Historic Estate01
Villa LenkaLucca & Garfagnana · Sleeps 14 · 7 bedrooms
From €2,150 / night
Pool: Private floodlit pool (20m × 10m)
A genuine 17th-century aristocratic villa, built in 1624 for Count Cosimo Bernardini…
Villas in Tuscany with private pools.
Private means private: the pool belongs to the house, not to a resort. Some are infinity lines above the vines, some are heated for April and October, some are fenced for the smallest swimmers, and the detail pages say which, and we will tell you honestly if a pool is wrong for your party.
Pool weather runs May to September, see Tuscany in June for the season at its best, or when to come for the honest overview. Travelling with children? The family activities start at the pool’s edge.
22 houses
Countryside Classic02
Villa BiondiCastiglion del Bosco · Sleeps 10 · 5 bedrooms
From €16,000 / night
Pool: Heated private pool, with a pool house
The estate's largest villa, 726 m², with five en-suite bedrooms for ten and a separate pool house.
Countryside Classic03
Villa OlivieraCastiglion del Bosco · Sleeps 6 · 3 bedrooms
From €11,000 / night
Pool: Heated infinity pool
Three en-suite bedrooms for six, an intimate, refined house at the edge of the borgo.
Restored Borgo04
Borgo BernardiniLucca & Garfagnana · Sleeps 24 · 12 bedrooms
From €3,300 / night
Pool: Private floodlit pool (18m × 8m)
A whole private hamlet, twelve en-suite bedrooms for up to twenty-four, made for a large gathering…
Restored Borgo05
Casale La PergolaCastelfalfi · Sleeps 6 · 3 bedrooms
From €12,000 / night
Pool: Private pool
A private house with its own pool inside the medieval borgo, a combination that almost never comes up in a historic Tuscan…
Countryside Classic06
Villa Sant'AnnaCastiglion del Bosco · Sleeps 10 · 5 bedrooms
From €14,500 / night
Pool: Heated private pool, with a tennis court and pool house
Five en-suite bedrooms for ten, with a separate pool house and a home-theatre room.
Historic Estate07
Villa San BartolomeoMontepulciano · Sleeps 12 · 6 bedrooms
From €1,900 / night
Pool: 25-metre outdoor infinity pool with panoramic lounge, plus an indoor pool heated to 38°C with hydromassage in the private wellness centre
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 Estate08
Villa ControniLucca & Garfagnana · Sleeps 24 · 12 bedrooms
From €3,150 / night
Pool: Private floodlit pool (18m × 8m), walled garden
A 19th-century Lucchese villa of real history, the Controni family's summer residence…
Countryside Classic09
Villa StabbiCastiglion del Bosco · Sleeps 11 · 6 bedrooms
From €15,500 / night
Pool: Heated private pool, with a pool house
Six en-suite bedrooms for eleven, across the main house, a guest annex and a pool house.
Countryside Classic10
Il FrantoioLucca & Garfagnana · Sleeps 8 · 4 bedrooms
From €1,050 / night
Pool: Private floodlit pool (8m × 4m, heatable on request)
An atmospheric conversion of a 16th-century olive mill, working until 1997, with original features and ancient oil jars in the…
Contemporary Masterwork11
Villa FarfallaLucca & Garfagnana · Sleeps 14 · 6 bedrooms
From €2,700 / night
Pool: Panoramic pool (26m × 5m) with hydromassage
An award-winning contemporary masterwork, designed by its owner-architects and named by National Geographic among Italy's most…
Countryside Classic12
Casale I BianchiCastelfalfi · Sleeps 10 · 5 bedrooms
From €18,000 / night
Pool: Private heated pool
The estate's largest villa, 550 m² and five master bedrooms, yet entirely private…
Countryside Classic13
Villa del FattoreLucca & Garfagnana · Sleeps 15 · 8 bedrooms
From €2,150 / night
Pool: Private floodlit pool (16m × 8m)
A classic restored Tuscan country home, terracotta, beams and frescoes, with rose-covered patios and a winter-garden conservatory.
Countryside Classic14
Villa MatteucciLucca & Garfagnana · Sleeps 14 · 7 bedrooms
From €1,700 / night
Pool: Private floodlit pool (12m × 6m); private lake
A characterful Tuscan farmhouse with genuine history, the home of Felice Matteucci, father of the combustion engine.
Countryside Classic15
Villa GauggioleCastiglion del Bosco · Sleeps 8 · 4 bedrooms
From €14,000 / night
Pool: Heated private pool, with a pool house and fitness room
Four en-suite bedrooms for eight, three in the main house, one in a private guest annex with its own shaded pergola.
Countryside Classic16
Villa AgrestoCastiglion del Bosco · Sleeps 12 · 6 bedrooms
Price on enquiry
Pool: Heated private pool and outdoor Jacuzzi
Six en-suite bedrooms for twelve, with a self-contained guest annex and kitchenette, room for a large family or group.
