Countryside Classic01
Casa LiliaChianti · 8 guests · 4 bedrooms
From €4,500 / week
Panoramic view · Olive grove
Four double bedrooms, each with its own bathroom, three of them opening straight onto the garden through floor-to-ceiling glass.
Luxury villas to rent in Tuscany
51 private villas in Tuscany, sleeping 4 to 37 guests; 45 have a pool of their own. Filter by area, group size and pool below, and every enquiry is answered personally within 24 hours.
51 villas
Historic Estate02
Villa San BartolomeoMontepulciano · 12 guests · 6 bedrooms
From €13,125 / week
Spa · Infinity pool
The only villa in the Val d'Orcia with a private wellness centre of its own: an indoor pool heated to 38°C with hydromassage…
Historic Estate03
Villa LenkaLucca & Garfagnana · 14 guests · 7 bedrooms
From €15,000 / week
Fully staffed · Private chef
A genuine 17th-century aristocratic villa, built in 1624 for Count Cosimo Bernardini…
Wellness Estate04
Tenuta Belvedere EstateChianti · 26 guests · 13 bedrooms
From €67,900 / week
Private chef · Spa
Complete exclusivity: the villa, both suites, the studio and every shared space, including the QB Cucina restaurant…
Countryside Classic05
Casale OlivaioChianti · 10 guests · 5 bedrooms
From €6,699 / week
Panoramic view · Olive grove
The whole farmhouse to yourselves: two self-contained lodgings joined into one home for up to ten, with the pool…
Restored Borgo06
Borgo BernardiniLucca & Garfagnana · 24 guests · 12 bedrooms
From €23,200 / week
Fully staffed · Private chef
A whole private hamlet, twelve en-suite bedrooms for up to twenty-four, made for a large gathering…
Countryside Classic07
Villa ElleSiena · 24 guests · 12 bedrooms
From €13,503 / week
Panoramic view · Pizza oven
Situated in sought-after Chianti wine country, within easy reach of Siena and Florence
Countryside Classic08
Villa AgrestoCastiglion del Bosco · 12 guests · 6 bedrooms
From €91,000 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Spa · Heated pool
Six en-suite bedrooms for twelve, with a self-contained guest annex and kitchenette, room for a large family or group.
Countryside Classic09
Villa MatteucciLucca & Garfagnana · 14 guests · 7 bedrooms
From €12,000 / week
Fully staffed · Private chef
A characterful Tuscan farmhouse with genuine history, the home of Felice Matteucci, father of the combustion engine.
Historic Estate10
Villa Poggio d'OroMontalcino · 24 guests · 12 bedrooms
From €30,730 / week
Panoramic view
A 600 m² terrace raised above the countryside, with Montalcino straight ahead, the Val d'Orcia to the east and, on clear days…
Historic Estate11
Villa CastellaroChianti · 13 guests · 7 bedrooms
From €8,500 / week
Private chef · Heated pool
A true Renaissance house: built in the fifteenth century for the Sernigi, Florentine merchants and art patrons…
Historic Estate12
Villa ControniLucca & Garfagnana · 24 guests · 12 bedrooms
From €22,000 / week
Fully staffed · Private chef
A 19th-century Lucchese villa of real history, the Controni family's summer residence…
Countryside Classic13
Casa dell'ErtaChianti · 14 guests · 7 bedrooms
From €7,810 / week
Spa · Infinity pool
Uninterrupted views of a medieval castle and the Chianti Classico hills from the pool, terraces and garden.
Countryside Classic14
Villa Casa del FiumeCastiglion del Bosco · 8 guests · 4 bedrooms
From €70,000 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Heated pool · Pizza oven
Four en-suite bedrooms for eight, including a pool house with its own living room and bedroom.
Countryside Classic15
Villa del FattoreLucca & Garfagnana · 15 guests · 8 bedrooms
From €15,000 / week
Private chef · Frescoed interiors
A classic restored Tuscan country home, terracotta, beams and frescoes, with rose-covered patios and a winter-garden conservatory.
Historic Estate16
Casale di Sant'AndreaCortona · 12 guests · 7 bedrooms
From €20,700 / week
Private chef · Infinity pool
More than seventy fenced acres of its own, meadows, olive groves, a deer park, woodland walks and a private lake.
Countryside Classic17
Villa BiondiCastiglion del Bosco · 10 guests · 5 bedrooms
From €112,000 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Heated pool · Working vineyard
The estate's largest villa, 726 m², with five en-suite bedrooms for ten and a separate pool house.
