Castiglione d'Orcia

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Satellite / Cable TV

Smart TV

Board Games

Library of Books

Entertainment

Bathrobes

Bathtub

Changing Table

Hair Dryer

Heated Towel Rail

Rain Shower

Toiletries

Bathroom

Cafetiere

Coffee Maker

Cooking Essentials

Dishwasher

Espresso Machine

Freezer

Fridge

High Chair

Kettle

Kitchen

Kitchen Utensils

Microwave

Oven

Pod Coffee Machine

Stove

Toaster

Kitchen & Dining

Black-Out Blinds

Cleaning Products

Cot / Crib

Dryer

Drying Rack

Extra Pillows and Blankets

Hangers

Iron

Ironing Board

Laundry Supplies

Luxury Bedding

Washing Machine

Bedroom & Laundry

Heated Pool

Outdoor Pool

Private Pool

Sauna

Sauna / Steam Room

Steam Room

Swimming Pool

Wellness & Fitness

Desk

Laptop Friendly Workspace

Wi-fi

Internet & Office

Air Conditioning

Central Heating

Fireplace

Temperature Control

Underfloor Heating

Heating & Cooling

Free Parking On Street

Free Parking On Premises

Valet Parking

Parking Available

Private Entrance

Self Check-in / Check-out

Step-Free Access

Parking & Access

Balcony

Balcony / Patio

Barbeque

Beach Essentials

Courtyard

Fenced Pool

Fenced Property

Garden

Hammock

Herb Garden

Outdoor Fireplace / Firepit

Outdoor Seating

Outdoor Shower

Patio / Terrace

Rooftop Terrace

Sun Loungers / Beach Chairs

Sun Umbrellas

Outdoor

Mosquito Net

Resort Access

Umbrellas

Nice to haves

Pets Allowed

Pets

Carbon Monoxide Detector

Child Friendly

Fire Extinguisher

First Aid Kit

Smoke Detector

Other

This villa captures the rustic charm of old Italy. Surrounded by 40 hectares of land boasting olive groves, vineyards, orchards, and meadows with grazing horses, it’s an idyllic escape into the Tuscan countryside. A country road leads to the UNESCO hamlet of Castiglione d'Orcia. The garden is home to a rustic outdoor cooking station, a large, shaded table, and a full outdoor lounge. There’s a touch of modernity to the private, heated pool and you’ll find a sauna hidden amid the trees. The main villa is split across two levels and is a vision of old-world Italy and there is a separate annexe with further bedrooms, a second full kitchen and an open-plan living room. 

Rusticana Retreat

Games Room

Baby Bath

Blender

Vacuum Cleaner

Hot Tub

Electricity Adaptors

Workplace

Wheelchair Access

Fenced Garden

Meeting / Conference Rooms

Old collides with new at this secluded villa in the middle of the south Tuscan hills. Days can be spent hopping between the vineyards of the Val d’Orcia or day-tipping to the UNESCO village of Castiglione d'Orcia, a short drive away. This Tuscan farmhouse is surrounded by forest-clad hills, creating a beautiful view from the myriad terraces and patios where you can dine and recline. A private pool awaits for hot days and there’s a barbecue with a view. Oodles of space inside allows big groups to spread out – across the cosy farmhouse living room, the family snug and a vast chill-out room with a teepee and boho-style lounge areas. 

Artistic Retreat

Private Parking

Free Parking

Immerse yourself in the heart of Tuscany with this charming villa, nestled along the historic Via Francigena. Beautifully restored, this home seamlessly blends traditional Tuscan features with modern comforts. And, thanks to its interconnecting apartments and plethora of outdoor space, it’s ideal for extended families or groups of friends, offering ample room for everyone. Dive into the refreshing pool, overlooking the Val d'Orcia hills, and savour delicious meals under the shaded pergola. If you can tear yourself away, an eighteen-minute drive takes you to San Quirico d'Orcia, where a selection of Italian eateries awaits. 

Tuscan Ornate

In the heart of the Val d'Orcia, this villa offers sweeping views as far as the eye can see. Montepulciano, San Quirico d'Orcia, and Seina further afield are all within driving distance – and all make great options for days out and about in the countryside. But even better than the location is the garden waiting for you back home. There's an ivy-covered pergola ideal for alfresco dining, a private pool overlooking the vineyards, and swings to keep little ones entertained. Inside, modern comforts blend with traditional character. Every bedroom has an en-suite bathroom, making this ideal for families or friends.

