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.

G
Grazia
From
Italy
The property is magnificient! The swimmimg pool is a dream. Rosa and Francesca go above and beyond to make your stay as comfortable as possibile. Super recommended!
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 154 reviews
Price from
US$239.37
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, 127 reviews
Price from
US$173.46
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 9.2
Superb - What previous guests thought, 313 reviews
Price from
US$231.84
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$536.35
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.

D
Domenico
From
Italy
Lapo is a great host and the house is just perfect, with an amazing view.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 17 reviews
Price from
US$3,763.39
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.

J
Joseph R
From
Canada
A wonderful place to stay in Gaiole...the accommodation is tastefully furnished with modern items. The bed was very comfortable. The owner/host Monica prepared a full and nourishing breakfast for me. Secure bicycle storage was provided free of charge at a location 300m from the hotel.
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 83 reviews
Price from
US$181.32
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.

Y
Yuliia
From
Netherlands
I can say I like this ! I loved this ,this felling full in love and fill like home ❤️❤️❤️Alessandra was incredible amazing ❤️thank you so much for accommodation, if honestly I wanna stay more then 1 day 😭
Scored out of 10, guest rating 8.3
Very good - What previous guests thought, 107 reviews
Price from
US$109.86
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.

A
Arnar
From
Iceland
Everything was fantastic. The staff, location, the wine, everything was perfect.
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 666 reviews
Price from
US$168.77
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
Jaka
From
Slovenia
Amazing stay at Borgo Casa. Kind and helpful staff. Location offers great views.
Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 353 reviews
Price from
US$218.31
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.

P
Piecha
From
Poland
Close to vineyards, located in an old castle, stunning views.
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 165 reviews
Price from
US$185.02
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 8.3
Very good - What previous guests thought, 107 reviews

Popular with guests booking holiday rentals in Gaiole in Chianti

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 257 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, 353 reviews

Popular with guests booking holiday rentals in Gaiole in Chianti

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 154 reviews

Popular with guests booking holiday rentals in Gaiole in Chianti

Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 163 reviews

Popular with guests booking holiday rentals in Gaiole in Chianti

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 71 reviews

Popular with guests booking holiday rentals in Gaiole in Chianti

Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 165 reviews

Popular with guests booking holiday rentals in Gaiole in Chianti

Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 313 reviews

Popular with guests booking holiday rentals in Gaiole in Chianti

Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 666 reviews

Popular with guests booking holiday rentals in Gaiole in Chianti

Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 1,245 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, 210 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$251.34 per night
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 120 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$194.28 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$115.64 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$157.27 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$203.82 per night
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 597 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$339.98 per night

Borgo Carpineto

Vagliagli
8.0+ review score
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 510 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$179.88 per night

Enjoy breakfast in Gaiole in Chianti and nearby

Scored out of 10, guest rating 7.1
Good - What previous guests thought, 419 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$139.62 per night
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 510 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$126.06 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 9.6
Exceptional - What previous guests thought, 27 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 9.1
Superb - What previous guests thought, 71 reviews

Featuring garden views, Castelli del Chianti provides accommodation with balcony, around 29 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.

Holiday Rentals with swimming pools in Gaiole in Chianti and nearby

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$462.56 per night
Scored out of 10, guest rating 7.0
Good - What previous guests thought, 59 reviews

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

From US$161.90 per night
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.

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.

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 57 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$140.18 per night

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, 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.

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

Casa Badia

Radda in Chianti
Free cancellation options available
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 85 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$109.28 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, 127 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.

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.

Agriturismo Vinci

Gaiole in Chianti
Free cancellation options available
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 23 reviews

Set in Gaiole in Chianti and only 30 km from Piazza Matteotti, Agriturismo Vinci offers accommodation with lake views, free WiFi and free private parking.

Nicchio

Gaiole in Chianti
Free cancellation options available

Located in Gaiole in Chianti in the Tuscany region, Nicchio has a balcony. Both free WiFi and parking on-site are available at the apartment free of charge.

Casa Vacanze Vertine

Gaiole in Chianti
Free cancellation options available
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 53 reviews

Set just 26 km from Piazza Matteotti, Casa Vacanze Vertine offers accommodation in Gaiole in Chianti with access to a spa and wellness centre, an open-air bath, as well as a 24-hour front desk.

Riecine

Gaiole in Chianti
Free cancellation options available

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

FAQ about holiday rentals in Gaiole in Chianti

Holiday rentals that guests love in Gaiole in Chianti

See all
Avg. price/night: US$168.89
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 666 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, 1,245 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, 1,245 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, 1,245 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, 158 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, 80 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$109.86
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