12 Best Luxury Villas in Tuscany: Ultimate Guide 2026
Timeless Wanderers: Posted December 22, 2025
Why a Villa Escape in Tuscany
Tuscany is the ultimate destination for travellers seeking rolling vineyards, picture-perfect hilltop towns, world-class wine, and the easy rhythms of rural Italy.
But what truly elevates a Tuscan escape is staying in your own luxury villa — a private home where you can savour slow breakfasts on sunlit terraces, take refreshing dips in a pool overlooking rolling hills, and unwind under starry skies with a glass of Chianti in hand.
A wide array of premium villa accommodations across Tuscany, from serene countryside estates to stylish retreats near historic centres — all with reliable booking, guest reviews, and secure payment options.
In this guide, we hand-pick 12 of the best luxury villas in Tuscany.
Each offers space, comfort, and upscale amenities like private pools, gardens, and scenic views, making them perfect for families, groups, or couples seeking a memorable holiday.
Whether you’re exploring Chianti’s wine roads, lounging in Val d’Orcia’s UNESCO landscapes, or discovering hidden medieval gems, these villas provide an unforgettable home base for your Tuscan adventure.
Table of Contents
We can help you plan your dream trip to Tuscany, with a personalised itinerary designed just for you.
After more than 20 years of travelling to Tuscany—and loving it so much we decided to make it our home—we now live here and explore the region at a relaxed, local pace.
Planning a trip to Tuscany is exciting, but choosing where to go, how long to stay, and how to get around can quickly become overwhelming.
That’s where we come in. We offer a personalised planning service that helps you decide exactly how to explore Tuscany, based on your travel style, budget, and pace.
Plus, we can help you plan scenic drives, time in hilltop towns, food and wine experiences, and those small local moments that make a trip truly special—making your Tuscany holiday easier, smoother, and full of memories you’ll treasure long after you return home.
Tips for Choosing Your Luxury Villa
Location matters:
For iconic countryside and hill towns, stay near Chianti or Val d’Orcia.
If you love wine tasting, Montepulciano and Chianti farm stays are ideal.
For a combination of sea + country vibes, Tuscany Coast agriturismi like Venturina Terme work beautifully.
Amenities to look for:
Private or shared swimming pools and expansive garden areas
On-site wine tastings or olive oil experiences
Farm-to-table meals or breakfasts sourced from the estate
Tuscany Villa Trip
Villa Bases (Luxury Villa Regions)
Chianti Wine Region
Greve in Chianti, Tuscany, Italy
Radda in Chianti, Tuscany, Italy
Castellina in Chianti, Tuscany, Italy
Val d’Orcia Villa Base
Pienza, Tuscany, Italy
Montepulciano, Tuscany, Italy
Castiglione d’Orcia, Tuscany, Italy
San Quirico d’Orcia, Tuscany, Italy
Arezzo / Eastern Tuscany Villas
Arezzo, Tuscany, Italy
Cortona Area Villa Base
Cortona, Tuscany, Italy
Florence Area Villa Base (Optional)
Florence, Tuscany, Italy
Pisa / Lucca Area Villa Base (Optional)
Pisa, Tuscany, Italy
- Lucca, Tuscany, Italy
Don’t have time to read the whole post? Here’s the quick version:
1. Agriturismo Villa Mazzi The beautifully restored farmhouse features elegant rooms, manicured gardens, and sweeping countryside views.
2. Agriturismo Nobile Located close to Montepulciano’s historic centre, this working farm is surrounded by vineyards and offers a relaxed yet refined countryside stay.
3. Agriturismo IL Casalino Just minutes from Pienza, Agriturismo Il Casalino delivers the postcard views that Val d’Orcia is famous for.
4. Vento d’Orcia The atmosphere is peaceful and unhurried, ideal for travellers who want to disconnect from busy itineraries.