Sunflower Sunset

Fall in love with the timeless charm of Tuscany from this home perched on the hills of Val D’Orcia. Outside, days can be spent by the saltwater pool and lounging under ancient oak trees. Upon arrival, you will be gifted with four bottles of wine from the estate – setting the tone for an unforgettable Italian stay. Housekeeping is available for an additional fee along with a range of extra services – including private chefs and local tours. It’s worth noting there is an unpaved track leading to the entrance of this home, but you will find it’s just a twenty-minute drive to Castiglione D’Orcia, while Montalcino is just a little further afield. 

Valley of Heaven

Nestled in the Tuscan countryside, this villa is a place for a family or group of friends to spend quality time together in the sunshine. From the hanging chair to sun loungers, the outside space offers ample opportunities to enjoy the views. Plus, there’s a covered terrace for alfresco dining. The sleeping quarters are on the lower ground floor with direct access to the garden and pool (something to keep in mind if you’re staying with young children), and the main bedroom has an open-concept en-suite, which may not be to everyone’s taste. If you fancy a change of scenery, the town of Castel del Piano is a short drive away.

The Italian Rose

Luxury Toiletries

Desk / Workplace

Single-Level Home

If you love the artsy side of life, you'll thrive in this contemporary loft. Colourful art pieces stand out, with some splashes of colour added by the feature walls. Natural light pours in through the large kitchen windows – the perfect chance to watch the morning birds fly by. You even get a lovely view of the courtyard from the bedroom too. 

Spend the day at Constanti winery – this is where your host works, so she will be more than happy to give you a tour of the place. Beautiful vineyards surround the loft and a wide range of wineries to sample some of the tastiest glasses of red.

Return home to sit at the dining table while the scent of a home-cooked Italian meal fills the room from the nearby kitchen. After you've eaten, pick a book off of the shelf, and snuggle up on the sofa while the moonlight shines through the windows. Pop the TV on for background noise or simply enjoy the peace and quiet that Montalcino brings.

Artistic Grapes

If views are what you’re after, this home has got you covered. From the pool to the portico, it comes with plenty of spots to soak up the scenery while sipping a glass of wine from one of the local vineyards. The wrought iron bedframes and other traditional fittings inside won’t be to everyone’s taste, but even the most cosmopolitan of guests will love the wooden beams and terracotta floors that feature in all the rooms here. And if not, an alfresco meal on the terrace is sure to take their mind off it.

Golden Panorama

Playground

Private Washing Machine

Ceiling Fans

EV Charger

Located in the heart of San Quirico d'Orcia, this apartment has romance written all over it. Inside, the Tuscan character beckons you to cosy up with your loved one after exploring the town's historic squares and local eateries. The kitchen is small but well-appointed, and though the living area lacks natural light, the private terrace more than makes up for it. Boasting views of the village church and the rolling hills in the Val d'Orcia, we can't think of a more idyllic setting to enjoy a glass of wine and a sunset meal for two.

The Maestro's Retreat

Enjoy the beautiful views of the valley, countryside, and forest from this renovated home's balcony or relax in the small, terraced garden area. This place has a hot tub too in the stone-built cellar, accessed from steep stairs in the living room (there's a bathroom down here too). If you're looking to cook elaborate meals, we should mention that this home just has a kitchenette. Still, there's a bakery 200 metres and a restaurant and bar 50 metres away, as well as a grocery shop 500 metres from this home in Seggiano. Further afield, the pretty town of Montalcino is 23 kilometres away.

Blue Umber

Outdoor Kitchen

This sprawling estate in Tuscany is the stuff that dreams are made of. Composed of the main farmhouse, two outbuildings, and a shared hall, along with plenty of outdoor space, it's perfect for large groups planning an escape to the Italian countryside. 

There are plenty of original features to admire, from the stone exterior to the arched brick doorways and vaulted wooden ceilings. With two kitchens and two indoor living rooms, everyone can make their own schedule and relax in style. Out in the garden, you'll find a sparkling swimming pool that invites you to cool off and plenty of sun loungers where you can catch some rays. And, when evening rolls around, the whole group can gather under the pergola for a fabulous alfresco dinner straight off the barbeque – don't forget the prosecco. 

It would be easy to while away your days without leaving this fabulous estate, but the rolling Tuscan countryside is waiting just outside the walls. You can drive to the medieval walled town of Lucignano in under twenty minutes, and admire the stunning views from its hilltop location. And, if you fancy a day trip, you can drive into the city of Siena in half an hour, or arrive at romantic Lake Trasimeno in forty minutes. 

