Top 5 Luxury Villas in Tuscany for an Exclusive Italian Escape

Why Tuscany, and why a villa right now?

Picture the first morning: shutters half open, a soft hum of cicadas outside, and the scent of espresso drifting across a stone terrace. With Luxury Tuscan Villas, you’re not just booking a place to sleep. You’re booking space — for slow lunches that stretch into golden evenings, for swim-before-breakfast mornings, and for that rare sense of privacy that makes Italy feel like it belongs to you.

Tuscany is made for this. It’s close enough to dip into Renaissance cities, yet rural enough to disappear into vineyards and cypress-lined lanes. And when the villa is right, you don’t need a packed itinerary. The villa becomes the destination — with a private chef on call, a driver when you want one, and day trips that feel effortless because someone else is handling the details. If you’d like to compare more options beyond these Luxury Tuscan Villas, our guide to The Best Private Villas in Tuscany for a Bespoke Luxury Getaway is a helpful next read.

Question for you: are you dreaming of a secluded countryside hideaway, or do you want a villa that sits near a buzzy town for evenings out?

If this list sparks your imagination, share it with the friend who always plans the group trip — Tuscany is better when you’ve got people to clink glasses with.

How we chose these Luxury Tuscan Villas

You’ll find plenty of “best villa” lists online. Ours is tighter, more intentional. Each villa in this edit earns its place for at least three reasons:

• A true sense of exclusivity (privacy, layout, and setting)
• A strong service story (chef, concierge, housekeeping, experiences)
• Location that enhances the escape (not just “in Tuscany”, but the right Tuscany)

We’ve also mixed styles — from restored estates to design-forward retreats — so you can choose a villa that matches the mood you want.

Still deciding whether a staffed villa is right for your trip? Here’s why many travellers choose a private villa in Tuscany for their next luxury getaway over a traditional hotel stay.

Villa 1 — A Chianti Hilltop Estate for Vineyard Views and Chef-Led Evenings

Best for: first-time Tuscany, friends’ trips, milestone birthdays

Chianti is Tuscany’s heartland: rolling vines, honey-stone villages, and roads that seem designed for leisurely drives with the roof down. A hilltop villa here gives you the classic “postcard Tuscany” feeling — but with modern comfort and the kind of exclusive privacy you can’t get in a hotel.

What makes this stay feel truly exclusive

• Panoramic vineyard views and sunset terraces for aperitivo
• Private pool with plenty of space around it (no “sunbed scramble”)
• Chef option for the nights you want restaurant-level food without leaving the villa
• A layout that suits groups: shared spaces for long dinners, plus bedrooms that still feel private

The rhythm of a perfect week here

Mornings are slow: fruit, pastries, espresso, then a swim. Midday might be a private winery visit, a market run for pecorino and peaches, or a guided e-bike ride through the vines. And evenings? They’re made for candlelight dinners at home, with local reds and the kind of laughter you only get when no one has to drive back.

Little touches we love arranging

• A welcome spread with regional wine and local olive oil
• A private driver for winery days (so you can taste freely)
• In-villa tastings led by a sommelier
• A chef-led Tuscan cooking evening, relaxed and hands-on

Awake & Wander link-in (explore more):
If this Chianti style speaks to you, we can shortlist Luxury Tuscan Villas with the same “hilltop + chef + views” formula — then tailor the extras (wine, wellness, drivers, guides) around how you actually like to travel. Where every journey begins with you.

For travellers who want to pair Luxury Tuscan Villas with a few nights of city elegance, our roundup of the top luxury hotels in Florence makes a perfect add-on.

Villa 2 — A Val d’Orcia Stone Villa for Cinematic Landscapes and Total Calm

Best for: couples, honeymoons, slow travel, wellness escapes

Val d’Orcia is the Tuscany you’ve seen in films: soft hills, cypress ribbons, and honey-coloured villages perched like paintings. It’s quieter than Chianti, and that’s the magic. If you want your Italian escape to feel like a deep exhale, this is the setting.

Why this is one of the most swoon-worthy Luxury Tuscan Villas

• A restored stone home with authentic character (beams, terracotta, arches)
• A pool set to maximise those “rolling hill” views
• Space for outdoor living: shady pergolas, long tables, and unhurried lunches
• Ideal positioning for day trips to places like Pienza and Montepulciano (without feeling “touristy” at home)

What you do here (and why it’s unforgettable)

You’ll wake to quiet. Not silence — softness. Birds, breezes, distant church bells. Days drift between pool time, countryside walks, and unplanned detours to small enotecas. And if you want a little sparkle, we can arrange a private tasting in Montepulciano or a sunset picnic with local wines.

Elevated add-ons that suit Val d’Orcia perfectly

• In-villa massage or a private yoga session at sunrise
• A photographer for couples or family trips (golden hour here is unreal)
• A curated “best of Val d’Orcia” day with driver + reservations handled
• A private chef for a pici pasta evening with regional pairings

Awake & Wander link-in (explore more):
If Val d’Orcia is calling your name, we’ll curate Luxury Tuscan Villas that match your pace — whether that’s full wellness retreat, honeymoon romance, or simply the rare joy of doing less (in the most beautiful place possible).



