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Holiday Rentals in Gaiole in Chianti

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The best holiday rentals in Gaiole in Chianti

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

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

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Popular with guests booking holiday rentals in Gaiole in Chianti

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 72 reviews

Popular with guests booking holiday rentals in Gaiole in Chianti

Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 81 reviews

Popular with guests booking holiday rentals in Gaiole in Chianti

Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 164 reviews

Popular with guests booking holiday rentals in Gaiole in Chianti

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 125 reviews

Popular with guests booking holiday rentals in Gaiole in Chianti

Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 310 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, 358 reviews

Popular with guests booking holiday rentals in Gaiole in Chianti

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 256 reviews

Popular with guests booking holiday rentals in Gaiole in Chianti

Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 163 reviews

Popular with guests booking holiday rentals in Gaiole in Chianti

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 1,259 reviews

Popular with guests booking holiday rentals in Gaiole in Chianti

Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 657 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, 207 reviews

31 km from The Mall Luxury Outlet in Cavriglia, Le Lappe offers accommodation with access to a hot tub and wellness packages.

From US$343.93 per night
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 113 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$181.87 per night
Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 63 reviews

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

From US$115.47 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$152.65 per night

Il Nespolo

Cavriglia
8.0+ review score
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 77 reviews

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

From US$203.52 per night

Borgo Carpineto

Vagliagli
8.0+ review score
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 508 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 9.3
Superb - What previous guests thought, 48 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$202.79 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 7 reviews

Boasting accommodation with a private pool, Tuscan Countryside Paradise with Pool is located in Cavriglia. This property offers access to a balcony, free private parking and free WiFi.

From US$540.40 per night

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

Relais Santa Cristina

Radda in Chianti
Free cancellation options available
Scored out of 10, guest rating 7.1
Good - What previous guests thought, 410 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$139.42 per night

Castello di Selvole

Vagliagli
Free cancellation options available
Scored out of 10, guest rating 7.0
Good - What previous guests thought, 58 reviews

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

From US$161.66 per night

Ciacchieri

Gaiole in Chianti
Free cancellation options available
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.

Casa Ciaccheri

Gaiole in Chianti
Free cancellation options available
Scored out of 10, guest rating 9.2
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.

Casa Ciaccheri 2

Gaiole in Chianti
Free cancellation options available
Scored out of 10, guest rating 9.6
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.

Casa Marcella nel cuore del Chianti

Gaiole in Chianti
Free cancellation options available
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 13 reviews

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

Castelli del Chianti

Gaiole in Chianti
Free cancellation options available
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 72 reviews

Featuring garden views, Castelli del Chianti provides accommodation with balcony, around 29 km from Piazza Matteotti.

Il Balcone

Gaiole in Chianti
Free cancellation options available
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.

Enjoy breakfast in Gaiole in Chianti and nearby

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 9.1
Superb - What previous guests thought, 125 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.

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, 54 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.

Gittori

Gaiole in Chianti
Breakfast options

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.

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.

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 204 reviews

Located on a hillside and surrounded by vineyards and cypress trees, Capanelle Wine Resort is around 500mt from Gaiole in Chianti's town centre.

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

Holiday Rentals with swimming pools in Gaiole in Chianti and nearby

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 10
Exceptional - What previous guests thought, 1 review

Situated in Gaiole in Chianti, Poggione features accommodation with private pool, free WiFi and free private parking for guests who drive.

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.

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 1 review

Situated in Gaiole in Chianti in the Tuscany region, Casa Dante features a balcony. Both free WiFi and parking on-site are accessible at the apartment free of charge.

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 8 reviews

Featuring air-conditioned accommodation with a terrace, Holiday Home Montechioccioli-2 by Interhome is set in Gaiole in Chianti. Guests staying at this holiday home have access to a balcony.

FAQ about holiday rentals in Gaiole in Chianti

Holiday rentals that guests love in Gaiole in Chianti

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Avg. price/night: US$168.64
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 657 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 9.3
Superb - What previous guests thought, 1,259 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 9.3
Superb - What previous guests thought, 1,259 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 9.3
Superb - What previous guests thought, 1,259 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, 81 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$109.70
Scored out of 10, guest rating 8.2
Very good - What previous guests thought, 105 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