Countryside Classic18
Il FrantoioLucca & Garfagnana · 8 guests · 4 bedrooms
From €7,500 / week
Private chef · Olive grove
An atmospheric conversion of a 16th-century olive mill, working until 1997, with original features and ancient oil jars in the…
Wellness Estate19
Villa Il CelleseChianti · 19 guests · 10 bedrooms
From €59,500 / week
Private chef · Spa
Nine hectares of organic land with its own vineyard, and the family's winery twenty minutes away…
Historic Estate20
Dimora Ghirlandaio EstateDimora Ghirlandaio · 37 guests · 20 bedrooms
From €91,000 / week
Fully staffed · Private chef
A private Renaissance hamlet taken whole: six independent houses around a formal garden, for up to 37 guests.
Historic Estate21
Borgo delle VigneChianti · 22 guests · 9 bedrooms
From €11,160 / week
Heated pool · Cinema room
Three separately restored stone farmhouses on one hilltop, a Main Villa, a Cottage and a one-bedroom Capanna annex…
Design Villa22
Podere MastrojanniMontalcino · 8 guests · 4 bedrooms
From €24,500 / week
Working vineyard · Pizza oven
Designed room by room by the artist Vittorio Corsini, every space one-of-a-kind, honest materials…
Countryside Classic23
Casa PernicellaChianti · 6 guests · 3 bedrooms
From €3,870 / week
Infinity pool · Heated pool
A carefully restored stone barn with three en-suite bedrooms, bathrobes and a kitchen equipped well beyond the usual.
Historic Estate24
Casale GherardiChianti · 18 guests · 9 bedrooms
From €20,300 / week
Infinity pool · Working vineyard
History on paper: a 1427 document from Bernardo di Bartolomeo Gherardi already describes this farm's forests, soil…
Historic Estate25
Villa della CappellaCortona · 18 guests · 9 bedrooms
From €10,150 / week
Private chapel · Frescoed interiors
A genuine 17th-century restoration: frescoed vaulted ceilings, painted walls and terracotta floors across more than 1,000 square…
Restored Borgo26
Casale La PergolaCastelfalfi · 6 guests · 3 bedrooms
From €84,000 / week
A private house with its own pool inside the medieval borgo, a combination that almost never comes up in a historic Tuscan…
Wellness Estate27
Solare del ChiantiChianti · 20 guests · 10 bedrooms
From €13,500 / week
Summer 2027: last free week
Spa · Gym
Room for a big family or group: sixteen in the main villa, twenty with the Poggiarello cottage.
Wellness Estate28
Tenuta La BarricaiaVal d'Orcia · 26 guests · 13 bedrooms
From €22,344 / week
Spa · Infinity pool
Thirteen en-suite bedrooms for up to twenty-six, eight in the main villa, five in a guest annex just metres away…
Historic Estate29
Villa Il ColtoArezzo · 12 guests · 6 bedrooms
From €4,570 / week
Heated pool · Panoramic view
A hilltop position with 360° views over the Valdarno and the Pratomagno hills.
Countryside Classic30
Villa GauggioleCastiglion del Bosco · 8 guests · 4 bedrooms
From €98,000 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Heated pool · Gym
Four en-suite bedrooms for eight, three in the main house, one in a private guest annex with its own shaded pergola.
Wellness Estate31
Villa FornacellaChianti · 12 guests · 6 bedrooms
From €9,500 / week
Spa · Heated pool
A full spa floor. Turkish bath, sauna and indoor jacuzzi, and a Technogym gym with views over Chianti.
Restored Borgo32
Casa MediciCastelfalfi · 6 guests · 3 bedrooms
From €56,000 / week
An address in the historic core of the borgo, with windows over the Medici Park, heritage you can see from the breakfast table.
Countryside Classic33
Villa VetrichinaVal d'Orcia · 12 guests · 6 bedrooms
From €7,875 / week
Infinity pool · Pizza oven
Complete seclusion at the end of a white road through oak woods, two kilometres from San Casciano dei Bagni and its thermal…
Countryside Classic34
Villa Sant'AnnaCastiglion del Bosco · 10 guests · 5 bedrooms
From €101,500 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Heated pool · Tennis court
Five en-suite bedrooms for ten, with a separate pool house and a home-theatre room.
Countryside Classic35
Podere PianoroChianti · 12 guests · 6 bedrooms
From €8,000 / week
Gym · Panoramic view
Six double bedrooms, all with en-suite showers, including the Gelsomino room at the top of the tower.