Trip To Tuscany

Ping Pong Table

Surrounded by rolling hills and lush trees as far as the eye can see, this Italian villa in the Lucciola Bella Nature Reserve offers picture-perfect seclusion. Split into five apartments – including an annexe and one suitable for guests with disabilities – it's a dream escape, whether for relaxation or celebrations. Inside, it's as charmingly rustic as you could hope, while outside there's a pool and plenty of space to dine and unwind. A car is essential for reaching amenities, but the idyllic location is totally worth it.

Tuscany Grace

Beach / Pool Towels

Offering panoramic valley views over the surrounding olive groves, this countryside spot invites guests to experience rural Tuscany at its finest. Just a short drive from Monticchiello, you'll have easy access to the town's shops and restaurants despite your countryside location. And with miles of valley routes in the local vicinity, it's the perfect spot for hikers and cyclists. At the villa, you'll have a private swimming pool and a covered terrace annexe with a fireplace, pizza oven and alfresco dining area to enjoy the Tuscan sunsets. While the interiors feel a little dated in terms of design, they don't seem out of place amid the traditional lifestyle of this part of Italy. 

The Pienza

Located in the pretty hilltop village of Montalcino, this home is a Tuscan gem with a lot to offer. There’s a beautiful garden with a pool and a hot tub to ensure optimum relaxation. You’ll also have a traditional wood-burning pizza oven and a fire-pit for magical evenings under the stars. Inside, the rooms are just as inviting with traditional and luxurious features. The main bedroom comes with a romantic bath tub and two of the bedrooms are located in the annexes for extra privacy. Daily breakfast and housekeeping are included in your stay. Plus, it couldn’t be better placed for adventures across Tuscany. From here, it’s just a short stroll into the village centre, while Pienza, Montepulciano and Siena are all within driving distance. 

The One Light

What this villa lacks in contemporary design, it makes up for with old-world character. It's traditionally Tuscan, from the timber ceilings down to the terracotta floors. While the dated and dark interiors won't be for everyone, we can't help but find it all rather charming – especially when the fire is blazing in the two brick hearths. On sunny days, the sprawling garden is a lovely spot to unwind, boasting a private pool and alfresco dining area. You can prepare meals in the pizza oven, or your host can arrange for a private chef to whip up an Italian feast. As for location, the Val d'Orcia is on your doorstep, with Pienza and Monticchiello both easily accessible by car.

Terracotta Roses

Sound System

With its rich peach-coloured frontage, stone walls, and terracotta tiled roof, from the outside, this home looks like a traditionally Tuscan place to stay. But you only need to head down to the elegant pool to realise it has all the modern comforts you’d want, with stylish sun loungers and day beds, outdoor sofas and chic hammocks to swing in. That’s not to say it doesn’t also have Tuscan charm, as you’ll find this aplenty when sitting under the pergola enjoying an alfresco meal. And inside, you’ll discover exposed wooden beams, a brick fireplace and enchanting archways. Cooking at home is a delight thanks to the outdoor kitchen, complete with hobs and a barbecue grill. You’ll also be able to explore 2,500 square metres of planted gardens, terraces and olive trees. At night, as the lights of the pool illuminate, relax on the terrace with a glass of local wine. 

Bria

Netflix

Streaming Services

Rice Maker

Welcome Hamper

Perched on the hills overlooking the Val d 'Orcia, this traditional farmhouse is immersed in the timeless beauty of the Tuscan countryside. And with its location just a short drive from the charming medieval town of San Quirico, you’ll find everything you could need to experience the beating heart of Italian living. 

Dating back to 1619, this atmospheric building has been thoughtfully restored into a sanctuary – the perfect setting for a restorative retreat. Anchored around a shared garden with spectacular views across the sweeping landscape, this is the kind of space that feels instantly inspiring. And the uplifting tone extends into this cosy first-floor apartment. From the traditional features to the rustic simplicity of the styling, there’s an abundance of character and warmth here. 

Days can be spent relaxing on the terrace, hiking, horseback riding, mountain biking and sampling delicious local products from the next-door farm (children will love meeting the resident animals). And for explorations further afield, you’ll find this home sits like a gateway to the region’s most beautiful towns and villages – Montepulciano, Cortona and the spectacular Siena are all within driving distance. 

Casa Rosana 

For a taste of authentic Italian living, this stylish home opens its doors to the beauty of southern Siena.

Located in the historic town of Montalcino (renowned for its Brunello wine), this is the perfect setting to experience the warmth and depth of Italian living. It feels traditional here with elegant styling that adds comfort and ease. From preparing your morning coffee in the kitchen to sitting in the private garden, this is the kind of space that inspires you to slow down and savour the moment. 

