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

Guest favorite
Guest suite in Gaiole in Chianti
Panoramic pool with Chianti hills views
1 bedroom, 1 bed, 1 private bath
Aug 28 – Sep 2
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4.98 out of 5 average rating, 52 reviews
Top guest favorite
Villa in Gaiole in Chianti
Pool, spa, and vineyard in Chianti
4.99 out of 5 average rating, 73 reviews, 4 bedrooms, 4 beds, 4 baths
Oct 24 – 31
Luxe
Home in Gaiole in Chianti
Restored 1700s farmhouse with spa and pool
5.0 out of 5 average rating, 22 reviews, 4 bedrooms, 4 beds, 5 baths
Aug 17 – 22
Top guest favorite
Villa in Gaiole in Chianti
Stone cottage with castle views in Chianti
4.93 out of 5 average rating, 46 reviews, 2 bedrooms, 2 beds, 2 baths
Oct 31 – Nov 7
Home in Gaiole in Chianti
Renovated Tuscan home among the vineyards
3 bedrooms, 6 beds, 2 baths
Aug 17 – 22
Top guest favorite
Villa in Gaiole in Chianti
Renovated villa on a Chianti winery
5.0 out of 5 average rating, 28 reviews, 5 bedrooms, 1 bed, 5 baths
Aug 29 – Sep 3
Guest favorite
Villa in Gaiole in Chianti
Stone villa with rooftop views and hot tub
5.0 out of 5 average rating, 6 reviews, 3 bedrooms, 3 beds, 3 baths
Aug 20 – 25
Apartment in Gaiole in Chianti
A 13th-century mill with a pool
1 bedroom, 2 beds, 1 bath
Aug 23 – 28
Villa in Gaiole in Chianti
Stone walls and a hot tub in Chianti
5.0 out of 5 average rating, 3 reviews, 1 bedroom, 1 bed, 1 bath
Aug 21 – 26
Guest favorite
Villa in Gaiole in Chianti
Stone villa on a Chianti wine estate
5.0 out of 5 average rating, 8 reviews, 2 bedrooms, 2 beds, 2 baths
Nov 1 – 6
Apartment in Gaiole in Chianti
200-year-old home with valley views and pool
3 bedrooms, 4 beds, 2 baths
Aug 29 – Sep 3
Guest favorite
Home in Radda in Chianti
Renovated farmhouse with fireplaces in Chianti
4.98 out of 5 average rating, 47 reviews, 3 bedrooms, 4 beds, 3 baths
Aug 18 – 23
Top guest favorite
Villa in Radda in Chianti
Organic winery villa in Chianti Classico
4.98 out of 5 average rating, 66 reviews, 5 bedrooms, 5 beds, 5 baths
Oct 26 – 31
Superhost
Tiny home in Reggello
Hot tub on a private Tuscan terrace
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
Apartment in San Gusmè
Medieval village immersed in Chianti
4.99 out of 5 average rating, 466 reviews, 2 bedrooms, 3 beds, 2 baths
Oct 26 – 31
Guest favorite
Apartment in Radda in Chianti
Exposed beams and terracotta among vineyards
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 3 beds, 4 baths
Sep 6 – 11
Apartment in Gaiole in Chianti
200-year-old home with valley views
3 bedrooms, 4 beds, 1 bath
Sep 23 – 28
Guest favorite
Villa in Gaiole in Chianti
Secluded Chianti villa with 180-degree views
5.0 out of 5 average rating, 30 reviews, 3 bedrooms, 4 beds, 3 baths
Oct 13 – 18