Holiday rentals near Gaiole in Chianti Stadium
We found 4,507 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals close to Gaiole in Chianti Stadium that provide the perfect home base for your trip. Whether you're travelling with your children and pets, with friends or just your children, holiday homes have the amenities that you need and want for your stay, which might include cable TV and a washer and dryer. You'll be sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Gaiole in Chianti Stadium
Showing deals for:19 Sept - 26 Sept
Image gallery for Exclusive panoramic villa with private pool between Florence and Siena.
1010 out of 10 rating
Exceptional
(15 reviews)
Exclusive panoramic villa with private pool between Florence and Siena.
Certaldo, Toscana
10% off
Price is AU$18,314
AU$18,314
AU$2,616 per night
includes taxes & fees
Image gallery for Stunning private Castle 9 BR - 8 BA with pool just 7 miles from Florence!
1010 out of 10 rating
Exceptional
(6 reviews)
Stunning private Castle 9 BR - 8 BA with pool just 7 miles from Florence!
Impruneta, Toscana
9% off
Price is AU$39,608
AU$39,608
AU$5,658 per night
includes taxes & fees
Image gallery for Breathtaking views of the Chianti hills, Tradition, Sustainability and Design
1010 out of 10 rating
Exceptional
(23 reviews)
Breathtaking views of the Chianti hills, Tradition, Sustainability and Design
Montespertoli
9% off
Price is AU$10,135
AU$10,135
AU$1,448 per night
includes taxes & fees
Image gallery for CHIANTI VILLA & studio, max12, super-large pool, hilltop secluded fab views,
9.89.8 out of 10 rating
Exceptional
(19 reviews)
CHIANTI VILLA & studio, max12, super-large pool, hilltop secluded fab views,
Gaiole in Chianti, Tuscany
9% off
Price is AU$7,176
AU$7,176
AU$1,025 per night
includes taxes & fees
Image gallery for Wonderful Villa - Air Bubble Massage Pool - WiFi - max.14peopl
1010 out of 10 rating
Exceptional
(39 reviews)
Wonderful Villa - Air Bubble Massage Pool - WiFi - max.14peopl
Greve in Chianti, Toscana
8% off
Price is AU$14,342
AU$14,342
AU$2,049 per night
includes taxes & fees
Image gallery for Lovely country house in the Chianti region, for 4 persons, near Siena
9.09.0 out of 10 rating
Wonderful
(10 reviews)
Lovely country house in the Chianti region, for 4 persons, near Siena
Castellina in Chianti, Tuscany
13% off
Price is AU$1,982
AU$1,982
AU$283 per night
includes taxes & fees
Image gallery for A Panoramic Tuscan Luxury - Villa Maria in Fronzano
1010 out of 10 rating
Exceptional
(71 reviews)
A Panoramic Tuscan Luxury - Villa Maria in Fronzano
Reggello, Toscana
5% off
Price is AU$15,031
AU$15,031
AU$2,147 per night
includes taxes & fees
Image gallery for Under the Tuscan sun
9.49.4 out of 10 rating
Exceptional
(9 reviews)
Under the Tuscan sun
Monteroni d'Arbia, Tuscany
8% off
Price is AU$1,690
AU$1,690
AU$241 per night
includes taxes & fees
Image gallery for GUFO: Peaceful apartment close to Tuscany 's best treasures, 1 mile from shops
9.69.6 out of 10 rating
Exceptional
(15 reviews)
GUFO: Peaceful apartment close to Tuscany 's best treasures, 1 mile from shops
Poggibonsi, Tuscany
8% off
Price is AU$1,670
AU$1,670
AU$239 per night
includes taxes & fees
Image gallery for Sangiovese Country House, apartment with pool in a small village in the hills of Chianti
1010 out of 10 rating
Exceptional
(17 reviews)
Sangiovese Country House, apartment with pool in a small village in the hills of Chianti
Tavarnelle Val di Pesa, Tuscany
6% off
Price is AU$2,357
AU$2,357
AU$337 per night
includes taxes & fees
Image gallery for Farmhouse 15th century in Chianti with private garden and lake
1010 out of 10 rating
Exceptional
(13 reviews)
Farmhouse 15th century in Chianti with private garden and lake
Radda in Chianti, Tuscany
8% off
Price is AU$2,092
AU$2,092
AU$299 per night
includes taxes & fees
Image gallery for BEAUTIFUL VILLA with private Pool in the heart of Chianti
1010 out of 10 rating
Exceptional
(21 reviews)
BEAUTIFUL VILLA with private Pool in the heart of Chianti
Castelnuovo Berardenga
5% off
Price is AU$14,993
AU$14,993
AU$2,142 per night
includes taxes & fees
Image gallery for Chic Tuscan apartment pool spectacular view modern comfort wifi air conditioning
9.89.8 out of 10 rating
Exceptional
(55 reviews)
Chic Tuscan apartment pool spectacular view modern comfort wifi air conditioning
Sovicille, Provincia di Siena
9% off
Price is AU$3,773
AU$3,773
AU$539 per night
includes taxes & fees
Image gallery for RONDINE: Peaceful farmhouse close to Tuscany 's treasures, 1mile from shops far