Follow the views of the Val d’Orcia and take a stroll through the charming streets of Montalcino, making a stop in one of the cafes or restaurants to enjoy the atmospheric beauty. Or wind your way through the rolling hills towards Siena – only a fifty–minute drive away. 

As the sun sets across the countryside, you’ll love coming home to this sanctuary in the trees. Open the doors and enjoy an evening in true Italian style – with beautiful food, wine and conversation.

Rosemary & Olive

Jacuzzi

Looking for the wow factor? This home fits the bill. Each room effortlessly blends Tuscan tradition with contemporary aesthetics – none more so than the living area, with its brick archways, stone walls and beamed ceilings. There's also an annexe offering even more space for groups, containing an additional kitchen and living room, as well as the fifth and sixth bedrooms (one of which is wheelchair-accessible). Outside, the swoon-worthy views from the infinity pool and Jacuzzi are hard to resist. Meanwhile, the shaded pergola is perfect for Aperol Spritzes at sundown. And did we mention daily maid service is included? If you can tear yourself away from this stunning home, Montefollonico is a thirty-minute walk, while Siena is an hour's drive.

The White Vine

Pool / Snooker Table

Safe

This villa has space for the whole family to spread out and get comfortable. With a games room and a private pool, there's never a dull moment here – and that's not even counting the many terraces where alfresco dining will no doubt be on the cards. Inside, you'll find a kitchen, dining room, and a living area on each floor. Nearly every room boasts exquisite views of the Brunello vineyards and surrounding countryside. You're also in a great position to explore the Val d'Orcia. Siena, Montepulciano, and Bagno Vignoni are all within driving distance.

Brunello Beauty

DVD Player

Stop scrolling and pack your bags if you’re seeking an unforgettable retreat to rural Tuscany. Here, you’ll be surrounded by the rolling hills of Montepulciano, three hectares of sprawling gardens, an orchard and a vegetable plot. With eight bedrooms, all of which are en-suite, this is a perfect spot for a large family getaway. Outside, soak up the Tuscan sun by the pool, or enjoy an alfresco meal prepared with your produce pickings on the covered terrace. And after a day exploring the local vineyards, you can sink into the Jacuzzi tub under the stars.

The Hilltop Sanctuary

Set on a farm, parts of which are more than 200 years old, you’ll find this apartment, which is light and bright thanks to the large arched windows. Outside, as you’d hope for – there are gorgeous vistas over the Tuscan countryside and instead of a farm pond, there’s now a beautiful shared pool, which is a short walk through the communal gardens. When you fancy exploring the area – go for a hike in the Val di Chiana, discover the medieval hilltop town of Montepulciano, or spend the day at one of the beaches at Lake Trasimeno.

The Tuscan Vineyard

Exercise Equipment

Lift Access

You can't beat the views of the beautiful Val D'Orcia, itself a UNESCO World Heritage Site, from this Tuscan farmhouse lying in the Siena Province on a private two-acre estate. Tear yourself away from the vistas, and you'll find a deft renovation, combining contemporary interiors and historic charm. An excellent choice for a large group of friends or family, there's plenty of space to spill out and feel at home here. Cool off from the Tuscan sun in the infinity pool. Put to use the vast, chef-worthy kitchen (we're talking two dishwashers, two ovens, and some) for a big dinner party – a private chef is bookable for fine dining. Or keep things easy and fire up the barbecue or pizza oven outside as breath-taking views of the valley spread out before you –  best seen beneath the pergola at sunset with a glass of something chilled. And on chiller nights, hunker down beside the fireplace with a good book – there are two living rooms to choose from. When it's time to lay your head, hop in the home's elevator and take your pick from the many bedrooms, boasting king-sized beds and separate bathrooms. We'll let you decide who lucks out on that ground floor suite with bi-folds opening onto the lawned gardens. Should you ever wish to leave this idyll, you'll find you're in an excellent base to uncover Tuscany's vineyards and historic villages, starting in Sarteano, just a ten-minute drive away. With its tempting trattorias and beguiling historic charms, you'll be off to a flying start.

Little Hills

Perfect for large groups, this stunning holiday home has plenty of space. It’s spread between the main house and a separate two-bedroom annex that also boasts a dining room for up to thirty-two guests – it’s a wonderful spot for a formal meal. For more relaxed dining, there’s the pergola with its barbecue and brick oven. The garden is filled with olive trees, cypresses, oaks, and roses, and offers spectacular views of the rolling hills of Tuscany. There’s a private pool to swim in and a yoga and meditation room for relaxing. You’ll have everything you need here. 