Countryside Classic36
Villa delle SorelleVal d'Orcia · 12 guests · 6 bedrooms
From €14,150 / week
Summer 2027: 2 weeks left
Heated pool · Gym
A 360-degree view over the Val d'Orcia, with Pienza on the skyline and the sun setting straight across the pool.
Countryside Classic37
Villa StabbiCastiglion del Bosco · 11 guests · 6 bedrooms
From €108,500 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Heated pool · Panoramic view
Six en-suite bedrooms for eleven, across the main house, a guest annex and a pool house.
Countryside Classic38
Casa FaraoniaChianti · 6 guests · 3 bedrooms
From €3,870 / week
Panoramic view · Pizza oven
A secluded single-storey house with 180-degree views over the Chianti Classico hills.
Historic Estate39
Villa ErbavoglioChianti · 18 guests · 9 bedrooms
From €17,400 / week
Working vineyard · Olive grove
Four private flats across two stone farmhouses on the Greve riverbank, each with its own kitchenette and living room…
Countryside Classic40
Casale I BianchiCastelfalfi · 10 guests · 5 bedrooms
From €126,000 / week
Heated pool · Working vineyard
The estate's largest villa, 550 m² and five master bedrooms, yet entirely private…
Restored Borgo41
Casa del VescovoCastiglion del Bosco · 5 guests · 2 bedrooms
From €35,000 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
A 200 m² two-bedroom suite in the heart of the borgo, in timeless Florentine style.
Contemporary Masterwork42
Villa FarfallaLucca & Garfagnana · 14 guests · 6 bedrooms
From €19,000 / week
Private chef · Panoramic view
An award-winning contemporary masterwork, designed by its owner-architects and named by National Geographic among Italy's most…
Contemporary Masterwork43
Stefano Ricci La RoccaCastelfalfi · 4 guests · 2 bedrooms
From €140,000 / week
Private chef · Panoramic view
The only Stefano Ricci-designed residence available to rent in Tuscany.
Restored Borgo44
Casa FontacciaCastiglion del Bosco · 4 guests · 2 bedrooms
From €56,000 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
A detached two-bedroom suite in the heart of the borgo, with its own private entrance.
Historic Estate45
Argentaia EstateMaremma · 18 guests · 9 bedrooms
Price on enquiry
Fully staffed · Private chef
Restored over a decade by artisans who handcrafted almost every element, locally quarried stone, hand-forged iron…
Countryside Classic46
Il FienileCastelfalfi · 6 guests · 3 bedrooms
From €70,000 / week
Working vineyard · Panoramic view
A restored barn with the volume and light only an old fienile gives: high ceilings, broad openings, a real sense of space.
Historic Estate47
Villa CastelloCastiglion del Bosco · 6 guests · 3 bedrooms
From €84,000 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Infinity pool · Heated pool
Built on medieval castle ruins, a three-storey house of real character, with a top-floor primary suite and panoramic views.
Countryside Classic48
Villa OddiCastiglion del Bosco · 12 guests · 6 bedrooms
From €91,000 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Heated pool · Tennis court
Six en-suite bedrooms for twelve, across the main house and a pool house, generous space for a large group.
Countryside Classic49
Villa OlivieraCastiglion del Bosco · 6 guests · 3 bedrooms
From €77,000 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Infinity pool · Heated pool
Three en-suite bedrooms for six, an intimate, refined house at the edge of the borgo.
Countryside Classic50
Villa ChiusaCastiglion del Bosco · 8 guests · 4 bedrooms
From €94,500 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Infinity pool · Heated pool
Four en-suite bedrooms for eight, including a private guest annex, and a separate pool house with a kitchenette.
Countryside Classic51
Villa AlbaCastiglion del Bosco · 6 guests · 3 bedrooms
From €63,000 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Heated pool
Three en-suite bedrooms for six, the most intimate of the estate's countryside villas, with a private guest annex.
Finite by design
That is the entire collection. There is no “view more”.
Choose your stay
Luxury villas in Tuscany, chosen around your stay
The right villa gives you more than a beautiful address. It gives your party the bedrooms, shared spaces and setting to enjoy time together. Our collection brings together countryside villas, historic villas and residences on Tuscan estates. Compare the location and layout alongside the photographs: a quiet retreat among vineyards makes for a different week from a villa close to a town.
Explore our luxury villas in Tuscany or read the best luxury villas shortlist for a closer look at individual villas. Each villa page lists its staffing and services, and a private chef can be arranged at every one. Our guide to villa rental costs explains what a quote should include.
