Pienza

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Bathtub

Hair Dryer

Bathroom

Coffee Maker

Dishwasher

Freezer

Fridge

Kitchen

Kitchen Utensils

Oven

High Chair

Kitchen & Dining

Cot / Crib

Iron

Washing Machine

Dryer

Hangers

Bedroom & Laundry

Outdoor Pool

Private Pool

Swimming Pool

Wellness & Fitness

Wi-fi

Laptop Friendly Workspace

Internet & Office

Air Conditioning

Fireplace

Heating & Cooling

Free Parking On Premises

Parking Available

Private Entrance

Parking & Access

Barbeque

Garden

Outdoor Seating

Patio / Terrace

Sun Loungers / Beach Chairs

Balcony

Outdoor

Pets Allowed

Pets

Child Friendly

Other

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

Entertainment

Microwave

Stove

Private Parking

Free Parking

Mosquito Net

Nice to haves

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

Heated Towel Rail

Rain Shower

Espresso Machine

Pod Coffee Machine

Ironing Board

Jacuzzi

EV Charger

Beach / Pool Towels

Courtyard

Sun Umbrellas

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

Satellite / Cable TV

Kettle

Central Heating

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

Toiletries

Cafetiere

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

Self Check-in / Check-out

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

Cooking Essentials

Toaster

Shared Pool

Balcony / Patio

Resort Access

Carbon Monoxide Detector

Smoke Detector

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

Cleaning Products

Drying Rack

Extra Pillows and Blankets

Free Parking On Street

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

Smart TV

Board Games

Library of Books

Bathrobes

Changing Table

Black-Out Blinds

Laundry Supplies

Luxury Bedding

Heated Pool

Sauna

Sauna / Steam Room

Steam Room

Desk

Temperature Control

Underfloor Heating

Valet Parking

Step-Free Access

Beach Essentials

Fenced Pool

Fenced Property

Hammock

Herb Garden

Outdoor Fireplace / Firepit

Outdoor Shower

Rooftop Terrace

Umbrellas

Fire Extinguisher

First Aid Kit

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

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

Playground

Private Washing Machine

Ceiling Fans

Single-Level Home

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

Gated Community

This converted Tuscan home provides a great base to explore one of Italy’s most iconic areas from. Though the interior perhaps lacks a bit of cosiness, it is well-kept and provides you with all you need for a comfortable stay, including a fully-equipped kitchen and a nice open-plan dining area which leads onto a private terrace. Guests can also make use of the resort’s facilities, such as the shared outdoor pool and rooftop. Make the most of the area by sampling some of its famous wines and visiting the picturesque towns. 

The Alighieri

DVD Library

DVD Player

Games Room

Sound System

Wine Cellar

Wine Cooler

Private Dryer

Exercise Equipment

Desk / Workplace

Safe

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

This apartment near Torrita di Siena has lovely views over this little slice of Tuscany from the terrace – perfect for alfresco meals. Or have a stroll through the communal gardens to the shared swimming pool. When you feel like exploring, visit Torrita di Siena with its pretty streets lined with stone-built houses or go for a hike around Mount Amiata. Alternatively, spend the day in one of the many parks in the area, such as Giardini Pubblici and Parco Via Ruffilli.

Tuscan Sweet

Nestled in a Tuscan country estate, this pet-friendly home offers the best of both worlds – a private terrace for alfresco dining and the option to share breakfast with your neighbours at the buffet. After snoozing by the communal pool, why not join a truffle hunt? Or rent a bike and cycle through the area. Maybe sipping local sundowners in the on-site bar will inspire a next-day trip to medieval Montepulciano, so you can see where that regional wine comes from.

Tuscan Getaway

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

Amazon Prime

Netflix

Sonos

Streaming Services

Welcome Hamper

Security Cameras

One of two three-bedroom apartments set within a traditional Tuscan farmhouse, it offers a welcome respite from the hustle and bustle of everyday life, overlooking the hilltop town of Montepulciano.

Despite its recent renovation, your hosts have done their utmost to maintain the period features that made this villa so special in the first place, so the original archways, exposed beams and wooden windows remain. However, stylish contemporary furnishings and a sleek kitchen bring it firmly up to date. All en-suite bedrooms complete the interior offering, each with views over the medieval town of Montepulciano, while guests staying in the main suite benefit from direct access to the balcony.

Vista a Montepulciano

Peaceful Tuscan retreats don’t get much better than this. This stunning home – spread between the main villa and an annex – is a special base in Italy, tucked amid the Tuscan Hills yet within easy reach of the art and culture of nearby Montepulciano and Pienza. This is a refined, stylish home designed to blend the antique and the modern. You can look forward to the villa’s original beamed ceilings and stone walls as well as a steel kitchen and contemporary features. We love the alfresco dining setup and the private infinity pool – it’s a breathtaking spot for admiring sunsets over Val D’Orcia. 

A Tuscan Rhapsody

This home is part of a resort set between the gorgeous valleys of Val d'Orcia and the Val di Chiana. The decor isn't the most exciting, but you can't beat this picturesque location. An easy drive from quaint villages and the city of Siena, it's the perfect starting point for exploring Tuscany. Spread over two floors, the first floor is dedicated to the large master suite, and we're big fans of the private terrace – perfect for enjoying a glass of wine at sunset. There's a communal swimming pool and solarium for relaxing during summer, and a wine bar and restaurant for trying some of the region's best wines. Your host can also help arrange a plethora of exciting activities, including truffle hunting, wine tastings and cooking classes.


