14 Best Luxury Vacation Rentals in the Tuscany Countryside
Timeless Wanderers: Posted January 18, 2026
Rolling Hills, Hilltop Towns & Vineyards: Where to Stay in Tuscany Countryside
Tuscany’s countryside is made for slowing down.
Rolling hills, hilltop towns, and endless vineyards create a setting where your accommodation becomes part of the dream.
Luxury vacation rentals give you space, privacy, and comfort to fully enjoy the landscape at your own pace.
From restored farmhouses and wine estates to elegant villas with private pools, these homes offer quiet mornings, relaxed afternoons, and easy access to charming towns.
All 14 properties featured here, are chosen for their comfort, location, and suitability for couples, families, or groups.
Whether you’re planning a romantic escape, a family retreat, or a friends’ getaway, these villas showcase the best of Tuscany’s countryside.
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.
“Let us plan your perfect trip with a custom itinerary designed just for you.
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How We Chose These Luxury Tuscany Vacation Rentals
Every property in this guide meets a clear set of criteria.
Each rental offers a genuine countryside or near-countryside setting, and provides the space and comfort expected from a luxury stay.
We focused on locations just outside towns or deep in rural areas, where a car is part of the experience and views, quiet, and outdoor living come naturally.
We selected these properties for quality, layout, and location for different travel styles — romantic escapes, family holidays, and group trips — rather than short-stay city breaks.
Don’t have time to read the whole post? Here’s the quick version:
1. Podere Spedalone – Val d’Orcia: well located for exploring Pienza, Bagno Vignoni, and Montepulciano
2.Villa Sassolini-Chianti Countryside– Set just outside a small Chianti town, peaceful surroundings with easy access to wineries and hill villages.
3. Castello di Vicarello – Maremma Hills: For couples looking for something truly special.
4. Borgo Santo Pietro – Near Chiusdino – This is a slow-paced stay best suited to couples celebrating a special trip.
5. Villa La Foce – Val d’Orcia – Ideal for couples, it offers a sense of calm and space, with elegant interiors and outdoor areas.
6. Villa Le Barone – Chianti Countryside – ideal for families who want a calm base with room for children to move around freely.
7. Villa Apparita – Siena Countryside – sits in a peaceful setting only a short drive from Siena, making it a practical and comfortable choice for families.
8. Fattoria di Corsignano – Val d’Orcia – Apartments are well laid out for longer stays, with kitchens and outdoor seating areas.
9. Luxury Villa on the Lucca’s hills – Its location makes it easy to combine countryside living with visits to Lucca and the Tuscan coast.
10. Tenuta di Artimino Apartments – Near Florence – This option works well for families who want countryside living and easy access to major sights.
11. Borgo Pignano – Volterra Countryside – Borgo Pignano is ideal for groups who want space and privacy.
12. Luxury Villa Sarteano – Val di Chiana & Val d’Orcia – This beautifully restored 18th-century farmhouse sits in the Tuscan countryside between Val di Chiana and Val d’Orcia.
13. Villa Poggio alle Corti – Exclusive Chianti Estate – Villa Poggio alle Corti is an exceptional Chianti estate set among vineyards and rolling hills.
14. Castello di Gabbiano – Chianti Classico – Set on a working wine estate, it offers apartments and suites within a historic castle setting
Best Romantic Luxury Villas in the Tuscany Countryside
1. Podere Spedalone – Val d’Orcia
Location: Near Pienza & Bagno Vignoni
Price range: €250–€350 per night
Set in the heart of the Val d’Orcia, Podere Spedalone is ideal for couples who want privacy, views, and a strong sense of place.
This restored countryside property sits among rolling hills with Panoramic views and quiet roads all around.
Rooms are simple, with stone walls, warm tones, and countryside views from almost every window.
Breakfast is often included, adding to the relaxed, slow-travel feel.
It’s well located for exploring Pienza, Bagno Vignoni, and Montepulciano, while still feeling removed from busy towns.
2. Villa Sassolini – Chianti Countryside
Location: Near Montevarchi, Chianti
Price range: €250–€350 per night
Villa Sassolini offers a romantic countryside stay with hotel-level comfort and service.
Set just outside a small Chianti town, it combines peaceful surroundings with easy access to wineries and hill villages.
Rooms are elegant without feeling formal, and the property includes a pool, gardens, and on-site dining for evenings when you don’t want to drive.
This is a great choice for couples who want a luxurious base in the countryside but still appreciate thoughtful service, excellent food, and a refined atmosphere rather than total isolation.
