Holiday rentals near Castle Arcidosso

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November 2025

December 2025

Discover a selection of holiday rentals within easy reach of Castle Arcidosso that can be your home away from home. Whether you’re travelling with friends, family or just with your pet, holiday homes have the best amenities for spending time at your holiday home, which might include a hot tub and a washer and dryer. No matter what you're looking for, you're sure to find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Castle Arcidosso

Showing deals for:30 Jan - 6 Feb

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$5,190 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$345 per night

includes taxes & fees

Exceptional

(11 reviews)

Iperbole country house, between Pienza and Montepulciano

Pienza, Toscana

5% off

for 7 nights, 1 villa

NZ$3,274 per night

includes taxes & fees

Exceptional

(14 reviews)

FARMH. PODERE CUNINA 25 KM SUD SIENA DAVANTI AL MONTALCINO TENENDO CUCINE CLAS

Buonconvento

8% off

for 7 nights, 1 room

NZ$296 per night

includes taxes & fees

Exceptional

(26 reviews)

Luxury Tuscan villa, spectacular views, beautiful pool and garden.

Pienza, Tuscany

5% off

for 7 nights, 1 villa

NZ$1,828 per night

includes taxes & fees

Exceptional

(40 reviews)

Tuscany romance. Rural charm between Montalcino and sea. Relax pur

Cinigiano, Tuscany

8% off

for 7 nights, 1 villa

NZ$935 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$1,111 per night

includes taxes & fees

Exceptional

(31 reviews)

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

Buonconvento

5% off

for 7 nights, 1 apartment

NZ$309 per night

includes taxes & fees

Exceptional

(12 reviews)

Villa D'Orchia, luxury organic farm with private pool in Val D'orcia, Sleeps 15.

Castiglione d'Orcia, Tuscany

44% off

for 7 nights, 1 villa

NZ$832 per night

includes taxes & fees

Exceptional

(7 reviews)

Südliche Toskana Modernes Ferienhaus in Alleinlage, Pool, 25km Meer, Haustiere

Campagnatico, Grosseto

8% off

for 7 nights, 1 home

NZ$316 per night

includes taxes & fees

Exceptional

(23 reviews)

Antico Podere La Martinella- Ground floor apartment

San Quirico d'Orcia, Tuscany

9% off

for 7 nights, 1 home

NZ$169 per night

includes taxes & fees

Exceptional

(17 reviews)

Charming ancient watching tower near Montepulciano and Val d'Orcia - Siena

Montepulciano

9% off

for 7 nights, 1 villa

NZ$994 per night

includes taxes & fees

Exceptional

(37 reviews)

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

Buonconvento

8% off

for 7 nights, 1 apartment

NZ$286 per night

includes taxes & fees

Exceptional

(44 reviews)

Charming Ancient Watch Tower with Swimming Pool in Val d'Orcia

Pienza, Siena

9% off

for 7 nights, 1 villa

NZ$960 per night

includes taxes & fees

Exceptional

(21 reviews)

FARMH. PODERE CUNINA 25 KM SUD SIENA / MONTALCINO PRENDENDO LEZIONI DI CUCINA

Buonconvento

8% off

for 7 nights, 1 room

NZ$387 per night

includes taxes & fees

Exceptional

(67 reviews)

Private and cozy retreat in Montalcino with private pool surrounded by vineyards

Montalcino, Tuscany

9% off

for 7 nights, 1 villa

NZ$847 per night

includes taxes & fees

Exceptional

(54 reviews)

Luxury Villa in Monticchiello, your heaven in Tuscany

Pienza, Toscana

17% off

for 7 nights, 1 apartment

NZ$242 per night

includes taxes & fees

Very good

(8 reviews)

IL Bagno - Podere 200 m from the Terme di Saturnia surrounded by a large garden

Saturnia, Tuscany

37% off

for 7 nights, 1 room

NZ$324 per night

includes taxes & fees

Exceptional

(8 reviews)