Countryside Classic17
Villa ChiusaCastiglion del Bosco · Sleeps 8 · 4 bedrooms
From €13,500 / night
Pool: Heated infinity pool, with a pool house
Four en-suite bedrooms for eight, including a private guest annex, and a separate pool house with a kitchenette.
Historic Estate18
Villa CastelloCastiglion del Bosco · Sleeps 6 · 3 bedrooms
From €12,000 / night
Pool: Heated infinity pool
Built on medieval castle ruins, a three-storey house of real character, with a top-floor primary suite and panoramic views.
Countryside Classic19
Villa Casa del FiumeCastiglion del Bosco · Sleeps 8 · 4 bedrooms
Price on enquiry
Pool: Heated private pool, with a pool house
Four en-suite bedrooms for eight, including a pool house with its own living room and bedroom.
Countryside Classic20
Villa AlbaCastiglion del Bosco · Sleeps 6 · 3 bedrooms
From €9,000 / night
Pool: Heated private pool
Three en-suite bedrooms for six, the most intimate of the estate's countryside villas, with a private guest annex.
Countryside Classic21
Villa OddiCastiglion del Bosco · Sleeps 12 · 6 bedrooms
Price on enquiry
Pool: Heated private pool, outdoor Jacuzzi and a tennis court
Six en-suite bedrooms for twelve, across the main house and a pool house, generous space for a large group.
Historic Estate22
Argentaia EstateMaremma · Sleeps 18 · 9 bedrooms
Price on enquiry
Pool: Heated saltwater infinity pool, 30 × 5 m
Restored over a decade by artisans who handcrafted almost every element, locally quarried stone, hand-forged iron…
Why the pool decides the shape of the day
Summer afternoons in Tuscany regularly reach 32 to 35C, and without a pool the hours between lunch and dinner are difficult to fill. With one, the day organises itself: a slow morning, a drive to a town for lunch, the long afternoon at the water, dinner on the terrace as the light goes. It is the single amenity that changes how a week is actually lived.
Not every Tuscan pool is built equal
Size matters more than guests expect. A 6x3 metre pool that looks adequate in photographs feels small at four in the afternoon with eight people in the house. Position matters as much: a south-facing terrace holds the sun until late afternoon, while a north-facing one starts losing the light by three. Heating extends the season into the shoulder months but adds running cost, and an infinity edge only earns its name when the ground beyond it actually falls away.
We have visited every house in this collection in person and checked the dimensions, the orientation and the heating against what the listing claims, so what you book is what you arrive to.
Where the pool villas are, region by region
The Chianti Classico zone has the widest choice of the standard family pool: an 8x4 or 10x5 rectangle on a stone terrace among olives and vines. These are the workhorses of the Tuscan market, reliably good and fairly priced. The Val d'Orcia is where pools turn ambitious, with infinity edges and more dramatic positioning, because the landscape itself is more dramatic. The Maremma coast pairs a family pool with a beach fifteen minutes away, which suits mixed-age groups. Around Lucca the pools tend to be smaller and set in walled gardens, better for couples and small families than for a crowd.
Practical notes before you book
Pool cleaning is normally included weekly, with daily service available at the larger estates and usually bundled with concierge. Covers are increasingly common as Italian rules on water use tighten. And if you have a specific requirement, a length you can swim laps in, a shallow end for grandchildren, lights for evening swimming, tell us at enquiry rather than assuming a listing covers it. Those are exactly the details that do not appear in photographs.
By region: Chianti for the widest choice, the Val d’Orcia for the infinity edges, the Maremma for pool and beach in one week, or near Lucca for walled-garden pools.
Frequently asked
- Are the pools private?
- Yes, every pool on this page belongs to its house alone. Villas inside estates (Castiglion del Bosco, Castelfalfi) may also have access to estate facilities, but the pool by your terrace is yours.
- When are the pools open?
- Most run from May to the end of September; heated pools stretch the season from April into October. If a specific month matters, tell us and we will match the house to it.
- Are the pools safe for young children?
- Several houses have fenced or gated pools, and we flag which when you tell us the ages in the party. No child-relevant detail is left to the arrival day.
- How big are the pools?
- Most sit between 8x4 and 10x5 metres, which is the comfortable range for a house sleeping eight to twelve. Size matters more than photographs suggest: a 6x3 pool looks adequate in a listing and feels small at four in the afternoon with eight people in the property. We publish the dimensions we have verified rather than the ones advertised.
- How warm is the water, and are any pools heated?
- Unheated pools sit around 26 to 28C by mid-July, cooler in spring and autumn. Heated pools stretch the season from April into October and are listed as such on each villa page; the heating adds running cost, which we state up front rather than at the end.