What makes Tuscany’s Luxury Private Villas unique compared to hotels?

Tuscany’s Luxury Private Villas offer total privacy, flexibility, and authenticity. Unlike hotels, you can immerse yourself in local life — from sunrise swims to dinners prepared by private chefs using ingredients from nearby farms. It’s a home-from-home experience infused with Italian elegance.

Which areas of Tuscany are best for Luxury Private Villas?

Top regions include Chianti and Florence for wine and culture, Val d’Orcia for panoramic countryside views, and the Tuscan Coast for seaside tranquillity. Each offers distinct landscapes, from vineyard-draped hills to olive groves and medieval towns.

Are private chefs or staff available at Luxury Private Villas?

Yes. Many Luxury Private Villas come with optional staff — including chefs, butlers, and housekeepers. Awake & Wander can arrange bespoke dining experiences such as truffle dinners, pizza-making nights, or poolside lunches.

Do Luxury Private Villas in Tuscany include pools and gardens?

Most do. Infinity pools overlooking vineyards, manicured gardens with pergolas, and terraces for al fresco dining are standard at many of Tuscany’s Luxury Private Villas. Some even have wellness areas, saunas, or private tennis courts.

When is the best time to book a Luxury Private Villa in Tuscany?

Spring (April–June) and autumn (September–October) offer the best mix of warm weather and quieter surroundings. Summer is ideal for families, while winter brings cosy villa stays with fireplaces and festive charm.

Can Awake & Wander arrange experiences during my villa stay?

Absolutely. We specialise in creating tailor-made itineraries for guests in Luxury Private Villas — including wine tastings, hot-air balloon rides, private art tours, or spa days. Every itinerary is designed around your preferences.

Are Tuscany’s Luxury Private Villas suitable for families and groups?

Yes. Villas range from romantic one-bedroom hideaways to large estates for 10–20 guests. Multi-generational families and wedding parties often choose Luxury Private Villas for their privacy, space, and shared living areas.

How does Awake & Wander protect my booking?

Every holiday booked through us is ATOL-protected and includes Supplier Failure Insurance, giving you complete peace of mind. You’ll enjoy the same security as a major tour operator with the personal service of an independent agency.

Can I request special amenities or celebrations in advance?

Yes. Whether it’s a milestone birthday, honeymoon, or private event, we can prepare your Luxury Private Villa with flowers, local wines, and bespoke touches — even private musicians or photographers on request.

How do I start planning my Tuscany villa holiday?

You can call 01495 400011 or fill in our enquiry form to begin. Our travel experts will handpick Luxury Private Villas that fit your vision and budget — ensuring every detail feels uniquely yours.

Luxury Private Villas in Tuscany – Bespoke Escapes Await

Few places stir the soul quite like Tuscany. A land of rolling vineyards, golden light, and cypress-lined hills, it has long been a sanctuary for artists, dreamers, and lovers of slow, elegant living. For discerning travellers, the region’s Luxury Private Villas offer something even more enchanting — privacy, indulgence, and that rare sense of timeless connection to place.

Whether you’re sipping Brunello beneath terracotta arches or waking to the sound of church bells echoing across the valley, Tuscany feels like it was designed for life’s finer moments. From the cultural riches of Florence to the rustic beauty of the Val d’Orcia, every corner invites you to settle in, slow down, and savour la dolce vita — privately, at your own pace.

At Awake & Wander Luxury Travel, we believe that where you stay should tell a story. That’s why our collection of Luxury Private Villas in Tuscany is handpicked for their character, location, and sense of exclusivity — villas where design meets heritage, and service feels effortless yet heartfelt.

In this guide, we explore some of Tuscany’s most exquisite private villas — each one designed to capture the spirit of bespoke travel.

Chianti & the Florence Countryside: Where Wine Meets Whispering Hills

Just south of Florence, the Chianti region feels like Tuscany distilled — rolling hillsides embroidered with olive trees, medieval hamlets crowned by stone towers, and miles of vineyards producing Italy’s finest wines. It’s here, amid this golden patchwork, that some of the most sought-after Luxury Private Villas in Tuscany are found. Looking for something equally romantic? Explore our hand-picked Romantic Getaways and Villa Escapes.

Villa Le Rose – Elegance Born from a Medici Legacy

Once a 15th-century estate belonging to the Medici family, Villa Le Rose embodies timeless grandeur with an intimate, contemporary twist. The villa’s sweeping cypress drive leads to honey-coloured façades and symmetrical gardens fragrant with lavender. Inside, high frescoed ceilings, original fireplaces, and marble floors evoke old-world aristocracy — yet modern comforts abound.