5. Castello di Velona Resort Guests are surrounded by vineyards and olive groves, with sweeping views.
6. La Moiana 1756 Surrounded by rolling Val d’Orcia countryside, it feels wonderfully secluded.
7. Agriturismo Podere Torre The setting feels rural and authentic, yet it remains conveniently close to village centres, wineries, and scenic driving routes.
8. Villa di Capovento- Castellina Surrounded by vineyards and olive groves, this elegant rural property delivers the classic Chianti landscape many travellers imagine.
9. Castello La Leccia – Castellina in Chianti Set on a historic estate, Castello La Leccia combines the romance of a Tuscan castle.
10. Agriturismo IL Piaggione Il Piaggione is particularly appealing to families and couples.
11. Castelo di Fonterutoli Castello di Fonterutoli Wine Resort offers a refined farm-stay experience rooted in Chianti Classico traditions.
12. Agriturismo Villa Toscano It’s location makes it ideal for longer stays, allowing guests to mix seaside visits with inland excursions.
1. Agriturismo Villa Mazzi – Montepulciano
Set among vineyards just outside Montepulciano, Agriturismo Villa Mazzi offers a refined yet authentic Tuscan farm stay experience.
The beautifully restored farmhouse features elegant rooms, manicured gardens, and sweeping countryside views that define this corner of Val d’Orcia.
Guests love the peaceful atmosphere, spacious outdoor areas, and easy access to Montepulciano’s historic centre and wine cellars.
The property produces its own wine and olive oil, adding to the immersive farm-stay experience.
With thoughtful interiors and a relaxed pace, Villa Mazzi is ideal for travellers who want countryside tranquillity without being isolated.
It works particularly well for couples and small families planning wine-focused itineraries.
Best for: Wine lovers, slow travel
Region: Montepulciano / Val d’Orcia
* Check availability and book your stay at Agriturismo Villa Mazzi here* Other accommodation in Tuscany.
2. Agriturismo Nobile – Montepulciano
Agriturismo Nobile combines authentic farmhouse character with a more boutique, comfort-focused feel.
Located close to Montepulciano’s historic centre, this working farm is surrounded by vineyards and offers a relaxed yet refined countryside stay.
Rooms are thoughtfully designed, balancing rustic Tuscan details with modern amenities, while the outdoor pool and garden areas provide space to unwind between sightseeing days
One of the highlights is the emphasis on local produce, with wine and olive oil from the estate adding depth to the farm-stay experience.
Its convenient location allows guests to explore Val d’Orcia’s most famous towns while returning each evening to quiet rural surroundings, making it especially appealing for couples and food-focused travellers.
Best for: Couples, food and wine travellers
Region: Montepulciano
* Check availability and book your stay at Agriturismo Nobile here* Other accommodation in Tuscany.
3. Agriturismo Il Casalino – Pienza
Just minutes from Pienza, Agriturismo Il Casalino delivers the postcard views that Val d’Orcia is famous for.
Surrounded by gently rolling hills, vineyards, and cypress-lined roads, this beautifully restored farmhouse offers a serene and timeless setting.
The accommodation feels elegant without being formal, with traditional materials, comfortable rooms, and terraces designed to make the most of the landscape.
Mornings here are slow and peaceful, while evenings often revolve around watching the light change across the valley.
Its location makes day trips to Pienza, Bagno Vignoni, San Quirico d’Orcia, and Montepulciano effortless.
Il Casalino is particularly well suited to couples and photographers seeking iconic scenery, tranquillity, and an authentic farm-stay experience.
Best for: Scenic stays, romantic escapes
Region: Val d’Orcia
* Check availability and book your stay at Agriturismo IL Casalino here* Other accommodation in Tuscany.
4. Vento d’Orcia – Pienza Countryside
Vento d’Orcia is a quietly luxurious farm stay that focuses on simplicity, comfort, and uninterrupted countryside views.
Set in the heart of Val d’Orcia, this property feels purposefully calm, with clean lines, well-designed spaces, and gardens that blend seamlessly into the surrounding hills.
