
Holiday rentals near Gaiole in Chianti Stadium
We found 4,974 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:14 Nov - 21 Nov
Image gallery for Wonderful Villa - Air Bubble Massage Pool - WiFi - max.14peopl

1010 out of 10 rating
Exceptional
(40 reviews)
Wonderful Villa - Air Bubble Massage Pool - WiFi - max.14peopl
Greve in Chianti, Toscana
7% off
Price is £6,188
£6,188
£884 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 £10,894
£10,894
£1,556 per night
includes taxes & fees
Image gallery for Exclusive panoramic villa with private pool between Florence and Siena.

1010 out of 10 rating
Exceptional
(16 reviews)
Exclusive panoramic villa with private pool between Florence and Siena.
Certaldo, Toscana
9% off
Price is £18,809
£18,809
£2,687 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
(76 reviews)
Exclusive 7BR-8BA Villa with pool, a few mins from town, yet in the countryside
Impruneta, Toscana
5% off
Price is £9,486
£9,486
£1,355 per night
includes taxes & fees
Image gallery for Exclusive Tuscan Winery Escape: Charming Villa with Pool & Breathtaking Views.

1010 out of 10 rating
Exceptional
(10 reviews)
Exclusive Tuscan Winery Escape: Charming Villa with Pool & Breathtaking Views.
Radda in Chianti, Provincia di Siena
5% off
Price is £8,843
£8,843
£1,263 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 £2,039
£2,039
£291 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
13% off
Price is £4,760
£4,760
£680 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 £8,261
£8,261
£1,180 per night
includes taxes & fees
Image gallery for "Borgo dei Fondi" La Loggia free wifi-free parking

9.89.8 out of 10 rating
Exceptional
(43 reviews)
"Borgo dei Fondi" La Loggia free wifi-free parking
Siena, Tuscany
6% off
Price is £1,111
£1,111
£159 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 £6,422
£6,422
£917 per night
includes taxes & fees
Image gallery for Typical Tuscan Countryside Cottage near Florence

1010 out of 10 rating
Exceptional
(28 reviews)
Typical Tuscan Countryside Cottage near Florence
Bagno a Ripoli, Tuscany
6% off
Price is £1,166
£1,166
£167 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 £1,877
£1,877
£268 per night
includes taxes & fees
Image gallery for BEAUTIFUL VILLA with private Pool in the heart of Chianti

1010 out of 10 rating
Exceptional
(25 reviews)
BEAUTIFUL VILLA with private Pool in the heart of Chianti
Castelnuovo Berardenga
6% off
Price is £5,731
£5,731
£819 per night
includes taxes & fees
Image gallery for EXCLUSIVE CHIANTI VILLA SPECTACULAR POOL TENNIS COURT 15 MIN TOFLORENCE

1010 out of 10 rating
Exceptional
(70 reviews)
EXCLUSIVE CHIANTI VILLA SPECTACULAR POOL TENNIS COURT 15 MIN TOFLORENCE
Impruneta, Tuscany
9% off
Price is £4,768
£4,768
£681 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 £964
£964
£138 per night
includes taxes & fees
Image gallery for Country Farmhouse with Magnificient Gardens near Siena, Tuscany

9.69.6 out of 10 rating
Exceptional
(24 reviews)
Country Farmhouse with Magnificient Gardens near Siena, Tuscany
Siena, Toscana
8% off
Price is £1,712
£1,712
£245 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
8% off
Price is £1,137
£1,137
£162 per night
includes taxes & fees
Image gallery for RELAX BETWEEN OLIVES AND WINEYARDS, NEAR FLORENCE

9.49.4 out of 10 rating
Exceptional
(9 reviews)
RELAX BETWEEN OLIVES AND WINEYARDS, NEAR FLORENCE
San Casciano in Val di Pesa, Tuscany
6% off
Price is £924
£924
£132 per night
includes taxes & fees
Image gallery for A Panoramic Tuscan Luxury - Villa Maria in Fronzano

1010 out of 10 rating
Exceptional
(74 reviews)
A Panoramic Tuscan Luxury - Villa Maria in Fronzano
Reggello, Toscana
5% off
Price is £8,177
£8,177
£1,168 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
13% off
Price is £585
£585
£84 per night
includes taxes & fees
Image gallery for Legnaia countryside luxury property, shared pool, ideal base to discover Tuscany

1010 out of 10 rating
Exceptional
(14 reviews)
Legnaia countryside luxury property, shared pool, ideal base to discover Tuscany
Siena, Toscana
9% off
Price is £1,779
£1,779
£254 per night
includes taxes & fees
Image gallery for Spectacular Villa sleeping 12, Large private Pool, 9 km South of Florence City