Guests can spend languid mornings by the private pool overlooking vineyards, followed by leisurely lunches prepared by a private chef using local ingredients from the nearby Sant’Ambrogio market. For evenings, Florence is only twenty minutes away — perfect for Michelin-star dining or a private art tour arranged by your Awake & Wander travel expert.

Castello di Ama Residence – A Vineyard Retreat for the Senses

Nestled in the heart of Chianti Classico, Castello di Ama Residence offers a completely different expression of Tuscan luxury. This working winery’s restored villa combines contemporary art installations with panoramic views of the Sangiovese vines that produce its celebrated wines. Suites feature rustic-chic interiors, limestone bathrooms, and terraces for sunset aperitivos.

Exclusive experiences include private tastings with the estate’s sommelier, candlelit dinners among the barrels, and bespoke spa treatments infused with grape seed oil — all arranged to your schedule.

Whether you’re travelling as a couple, a family, or a group of friends, the Chianti hills deliver the perfect rhythm: unhurried, graceful, and entirely yours.

Chianti & the Florence Countryside: Where Wine Meets Whispering Hills

Just south of Florence, the Chianti region feels like Tuscany distilled — rolling hillsides embroidered with olive trees, medieval hamlets crowned by stone towers, and miles of vineyards producing Italy’s finest wines. It’s here, amid this golden patchwork, that some of the most sought-after Luxury Private Villas in Tuscany are found. Explore more about Tuscany’s regions and cultural highlights on the official Visit Tuscany website.

Villa Le Rose – Elegance Born from a Medici Legacy

Castello di Ama Residence – A Vineyard Retreat for the Senses

Whether you’re travelling as a couple, a family, or a group of friends, the Chianti hills deliver the perfect rhythm: unhurried, graceful, and entirely yours.

The Val d’Orcia & Siena Countryside: Tuscany’s Timeless Heart

If Chianti is Tuscany’s crown, the Val d’Orcia is its beating heart. Recognised as a UNESCO World Heritage Site, this region is defined by vast, cinematic beauty — wheat fields turning from green to gold, solitary farmhouses perched on sun-drenched hills, and the distant silhouette of cypress trees guiding the road like brushstrokes on a Renaissance painting.

For those seeking Luxury Private Villas that embody the romance of rural Italy, there’s nowhere quite like it. The Val d’Orcia invites stillness. It’s where time moves gently, and every sunset feels like a private performance.

Villa La Foce – A Noble Garden Estate Overlooking Infinity

Perched above the rolling hills near Pienza, Villa La Foce is one of Tuscany’s most storied estates. Once home to the writer Iris Origo, it’s now available for exclusive stays, offering guests a rare glimpse into aristocratic life. The villa’s gardens, designed by Cecil Pinsent, are among the most celebrated in Italy — a blend of Italian symmetry and English romanticism that unfurls toward the horizon.

Inside, antique furniture meets soft, understated luxury: linen-draped beds, terracotta floors, and windows framing dreamlike views. A team of staff discreetly tends to every need, from organising daily breakfasts to arranging guided tours of nearby Montepulciano’s vineyards.

For those seeking cultural immersion, Siena’s Gothic architecture and medieval palio traditions are only an hour’s drive away. But most guests find it hard to leave — afternoons melt into golden evenings on the terrace, where Brunello di Montalcino glows like liquid amber in the light.

Borgo Finocchieto – Where Old World Charm Meets Modern Grandeur

Just outside Buonconvento lies Borgo Finocchieto, a meticulously restored medieval hamlet once abandoned and now reborn as one of Italy’s most exclusive private villa complexes. Comprising five separate buildings — from the grand Manor House to smaller guest residences — the borgo can host up to 44 guests in utter privacy.

This is Tuscany on an epic scale: think candlelit banquets beneath vaulted ceilings, private cooking lessons with local chefs, or a sunset concert performed just for you in the borgo’s stone courtyard. Yet for all its grandeur, there’s warmth here — a sense of community that makes every gathering feel authentic rather than ostentatious.

Each suite balances rustic Tuscan textures with elegant modern touches: exposed beams, travertine bathrooms, and handcrafted furniture sourced from nearby artisans. The infinity pool overlooks patchwork hills, and guests can enjoy wine tastings, truffle hunts, and e-bike tours arranged exclusively through Awake & Wander Luxury Travel.

