Holiday rentals near Gaiole in Chianti Stadium
We found 4,536 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:7 Nov - 14 Nov
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
7% off
Price is AU$12,509
AU$12,509
AU$1,787 per night
includes taxes & fees
Image gallery for Medieval Castle 15 km from Florence, in the heart of "Chianti Classico" region
1010 out of 10 rating
Exceptional
(23 reviews)
Medieval Castle 15 km from Florence, in the heart of "Chianti Classico" region
Greve in Chianti, Toscana
9% off
Price is AU$21,621
AU$21,621
AU$3,089 per night
includes taxes & fees
Image gallery for Gorgeous villa with new pool in the heart of Chianti (wi fi and whirlpool)
9.29.2 out of 10 rating
Wonderful
(7 reviews)
Gorgeous villa with new pool in the heart of Chianti (wi fi and whirlpool)
Radda in Chianti, Toscana
8% off
Price is AU$4,085
AU$4,085
AU$584 per night
includes taxes & fees
Image gallery for Villa in the Heart of Chianti
1010 out of 10 rating
Exceptional
(36 reviews)
Villa in the Heart of Chianti
Greve in Chianti, Tuscany
14% off
Price is AU$5,632
AU$5,632
AU$805 per night
includes taxes & fees
Image gallery for Large estate with private pool comprising 7 apartments - up to 24 people
9.49.4 out of 10 rating
Exceptional
(36 reviews)
Large estate with private pool comprising 7 apartments - up to 24 people
Greve in Chianti, Toscana
14% off
Price is AU$9,352
AU$9,352
AU$1,336 per night
includes taxes & fees
Image gallery for Exclusive Tuscan Winery Escape: Charming Villa with Pool & Breathtaking Views.
1010 out of 10 rating
Exceptional
(9 reviews)
Exclusive Tuscan Winery Escape: Charming Villa with Pool & Breathtaking Views.
Radda in Chianti, Provincia di Siena
5% off
Price is AU$17,814
AU$17,814
AU$2,545 per night
includes taxes & fees
Image gallery for ALL PROPERTY 7BR- Charming Tuscan Villa with pool, hot tub, A/C,Siena 15 km
1010 out of 10 rating
Exceptional
(120 reviews)
ALL PROPERTY 7BR- Charming Tuscan Villa with pool, hot tub, A/C,Siena 15 km
Sovicille, Italy
23% off
Price is AU$12,752
AU$12,752
AU$1,822 per night
includes taxes & fees
Image gallery for Beautiful Tuscan home between Florence & Siena
1010 out of 10 rating
Exceptional
(5 reviews)
Beautiful Tuscan home between Florence & Siena
San Casciano in Val di Pesa
9% off
Price is AU$18,654
AU$18,654
AU$2,665 per night
includes taxes & fees
Image gallery for Beautifully restored farmhouse in Greve, heart of Chianti
9.89.8 out of 10 rating
Exceptional
(26 reviews)
Beautifully restored farmhouse in Greve, heart of Chianti
Greve in Chianti, Chianti
5% off
Price is AU$7,202
AU$7,202
AU$1,029 per night
includes taxes & fees
Image gallery for House in Chianti - La Capanna
1010 out of 10 rating
Exceptional
(5 reviews)
House in Chianti - La Capanna
Greve in Chianti, Tuscany
9% off
Price is AU$2,033
AU$2,033
AU$290 per night
includes taxes & fees
Image gallery for Exclusive 7BR-8BA Villa with pool, a few mins from town, yet in the countryside
1010 out of 10 rating
Exceptional
(75 reviews)
Exclusive 7BR-8BA Villa with pool, a few mins from town, yet in the countryside
Impruneta, Toscana
5% off
Price is AU$19,040
AU$19,040
AU$2,720 per night
includes taxes & fees
Image gallery for Special offer Newly renovated fine detached villa with fireplace.
8.68.6 out of 10 rating
Excellent
(11 reviews)
Special offer Newly renovated fine detached villa with fireplace.
Castelnuovo Berardenga, Tuscany
8% off
Price is AU$1,295
AU$1,295
AU$185 per night
includes taxes & fees
Image gallery for FABULOUS 6BR HOME WITH WONDERFUL SWIMMING POOL & GARDEN IN THE HEART OF TUSCANY!
1010 out of 10 rating
Exceptional
(20 reviews)
FABULOUS 6BR HOME WITH WONDERFUL SWIMMING POOL & GARDEN IN THE HEART OF TUSCANY!