The atmosphere is peaceful and unhurried, ideal for travellers who want to disconnect from busy itineraries and embrace slow Tuscan living.
Its location near Pienza allows easy access to the region’s most beautiful villages, while evenings are best spent on the property enjoying the silence and wide-open views.
Vento d’Orcia is particularly popular with couples and solo travellers looking for a refined, adult-friendly retreat in one of Tuscany’s most scenic landscapes.
Best for: Couples, photography lovers
Region: Val d’Orcia
* Check availability and book your stay at Vento d’Orcia here* Other accommodation in Tuscany.
5. Castello di Velona Resort, Thermal Spa & Winery – Val d’Orcia
Overlooking the rolling hills of Val d’Orcia, Castello di Velona Resort delivers a true 5-star Tuscan countryside experience.
Set within a restored medieval castle, the property combines historic grandeur with refined modern luxury.
Guests are surrounded by vineyards and olive groves, with sweeping views that stretch across one of Tuscany’s most celebrated landscapes.
A major highlight is the on-site thermal spa, fed by natural hot springs and designed for total relaxation after days of exploring nearby hill towns.
Despite its secluded setting, the resort is well positioned for visits to Castiglione d’Orcia, Montalcino, and Pienza.
Castello di Velona is ideal for travellers seeking elegance, wellness, and iconic Val d’Orcia scenery.
Best for: Luxury quiet countryside stay.
Region: Val d’Orcia
* Check availability and book your stay at Castello di Velona Resort here* Other accommodation in Tuscany.
6. La Moiana 1756 – Castiglione d’Orcia
Highly rated and beautifully restored, La Moiana 1756 is a refined farm stay that blends historic character with understated elegance.
Dating back to the 18th century, the property retains its original charm while offering modern comforts and a tranquil atmosphere.
Surrounded by rolling Val d’Orcia countryside, it feels wonderfully secluded, making it ideal for travellers seeking rest and privacy.
The interiors are warm and tasteful, with attention paid to detail rather than excess.
Outdoor spaces invite quiet moments spent reading, walking, or simply enjoying the views.
La Moiana 1756 is best suited to couples or solo travellers looking for a boutique-style agriturismo where the focus is on calm, quality, and a strong sense of place.
Best for: Boutique lovers, peaceful retreats
Region: Val d’Orcia
* Check availability and book your stay at La Moiana 1756 – Castiglione d’Orcia here* Other accommodation in Tuscany.
7. Agriturismo Podere Torre – Greve in Chianti
Set among vineyards near Greve in Chianti, Agriturismo Podere Torre is an excellent choice for travellers exploring Tuscany’s most famous wine region.
This working farm combines classic Chianti scenery with comfortable, traditional accommodation and panoramic countryside views.
The setting feels rural and authentic, yet it remains conveniently close to village centres, wineries, and scenic driving routes.
Guests appreciate the balance between exploration and downtime, with outdoor areas that encourage relaxed afternoons and peaceful evenings.
The atmosphere is welcoming and unpretentious, making it a reliable base for wine lovers who want to experience Chianti beyond busy tasting rooms.
Podere Torre works especially well for couples and small groups planning a wine-focused itinerary.
Best for: Chianti wine routes
Region: Chianti
* Check availability and book your stay at Agriturismo Podere Torre – Greve in Chianti here* Other accommodation in Tuscany.
8. Villa di Capovento – Castellina in Chianti
Villa di Capovento offers a refined farm-stay experience in the rolling hills near Castellina in Chianti.
Surrounded by vineyards and olive groves, this elegant rural property delivers the classic Chianti landscape many travellers imagine.
The accommodation preserves its rustic character while offering high standards of comfort, making it easy to settle in and unwind.
Outdoor spaces are designed for enjoying Tuscany’s long evenings, whether with a glass of local wine or a simple home-cooked meal.
Its location places guests within easy reach of Castellina, Radda, and Greve, making it a practical and scenic base.
Villa di Capovento is ideal for travellers who want authenticity paired with a polished, relaxed atmosphere.