1010 out of 10 rating
Exceptional
(14 reviews)
RONDINE: Peaceful farmhouse close to Tuscany 's treasures, 1mile from shops far
Poggibonsi, Tuscany
8% off
Price is AU$1,724
AU$1,724
AU$246 per night
includes taxes & fees
Image gallery for Ancient house in Chianti Hills with private lake and garden
1010 out of 10 rating
Exceptional
(5 reviews)
Ancient house in Chianti Hills with private lake and garden
Radda in Chianti, Tuscany
8% off
Price is AU$1,950
AU$1,950
AU$279 per night
includes taxes & fees
Image gallery for Stone Farmhouse in Chianti Hill between Florence, Siena private veranda and lake
1010 out of 10 rating
Exceptional
(33 reviews)
Stone Farmhouse in Chianti Hill between Florence, Siena private veranda and lake
Radda in Chianti, Tuscany
8% off
Price is AU$2,401
AU$2,401
AU$343 per night
includes taxes & fees
Image gallery for PASSERO:Peaceful farmhouse close to Tuscany 's best treasures, 1 mile from shops
9.29.2 out of 10 rating
Wonderful
(20 reviews)
PASSERO:Peaceful farmhouse close to Tuscany 's best treasures, 1 mile from shops
Poggibonsi, Tuscany
7% off
Price is AU$2,408
AU$2,408
AU$344 per night
includes taxes & fees
Image gallery for Ancient Cottage in Chianti
9.49.4 out of 10 rating
Exceptional
(8 reviews)
Ancient Cottage in Chianti
Castellina in Chianti, Tuscany
9% off
Price is AU$1,566
AU$1,566
AU$224 per night
includes taxes & fees
Image gallery for Ancient stone farmhouse on a top of Chianti Hill with private garden and lake
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Ancient stone farmhouse on a top of Chianti Hill with private garden and lake
Radda in Chianti, Tuscany
8% off
Price is AU$1,846
AU$1,846
AU$264 per night
includes taxes & fees
Image gallery for Studio in Chianti Villa in heart of Tuscany, super-large pool, 14 ha property
8.48.4 out of 10 rating
Very good
(10 reviews)
Studio in Chianti Villa in heart of Tuscany, super-large pool, 14 ha property
Gaiole in Chianti, Toscana
8% off
Price is AU$1,767
AU$1,767
AU$252 per night
includes taxes & fees
Image gallery for old barn on Via Francigena
9.89.8 out of 10 rating
Exceptional
(11 reviews)
old barn on Via Francigena
Siena, Toscana
13% off
Price is AU$1,544
AU$1,544
AU$221 per night
includes taxes & fees
Image gallery for Charming House Siena center
9.89.8 out of 10 rating
Exceptional
(8 reviews)
Charming House Siena center
Siena, Toscana
8% off
Price is AU$2,455
AU$2,455
AU$351 per night
includes taxes & fees
Image gallery for A luxury escape in Chianti, great landscape, stunning views, swimming pool
9.09.0 out of 10 rating
Wonderful
(19 reviews)
A luxury escape in Chianti, great landscape, stunning views, swimming pool
Greve in Chianti, Tuscany
8% off
Price is AU$3,026
AU$3,026
AU$432 per night
includes taxes & fees
Image gallery for 2 bedrooms, large pool, stunning views of San Gimignano, Tuscany, private garden
8.48.4 out of 10 rating
Very good
(9 reviews)
2 bedrooms, large pool, stunning views of San Gimignano, Tuscany, private garden
San Gimignano, Tuscany
9% off
Price is AU$2,918
AU$2,918
AU$417 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Gaiole in Chianti Stadium
country house in the Chianti area
Sleeps 4 · 2 bedrooms · 1 bathroom
8.68.6 out of 10
Excellentexcellent
14 reviews(14 reviews)
The Casina of San Polo in Chianti
Sleeps 5 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
12 reviews(12 reviews)
Apartment 'Un Oasi Di Tranquillità' with Mountain View, Private Garden and Wi-Fi
Sleeps 4 · 2 bedrooms · 1 bathroom
Our cottage, in the beautiful Tuscan countryside, not far from the cities of art
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Beautiful apartment
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
Holiday apartment embedded in the Tuscan landscape
Sleeps 2 · 1 bedroom · 1 bathroom
8.88.8 out of 10
Excellentexcellent
3 reviews(3 reviews)
Top rated rentals - Gaiole in Chianti Stadium
Amazing house like a dream.
1010 out of 10
Exceptionalexceptional
26 reviews(26 reviews)
Fabulous in Chianti
1010 out of 10
Exceptionalexceptional
57 reviews(57 reviews)
Amazing
1010 out of 10
Exceptionalexceptional
95 reviews(95 reviews)
Beautiful farmhouse in Chianti
1010 out of 10
Exceptionalexceptional
137 reviews(137 reviews)
Loved our Tuscan villa!
1010 out of 10
Exceptionalexceptional
142 reviews(142 reviews)
A slice of Tuscan heaven
1010 out of 10
Exceptionalexceptional
63 reviews(63 reviews)
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value