Between these two extraordinary retreats, travellers can choose between heritage and reinvention — a noble villa steeped in history or a reimagined borgo blending tradition and indulgence. Both represent the essence of Luxury Private Villas in Tuscany: spaces that restore your senses while reconnecting you to life’s quieter pleasures.

Beyond the Villas: Curated Experiences in the Val d’Orcia

At Awake & Wander, we believe every stay should feel tailor-made. Whether you’re travelling for a milestone celebration or a soul-nourishing escape, our travel specialists curate bespoke experiences that transform Tuscany into your private playground:

Private Vineyard Picnics – Enjoy exclusive access to boutique wineries in Montalcino, complete with a personal sommelier and chef-prepared tasting menu.
Hot-Air Balloon Rides at Dawn – Watch the Val d’Orcia awaken beneath you, mist curling through valleys like soft silk.
Artisan Market Tours – Shop for hand-painted ceramics, olive oils, and Pecorino di Pienza with a local expert who knows every hidden stall.
Wellness at the Source – Visit the thermal springs of Bagno Vignoni for a rejuvenating soak followed by an al-fresco lunch under olive trees.

After each day’s discoveries, return to your villa’s serenity — perhaps with an Aperol spritz by the firepit or a massage in the garden pavilion. Tuscany’s true luxury lies not in excess, but in effortless beauty.

The Tuscan Coast & Maremma Region: Coastal Calm Meets Countryside Chic

Tuscany isn’t only vineyards and hill towns — its coast, stretching from Livorno to Monte Argentario, offers a lesser-known but equally enchanting escape. Here, pine forests give way to golden beaches, and ancient watchtowers guard turquoise coves. For travellers who love the idea of Luxury Private Villas paired with the sea breeze, Maremma and the Argentario peninsula deliver Tuscany at its most unexpected and indulgent.

Villa La Sughera – A Seaside Sanctuary in Monte Argentario

On the slopes above Porto Ercole, Villa La Sughera feels like a secret retreat. Its modernist design contrasts beautifully with the wildness of the coast — clean lines, wide terraces, and floor-to-ceiling windows that open onto sweeping sea views. Inside, interiors blend coastal minimalism with Tuscan warmth: soft linen sofas, natural stone, and handcrafted décor inspired by the region’s maritime heritage.

Guests can start the day with yoga on the terrace, spend afternoons exploring the hidden coves of Cala Galera by private boat, and end with a candlelit dinner prepared by an in-villa chef using the day’s catch. The property’s infinity pool mirrors the horizon, creating the illusion of floating between sky and sea.

For those craving adventure, Awake & Wander can arrange scuba diving trips to Giglio Island, sunset sails, or a private beach picnic on the Feniglia dunes — all while your villa remains your personal sanctuary by the sea.

Tenuta di Poggio Cavallo – Maremma’s Wild Heart, Refined

Inland from the coast, the Tenuta di Poggio Cavallo sits amid 300 hectares of olive groves and wildflower meadows. This restored 18th-century estate captures the essence of rural Maremma — tranquil, untamed, and authentically Italian.

The villa’s honey-coloured walls and shaded loggias frame views of the Ombrone River. Inside, vaulted ceilings, terracotta floors, and antique furnishings speak of history, while the swimming pool, wine cellar, and private equestrian centre add layers of refined indulgence.

Guests can join local cowboys — known as butteri — for a horseback ride through the wetlands, followed by an olive-oil tasting or dinner beneath the stars. Each evening, the scent of rosemary and sea salt drifts through the air, reminding you that Tuscany’s magic lies in its contrasts. For wellness seekers, explore our favourite Luxury Spa Hotels Worldwide.

Why the Tuscan Coast Belongs on Your Luxury Villa Shortlist

While many travellers gravitate to Chianti or Siena, the Tuscan coast remains a secret shared by those in the know. It’s where rustic meets Riviera — perfect for honeymooners, multi-generation families, or groups of friends seeking a slower pace.

From vineyard-dotted hillsides to hidden beaches, these Luxury Private Villas invite you to experience Tuscany differently: private, peaceful, and endlessly beautiful.

And with Awake & Wander Luxury Travel, your coastal escape is more than just a booking. It’s a personally curated journey, where every meal, excursion, and sunset is designed around you.

