Skip to main content

Holiday Rentals in Gaiole in Chianti

Find the holiday rentals that appeal to you the most

Holiday Rentals for every style

Find the right holiday rental for you in Gaiole in Chianti

The best holiday rentals in Gaiole in Chianti

Check out our pick of great holiday rentals in Gaiole in Chianti

Filter by:

Review score

BORGO A MONTI di Sotto

Gaiole in Chianti

20 km from Piazza del Campo, BORGO A MONTI di Sotto is a recently renovated property located in Gaiole in Chianti and provides air-conditioned rooms with free WiFi and private parking.

J
Julia
From
Germany
The apartment was amazing. Everything was super clean. The pool and also view of the Pool is a dream. The kitchen is equipped with all the basics you need and there was also a welcome package and a bottle of wine. We would always come back!
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 153 reviews
Price from
US$240.41
1 night, 2 adults

Cavarchino B&B

Gaiole in Chianti

Featuring a garden and views of pool, Cavarchino B&B is a bed and breakfast situated in a historic building in Gaiole in Chianti, 30 km from Piazza Matteotti.

D
David
From
Australia
This was my third visit, so that speaks for itself. Very comfortable and welcoming. I’ll be back for a fourth visit!
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 129 reviews
Price from
US$174.21
1 night, 2 adults

Badia a Coltibuono Wine Resort

Gaiole in Chianti

Badia a Coltibuono, Abbey of 1051, is the first wine resort in Chianti that offers a truly exceptional experience.

M
Maree
From
Australia
The staff were amazing and very friendly. They were genuinely wanting to make each visitors experience the best it could be.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 321 reviews
Price from
US$232.84
1 night, 2 adults

Casa Vacanze Chianti Summer

Gaiole in Chianti

Boasting air-conditioned accommodation with a private pool, Casa Vacanze Chianti Summer is situated in Gaiole in Chianti.

M
Mark
From
United Kingdom
We had the whole lower floor of the house with our own living room and kitchen as well as bathroom and bedroom. There is a swimming pool and outside table for breakfast in the sunshine. It is very well situated as it is a very short walk into the centre for restaurants and bars. There is also sheltered parking at the house
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 12 reviews
Price from
US$538.67
1 night, 2 adults

Podere Erbolino

Gaiole in Chianti

Located in Gaiole in Chianti in the Tuscany region, Podere Erbolino has a balcony. A hot tub is available for guests.

T
Tóth
From
Hungary
Beautiful villa and garden in the Chianti hills with amazing panorama, maximum silence and relaxation! Great place to stay and to run excursions in the region from here. Fully equiped house with all necessary stuff for longer stay. Lapo the owner was very kind and helpful in all matters and questions we had, suggested really good places to see and try. Very flexible, we could check-in earlier on arrival and check-out with no hurry on departure day.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 18 reviews
Price from
US$4,104.10
1 night, 2 adults

B&B L'Eroico

Gaiole in Chianti

Offering a garden and city view, B&B L'Eroico is set in Gaiole in Chianti, 30 km from Piazza Matteotti and 30 km from Piazza del Campo.

в
валентина
From
Russia
Splendid breakfast,good fresh room and great Monica!
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 83 reviews
Price from
US$182.11
1 night, 2 adults

Agriturismo "Crocino in Chianti"

Gaiole in Chianti

Offering pool views, Agriturismo "Crocino in Chianti" is an accommodation located in Gaiole in Chianti, 26 km from Piazza del Campo and 27 km from Piazza Matteotti.

K
Keith
From
United Kingdom
The host Alissandra ( I think) was brilliant booked a meal at a local restaurant and her home produced olive oil and wine is lovely
Scored out of 10, guest rating 8.3
Very good - What previous guests thought, 107 reviews
Price from
US$110.33
1 night, 2 adults

Castello Di Meleto

Gaiole in Chianti

Offering an open-air bath and garden view, Castello Di Meleto is set in Gaiole in Chianti, 29 km from Piazza Matteotti and 30 km from Piazza del Campo.

M
Martin Ervik
From
Norway
Perfect place for a Chianti experience
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 673 reviews
Price from
US$169.49
1 night, 2 adults

Borgo Casa al Vento

Gaiole in Chianti

Borgo Casa Al Vento is in the Tuscan countryside, 3 km from Gaiole In Chianti. It offers sport activities and a panoramic pool.

