Luxury Villa Rentals
in Tuscany & Umbria
Hand-picked tuscany luxury villas, personally curated by our team of travel specialists with over two decades of sourcing the finest properties across Tuscany and Umbria.
Our Collection
Tuscany Luxury Villas, Personally Chosen
Every tuscany villa rental in our portfolio has been personally curated and selected for its exceptional character, comfort, and location across the region.
Where to Stay
Explore Tuscany by Region
From the iconic cypress-lined hills of Chianti to the crystal waters of the Tuscan coast, every region offers a different flavour of tuscany holiday living.
Celebrations
Weddings in Tuscany
Say "I do" surrounded by rolling hills, ancient olive groves, and golden light. Our villas provide the ultimate setting for unforgettable destination weddings.
Ceremony Planning
Intimate garden ceremonies or grand terrace celebrations with breathtaking Tuscan panoramas as your backdrop.
Wedding Banquet
Bespoke menus crafted by acclaimed chefs, featuring the finest local ingredients and regional wines.
Photography & Film
World-class photographers and cinematographers to capture every moment of your magical day.
Floral Design
Stunning arrangements from Tuscan blooms, from romantic arches to cascading table centrepieces.
Entertainment
Live musicians, DJs, and performers curated to set the perfect mood from aperitivo to last dance.
Full Coordination
A dedicated wedding planner handles every detail, so you and your guests simply enjoy la dolce vita.
Our Story
Two Decades of Travel Expertise
Founded by a British couple who fell in love with Tuscany, TuscanyHolidays began with a simple belief: the best holidays come from local knowledge and personal attention.
What started with a handful of carefully chosen farmhouses has grown into a curated collection of exceptional properties across Tuscany, Umbria, and the Italian coast, each one personally curated by our team.
We remain proudly independent, a small team of passionate travel experts who know every property, every owner, and every hidden trattoria worth visiting.
Personally Curated
Every villa vetted by our team before joining our collection.
Bespoke Service
Dedicated travel specialist assigned to your booking from enquiry to departure.
The Villa Advantage
Why Rent a Villa in Tuscany?
Tuscany villa rentals offer something a hotel simply cannot: the complete run of a private property, from the first cup of morning coffee on a sun-warmed terrace to a midnight dip in your own pool. Here is why a private villa is the definitive way to do a Tuscany holiday.
Privacy a Hotel Cannot Match
A tuscany villa rental gives your group the complete run of the property, private pool, olive grove, and sun-warmed terrace included. No shared dining rooms, no lobby check-ins, no compromise.
Perfect for Families & Groups
Our Tuscany luxury villas accommodate large families and groups under one roof. Birthdays, anniversary retreats, multi-family summers, a single Tuscany holiday villa transforms a trip into a shared memory.
The Whole of Tuscany on Your Doorstep
Based in a rental villa in Tuscany, you are within an hour's drive of Siena, Florence, San Gimignano, Montalcino, and the Maremma coast. Day trips are effortless; coming home to your private terrace is even better.
Authentic Italian Living
Cook with produce from the Thursday market in Greve, uncork a Brunello from the local cantina, and dine under the stars. A Tuscany holiday villa is not an accommodation, it is a way of living Italian.
Explore Tuscan food and cuisine →Tuscany Regions at a Glance
| Region | Landscape | Best For | Nearest City |
|---|---|---|---|
| Chianti → | Vine-covered hills, olive groves | Wine touring, Florence & Siena day trips | Florence (45 min) |
| Val d'Orcia → | UNESCO cypress avenues, wheat valleys | Photography, Brunello wine, hilltop towns | Siena (50 min) |
| Tuscan Coast → | Maremma coastline, pine forest | Beach, seafood, Etruscan history | Grosseto (30 min) |
| Umbria → | Green valleys, hill towns | Truffles, quieter pace, Assisi & Orvieto | Perugia (20 min) |
4
Tuscany regions covered
20+
Years travel sourcing experience
100%
Personally curated
Seasonal Guide
Best Time to Visit Tuscany
Tuscany rewards visitors in every season, but the right time depends on what you want from the holiday. Here is what each season offers for a private villa stay.
Spring
April - June
Best for scenery & wine touring
The hillsides are green, the wildflowers are out, and the light is clear and warm without the August heat. Val d'Orcia looks exactly like the postcards. Chianti's vine shoots are emerging and the cantinas welcome visitors without queues. Prices are lower than peak and availability is good if you book a few months ahead.
Summer
July - August
Peak season, pool weather
The hottest and busiest period, particularly mid-July to mid-August. Temperatures regularly reach 35°C in the interior, making a private pool essential rather than optional. Towns fill with visitors but your villa grounds remain a cool, private retreat. Book 9-12 months ahead for the best properties.
Autumn
September - October
Best for food, wine & harvest
Many experienced villa guests consider this the finest season. Grape harvest begins in late August and runs through September; truffle season opens in Umbria from late September. The light turns golden, the crowds thin, and restaurants shift to the autumn menu. Temperatures remain warm enough for afternoon swims well into October.
Winter
November - March
Off-season, quiet & affordable
Most villa rental activity pauses between November and March, though a small number of properties remain available at significantly lower rates. Florence and Siena are at their quietest and most atmospheric. Umbria's hill towns, Assisi, Spoleto, Orvieto, feel genuinely local. Not swimming weather, but ideal for culture and food.
Frequently Asked Questions
Frequently Asked Questions
When is the best time to rent a villa in Tuscany?
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May to June and September to October offer the ideal balance of warm weather, quieter roads, and better availability. The landscape is at its most dramatic in spring, wildflowers, green hillsides, and the vine shoots just emerging. September brings the grape harvest, cooler evenings, and truffle season beginning in Umbria. July and August are peak season: hotter, busier, and priced accordingly. For families tied to school holidays, mid-August in a private villa still works well, you have the pool and the property to yourselves even when the towns are full.
Which region of Tuscany is best for a villa holiday?
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It depends on what draws you. Chianti suits wine-lovers and anyone wanting easy day trips to Florence and Siena, rolling vine-covered hills, hilltop villages, and the famous Chiantigiana road. Val d'Orcia is the UNESCO postcard: cypress avenues, Pienza, Montepulciano, and Montalcino within easy reach. The Tuscan Coast (Maremma) is the choice for beach access alongside countryside, quieter than the Amalfi, with good seafood and Etruscan sites. Umbria sits just across the border: greener, quieter, and typically 20-30% more affordable than comparable Tuscan properties, with Assisi, Orvieto, and Spoleto all within reach.
How far in advance should I book a Tuscany villa?
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For peak summer dates, particularly the last two weeks of July and first two weeks of August, 9 to 12 months ahead is the realistic window for the best properties. Many of our most popular villas are taken for these weeks before the previous season ends. For shoulder season (May, June, September, October), 3 to 6 months is usually sufficient, though earlier is always better for larger villas accommodating 10 or more guests. If you have a specific property in mind, contact us regardless of timing, last-minute cancellations do happen, and we keep a waiting list.
From the Blog
Tuscany Holiday Planning Guides
Expert advice on choosing the right region, the best time to visit, and how to make the most of your tuscany villa holiday.