Lucignano, Tuscany
9% off
Price is AU$7,951
AU$7,951
AU$1,136 per night
includes taxes & fees
Image gallery for Le Redi: sustainable geothermal country villa, amazing views over Chianti hills
9.89.8 out of 10 rating
Exceptional
(44 reviews)
Le Redi: sustainable geothermal country villa, amazing views over Chianti hills
Castelnuovo Berardenga, Tuscany
14% off
Price is AU$2,959
AU$2,959
AU$423 per night
includes taxes & fees
Image gallery for Agriturismo San Silvestro - Your home with pool in the hills of Chianti
9.49.4 out of 10 rating
Exceptional
(25 reviews)
Agriturismo San Silvestro - Your home with pool in the hills of Chianti
Barberino Val d'Elsa, Tuscany
9% off
Price is AU$2,275
AU$2,275
AU$325 per night
includes taxes & fees
Image gallery for Single-level Villa, panoramic position, AC, 6x16m private Pool, Whirlpool & Spa
1010 out of 10 rating
Exceptional
(146 reviews)
Single-level Villa, panoramic position, AC, 6x16m private Pool, Whirlpool & Spa
Castellina in Chianti, Tuscany
12% off
Price is AU$5,673
AU$5,673
AU$810 per night
includes taxes & fees
Image gallery for FALCO: Peaceful farmcottage close to Tuscany 's treasures, 1 mile from shops
9.49.4 out of 10 rating
Exceptional
(18 reviews)
FALCO: Peaceful farmcottage close to Tuscany 's treasures, 1 mile from shops
Poggibonsi, Tuscany
8% off
Price is AU$1,946
AU$1,946
AU$278 per night
includes taxes & fees
Image gallery for Stunning Villa: 24 guests, private SwimmingPool
9.89.8 out of 10 rating
Exceptional
(28 reviews)
Stunning Villa: 24 guests, private SwimmingPool
Sovicille, Provincia di Siena
14% off
Price is AU$16,505
AU$16,505
AU$2,358 per night
includes taxes & fees
Image gallery for BEAUTIFUL VILLA with private Pool in the heart of Chianti
1010 out of 10 rating
Exceptional
(24 reviews)
BEAUTIFUL VILLA with private Pool in the heart of Chianti
Castelnuovo Berardenga
6% off
Price is AU$11,402
AU$11,402
AU$1,629 per night
includes taxes & fees
Image gallery for "Borgo dei Fondi" Il Forno Primo Piano free wifi-free parking
9.69.6 out of 10 rating
Exceptional
(35 reviews)
"Borgo dei Fondi" Il Forno Primo Piano free wifi-free parking
Siena, Tuscany
6% off
Price is AU$2,158
AU$2,158
AU$308 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$1,673
AU$1,673
AU$239 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$1,673
AU$1,673
AU$239 per night
includes taxes & fees
Image gallery for Secluded Villa, private heated Pool, Wi-fi and TV. Secure Payment
9.29.2 out of 10 rating
Wonderful
(25 reviews)
Secluded Villa, private heated Pool, Wi-fi and TV. Secure Payment
Civitella in Val di Chiana, Province of Arezzo
8% off
Price is AU$3,734
AU$3,734
AU$533 per night
includes taxes & fees
Image gallery for The Photographer's House
1010 out of 10 rating
Exceptional
(11 reviews)
The Photographer's House
Colle di Val d'Elsa, Toscana
14% off
Price is AU$1,197
AU$1,197
AU$171 per night
includes taxes & fees
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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
9.69.6 out of 10
Exceptionalexceptional
13 reviews(13 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)
Awesome apartment in Castelfranco Piandiscò
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
B&B San Paterno Classic Retrò room Double or Twin
Sleeps 2 · 1 bedroom
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Top rated rentals - Gaiole in Chianti Stadium
Amazing
1010 out of 10
Exceptionalexceptional
140 reviews(140 reviews)
We loved our stay! The Farmhouse is really lovely and the view out the back is exceptional. We enjoyed a lot of home cooked meals with the most stunning view. Daniele was amazing to communicate with as well. Definitely hope to be back one day!
Rebekah T.
Stayed July 2025
Beautiful Tuscan Villa
1010 out of 10
Exceptionalexceptional
102 reviews(102 reviews)
We had the most beautiful stay, check in was very easy and communication was wonderful.
We also booked Elisa who is a private chef that Simone recommended and she was so wonderful, food and hospitality was amazing and highly recommended.
Villa is an easy drive to Siena and also a local supermarket.
Highly recommended, the views and villa are just spectacular.
laura b.
Stayed June 2024
A slice of Tuscan heaven
1010 out of 10
Exceptionalexceptional
66 reviews(66 reviews)
My family, including my parents and children, spent the most wonderful week at this beautiful property! The house and private outdoor terrace is huge, with lots of different spaces to spend eating and drinking and relaxing. The pool was incredible - the kids loved the diving board and making friends with other children who were also staying in the hamlet.
It was the perfect house for us to spend a week relaxing in Tuscany!
Amanda O.
Stayed Aug 2019
Amazing
1010 out of 10
Exceptionalexceptional
73 reviews(73 reviews)
Our stay was incredible! Everything as per pictures, Sergio and Elena were very helpful!! Would definitely recommend this place ! You can’t get a better view or place than this!!
Jenelle C.
Stayed Apr 2019
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