J
Joel
From
Australia
After reading some questionable reviews, we were pleasantly surprised at how beautiful this accomodation was. Our room itself was large, clean, air conditioned and what appeared like a newly renovated bathroom. The room was cleaned daily. While some fixtures are clearly older than others, it was part of the charm. They had great options for experiences hosted on site which allowed us to experience all we had hoped for by staying in the gorgeous Tuscan countryside. We personally loved the BBQ hosted on the Friday night which was a surprising touch. The food was amazing, accompanied by a beautiful bottle of their wine and live music. The wine tasting and cooking class were also great. Pool area was clean and great spot for relaxing. We are from Australia and would go out of our way to come back to this beautiful accomodation.
Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 355 reviews
Price from
US$219.25
1 night, 2 adults

Rocca Di Castagnoli

Gaiole in Chianti

Rocca di Castagnoli is surrounded by its vineyards and features a restaurant and free WiFi. It offers guest rooms and independent apartments.

R
Relika
From
Estonia
I loved the hotel, it was little beautiful medivial village, sorrounded by mountins and Tuscany atmosphere. Ladies in reception were so kind and happy all the time:) Nice breakfast - at least for us there were many options we liked. They produce wine and we enjoyed the wine tasting as well. Thank you for everything!
Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 162 reviews
Price from
US$185.82
1 night, 2 adults
All holiday rentals in Gaiole in Chianti

Most booked holiday rentals in Gaiole in Chianti and surroundings in the past month

See all

Popular with guests booking holiday rentals in Gaiole in Chianti

Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 157 reviews

Popular with guests booking holiday rentals in Gaiole in Chianti

Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 258 reviews

Popular with guests booking holiday rentals in Gaiole in Chianti

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 70 reviews

Popular with guests booking holiday rentals in Gaiole in Chianti

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 153 reviews

Popular with guests booking holiday rentals in Gaiole in Chianti

Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 161 reviews

Popular with guests booking holiday rentals in Gaiole in Chianti

Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 355 reviews

Popular with guests booking holiday rentals in Gaiole in Chianti

Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 162 reviews

Popular with guests booking holiday rentals in Gaiole in Chianti

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 321 reviews

Popular with guests booking holiday rentals in Gaiole in Chianti

Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 673 reviews

Popular with guests booking holiday rentals in Gaiole in Chianti

Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 1,232 reviews

Highly rated holiday rentals in Gaiole in Chianti and nearby

Le Lappe

Cavriglia
8.0+ review score
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 208 reviews

Set in Cavriglia, 31 km from The Mall Luxury Outlet, Le Lappe offers accommodation with a hot tub and wellness packages. This farm stay features a pool with a view, a garden and free private parking.

From US$305.79 per night
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 123 reviews

Located just 38 km from Piazza Matteotti, Agriturismo La Forra features accommodation in Cavriglia with access to a bar, a shared lounge, as well as a concierge service.

From US$195.07 per night
Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 62 reviews

Boasting quiet street views, Camere e Appartamenti Baldini Romanita provides accommodation with patio, around 18 km from Piazza Matteotti.

From US$116.12 per night

Villino Chianti

Cavriglia
8.0+ review score
Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 31 reviews

Situated in Cavriglia, the recently renovated Villino Chianti features accommodation 30 km from The Mall Luxury Outlet and 36 km from Piazza Matteotti.

From US$157.95 per night

Il Nespolo

Cavriglia
8.0+ review score
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 80 reviews

Featuring air-conditioned accommodation with a terrace, Il Nespolo is set in Cavriglia. With garden views, this accommodation offers a balcony.

From US$204.65 per night
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 601 reviews

Set in 600 hectares of beautiful Chianti countryside 20 minutes from Siena, Wine Resort Dievole offers different types of recently renovated apartment-suites and rooms in a large complex.

From US$678.11 per night

Borgo Carpineto

Vagliagli
8.0+ review score
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 511 reviews

Borgo Carpineto features a hot tub and free private parking, and is within 16 km of Piazza del Campo and 30 km of Piazza Matteotti.

Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 46 reviews

Located within 35 km of Piazza Matteotti and 44 km of Piazza del Campo in Cavriglia, Tenuta San Jacopo - Agriturismo provides accommodation with seating area.