Villa 3 — A Design-Led Florence Hills Villa for Art, Shopping, and Seamless Day Trips

Best for: culture lovers, foodies, “a bit of everything”, multi-gen families

If you want Tuscany’s countryside calm without giving up city sparkle, stay in the hills around Florence. You’ll get olive groves, private terraces, and that warm villa stillness — plus the option to be in the city for a late lunch, the Uffizi, or a beautifully simple dinner that turns into a walk across the Arno.

This is where Luxury Tuscan Villas really shine for travellers who like choice. You can go full slow-living at the villa, then dip into Florence whenever you fancy. No pressure, no rigid schedule.

What makes this villa feel “exclusive” (not just “nice”)

• A sleek, design-forward interior (clean lines, natural materials, curated art)
• Multiple outdoor zones: shaded lounge, dining terrace, sunset spot
• Concierge-ready set-up for museum tickets, private guides, restaurant bookings
• Easy logistics: short transfers, smooth arrivals, and less time spent driving

How a week here tends to flow

• Day 1–2: settle in, pool time, chef dinner at home
• Day 3: Florence with a private guide (art and hidden streets), gelato break, dinner back in the hills
• Day 4: a Chianti tasting day by driver (no navigating, no parking stress)
• Day 5: villa reset day — massage, long lunch, book by the pool

Elevated extras we love for the Florence hills

• Private art historian for the Uffizi or Accademia (timed entry handled)
• A craft and artisan route: leather, ceramics, jewellery — the pieces you keep forever
• Chef + sommelier pairing night at the villa for a restaurant-level evening without the noise

Awake & Wander link-in (explore more):

If this “villa serenity + Florence energy” blend is your sweet spot, we’ll shortlist Luxury Tuscan Villas in the right pockets — then build your week around what you love (art, food, shopping, wine, or all four). Where every journey begins with you.

Villa 4 — A Maremma Coastal-Countryside Retreat for Beach Days and Barefoot Luxury

Best for: repeat Italy travellers, privacy seekers, families who want variety

Most lists lean hard into Chianti and Val d’Orcia. But for an exclusive escape, Tuscany’s Maremma is the power move. It’s more under-the-radar: wild beaches, pine-backed shores, nature reserves, hot springs, and countryside estates where the vibe is effortlessly chic.

If you want Luxury Tuscan Villas that feel different — less postcard, more “insider Tuscany” — this is the region.

What makes this one special

• A villa that balances countryside seclusion with easy beach access
• Large pool + outdoor living built for long summer days
• Space that suits families and friends: room to spread out, gather, and still breathe
• The option to mix in experiences beyond wine: boat days, beaches, thermal springs, horseback riding

The kind of days you’ll remember

Morning swim, then a coastal drive for a lazy beach lunch. Back for an afternoon by the pool while someone preps aperitivo. Or swap it: a thermal springs morning, vineyard lunch, sunset back at the villa. It’s a choose-your-own-adventure Tuscany — but still deeply relaxed.

Add-ons that elevate Maremma beautifully

• Private boat charter for hidden coves and sea swims
• A chef who leans coastal: grilled fish, bright salads, local whites
• Hot springs day with a driver so you don’t think about timing
• A family-friendly pizza night (dough tossing encouraged)

Awake & Wander link-in (explore more):

If you like the sound of Tuscany with beach energy, we can curate Luxury Tuscan Villas in Maremma that match your style — from barefoot-luxe to ultra-private estates — and layer in the experiences that make it feel truly tailored.

If you’re building a wider itinerary, our Italy overview—Luxury Travel in Italy: The Best Hotels and Villas in Tuscany—pulls together standout stays and experiences in one place.

Villa 5 — Luxury Tuscan Villas in Lucca: Walled-City Charm with a Private Countryside Base

Best for: stylish families, food lovers, couples who want evenings out, “quiet but not remote”

Lucca is one of Tuscany’s loveliest surprises — a small, elegant walled city with tree-lined ramparts, candlelit trattorias, and a calmer, more local feel than Florence. Base yourself in the countryside just outside the walls and you get the best mix: villa privacy by day, walkable charm by night.

This is a brilliant choice if you want Luxury Tuscan Villas that feel exclusive and peaceful, but still connected to real life — markets, cafés, small concerts, and that simple Italian joy of an evening passeggiata.

Why this villa earns its “exclusive escape” status

• A private countryside setting with easy access back into Lucca
• Pool + garden that actually invites you to spend the whole day outside
• Interiors that feel polished yet comfortable (think linen, stone, soft neutrals)
• Ideal for short scenic drives to the coast (Versilia beaches) or nearby hill towns

The Lucca rhythm (the one people fall in love with)

Mornings at the villa: slow breakfasts, a swim, then a gentle plan — or none at all. Late afternoon, you dress up a little and head into Lucca for aperitivo. Maybe you cycle the ramparts, browse small boutiques, then settle into a long dinner where the second bottle of wine is never a mistake.