9.89.8 out of 10 rating
Exceptional
(103 reviews)
Spectacular Villa sleeping 12, Large private Pool, 9 km South of Florence City
Impruneta, Tuscany
7% off
Price is £5,805
£5,805
£829 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
(59 reviews)
Chic Tuscan apartment pool spectacular view modern comfort wifi air conditioning
Sovicille, Provincia di Siena
9% off
Price is £1,892
£1,892
£270 per night
includes taxes & fees
Image gallery for La Vecchia Posta | Charming home near Chianti and Art Cities – 2 Beds, 3 Baths

1010 out of 10 rating
Exceptional
(10 reviews)
La Vecchia Posta | Charming home near Chianti and Art Cities – 2 Beds, 3 Baths
Cavriglia, Toscana
16% off
Price is £1,128
£1,128
£161 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)
"La Casina delle Fate" a pretty little house in Tuscany
Sleeps 2 · 2 bedrooms
1010 out of 10
Exceptionalexceptional
63 reviews(63 reviews)
B&B San Paterno Classic Retrò room Double or Twin
Sleeps 2 · 1 bedroom
1010 out of 10
Exceptionalexceptional
1 review(1 review)
The Casina of San Polo in Chianti
Sleeps 5 · 1 bedroom · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
14 reviews(14 reviews)
Charming double bedroom in cottage in enchanting Monteaperti with WiFi, AC
Sleeps 2 · 1 bedroom · 1 bathroom
Chianti dreaming in Radda-3 independent bedrooms with private bathroom and TV
Sleeps 8 · 3 bedrooms · 3+ bathrooms
Top rated rentals - Gaiole in Chianti Stadium
Excellent apartment in outstanding location in the heart of Siena
1010 out of 10
Exceptionalexceptional
71 reviews(71 reviews)
A very spacious and comfortable apartment with all amenities provided. Aircon would have been a bonus given that we were in a heat wave of 39 deg C but the apartment description stated fans and that's what we had. Experiencing a Palio is a never forgotten time - such history, such passion, such brotherhood!
Jerry C.
Stayed Jun 2025
Outstanding villa
1010 out of 10
Exceptionalexceptional
68 reviews(68 reviews)
We had the most amazing time in an outstanding villa with stunning views and sunsets. The villa is spacious and very comfortable, plenty of areas to eat outside, a large shared swimming pool that was never busy and beautifully tended gardens. Honestly the best villa we have stayed in. Perfect for 6 to 8 people and everything you need provided to cook in or bbq. It’s a 10 minute drive down a dirt track but worth it! Great villages nearby and close to Siena and Florence (1 hr by car). Thank you Anna and Paul
Gini A.
Stayed Jun 2025
Absolutely beautiful villa
1010 out of 10
Exceptionalexceptional
117 reviews(117 reviews)
We went as a group of 10 friends. The villa is outstanding. Enough rooms and private bathrooms for all. The most wonderful garden and pool area. Private chef was worth every penny. Wonderful experience.
Karen O.
Stayed Sept 2024
Peaceful and relaxing
1010 out of 10
Exceptionalexceptional
63 reviews(63 reviews)
We had an amazing relaxing time. The hosts were excellent and friendly and also respected our privacy. The view from the house and pool was beautiful. The pool area is secluded and clean. The house was well equipped and the beds were very comfortable. The spare bedroom acted as a living room with big TV. The little village had a very good well stocked co-op and lovely resturants. We will be returning!
Pamela F.
Stayed Jun 2024
Perfect for us!
1010 out of 10
Exceptionalexceptional
29 reviews(29 reviews)
Possibly best equipped holiday rental we've been to! Great location in countryside with wonderful views , yet very easy access to civilisation , Autostrada and railway station - Florence 40 mins by train!
Sara is a great host helpful when needed and a mine of local information. In all we would heartily recommend it as a Tuscan base.
Paul H.
Stayed May 2024
A great place for a family holiday
1010 out of 10
Exceptionalexceptional
45 reviews(45 reviews)
Valter and his wife are kind and welcoming hosts. The apartment was well laid out and had everything we wanted. The garden was very well kept with a big pool which we spent lots of time in. Great location close to Florence and within an easy drive of Siena, with lovely local restaurants and shops within a short drive. The road by the house can be a bit busy / noisy, but that didn’t detract from an excellent holiday.
Charlie H.
Stayed Aug 2023
Excellent stay
1010 out of 10
Exceptionalexceptional
140 reviews(140 reviews)
Everything was perfect: thank you
Richard D.
Stayed Jul 2023
Break with friends
1010 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
Beautiful house and location. Lovely village as well with cafes and small shops. Well located for Sienna and Florence and the rest of Tuscany
Mike V.
Stayed Apr 2023
- 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, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value