From US$180.62 per night

Enjoy breakfast in Gaiole in Chianti and nearby

Scored out of 10, guest rating 7.1
Good - What previous guests thought, 421 reviews

The Relais Santa Cristina is a renovated country house in the heart of the Chianti wine country, outside Siena. It offers panoramic views, an outdoor pool and free parking.

From US$140.20 per night
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 512 reviews

Featuring a garden, Agriturismo Oliviera Winery is located in Vagliagli in the Tuscany region, 13 km from Piazza del Campo and 30 km from Piazza Matteotti.

From US$126.60 per night
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Boasting air-conditioned accommodation with a private pool, Ciacchieri is situated in Gaiole in Chianti. This property offers access to a balcony, free private parking and free WiFi.

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 4 reviews

Situated in Gaiole in Chianti, 27 km from Piazza Matteotti and 28 km from Piazza del Campo, Casa Ciaccheri offers air conditioning.

Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 26 reviews

Located in Gaiole in Chianti, 30 km from Piazza Matteotti and 31 km from Piazza del Campo, Casa Ciaccheri 2 provides air-conditioned accommodation with a balcony and free WiFi.

Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 14 reviews

Featuring garden views, Casa Marcella nel cuore del Chianti provides accommodation with a garden and a balcony, around 27 km from Piazza Matteotti.

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Set in Gaiole in Chianti, 30 km from Piazza Matteotti and 31 km from Piazza del Campo, Il Balcone offers air-conditioned accommodation with a balcony and free WiFi.

Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 8 reviews

Featuring accommodation with a pool with a view, mountain view and a patio, Borgo di Gaiole - Casa BD - apartment with a view & travel guide is situated in Gaiole in Chianti.

These holiday rentals in Gaiole in Chianti and nearby have options with free cancellation

Holiday home Belvedere

Montevarchi
Free cancellation options available

Boasting accommodation with a private pool, pool view and a patio, Holiday home Belvedere is situated in Montevarchi. This property offers access to a balcony, free private parking and free WiFi.

From US$464.56 per night

Castello di Selvole

Vagliagli
Free cancellation options available
Scored out of 10, guest rating 7.0
Good - What previous guests thought, 57 reviews

Set in a historical hills of Chianti Classico, Castello di Selvole is a winery offering hospitality with an outdoor pool.

From US$162.56 per night

Casa Badia

Radda in Chianti
Free cancellation options available
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 84 reviews

Casa Badia has quiet street views, free WiFi and free private parking, situated in Radda in Chianti, 18 km from Piazza Matteotti.

From US$109.73 per night

Cavarchino B&B

Gaiole in Chianti
Free cancellation options available
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 129 reviews

Featuring a garden and views of pool, Cavarchino B&B is a bed and breakfast situated in a historic building in Gaiole in Chianti, 30 km from Piazza Matteotti.

From US$174.21 per night

Il Colombaio by VacaVilla

Gaiole in Chianti
Free cancellation options available
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 3 reviews

Situated in Gaiole in Chianti, Il Colombaio by VacaVilla features accommodation with private pool, free WiFi and free private parking for guests who drive.

La Loggetta - Apartments

Gaiole in Chianti
Free cancellation options available
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 58 reviews

Set in Gaiole in Chianti and only 30 km from Piazza Matteotti, La Loggetta - Apartments offers accommodation with pool views, free WiFi and free private parking.

From US$140.78 per night

Gittori

Gaiole in Chianti
Free cancellation options available

Boasting air-conditioned accommodation with a private pool, Gittori is situated in Gaiole in Chianti. This property offers access to a balcony, free private parking and free WiFi.

Capanna di Camporata

Gaiole in Chianti
Free cancellation options available

Located in Gaiole in Chianti, Capanna di Camporata offers accommodation with a private pool. This property offers access to a balcony, free private parking and free WiFi.

Holiday Rentals with swimming pools in Gaiole in Chianti and nearby

Situated in Gaiole in Chianti, 28 km from Piazza Matteotti and 29 km from Piazza del Campo, Villa Radda by Mmega offers air conditioning.

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 3 reviews

Located in Gaiole in Chianti and only 30 km from Piazza Matteotti, Podere Il Trebbio, porzione di villa provides accommodation with mountain views, free WiFi and free private parking.