Best for: Wine country stays
Region: Chianti
* Check availability and book your stay at Villa di Capovento- Castellina in Chianti here* Other accommodation in Tuscany.
9. Castello La Leccia – Castellina in Chianti
Set on a historic estate, Castello La Leccia combines the romance of a Tuscan castle with the warmth of a countryside farm stay.
Surrounded by vineyards and rolling hills, the property offers elegant accommodation that feels both timeless and welcoming.
The sense of space and history is one of its strongest appeals, along with the carefully maintained grounds and scenic views.
While the setting feels secluded, it remains well positioned for exploring Chianti Classico villages and wineries.
Castello La Leccia is particularly well suited to couples celebrating a special occasion or travellers looking for a stay that feels distinctly Tuscan, atmospheric, and quietly luxurious without being overly formal.
Best for: Romantic stays, special occasions
Region: Chianti
* Check availability and book your stay at Castello La Leccia – Castellina in Chianti here* Other accommodation in Tuscany.
10. Agriturismo Il Piaggione – Venturina Terme
Agriturismo Il Piaggione offers a slightly different take on the Tuscan farm stay, combining countryside charm with proximity to the coast.
Located near Venturina Terme, this property is surrounded by open land and features outdoor spaces ideal for relaxation, including a pool and gardens.
The atmosphere is laid-back and welcoming, making it a good option for longer stays or travellers who want variety in their itinerary.
From here, guests can easily combine rural exploration with visits to nearby beaches, thermal spas, and historic villages.
Il Piaggione is particularly appealing to families and couples looking for a balance of nature, comfort, and flexibility beyond inland Tuscany.
Best for: Coast + countryside
Region: Tuscan Coast
* Check availability and book your stay at Agriturismo IL Piaggione* Other accommodation in Tuscany.
11. Castello di Fonterutoli Wine Resort – Castellina in Chianti (Near Siena)
Set on a historic wine estate just north of Siena, Castello di Fonterutoli Wine Resort offers a refined farm-stay experience rooted in Chianti Classico traditions.
Surrounded by vineyards and rolling hills, the property blends contemporary design with centuries-old rural architecture, creating a stay that feels both luxurious and authentic.
Accommodation is spread across restored stone buildings, offering privacy, space, and sweeping countryside views.
Guests can enjoy peaceful mornings, scenic walks through the vineyards, and easy access to nearby Chianti villages.
Its location makes it an excellent base for exploring Siena, Castellina in Chianti, and Radda.
This farm stay is ideal for travellers seeking wine-country elegance, tranquillity, and a strong sense of place.
Best for: Wine Tasting, relaxed travel
Region: Tuscan Coast
* Check availability and book your stay at Castelo di Fonterutoli* Other accommodation in Tuscany.
12. Agriturismo Villa Toscana – Campiglia Marittima
Located near Campiglia Marittima and close to Baratti Beach, Agriturismo Villa Toscana offers a well-rounded farm-stay experience with easy access to both countryside and coast.
The property sits in a peaceful rural setting, with outdoor spaces designed for relaxing after days spent exploring nearby beaches, hill towns, and archaeological sites.
Accommodation is comfortable and practical, appealing to travellers who want space and simplicity rather than overly formal luxury.
Its location makes it ideal for longer stays, allowing guests to mix seaside visits with inland excursions at an easy pace.
Villa Toscana is a great choice for travellers seeking variety, authenticity, and a less-crowded side of Tuscany.
Best for: Longer stays, mixed itineraries
Region: Tuscan Coast
* Check availability and book your stay at Agriturismo Villa Toscano* Other accommodation in Tuscany.
Sightseeing & Day Trip Stops
Siena, Tuscany, Italy — Day trip from Chianti
San Gimignano, Tuscany, Italy — Medieval hill town
Bagno Vignoni, Tuscany, Italy — Thermal pool village
Montepulciano Historic Centre — Wine & views
Chianti Vineyards & Wineries — ( “Chianti wine region” broadly)
Val d’Orcia Scenic Drives — (use “Val d’Orcia, Tuscany” as a general region)
How to Get Around Tuscany
A rental car is essential for staying at luxury farm stays in Tuscany.
