Holiday rentals near Pista Internazionale di Siena

We found 3,541 holiday rentals — enter your dates for availability

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October 2025

November 2025

Holiday rentals with weekly discounts - Pista Internazionale di Siena

Showing deals for:23 Jan - 30 Jan

Exceptional

(13 reviews)

Recently restored Villa in Tuscany, sleeps 12, sw.pool, gym, big garden.

San Giovanni d'Asso, Provincia di Siena

9% off

for 7 nights, 1 villa

NZ$4,785 per night

includes taxes & fees

Villa Le Caggia.........your home away from home in Tuscany!!!! .

Exceptional

(9 reviews)

ALL PROPERTY 7BR - Charming Tuscan Villa with pool, hot tub, A/C,Siena 15 km

Sovicille, Toscana

22% off

for 7 nights, 1 villa

NZ$2,220 per night

includes taxes & fees

Exceptional

(40 reviews)

PRIVATE VILLA IN THE HEART OF CHIANTI with pools and stunning views

Castelnuovo Berardenga, Tuscany

9% off

for 7 nights, 1 villa

NZ$1,507 per night

includes taxes & fees

Exceptional

(11 reviews)

"Borgo dei Fondi" Splendid Farmhouse free wifi-free parking

Siena, Tuscany

5% off

for 7 nights, 1 villa

NZ$1,567 per night

includes taxes & fees

Wonderful

(6 reviews)

Wonderful apartment in a Tuscan farmhouse with swimming pool and panoramic terrace

Casole d'Elsa, Tuscany

8% off

for 7 nights, 1 apartment

NZ$229 per night

includes taxes & fees

Exceptional

(13 reviews)

Exclusive Villa 18th century, with pool. Fine winery in Chianti central Tuscany

Bucine, Tuscany

25% off

for 7 nights, 1 home

NZ$4,057 per night

includes taxes & fees

Exceptional

(25 reviews)

Country Farmhouse with Magnificient Gardens near Siena, Tuscany

Siena, Toscana

8% off

for 7 nights, 1 room

NZ$445 per night

includes taxes & fees

Exceptional

(25 reviews)

Villa Banditello, secluded, panoramic view over Montepulciano valley.

Torrita di Siena, Tuscany

9% off

for 7 nights, 1 home

NZ$520 per night

includes taxes & fees

Exceptional

(13 reviews)

Beautiful farmhouse nestled in very sweet hills just a few minutes from Siena

Siena, Provincia di Siena

9% off

for 7 nights, 1 home

NZ$1,938 per night

includes taxes & fees

Exceptional

(13 reviews)

15th century barn fully renovated in a stylish style with gorgeous swimming pool

Monteriggioni, Provincia di Siena

9% off

for 7 nights, 1 villa

NZ$1,599 per night

includes taxes & fees

Exceptional

(23 reviews)

FARMH. PODERE CUNINA 25 KM SUD SIENA DI FRONTE AL MONTALCINO PRENDENDO CUCINE DI CUCINA

Buonconvento

8% off

for 7 nights, 1 room

NZ$343 per night

includes taxes & fees

Wonderful

(7 reviews)

Gorgeous villa with new pool in the heart of Chianti (wi fi and whirlpool)

Radda in Chianti, Toscana

8% off

for 7 nights, 1 villa

NZ$667 per night

includes taxes & fees

Exceptional

(64 reviews)

Arco al Poggio, Arceno Rentals Club, Spacious Chianti Apt, Pool, Concierge, WiFi

Castelnuovo Berardenga, Toscana

14% off

for 7 nights, 1 apartment

NZ$573 per night

includes taxes & fees

Exceptional

(34 reviews)

Beautiful house on garden with shared pool just a few minutes Siena Tuscany

Siena, Tuscany

9% off

for 7 nights, 1 home

NZ$1,289 per night

includes taxes & fees

Exceptional

(25 reviews)

Wonderful new villa in Maremma, near Montalcino and Castiglione della Pescaia

Montalcino, Toscana

9% off

for 7 nights, 1 villa

NZ$1,114 per night

includes taxes & fees

Exceptional

(8 reviews)

Apartment in renovated farmhouse in typical Chianti Tuscan village

Castelnuovo Berardenga, Toscana

7% off

for 7 nights, 1 home

NZ$285 per night

includes taxes & fees

Exceptional

(17 reviews)

Legnaia countryside luxury property, shared pool, ideal base to discover Tuscany

Siena, Toscana

14% off

for 7 nights, 1 home

NZ$675 per night

includes taxes & fees

Exceptional

(24 reviews)

Idyllic guest house in Tuscan country house style with swimming pool

Sinalunga, Siena

8% off

for 7 nights, 1 home

NZ$313 per night

includes taxes & fees

Find spaces that suit your style

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Condo/Apartment

Find the best place to stay - Pista Internazionale di Siena

Premier Host

Farmhouse in the heart of the real chiantishire

Sleeps 4 · 2 bedrooms

Beautiful view of the entire property - main house + 2 guesthouses

Premier Host

ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views

Sleeps 23 · 11 bedrooms · 11+ bathrooms

MAGNIFICENT 9BR VILLA WITH HEATED POOL & STUNNING VIEWS IN TOP CHIANTI LOCATION!

Sleeps 18 · 9 bedrooms · 7+ bathrooms

Top rated rentals - Pista Internazionale di Siena

Premier Host

Secret Val D’Orcia

We have stayed in the Val D’Orcia before - it’s an area we love, but this was really next level.Privacy, huge beautiful grounds and amazing views from every window!Wonderful hosts who went out of their way to make this the most special stay - thank you, it was amazing!

Vernon H.

Stayed May 2025

Premier Host

A wonderful Tuscan getaway

A wonderful, picturesque place to stay, only an hour out of Florence. Grazia, our hostess, was incredibly accommodating and a delight to talk with. My biggest complaint is that I didn’t get to stay longer! We will be back, and will definitely recommend to all who want a relaxing Tuscan experience.

Alicia D.

Stayed May 2023

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Enjoy full kitchens, laundry, pools, gardens and more
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