3. Castello di Vicarello – Maremma Hills
Location: Near Cinigiano, Southern Tuscany
Price range: €600–€750 per night
For couples looking for something truly special, Castello di Vicarello offers privacy, space, and a dramatic countryside setting.
Set high in the Maremma hills, this restored estate feels remote but carefully curated, with beautifully designed suites, panoramic views, and exceptional attention to detail.
Outdoor terraces, quiet walking paths, and a pool overlooking the landscape make it easy to spend full days on site.
It’s ideal for a romantic escape where the accommodation itself is as memorable as the surrounding region.
4. Borgo Santo Pietro – Near Chiusdino
Location: Siena countryside
Price range: €900–€1,600 per night
Borgo Santo Pietro sits on a large rural estate surrounded by gardens, fields, and woodland, offering couples a peaceful and immersive countryside experience.
The rooms and suites are individually styled, with generous space and views across the property.
Guests can enjoy long walks, quiet afternoons by the pool, and relaxed dining without leaving the estate.
While it’s in the countryside, it’s well placed for visiting Siena and nearby hill towns.
This is a slow-paced stay best suited to couples celebrating a special trip.
Read my full guide
The 14 Best Things to Do in Tuscany: The Complete Guide (2026)
5. Villa La Foce – Val d’Orcia
Location: Near Chianciano Terme
Price range: €500–€850 per night
Villa La Foce is a beautifully restored countryside property known for its gardens and views over the Val d’Orcia landscape.
Ideal for couples, it offers a sense of calm and space, with elegant interiors and outdoor areas designed for lingering rather than sightseeing.
The villa is well positioned for exploring southern Tuscany while still feeling secluded.
Evenings here are quiet, with open skies and little distraction, making it a strong choice for travellers who want a romantic stay in the countryside.
Best Luxury Villas in the Tuscany Countryside for Families
6. Villa Le Barone – Chianti Countryside
Location: Near Panzano in Chianti
Price range: €400–€700 per night
Villa Le Barone is a relaxed countryside property that works especially well for families who want space, comfort, and an easygoing atmosphere.
Set among vineyards and olive groves, the villa offers family-sized rooms, a large pool, gardens, and on-site dining, making day-to-day life simple.
The Villa feels rural but not remote, with Panzano and Greve in Chianti nearby for groceries and meals.
It’s ideal for families who want a calm base with room for children to move around freely.
7. Villa Apparita – Siena Countryside
Location: Just outside Siena
Price range: €650–€1,100 per night
Villa Apparita sits in a peaceful countryside setting only a short drive from Siena, making it a practical and comfortable choice for families.
The villa offers generous indoor space, multiple bedrooms, a private pool, and shaded outdoor areas for long afternoons at home.
Its proximity to Siena allows for easy sightseeing without long drives, while the rural setting provides quiet evenings and open space.
This villa suits families who want Tuscany living without being far from Siena.
8. Fattoria di Corsignano – Val d’Orcia
Location: Near Pienza
Price range: €300–€550 per night
Set on a working olive and wine estate, Fattoria di Corsignano offers a family-friendly countryside stay with the flexibility of apartment-style accommodation.
Families benefit from shared outdoor space, a pool, and plenty of room for children to explore safely.
Apartments are well laid out for longer stays, with kitchens and outdoor seating areas.
The location near Pienza makes day trips easy while keeping the feel rural and relaxed.
This is a strong option for families who prefer independence over formal luxury.
9. Luxury Villa on the Lucca’s hills
Location: Capannori, near Lucca
Price range: €850–€1050 per night
Luxury Villa on the Lucca’s hills with private pool, BBQ, tennis court, PingPong.
Offering families a peaceful base with views across olive groves and countryside.
The villa includes a private pool, multiple bedrooms, and outdoor dining areas ideal for shared meals.
Its location makes it easy to combine countryside living with visits to Lucca and the Tuscan coast.
This villa suits families who want outdoor space, privacy, and a comfortable home base rather than resort-style accommodation.
Read this guide next
10. Tenuta di Artimino Apartments – Near Florence
Location: Montalbano Hills
Price range: €280–€400 per night
Tenuta di Artimino offers apartment-style countryside accommodation on a historic estate, making it a practical choice for families.
The property includes pools, walking paths, and open space, while apartments provide kitchens and flexible sleeping arrangements.
Located in the Montalbano hills, it’s well positioned for trips to Florence, Pisa, and the wider Tuscan countryside.
This option works well for families who want countryside living with facilities and easy access to major sights.
