Gaiole in Chianti Rentals

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

Nusenna villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$255

Tower Gates - luxury villa in Chianti!

Gaiole in Chianti villa

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 14

Price per night from

$768

Casa il Mandorlo private garden - pool

Gaiole in Chianti house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

Price per night from

$134

Hermitage Cloister

Gaiole in Chianti apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

Price per night from

$349

Hermitage Granary

Gaiole in Chianti apartment

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$378

Amazing stay in the heart of Tuscany, Chianti area

Gaiole in Chianti house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$256

Podere Lucignano Secondo - Charming Tuscan Villa

Nusenna villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$573

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

$2,349

Villa il Roseto

Gaiole in Chianti house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$1,197

Hermitage Magnolia

Gaiole in Chianti apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$378

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

$183

Villa Herakles

Gaiole in Chianti house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 54 minutes

Price per night from

$1,272

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

Nusenna villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$305

The Nibbio

Gaiole in Chianti house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$209

Hermitage factor

Gaiole in Chianti apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

Price per night from

$224

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

$105

Barn overlooking the vineyards

Gaiole in Chianti barn

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$159

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

$635

A HOLIDAY IN THE HEART OF CHIANTI

Gaiole in Chianti villa

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 6

Price per night from

$183

UNA VACANZA DA SOGNO

Gaiole in Chianti house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$220

Chianti house, Florence, Siena, Arezzo, Tuscany

Montefienali guest house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$82

TOSCANAFERIEN - PODERE L'AQUILA - OSKAR SIGRIST

Gaiole in Chianti apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$103

LUXURY APARTMENT WITH PRIVATE GARDEN & VIEWS IDEAL FOR COUPLES

Gaiole in Chianti apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$112

Il Borghetto, Gaiole-in-Chianti

Lecchi b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$134

PODERE MONTELUCCI - GAIOLE IN CHIANTI

Gaiole in Chianti villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$574

Casa Ciaccheri

Gaiole in Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$146

Apartment LA LOGGIA in the heart of Chianti Senes

Gaiole in Chianti apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$171

Vertine Spa Apartment

Gaiole in Chianti townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

Price per night from

$244

La Canonica di Vertine

Gaiole in Chianti house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

Price per night from

$696

Abbey of 1051

Gaiole in Chianti apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$268

Casale Montelucci

Gaiole in Chianti villa

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

Price per night from

$692

Villa Fauno A

Rietine apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 54 minutes

Price per night from

$561

Villa Radda - Villa with pool near Gaiole in Chianti

Gaiole in Chianti villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

Price per night from

$663

Canonica

Gaiole in Chianti villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

Price per night from

$602

Mulino nel Chianti 10, Emma Villas

Gaiole in Chianti villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$761

Montefienali Hamlet Aprt Il Portico n. 7

Nusenna apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Price per night from

$195

Il Colombaio by VacaVilla

Gaiole in Chianti villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$286

Villa Fauno D

Rietine apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 54 minutes

Price per night from

$561

Viewing 38 of 2,133
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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