO
Traumblick in die Toskana vom Landhaus mit Pool auf Hügel zw. Siena u. Florenz
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Located in a rural area, this welcoming cottage lets you experience it all in Castelnuovo Berardenga. Jump into your ...
From $185 per night (USD)
VRBO
From $3958 per night (USD)
Expedia
Private Villa with private pool, sauna, A/C, WIFI, hot tub, TV, patio, close to Greve In Chianti
Bedrooms:
7
Bathrooms:
5
Sleeps:
11
Villa Castiglioni is a lovely holiday home with air conditioning, WiFi internet and private pool. The property can sle ...
From $3958 per night (USD)
Expedia
From $168 per night (USD)
VRBO
Adorable house in charming Chianti hamlet btwn Siena, Arezzo and Florence
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Casa Secciano is located strategically between these 3 artistic cities allowing for easy access to tourist sites, but at ...
From $168 per night (USD)
VRBO
From $238 per night (USD)
Expedia
LA LOGGIA. HOUSE WITH STUNNING VIEW ABOVE THE CHIANTI REGION AND PANORAMIC POOL
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
LA LOGGIA House, renovated in 2015, is a large independent apartment, ideal to be rented by those who love nature, tranq ...
From $238 per night (USD)
Expedia
From $258 per night (USD)
VRBO
LA TORRE, AN EAGLE NEST ABOVE THE TUSCANY LANDSCAPE
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Casa La Torre is located in an ancient palace overlooking the small hamlet of Rosennano. Its renovation was completed in ...
From $258 per night (USD)
VRBO
From $188 per night (USD)
VRBO
Townhouse Casa Gorizia - Authentic Tuscany
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Set in a medieval hamlet amongst the Tuscan Hills, Montebenichi feels a world away and yet is close to some of Tuscany's ...
From $188 per night (USD)
VRBO
From $131 per night (USD)
VRBO
In the heart of Chianti: view over the valley, relaxation & art, wine & sun
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Val delle Corti is a small winery in Radda in Chianti. The ‘Capanna’, an old, tastefully restored natural stone hay bar ...
From $131 per night (USD)
VRBO
From $260 per night (USD)
VRBO
Apartment in an idyllic holiday complex in the middle of the winery T6
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Three-room apartment for 6 people: ground floor or first floor, living room with double sofa bed, kitchenette, one doubl ...
From $260 per night (USD)
VRBO
From $2629 per night (USD)
VRBO
Luxury Villa in Radda Chianti,heatable Pool,Aircon,SPA room,gym room,sleep 10
Bedrooms:
7
Bathrooms:
6
Sleeps:
12
This charming wine estate with panoramic views is located on the hills at just 1.5 km from Radda in Chianti, a lovely me ...
From $2629 per night (USD)
VRBO
From $145 per night (USD)
VRBO
Holiday apartment Pievasciata for 1 - 4 persons with 2 bedrooms - Holiday apartment
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
ED Refnr. 2077187 Immerse yourself in the heart of Tuscany with this exquisite holiday home. The 80-100 square metre Tu ...
From $145 per night (USD)
VRBO
From $102 per night (USD)
VRBO
Apartment in an idyllic holiday complex in the middle of the B2 winery
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Two-room apartment for 2 people: ground floor or first floor, living room, kitchenette, double room, bathroom with showe ...
From $102 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 $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 $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

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Results: 113 Rentals