Most farm stays are located along country roads with limited public transport.
Florence and Pisa airports are the easiest arrival points, with car hire available directly at the terminals.
Driving allows flexibility, scenic detours, and access to villages, wineries, and viewpoints not reachable otherwise.
For more comfort and convenience, compare these car rentals: DISCOVER CARS or RENTALCARS
One-Week Tuscany Villa Itinerary
Luxury Slow Travel from Chianti to Val d’Orcia
This itinerary is designed for travellers staying in one or two luxury villas, allowing time to settle in, explore nearby towns, and truly enjoy the villa experience — pools, views, and long Tuscan evenings.
Day 1 – Arrive in Florence or Pisa & Drive to Your Villa
Arrive at Florence or Pisa Airport, pick up your rental car, and drive straight to your villa.
Resist the urge to squeeze in sightseeing today — Tuscany is best enjoyed slowly.
Stop at a local Coop or Conad supermarket near your villa to stock up on wine, bread, olive oil, and breakfast essentials.
Spend the evening settling in, enjoying the views, and having your first al fresco dinner as the sun sets over the hills.
Overnight: Luxury villa in Chianti or near Florence
Day 2 – Chianti Wine Roads & Hill Towns
Spend your first full day exploring the Chianti Classico region.
Scenic drives connect charming towns like Greve in Chianti, Radda, and Castellina, each perfect for a relaxed wander, coffee in the piazza, and boutique shopping.
Choose one winery to visit rather than rushing between several.
Return to your villa mid-afternoon for pool time, a nap, or a simple dinner cooked at home.
Overnight: Same Chianti-based villa
Day 3 – Siena or San Gimignano Day Trip
From Chianti, take a day trip to Siena to explore its medieval streets, cathedral, and the famous Piazza del Campo.
Alternatively, visit San Gimignano, known for its towers and vineyard views.
Return to your villa by late afternoon to avoid crowds and enjoy a quiet evening — this balance of sightseeing and downtime is what makes villa travel special.
Overnight: Same villa
Day 4 – Drive to Val d’Orcia (Villa Change or Long Day Trip)
Today you’ll head south into the iconic landscapes of Val d’Orcia — one of Tuscany’s most beautiful regions.
If you’re changing villas, this is the ideal midpoint.
Stop in Montepulciano or Pienza en route, then continue to your Val d’Orcia villa.
Spend the afternoon soaking up the scenery, swimming, and enjoying uninterrupted countryside views.
Overnight: Luxury villa in Val d’Orcia
Day 5 – Pienza, Bagno Vignoni & San Quirico d’Orcia
Explore Val d’Orcia at an easy pace.
Start with Pienza, famous for pecorino cheese and panoramic viewpoints, then continue to Bagno Vignoni to see its unique thermal pool piazza.
End the day in San Quirico d’Orcia, wandering through quiet lanes before returning to your villa for dinner and sunset views.
Overnight: Same Val d’Orcia villa
Day 6 – Cortona or Arezzo
Choose between Cortona, perched high above the Val di Chiana, or Arezzo, a lively city with rich history and antique markets.
Both offer a contrast to Val d’Orcia’s open landscapes.
Return to your villa early evening for a final swim, a celebratory dinner, or even a private chef experience if your villa offers it.
Overnight: Same villa
Day 7 – Leisure Morning & Departure
Enjoy a slow final morning — breakfast on the terrace, one last swim, and a final walk through the countryside. Drive back to Florence or Pisa, allowing time for a relaxed return.
Why This Itinerary Works for Villa Stays
Minimises hotel hopping
Leaves time to actually enjoy the villa
Balances sightseeing with downtime
Perfect for couples, families, and small groups
Ideal for luxury villas in rural Tuscany
Frequently Asked Questions
1. Are all these farm stays bookable on Booking.com?
Yes, every property listed is available on Booking.com.