"Il Focolare" Superior Apartment in Monticchiello

Pienza, Toscana

5% off

for 7 nights, 1 home

NZ$223 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Castle Arcidosso

Showing deals for: 30 Jan - 2 Feb

Private and cozy retreat in Montalcino with private pool surrounded by vineyards

Sleeps 6 · 2 bedrooms · 2 bathrooms

for 3 nights, 1 villa

NZ$985 per night

includes taxes & fees

Breakfast, lunch and dinner with lake, vineyard and olive groves in front of you

Premier Host

INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING

Sleeps 10 · 4 bedrooms · 2 bathrooms

for 3 nights, 1 home

NZ$668 per night

includes taxes & fees

Premier Host

Charming Ancient Watch Tower with Swimming Pool in Val d'Orcia

Sleeps 13 · 4 bedrooms · 4 bathrooms

for 3 nights, 1 villa

NZ$1,076 per night

includes taxes & fees

Premier Host

Montalcino: Private villa in the heart of Tuscany, private pool,panoramic view!

Sleeps 6 · 3 bedrooms · 4 bathrooms

for 3 nights, 1 villa

NZ$1,004 per night

includes taxes & fees

Top rated rentals - Castle Arcidosso

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

Fabulous Experience

This is a modern apartment in a peaceful authentic walled city in the heart of Tuscany- Monticchiello! It has great restaurants- Daria and La Porta to name just two. It is located close to Pienza, Montipulicano, Montalcino and the Brunello wine country. Francesco is the host and owner. He provides a wonderful breakfast and free laundry service. He is very responsive and takes great care of his guests. The four of us had a wonderful time there and highly recommend this town and property. You will not be disappointed.

John M.

Stayed Sept 2022

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Holiday rentals with weekly discounts - Castle Arcidosso

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

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

Iperbole country house, between Pienza and Montepulciano

FARMH. PODERE CUNINA 25 KM SUD SIENA DAVANTI AL MONTALCINO TENENDO CUCINE CLAS

Luxury Tuscan villa, spectacular views, beautiful pool and garden.

Hortulanus private Luxury Estate

Tuscany romance. Rural charm between Montalcino and sea. Relax pur

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

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

Villa D'Orchia, luxury organic farm with private pool in Val D'orcia, Sleeps 15.

Südliche Toskana Modernes Ferienhaus in Alleinlage, Pool, 25km Meer, Haustiere

Antico Podere La Martinella- Ground floor apartment

Charming ancient watching tower near Montepulciano and Val d'Orcia - Siena

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

Charming Ancient Watch Tower with Swimming Pool in Val d'Orcia

Eco house with pool and fantastic views

FARMH. PODERE CUNINA 25 KM SUD SIENA / MONTALCINO PRENDENDO LEZIONI DI CUCINA

Private and cozy retreat in Montalcino with private pool surrounded by vineyards

Luxury Villa in Monticchiello, your heaven in Tuscany

IL Bagno - Podere 200 m from the Terme di Saturnia surrounded by a large garden

"Il Focolare" Superior Apartment in Monticchiello

Find spaces that suit your style

Find the best place to stay - Castle Arcidosso

Private and cozy retreat in Montalcino with private pool surrounded by vineyards

The House of Alice, charm and relaxation

INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING

Charming Ancient Watch Tower with Swimming Pool in Val d'Orcia

Montalcino: Private villa in the heart of Tuscany, private pool,panoramic view!

Il Poggio dell'Eremita

Top rated rentals - Castle Arcidosso

Secret Val D’Orcia

Fabulous Experience

Peace of mind

More quality time

All the privacy of home

More for less

Holiday Rental options near Castle Arcidosso

More Holiday Rentals ideas

People also search for

Holiday rentals near Castle Arcidosso

Holiday rentals with weekly discounts - Castle Arcidosso

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

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

Find spaces that suit your style

Find the best place to stay - Castle Arcidosso

Private and cozy retreat in Montalcino with private pool surrounded by vineyards

Top rated rentals - Castle Arcidosso

Secret Val D’Orcia

Peace of mind

More quality time

All the privacy of home

More for less

Holiday Rental options near Castle Arcidosso

More Holiday Rentals ideas

People also search for