The Tuscan Farmhouse

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

Luxury Toiletries

There's nothing more magical and romantic than the sight of an ancient hilltop Tuscan town, surrounded by rolling hills and cypress trees, and here it's what you'll be waking up to each morning. Set just outside the walls of Montepulciano, surrounded by vineyards and olive trees, this traditional farmhouse has been lovingly modernised by your host to create a perfect, authentic experience of life in this beautiful region.

Divided into two apartments, each with three good-size bedrooms, it's easily connected to form a really spacious single home. Set on three levels, you'll have all the character features you'd hope for – terracotta floors, arched windows and heavily beamed ceilings – while much of the home has been updated to offer modern kitchens and luxurious ensuite bathrooms. At the front is a large lawn suitable for kids to play on or adults to sit and read, while the rear patio faces that incredible view of the town.

Walk or drive into Montepulciano in just minutes to explore its medieval buildings, or head further afield for day trips – Siena and Perugia are both less than an hour away by car.

Il Doppio

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

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

This stunning Tuscan villa is set amid rolling hills and cypress trees, offering breathtaking views of Pienza and the Val d’Orcia. The large garden blends seamlessly with the surrounding wheat fields, while the inviting pool and sun-drenched solarium promise total relaxation. Inside, rustic charm meets authentic tradition with terracotta floors, exposed beams, and restored antique furniture. A spacious hall on the ground floor is ideal for weddings or special events, with space for up to one hundred people. In addition to the upstairs bedrooms, there’s a fully equipped one-bedroom apartment in a separate annex. We'd recommend hiring a car, plus it's also worth noting the host doesn't accept group stays with guests under the age of twenty-three. It's otherwise the perfect place for a peaceful, unforgettable escape in the heart of Tuscany.

 Cypress Skies

Pool / Snooker Table

This stunning home is a perfect base for a relaxing Tuscan escape. It’s been beautifully restored and renovated to blend its historic splendour with modern amenities and luxuries. There are elegant lounges to entertain in, and a huge kitchen perfect for whipping up feasts. You can dine alfresco beneath the pergola, on the covered terrace, or in the dining room. Outside, there’s a dreamy swimming pool, delightful gardens, and sweeping views of the surrounding hills. Inside, each comfortable bedroom has its own bathroom, and there are desks for those feeling creative. 

Tuscany's Charms

Nestled within a private estate, this traditional Tuscan farmhouse offers beautiful views and the ideal setting for a romantic Italian escape. Outside, lazy days can be spent strolling through olive groves, lounging by the private pool (open seasonally) and sipping drinks on the terrace. Inside, some of the furnishings are a little dated, but there’s plenty of character and an abundance of space across the eight bedrooms – one of which is located in a separate apartment and includes its own kitchen. You will need a car to explore further afield, but it’s just 2 kilometres to the historic centre of Montefollonico, with easy access to Lake Trasimeno. 

Sweet, Sweet Tuscany 

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

Whereas years ago you would have found a farmhouse on this site, visitors are today greeted by a villa that marries rustic charm and modern amenities.

Trust us when we say that you won't find it difficult to relax here, thanks to the beautiful views of vineyards and the ancient walled city of Montepulciano in the distance. As you would hope, there are plenty of spots where you can admire this scenic vista, whether it's out on the balcony, the terrace or the large front lawn.

Inside, there are a pair of kitchens, dining rooms and living rooms, which offers an extra degree of flexibility if you're travelling in a big group. There are terracotta tiles and wooden ceiling beams throughout to remind you of the home's heritage, but contemporary kitchens and pristine bathrooms show you how much effort the host has gone to in order to bring the address up to date.

Montepulciano and its impressive collection of Renaissance-era architecture can be reached in around ten minutes' walk. The wider region is famous for its wine production and there are lots of wineries you can visit to learn a little more about the process. Who knows, you might even be able to sample some of the local produce, too.



Rural Idyll

Juicer

You can take your pick from Tuscany's best bits with a stay at this modern apartment. The historic towns of Val d'Orcia and the famous cities of Florence, Perugia, Siena, Arezzo, and Orvieto are all within easy reach. Set within the grounds of a 200-year-old farm estate, while little of the historic charm remains inside the home, the fuss-free interiors are well-suited to a family holiday. Outside, the private veranda with an alfresco dining set-up is tailor-made for evening meals. While over on the grounds, there's a communal swimming pool which you'll share with the thirteen other lodgings and an on-site bar to grab breakfast and obligatory sundowners.

Tuscany's Holy Grail

It's homes like this that give Tuscany its reputation as a blissful place which to retreat for a week or three. The surrounding landscape of vineyards and rolling hillsides is as picturesque as you could possibly imagine, while the home itself is bursting with character.

Much of this is down to its long history. Built at the end of the 18th century as a mill, it was converted into a farmhouse before becoming the handsome getaway you see today. This heritage is writ large across the interior, with stone archways, wooden ceiling beams and terracotta tiles underfoot a treat for those that melt at the sight of rustic design – which includes us. The more contemporary features – including the freestanding bathtub and modern kitchen – have been tastefully added to retain this inimitable charm.

Outside, it's a slightly different story. The hot tub and swimming pool in the middle of the garden are comparatively recent additions to the address but are no less welcome for it. As well as that, there are a couple of spots for alfresco feasts to dine among the fragrant flowers and trees that fill the grounds.

Although the location is certainly secluded, you don't have to venture far to find things to see and do. The medieval hilltop town of Montepulciano is only 4.5km away and is famous for its Renaissance-era buildings and globally-coveted wine. A little further afield, the cities of Perugia and Siena are 63 and 67km away respectively, so well within range for a day trip.

Rustic Idyll

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