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 20 reviews

Located in Gaiole in Chianti, Casina provides accommodation with a private pool, a patio and mountain views. This property offers access to a terrace and free private parking.

Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 9 reviews

Featuring a garden, private pool and garden views, Il Molinaccio is set in Gaiole in Chianti. This property offers access to a patio, a pool table, free private parking and free WiFi.

Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 355 reviews

Borgo Casa Al Vento is in the Tuscan countryside, 3 km from Gaiole In Chianti. It offers sport activities and a panoramic pool.

From US$211.93 per night
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 5 reviews

Situated in Gaiole in Chianti and only 30 km from Piazza Matteotti, Montemarcoli features accommodation with mountain views, free WiFi and free private parking.

Featuring air-conditioned accommodation with a private pool, garden view and a patio, Sestuccia is located in Gaiole in Chianti.

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 3 reviews

Featuring pool views, Sestuccina provides accommodation with an open-air bath and a balcony, around 28 km from Piazza Matteotti.

FAQ about holiday rentals in Gaiole in Chianti

Holiday rentals that guests love in Gaiole in Chianti

See all
Avg. price/night: US$169.62
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 673 reviews
I have been to this castle a lot of times and I love it. You instantly relax when you get arrive and the buildings and vibe is just lovely. There was 8 of us this time. Village nearby is lovely and it is a short drive to other places. Breakfast is lovely and there are two beautiful pools (Although they were covered in wasps!!)
Guest review by
Fiona
Group
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 1,232 reviews
Beautiful agriturismo in the Chianti area about half an hour from Siena. We loved everything about this agriturismo: the friendly welcome, the spacious and well-equipped room, the light dinner that the agriturismo offers, the beatuiful building and garden, and the location: San Sano. A very small, picturesque Tuscan village. We shall be back for sure!
Guest review by
Ulrike
Family with young children
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 1,232 reviews
This place is a little oasis where you can relax and enjoy the feeling of a tiny tuscan village and a huge wineyard. It is lucky that they dont upload new pictures of the property, otherwise they wouldnt have any vacancy :D Everything is covered with flowers, room and pool is clean, breakfast is really good with excellent background music, lot of things to see nearby. We also enjoyed the kind service of Lorena who is super sweet! We had the chance to meet with the owner and take a winetour which was really interesting.
Guest review by
Veronika
Young couple
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 1,232 reviews
Very friendly staff, with good breakfast and lunch/dinner options featuring local products and wine from their own winery. Everything was super clean, including the rooms and the pool area. It is a great small village for people who want to enjoy the nature and chill vibes of the Chianti area.
Guest review by
Mariya
Young couple
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 63 reviews
A beautiful and quiet Tuscany villa in the middle of olive groves and a very kind and hospitable host
Guest review by
Vladimír
Family with young children
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 157 reviews
Location (Chianti region, tiny village on a hill), characteristics of the room (design) and the very friendly and helpful owner.
Guest review by
maurice
Young couple
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 78 reviews
When we arrived at the accommodation, surrounded by a beautiful landscape, our hostess Jasmin welcomed us and showed us around the stunningly beautiful property. We immediately felt at home, which was mainly due to the great service and the extravagant interior design. The entire house is incredibly tastefully furnished and invites you to relax. The rooms are very comfortable and wonderfully equipped. We left the villa with a homemade peach cake and are already looking forward to our next visit!
Guest review by
Heinersdorff
Young couple
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 63 reviews
Very charming old Tuscan villa with a lot of space. There was a huge living room with lots of space. Nice Garden area with lots of seating space and grill station.
Guest review by
Christopher
Group
Avg. price/night: US$110.31
Scored out of 10, guest rating 8.3
Very good - What previous guests thought, 107 reviews
Alessandra was a delight! She was friendly, helpful with answering questions about the area and available for our needs. The room was beautiful comfortable and very clean. The grounds on property were beautiful, lush and green ,with flowers, olive trees and grapes. The location was peaceful and easy walking distance to little village. We got the breakfast which was extra but was well worth it. Alessandra set up our breakfast in the shared kitchen. We had espresso, fruit, yogurt and croissant. We enjoyed our visit and would stay here again.
Guest review by
Diana
Young couple