Booking Protections & Peace of Mind

When you book your Luxury Private Villa in Tuscany through Awake & Wander Luxury Travel, you’re not just choosing elegance — you’re choosing peace of mind.

As a UK-based independent travel agency with ATOL protection and Supplier Failure Insurance, every bespoke trip is fully safeguarded from the moment you enquire to the moment you return home. We work directly with trusted villa owners and local partners across Tuscany to ensure complete transparency, quality, and flexibility.

Whether you’re reserving a centuries-old Chianti estate or a coastal hideaway in Monte Argentario, you’ll enjoy the reassurance of financial protection and personalised support at every step.

Why Choose Awake & Wander for Your Tuscany Escape

At Awake & Wander Luxury Travel, we don’t sell holidays — we design stories that belong only to you. Every itinerary is handcrafted by our expert team, blending Italy’s finest villas with immersive experiences and seamless service.

We believe the art of travel lies in personal connection:

You’ll speak with real travel designers who know Tuscany intimately.

You’ll receive tailored recommendations that reflect your style and pace.

And you’ll enjoy round-the-clock support before and during your stay.

Our mission is simple: to create journeys that feel effortless, inspiring, and deeply individual. Because, as our philosophy reminds us —

Where every journey begins with you.

Start Planning Your Bespoke Villa Escape

Whether it’s a vineyard estate surrounded by olive groves, a Renaissance mansion near Florence, or a chic coastal villa overlooking the Tyrrhenian Sea, Tuscany’s Luxury Private Villas promise a getaway unlike any other.

Speak with our team today on 01495 400011, or use our online enquiry form to start designing your own tailor-made Tuscan retreat. You can also explore more inspiration through our website’s holiday search tool — where your perfect journey awaits, crafted as uniquely as you are.

Tuscany is waiting — the only question is:

Which villa will you call yours?

What makes Tuscany’s Luxury Private Villas unique compared to hotels?
Tuscany’s Luxury Private Villas offer total privacy, flexibility, and authenticity. Unlike hotels, you can immerse yourself in local life — from sunrise swims to dinners prepared by private chefs using ingredients from nearby farms. It’s a home-from-home experience infused with Italian elegance.
Which areas of Tuscany are best for Luxury Private Villas?
Top regions include Chianti and Florence for wine and culture, Val d’Orcia for panoramic countryside views, and the Tuscan Coast for seaside tranquillity. Each offers distinct landscapes, from vineyard-draped hills to olive groves and medieval towns.
Are private chefs or staff available at Luxury Private Villas?
Yes. Many Luxury Private Villas come with optional staff — including chefs, butlers, and housekeepers. Awake & Wander can arrange bespoke dining experiences such as truffle dinners, pizza-making nights, or poolside lunches.
Do Luxury Private Villas in Tuscany include pools and gardens?
Most do. Infinity pools overlooking vineyards, manicured gardens with pergolas, and terraces for al fresco dining are standard at many of Tuscany’s Luxury Private Villas. Some even have wellness areas, saunas, or private tennis courts.
When is the best time to book a Luxury Private Villa in Tuscany?
Spring (April–June) and autumn (September–October) offer the best mix of warm weather and quieter surroundings. Summer is ideal for families, while winter brings cosy villa stays with fireplaces and festive charm.
Can Awake & Wander arrange experiences during my villa stay?
Absolutely. We specialise in creating tailor-made itineraries for guests in Luxury Private Villas — including wine tastings, hot-air balloon rides, private art tours, or spa days. Every itinerary is designed around your preferences.
Are Tuscany’s Luxury Private Villas suitable for families and groups?
Yes. Villas range from romantic one-bedroom hideaways to large estates for 10–20 guests. Multi-generational families and wedding parties often choose Luxury Private Villas for their privacy, space, and shared living areas.
How does Awake & Wander protect my booking?
Every holiday booked through us is ATOL-protected and includes Supplier Failure Insurance, giving you complete peace of mind. You’ll enjoy the same security as a major tour operator with the personal service of an independent agency.
Can I request special amenities or celebrations in advance?
Yes. Whether it’s a milestone birthday, honeymoon, or private event, we can prepare your Luxury Private Villa with flowers, local wines, and bespoke touches — even private musicians or photographers on request.
How do I start planning my Tuscany villa holiday?
You can call 01495 400011 or fill in our enquiry form to begin. Our travel experts will handpick Luxury Private Villas that fit your vision and budget — ensuring every detail feels uniquely yours.