Best Luxury Villas in the Tuscany Countryside for Groups
11. Borgo Pignano – Volterra Countryside
Location: Near Volterra
Price range: €900–€1,500 per night
Borgo Pignano is ideal for groups who want space, privacy, and a strong sense of place.
Set on a large rural estate, it offers beautifully restored buildings, generous communal areas, and sweeping countryside views.
Groups can spread out across the property while still sharing meals, pool time, and outdoor terraces.
The atmosphere is relaxed, with options for on-site dining and different experiences.
Its location near Volterra makes it easy to combine countryside living with cultural day trips.
12. Luxury Villa Sarteano – Val di Chiana & Val d’Orcia
Sarteano, Siena Province, Tuscany
Approx. €1,800–€3,500+ per night (varies by season & group size)
This beautifully restored 18th-century farmhouse sits in the Tuscan countryside between Val di Chiana and Val d’Orcia, offering a truly luxurious escape for groups of up to ~16 guests.
It combines traditional stone architecture with modern design and upscale amenities like a private pool, panoramic views, and extensive gardens.
There’s also a wellness area with sauna and gym, making it ideal for extended stays or special occasions.
Outdoor spaces include a tennis court and bowling green, while interiors are spacious, perfect for friends or families who want comfort, privacy, and room to spread out together.
13. Villa Poggio alle Corti – Exclusive Chianti Estate
Greve in Chianti, Tuscany Countryside
Approx. €6,000–€18,000+ per week (seasonal pricing varies)
Villa Poggio alle Corti is an exceptional Chianti estate set among vineyards and rolling hills, ideal for larger groups seeking privacy and refined comfort.
The historic villa offers generous living spaces, multiple bedrooms, and beautifully maintained gardens designed for shared time without feeling crowded.
Outdoor terraces, a private pool, and estate views encourage slow days and long evenings at home.
With its peaceful countryside setting and easy access to Chianti towns, this villa suits celebrations, extended family stays, or group trips with space, and atmosphere.
14. Castello di Gabbiano – Chianti Classico
Location: Near Mercatale Val di Pesa
Price range: €350–€400 per night
Castello di Gabbiano combines countryside accommodation with the scale needed for group travel.
Set on a working wine estate, it offers apartments and suites within a historic castle setting, along with shared outdoor spaces and vineyard views.
Groups benefit from on-site facilities, dining options, and room to gather without needing to manage an entire private villa.
It’s a great option for friends travelling together who want Chianti scenery with added convenience.
Best Parts of the Tuscany Countryside to Stay
Choosing the right area in Tuscany depends on how you like to travel.
Val d’Orcia is one of the most scenic parts of the region, known for its rolling hills, cypress-lined roads, and towns like Pienza and Montalcino.
It’s ideal for slow travel and longer stays.
Chianti countryside sits between Florence and Siena and works well if you want vineyards, wine estates, and easier access to cities.
The Siena countryside offers classic Tuscan landscapes with fewer crowds, while still being well connected.
The Lucca hills combine rural settings with access to the coast and historic towns.
Further south, Maremma feels wilder and more spacious, with beaches, olive groves, and a quieter pace.
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
FAQs About Luxury Vacation Rentals in the Tuscany Countryside
Are these rentals available on Booking.com and VRBO
Yes. Every property listed is available on Booking.com or VRBO, though availability and pricing vary by season.
Do I need a car when staying in the countryside?
Yes. A car is essential for exploring villages, wineries, and nearby towns.
Are these villas suitable for longer stays?
Many are ideal for longer stays, offering kitchens, outdoor space, and room to settle in.
What’s the best time of year to stay in the Tuscan countryside?
Late spring and early autumn are ideal. Summer is popular but busier and more expensive.
Are these properties child-friendly?
Family-focused villas offer pools, gardens, and flexible layouts, but always check safety features.
Do prices include cleaning and local taxes?
This varies by property and platform, so always confirm final costs before booking.
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
Staying in the Tuscany countryside offers a very different experience from city travel.
Space, quiet, and landscape become part of daily life, whether you’re cooking at home, enjoying long evenings outdoors, or exploring small towns at an unhurried pace.
Luxury vacation rentals allow you to experience Tuscany on your own terms, with comfort and privacy that hotels often can’t offer.
Whether you’re planning a romantic escape, a family holiday, or a trip with friends, choosing the right countryside base can shape the entire experience.
These 14 carefully selected rentals offer some of the best ways to enjoy Tuscany slowly, comfortably, and well beyond the tourist trail.
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 –OMIO – 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.