Vacation rentals near Castello di Radda Winery
We found 5,991 vacation rentals — enter your dates for availability
If you want to to stay within easy reach of Castello di Radda Winery, scroll through and discover vacation rentals to find the perfect one for your trip. Whether you’re staying in a vacation home with family or friends, you'll have the best amenities for spending time at your home away from home, which might include a fireplace and a washer and dryer. Whatever you're looking for, you'll be sure to find a rental to meet everyone's needs, including a place that's non-smoking or offers accessibility.
Vacation rentals with weekly discounts - Castello di Radda Winery
Showing deals for:Nov 7 - Nov 14
Image gallery for Cascina Galileo
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Cascina Galileo
Florence, Città Metropolitana di Firenze
5% off
Price is CA $593
CA $593
CA $4,957 total
CA $4,957 total
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
10% off
Price is CA $1,153
CA $1,153
CA $11,147 total
CA $11,147 total
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
10% off
Price is CA $2,601
CA $2,601
CA $19,319 total
CA $19,319 total
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
10% off
Price is CA $2,149
CA $2,149
CA $16,609 total
CA $16,609 total
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 CA $2,282
CA $2,282
CA $16,969 total
CA $16,969 total
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
10% off
Price is CA $432
CA $432
CA $3,652 total
CA $3,652 total
includes taxes & fees
Image gallery for VILLA BELSOLE - Certaldo Tuscany HEATED POOL and electric car recharge
1010 out of 10 rating
Exceptional
(38 reviews)
VILLA BELSOLE - Certaldo Tuscany HEATED POOL and electric car recharge
Certaldo, Tuscany
19% off
Price is CA $973
CA $973
CA $8,500 total
CA $8,500 total
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
25% off
Price is CA $1,502
CA $1,502
CA $11,319 total
CA $11,319 total
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
15% off
Price is CA $1,089
CA $1,089
CA $8,303 total
CA $8,303 total
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
7% off
Price is CA $253
CA $253
CA $2,088 total
CA $2,088 total
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
15% off
Price is CA $1,974
CA $1,974
CA $14,665 total
CA $14,665 total
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
10% off
Price is CA $1,096
CA $1,096
CA $8,395 total
CA $8,395 total
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
15% off
Price is CA $136
CA $136
CA $1,072 total
CA $1,072 total
includes taxes & fees
Image gallery for Happy holidays in Chianti, among olives and vineyards, From Florence
9.69.6 out of 10 rating
Exceptional
(18 reviews)
Happy holidays in Chianti, among olives and vineyards, From Florence
San Casciano in Val di Pesa, Toscana
5% off
Price is CA $147
CA $147
CA $1,288 total
CA $1,288 total
includes taxes & fees
Image gallery for Cozy newly renovated 4 Bdr Villa with garden in Florence, great central location
9.89.8 out of 10 rating
Exceptional
(56 reviews)
Cozy newly renovated 4 Bdr Villa with garden in Florence, great central location
Florence, Toscana
5% off
Price is CA $956
CA $956
CA $8,049 total
CA $8,049 total
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
7% off
Price is CA $1,341
CA $1,341
CA $10,158 total
CA $10,158 total
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
10% off
Price is CA $202
CA $202
CA $1,743 total
CA $1,743 total
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
10% off
Price is CA $370
CA $370
CA $3,090 total
CA $3,090 total
includes taxes & fees
Image gallery for Beautiful Private & Luxurious Tuscan Villa Near Siena/Scenic Views/Crete Senesi
1010 out of 10 rating
Exceptional
(86 reviews)
Beautiful Private & Luxurious Tuscan Villa Near Siena/Scenic Views/Crete Senesi
Castelnuovo Berardenga
5% off
Price is CA $609
CA $609
CA $4,719 total
CA $4,719 total
includes taxes & fees
Image gallery for Holiday home in the Florentine Chianti half an hour from Florence
9.89.8 out of 10 rating
Exceptional
(57 reviews)
Holiday home in the Florentine Chianti half an hour from Florence
Montespertoli, Toscana
10% off
Price is CA $362
CA $362
CA $2,769 total
CA $2,769 total
includes taxes & fees
Image gallery for Charming Farmhouse with Private Pool among Vineyards
9.49.4 out of 10 rating
Exceptional
(50 reviews)
Charming Farmhouse with Private Pool among Vineyards
Greve in Chianti, Firenze
10% off
Price is CA $1,024
CA $1,024
CA $8,452 total
CA $8,452 total
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 CA $1,948
CA $1,948
CA $14,505 total
CA $14,505 total
includes taxes & fees
Image gallery for Tuscan village in SIena. farmhouse surrounded by garden,pool and panoramic view
1010 out of 10 rating
Exceptional
(43 reviews)
Tuscan village in SIena. farmhouse surrounded by garden,pool and panoramic view
Asciano, Toscana
5% off
Price is CA $380
CA $380
CA $3,067 total
CA $3,067 total
includes taxes & fees
Image gallery for HillsideVilla overlooking the Tuscan landscape between Florence Arezzo and Siena
1010 out of 10 rating
Exceptional
(28 reviews)
HillsideVilla overlooking the Tuscan landscape between Florence Arezzo and Siena
Loro Ciuffenna, Tuscany
6% off
Price is CA $286
CA $286
CA $2,539 total
CA $2,539 total
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Castello di Radda Winery
Farmhouse in the heart of the real chiantishire
Sleeps 4 · 2 bedrooms
1010 out of 10
Exceptionalexceptional
140 reviews(140 reviews)
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Sleeps 23 · 11 bedrooms · 11+ bathrooms
1010 out of 10
Exceptionalexceptional
60 reviews(60 reviews)
MAGNIFICENT 9BR VILLA WITH HEATED POOL & STUNNING VIEWS IN TOP CHIANTI LOCATION!
Sleeps 18 · 9 bedrooms · 7+ bathrooms
1010 out of 10
Exceptionalexceptional
40 reviews(40 reviews)
Traditional Tuscan farmhouse with stunning views
Sleeps 8 · 3 bedrooms · 3+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
97 reviews(97 reviews)
Beautiful stone house with garden and private pool.
Sleeps 5 · 1 bedroom · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
63 reviews(63 reviews)
Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany
Sleeps 10 · 5 bedrooms · 5 bathrooms
1010 out of 10
Exceptionalexceptional
103 reviews(103 reviews)
Top rated rentals - Castello di Radda Winery
Exceptional stay
1010 out of 10
Exceptionalexceptional
45 reviews(45 reviews)
Definitely works for me.
1010 out of 10
Exceptionalexceptional
62 reviews(62 reviews)
Charming Villa
1010 out of 10
Exceptionalexceptional
73 reviews(73 reviews)
Amazing location!
1010 out of 10
Exceptionalexceptional
76 reviews(76 reviews)
Great location
1010 out of 10
Exceptionalexceptional
105 reviews(105 reviews)
Breathtaking Property
1010 out of 10
Exceptionalexceptional
96 reviews(96 reviews)
quick surprise getaway
1010 out of 10
Exceptionalexceptional
43 reviews(43 reviews)
Fantastic stay for 4 weeks
1010 out of 10
Exceptionalexceptional
140 reviews(140 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, yards and more
More for lessMore space, more privacy, more amenities — more value