Tuscany’s Charm

Located in the Tuscan countryside, this home in Torrita di Siena offers endless peace, quiet and picturesque scenery. With views stretching to Lake Trasimeno, it's a spot for those keen to reconnect with nature while discovering the attractions of Tuscany. There's a shared swimming pool on-site, and you'll have your own private garden space here. The alfresco dining area is perfect for sitting with a glass of local wine and an Italian aperitivo. Meanwhile, the open-plan living area makes for a sociable living space to kick back after a long day of exploring.

Casa di Siena

DVD Library

Wine Cellar

Wine Cooler

Private Dryer

Bookended by the olive groves, cypress trees and rolling green hills of Southern Tuscany is this 1960s-style architectural feat designed and curated by a sculptor and architect duo. Perfect for two couples or a small group of friends looking to explore the region, this cleverly converted warehouse is airy and open-plan with large crittall-style windows looking out over the vineyard and rambling countryside beyond. We particularly liked the stone fireplace and curated pieces of art dotted around that make for a real visual statement. Through to the bedrooms, where you'll find minimalist interiors, crisp white bed linens and antique objects that combines traditional touches with modern influence. Spend mornings idly relaxing underneath the warm Tuscan sun by the stunning 20-metre lap pool or recharging in the sauna, before cycling to the nearby village of Montisi. Take a half-hour drive to the famous vineyards of Montepulciano and bring a few bottles of vino back with you – to be chilled in the home's wine cellar and enjoyed out on the terrace, as you look out across the medieval ruins of Montelifrè Castle. Be it wine, history, interior design, or art, this home delivers in spades. 

Architectural Narrative

Shared Pool

Situated on a private resort, this villa drops you in the heart of the Tuscan countryside to indulge in pure rest and relaxation. Set over two floors, there’s plenty of space for guests to spread out, plus an inviting private terrace to soak up the rural vistas. Cool off from the Italian heat in the seasonal communal pool, while a visit to the on-site wine bar is a must to taste some local delights. For an additional fee, you can also enjoy a delicious breakfast buffet, an Italian cooking class or a truffle hunting experience. 

Tuscan White

Boasting traditional Tuscan charm, this countryside villa welcomes up to ten guests, making it an excellent choice for a family or group of friends looking for a restful getaway. Inside, there’s plenty of space for the group to spread out, then come together for meals in the garden. The private pool is sure to be a hit, and the covered terrace is an ideal spot to enjoy a tipple or two. Buonconvento is the closest village, but if you’d like to explore further afield, Siena is easily reached by car.

Green in Bloom

Providing sweeping views of the Tuscan countryside, this rustic villa guarantees a restful break for a family or group of friends. While the traditional, worn-in interior won’t be to everyone’s taste, we think it’s charming. Outside, there’s a heated swimming pool, a dining terrace and loungers for sunbathing sessions. Plus, there is a vegetable patch and orchard – feel free to help yourself to fresh produce. If you’d prefer to let the professionals take care of dinner, the closest restaurant is 3 kilometres from the home while Sarteano town is 8 kilometres away.

Carmine Sunset

Located just a ten-minute drive from the town of Castel del Piano in Tuscany, this renovated farmhouse villa is full of historic charm. Boasting many of its original early twentieth-century features, including beamed ceilings, terracotta floors and travertine tile showers, its rooms nod to an Italy of the past while elevating rustic traditionalism in comfortable style. Head outside to the garden where cypress and olive trees create a natural frame around the panoramic countryside vistas, then spend the day taking dips in the pool, playing some ping pong and idling the sunny hours away in the hammock. Gather together for cocktails in the garden while you watch the sun set over the hills, then fire up the brickwork barbecue for an al fresco dinner. Gather on the master bedroom’s private terrace for a starlit nightcap, then tuck yourself in bed for a serene night’s sleep in your peaceful country surroundings. 

Il Mugnaio

This home, composed of three suites and two cottages, sits on an exclusive estate just 1 kilometre from the historic centre of Montepulciano. It’s in a breathtaking spot overlooking a vineyard-filled valley, with the marvellous views visible from inside and out – the living room boasts floor-to-ceiling arched windows. The outside space is stunning, with a private pool and gardens filled with fragrant roses, fruit trees, and even a vegetable patch. We love the rustic touches that sit alongside modern amenities – you get the best of both worlds here. 

Sunflower Hill

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We selected the 2108 homes worth renting in this location

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Home spotlights in Castiglione d'Orcia

We selected the top 3% holiday homes in Castiglione d'Orcia

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