2. What makes a farm stay “luxury”?
High-quality restoration, scenic locations, pools, refined interiors, and excellent guest reviews.
3. Are farm stays suitable for families?
Many are, especially those with pools and larger rooms or apartments.
4. Do farm stays include breakfast?
Most do, often featuring local or homemade products.
5. Is a car necessary?
Yes, a car is strongly recommended.
6. When is the best time to stay at a Tuscan farm stay?
May–June and September–October offer the best weather and fewer crowds.
7. Do these farm stays produce wine or olive oil?
Many do, especially in Chianti and Val d’Orcia.
8. Are farm stays quiet at night?
Yes — peaceful evenings are one of their biggest appeals.
For more comfort and convenience, compare these car rentals: DISCOVER CARS or RENTALCARS
Do You Need Travel Insurance for Tuscany?
(Short Answer: Yes — It’s Still a Smart Idea)
Travel insurance isn’t legally required to visit Tuscany, but it’s one of the smartest things you can have when travelling in Italy.
Even in a relaxed destination like Tuscany, things can go wrong — from delayed flights and lost luggage to medical issues, rental car damage, or unexpected trip cancellations.
And while Italy has excellent healthcare, medical treatment for visitors can still be costly without proper coverage.
As long-term travellers living in Italy, we’ve found SafetyWing to be a practical option for trips around Europe, offering coverage for medical care, travel delays, and lost belongings without complicated fine print.
SafetyWing
(Best for Long-Term Travel & Affordability)
We personally use SafetyWing, and have since 2019.
It’s perfect for travelling, spending multiple weeks or a whole year abroad.
You can get a Quote here.
It’s the kind of insurance you hope you never need—but you’ll be very glad you have if something unexpected happens.
Final Thoughts
Luxury farm stays in Tuscany offer something hotels simply can’t: space, silence, scenery, and a true connection to the land.
Whether you choose Chianti’s vineyards, Val d’Orcia’s iconic hills, or the Tuscan coast, Booking.com makes it easy to book trusted agriturismi with confidence.
These 12 properties showcase the very best of rural Tuscany — authentic, comfortable, and unforgettable.
PLAN YOUR TUSCANY ADVENTURE
These are our favorite companies we use when planning a trip, they consistently have the best prices, great customer service, and overall, are better than their competitors.
BOOK YOUR FLIGHT – Going is a great search engine if you are flexible about your travel destination and dates. Sign up for their newsletter and get the latest deals on destinations around the world. GOING is our new go to.
CAR RENTAL – We recommend using Discover Cars or Rental Cars when booking a car rental, they work with hundreds of companies worldwide to help you find the best car for your needs.
TRAINS – TRAINLINE – is our favorite, this site is very reliable and easy to use.
BUS – OMIO – this website allows you to book train or bus tickets to travel from city to city the best and cheapest way. FLIXBUS is another terrific website with routes between 20 European countries.
ACCOMMODATIONS
BOOKING.com – is our go to for hotel searches around the world, we find they always have the cheapest rates and offer different payment options. In addition, VRBO is another terrific website for all types of accommodations.
HOSTELWORLD – is great if you’re traveling on a budget, and if you need a cheap place to stay.
SIGHTSEEING TOURS
GET YOUR GUIDE – is our favorite; they have stacks of tours and excursions available in cities all over the world. VIATOR is another great website for all types of tours.
TAKE WALKS – This walking tour company provides inside access to attractions and places you can’t get elsewhere.
TRAVEL INSURANCE
SAFETY WING – is our go to travel medical insurance company, especially for longer trips. You can either purchase a monthly plan or a plan for specific trip dates (i.e. 1-2 week trips). They cover people from all over the world, while outside their home country.
ARC’TERYX – is a go to reliable brand for outdoor adventure and travel, their wide range includes light weight durable, easy to clean travel gear.
Check out our RESOURCE PAGE for more additional planning.