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Search results; Over 1,000 homes in Gaiole in Chianti

Guest favorite
This restored 1700s stone house gives you vineyard views and a jacuzzi in Gaiole in Chianti
2 bedrooms, 2 beds, 1 private bath
Oct 6 – 11
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4.86 out of 5 average rating, 293 reviews
Top guest favorite
This Gaiole in Chianti villa gives you a private pool, spa, and vineyard views
4.99 out of 5 average rating, 73 reviews, 4 bedrooms, 4 beds, 4 baths
Oct 24 – 31
Luxe
Soak in valley views from the heated pool at this restored 1700s Gaiole villa
5.0 out of 5 average rating, 22 reviews, 4 bedrooms, 4 beds, 5 baths
Aug 17 – 22
Top guest favorite
This stone-built Gaiole in Chianti villa gives you vineyard views and a heated jacuzzi
4.93 out of 5 average rating, 46 reviews, 2 bedrooms, 2 beds, 2 baths
Oct 31 – Nov 7
This renovated Tuscan home in Gaiole in Chianti gives you vineyard views and a pool
3 bedrooms, 6 beds, 2 baths
Aug 17 – 22
Top guest favorite
This Gaiole in Chianti villa puts you among vineyards with a private pool and winery
5.0 out of 5 average rating, 28 reviews, 5 bedrooms, 1 bed, 5 baths
Aug 29 – Sep 3
Guest favorite
Wake to church-tower views from this stone villa in Gaiole in Chianti
5.0 out of 5 average rating, 6 reviews, 3 bedrooms, 3 beds, 3 baths
Aug 20 – 25
A converted windmill in Gaiole in Chianti where you’ll find a pool and garden
1 bedroom, 2 beds, 1 bath
Aug 23 – 28
Soak in the hot tub among olive groves at this Gaiole in Chianti villa
5.0 out of 5 average rating, 3 reviews, 1 bedroom, 1 bed, 1 bath
Aug 21 – 26
Guest favorite
Take in vineyard views from this stone villa on a Gaiole in Chianti wine estate
5.0 out of 5 average rating, 8 reviews, 2 bedrooms, 2 beds, 2 baths
Nov 1 – 6
Valley views and a private terrace await you at this historic Gaiole in Chianti apartment
3 bedrooms, 4 beds, 2 baths
Aug 29 – Sep 3
Guest favorite
This renovated Tuscan farmhouse in Radda gives you olive grove views from the terrace
4.98 out of 5 average rating, 47 reviews, 3 bedrooms, 4 beds, 3 baths
Aug 18 – 23
Top guest favorite
This Radda in Chianti villa puts you on an organic winery with a private pool
4.98 out of 5 average rating, 66 reviews, 5 bedrooms, 5 beds, 5 baths
Oct 26 – 31
Superhost
Soak in your private hot tub overlooking Tuscan hills at this Reggello tiny house
New place to stay, 1 bedroom, 1 bed, 1 bath
Aug 23 – 28
Top guest favorite
Room in Gaiole in Chianti
Argentina. Welcome to our small village, L...
4.98 out of 5 average rating, 145 reviews, 1 double bed, 1 bath
Mar 18 – 23
Top guest favorite
This San Gusmè apartment puts you in a quiet medieval village amid Chianti
4.99 out of 5 average rating, 466 reviews, 2 bedrooms, 3 beds, 2 baths
Oct 26 – 31
Guest favorite
Exposed beams and terracotta floors greet you at this renovated Radda in Chianti apartment
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 3 beds, 4 baths
Sep 6 – 11
Valley views and a private terrace greet you at this historic Gaiole in Chianti apartment
3 bedrooms, 4 beds, 1 bath
Sep 23 – 28
Guest favorite
This secluded Gaiole in Chianti villa gives you a private pool and 180-degree views
5.0 out of 5 average rating, 30 reviews, 3 bedrooms, 4 beds, 3 baths
Oct 13 – 18