Little upgrades that make this stay sing

• A private chef for two villa nights (and two nights out in Lucca — best of both)
• A guided food walk through Lucca’s markets and bakeries
• A driver on standby for beach days, winery visits, and stress-free evenings
• A family-friendly “Italian classics” cooking session at the villa

Awake & Wander link-in (explore more):

If you want Tuscany with a strong sense of place — not just countryside views — we’ll curate Luxury Tuscan Villas near Lucca that match your pace and style, then add the experiences that make it feel personal, easy, and completely yours. Where every journey begins with you.

How to choose between Luxury Tuscan Villas (without overthinking it)

Villa lists can feel overwhelming because everything looks beautiful. Here’s the simplest way to narrow it down — fast.

1) Pick your “Tuscany mood” first

• Postcard vineyards + classic villages: Chianti
• Cinematic landscapes + deep calm: Val d’Orcia
• Art + restaurants + easy logistics: Florence hills
• Beach days + wild nature + privacy: Maremma
• Charming evenings out + relaxed elegance: Lucca

Once you choose the mood, the right villa shortlist becomes obvious.

2) Decide what “luxury” means for you

For some travellers, luxury is a chef and daily housekeeping. For others, it’s a heated pool, a gym, or bedrooms that feel like boutique suites. When we plan Luxury Tuscan Villas for clients, we start with your non-negotiables and build from there.

A few questions that instantly clarify things:

• Do you want staff on-site, or discreet service on request?
• Is walking distance to a village important, or do you prefer isolation?
• Are you a pool-all-day family, or are you out exploring most days?
• Do you prefer traditional charm or modern design?

3) Don’t underestimate layout

A villa can be gorgeous and still wrong for your group. We look closely at:

• Bedroom privacy (especially for couples travelling together)
• Bathroom ratios (the silent hero of a happy group trip)
• Outdoor shade, dining areas, and whether the pool space works for your style

Best time to book Luxury Tuscan Villas for an exclusive escape

Tuscany is lovely most of the year, but your experience changes a lot by season.

Spring (April–May)

Fresh landscapes, comfortable temperatures, fewer crowds. Perfect for food, wine, and exploring without the heat

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Summer (June–August)

Peak villa season: long days, warm nights, pool weather. The trade-off is higher demand — the most sought-after villas often go early.

Early autumn (September–October)

One of the best times for a villa escape: golden light, vineyard energy, and a slower, more romantic pace.

Winter (November–March)

Quiet, cosy, and great for city-focused trips with a countryside base — though many villas reduce services or close pools.

A useful rule: if you’re aiming for the very best Luxury Tuscan Villas (prime locations + strong service + standout pools), it pays to plan earlier than you think — especially for July/August or large groups.

What’s typically included in Luxury Tuscan Villas (and what to double-check)

Even among Luxury Tuscan Villas, “luxury” can mean different things. Here’s what’s commonly included — and the few details that stop surprises later. For seasonal events, regional highlights, and practical planning inspiration, the official Tuscany tourism portal is a trusted resource before you travel.”

Usually included

• Exclusive use of the villa and grounds
• A private pool (seasonal opening can vary)
• Kitchen essentials and dining space for entertaining
• Wi-Fi, air con (not always throughout older villas), and parking
• A local property manager or concierge contact

Often optional, but worth adding

• Private chef (one-night splurge or full stay)
• Housekeeping frequency upgrades
• Driver services for winery days and evenings out
• Wine tours, truffle hunting, Vespa days, guides, and wellness treatments

Quick checklist we run with clients

• Bedroom privacy + bathroom ratios
• Pool heating, fencing (for little ones), and exact pool season dates
• A/C coverage (especially for July–August)
• Any local rules (quiet hours, event permissions, arrivals)
• Distance to the closest town for restaurants/markets

Our Take:

"The best Tuscan luxury isn’t loud. It’s the quiet confidence of having everything handled — while you do absolutely nothing… beautifully.”
– Awake & Wander Luxury Travel

Booking protections when you travel with Awake & Wander Luxury Travel

As a UK-based independent travel agency, we plan your trip with confidence built in — not just beautiful stays.



• ATOL protection applies where your booking meets the legal definition of an ATOL-protected package/flight arrangement.
• We also provide Supplier Failure Insurance, adding reassurance if an end supplier fails.
• Most importantly, you have a real team to contact if plans change — plus support if disruption happens while you’re away.

Why book your Luxury Tuscan Villas with Awake & Wander Luxury Travel

The difference is in the curation — and the way your stay flows. We don’t just point you to a property. We match you to the right region, the right layout, and the right level of service, then weave in the extras that make your villa feel like it was waiting for you all along.

If you’d like a shortlist of Luxury Tuscan Villas that fit your dates, group size, and style, call 01495 400011 or use our enquiry form. You can also use our website’s search tool to start shaping a bespoke holiday “as unique as you are.”

Where every journey begins with you.

Frequently Asked Questions