Large villas in Tuscany for families and celebrations
For a family reunion, a holiday with friends or a milestone birthday, start with our large villas in Tuscany. Narrow your search to villas for 16 guests or villas for 20 or more, 14 of our villas sleep 16 or more. Each villa page lists bedrooms and bathrooms, and we send floor plans showing annexes and dining space on request.
Villa Elle and Villa della Cappella are useful starting points for a larger-group shortlist. For a 30th, 40th, 50th or 70th birthday, our birthday celebrations guide helps you plan the stay. Visiting guests, catering and music for an event are agreed with the owner before you book.
Tuscany villas with a private pool
A pool for your party alone can shape the whole holiday: mornings at the villa, a swim after sightseeing and time together on the terrace. Browse our Tuscany villas with private pools to focus on the 45 villas with a pool of their own; the others share estate pools, and each villa page says which.
Most villa pools open from May to late September, and heated pools from April to October; 21 of ours list a heated pool. For young children we send current photographs of the pool boundary and gates before you book.
By sub-region
Tuscany,
region by region.
Chianti for Florence and Siena, the Val d’Orcia for the classic landscape, the Lucca countryside for families and the Maremma for the coast. Our regional guides compare each area, with drive times to towns and airports; a countryside villa means a car for most outings.
Browse Tuscany by region →Frequently asked
Things travellers
often want to know.
Practical answers about choosing a villa, private pools, group stays and rental terms. For details specific to a villa, send us your dates and requirements.
- How do I choose a luxury villa in Tuscany?
- Choose the area first, then the size. Our 51 villas sleep from 4 to 37 guests across 12 areas of Tuscany: Chianti for Florence and Siena, the Val d'Orcia for the classic landscape, the Lucca countryside for families and the Maremma for the coast. Then compare bedrooms, bathrooms and the pool on each villa page.
- Do you have large villas in Tuscany for 16 or more guests?
- Yes: 14 villas sleep 16 or more, and 9 sleep 20 or more. The largest, Dimora Ghirlandaio Estate, sleeps 37. Each villa page lists its bedrooms and bathrooms, and we send floor plans on request.
- Do all your Tuscany villas have a private pool?
- Most do: 45 of our 51 villas have a pool of their own. The rest share estate pools, and each villa page states which. The private-pool collection shows only villas with their own pool.
- Are private pools heated or fenced?
- 21 villas list a heated pool, including Villa San Bartolomeo, Villa Agresto, Villa Castellaro and 18 more. Fencing is not standard in Tuscany, so for young children we send current photographs of the pool boundary and gates before you book.
- How much does a luxury villa in Tuscany cost?
- Every villa card shows its current weekly from-rate, or price on enquiry. Rates change with the season and are highest in July and August. Our guide to villa costs gives typical budgets and what a quote should include.
- What's included in a villa rental?
- The whole villa for your party for the dates you book, with the staffing and services listed on each villa page. A private chef, groceries, transfers and experiences are quoted separately. Our staffing guide explains what each role does.
- Can you help arrange a private chef?
- Yes, at every villa in the collection: for one celebration dinner or every evening of your stay. Tell us dates, numbers and any dietary needs, and we quote the chef and grocery costs before you confirm.
- Can I book a large villa for a birthday or family reunion?
- Yes. 29 villas sleep 12 or more, and 33 are listed for weddings, family celebrations or corporate retreats. Visiting guests, catering and music for an event are agreed with the owner before you book.
- Which part of Tuscany should I stay in?
- Chianti for a first visit with Florence and Siena in reach, the Val d'Orcia for the classic landscape, the Lucca countryside for families and Pisa airport, and the Maremma for beaches. Our guide to choosing a base compares them, with drive times.
- Are children and pets welcome?
- We confirm both with the owner before you book. Tell us the children's ages and any pets, and we check cots, high chairs, stairs, pool access and the pet policy for the villas you like.
- How do booking and cancellation work?
- Send your dates and group size; we reply within 24 hours with availability and the rate. You then sign the rental contract and pay a deposit to confirm, with the balance due before arrival. Cancellation terms are set out in the contract and our booking terms.
Find the right villa for your stay.
Start with your party size, a city you want to visit, or the kind of villa you have in mind. Compare bedroom layouts and facilities as well as sleeping capacity.
By party size
Near a city
Enquire
Every enquiry is answered personally.
Tell us your dates, the size of your party and the kind of trip you are imagining, and Smaranda will reply with availability, full rates and a considered recommendation, usually within a working day. Include any requirements for en-suite bedrooms, pool heating, accessibility or a celebration so we can check the details that matter to your party.