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Gaiole in Chianti Rentals

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2,514 Houses

Podere Lucignano Secondo - Apt. La Mangiatoia (ground floor)

Nusenna villa

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$213

Tower Gates - luxury villa in Chianti!

Gaiole in Chianti villa

7 bedrooms / 4 bathrooms / sleeps 14

Responds fast! avg. 1 hour 43 minutes

Price per night from

$783

Casa il Mandorlo private garden - pool

Gaiole in Chianti house

2 bedrooms / 1 bathroom / sleeps 2

Price per night from

$125

Hermitage Cloister

Gaiole in Chianti apartment

4 bedrooms / 3 bathrooms / sleeps 7

Price per night from

$681

Hermitage Granary

Gaiole in Chianti apartment

4 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$681

Amazing stay in the heart of Tuscany, Chianti area

Gaiole in Chianti house

5 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$239

Gaiole Suites - Gaiole Suites 4

Gaiole in Chianti house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$88

Podere Lucignano Secondo - Charming Tuscan Villa

Nusenna villa

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$481

Le Pratola Luxury Villa in Chianti with Heated Pool, top rated reviews.

Gaiole in Chianti villa

5 bedrooms / 6 bathrooms / sleeps 13

“Unforgettable Vacation!” My family and I (six of us) stayed at Le Pratola for a week in June. We had such a great time. The villa is beautiful and comfortable, and the views of the Tuscan hills are stunning. The team at Le Pratola is amazing. Laura, the cleaning lady, is a doll. The cooking class with Barbara is so much fun! Elena and Monica's (the personal chefs) meals are delicious. The villa is beautifully decorated and so comfortable. We all had the best vacation! We will definitely recommend the villa to family and friends. It was the best trip we've ever been on! We would like to thank the team at Le Pratola for making our vacation to Tuscany so special.

Price per night from

$2,190

Villa il Roseto

Gaiole in Chianti house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,022

Gaiole Suites - Gaiole Suites 6

Gaiole in Chianti house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$72

Hermitage Magnolia

Gaiole in Chianti apartment

3 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$568

San Sano hamlet in the Heart of the Chianti, the Best choice in Tuscany !

Gaiole in Chianti house

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$171

Gaiole Suites - Gaiole Suites 9

Gaiole in Chianti house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$88

Villa Herakles

Gaiole in Chianti house

4 bedrooms / 5 bathrooms / sleeps 8

Responds fast! avg. 1 hour 47 minutes

Price per night from

$704

Gaiole Apartment - Gaiole Apartment 15

Gaiole in Chianti house

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$67

Podere Lucignano Secondo - Apt. Le Logge (first floor)

Nusenna villa

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$268

The Nibbio

Gaiole in Chianti house

3 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$195

Hermitage factor

Gaiole in Chianti apartment

2 bedrooms / 1 bathroom / sleeps 3

Price per night from

$341

Gaiole Suites - Gaiole Suites 3

Gaiole in Chianti house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$88

Gaiole Suites - Gaiole Suites 1

Gaiole in Chianti house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$88

Gaiole Suites - Gaiole Suites 2

Gaiole in Chianti house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$88

Gaiole Apartment - Gaiole Apartment 13

Gaiole in Chianti house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$67

Casa Felice is a 2 bedroom apartment in village of Gaiole, sleeps 6, shared pool

Gaiole in Chianti apartment

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$96

Barn overlooking the vineyards

Gaiole in Chianti barn

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$148

Private secluded retreat in the Chianti hills between Siena and Florence

Gaiole in Chianti villa

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$592

A HOLIDAY IN THE HEART OF CHIANTI

Gaiole in Chianti villa

2 bedrooms / 4 bathrooms / sleeps 6

Price per night from

$171

UNA VACANZA DA SOGNO

Gaiole in Chianti house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$171

Chianti house, Florence, Siena, Arezzo, Tuscany

Montefienali guest house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$76

TOSCANAFERIEN - PODERE L'AQUILA - OSKAR SIGRIST

Gaiole in Chianti apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$96

LUXURY APARTMENT WITH PRIVATE GARDEN & VIEWS IDEAL FOR COUPLES

Gaiole in Chianti apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$141

Il Borghetto, Gaiole-in-Chianti

Lecchi b&b

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$125

PODERE MONTELUCCI - GAIOLE IN CHIANTI

Gaiole in Chianti villa

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$535

Casa Ciaccheri

Gaiole in Chianti apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 57 minutes

Price per night from

$137

Apartment LA LOGGIA in the heart of Chianti Senes

Gaiole in Chianti apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$159

Montechioccioli

Castagnoli house

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 2 hours 47 minutes

Price per night from

$113

Montelucci

Barbischio house

4 bedrooms / 4 bathrooms / sleeps 14

Responds fast! avg. 2 hours 47 minutes

Price per night from

$520

Il Molino

Castagnoli house

5 bedrooms / 5 bathrooms / sleeps 9

Responds fast! avg. 2 hours 50 minutes

Price per night from

$384

Viewing 38 of 2,514
rentals in Gaiole in Chianti

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Top Destination reviews

Le Pratola Luxury Villa in Chianti with Heated Pool, top rated reviews.
Real Life ... Under The Tuscan Sun

My family and I spent one week in this fabulous villa. The villa and the surrounding property are magnificent. Margherita made every effort to maintain communication throughout our stay to make sure we were enjoying ourselves and had everything we needed. She helped arrange so much for us ... transportation for sightseeing, reservations at restaurants, babysitter, car rental, and recommendations of things to do. One of the very biggest highlights of our stay was having this fabulous, adorable little Italian woman come in to cook meals for us. We loved everything that she made and would have loved to have her there every night. Her cooking was a real treat enjoyed outdoors with the vineyard as our background. I very much liked that we had another lovely caring Italian lady that came in every day to clean the downstairs of the villa ( we added that she also do the upstair bedrooms and baths as an extra charge ). It represented to me that Margherita took prided in her villa and making sure her guests were cared for and comfortable. I think it is very important to know, however, that the location is somewhat isolated and that you do need a car to get around. I had no idea where I was and it took a bit to figure that out and feel comfortable. I probably should have done my homework before arriving but it all worked out. Thanks for a lovely holiday Margherita!!!see more

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