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.
Villas near Siena
Siena rewards a well-planned day far more than it rewards sleeping there, which is why the villas below sit in the country around it rather than inside the walls.
31 villas near Siena in our collection, sleeping 4 to 26 guests; 28 have a private pool and 17 list a heated pool. The largest, Tenuta Belvedere Estate, sleeps 26. A private chef can be arranged at every villa.
31 villas
Countryside Classic02
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…
Wellness Estate03
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 Classic04
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
Wellness Estate05
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 Estate06
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…
Countryside Classic07
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 Classic08
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.
Historic Estate09
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…
Countryside Classic10
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.
Historic Estate11
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…
Wellness Estate12
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…
Countryside Classic13
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 Classic14
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.
Wellness Estate15
Solare del ChiantiChianti · 20 guests · 10 bedrooms
From €13,500 / week
Spa · Gym
Room for a big family or group: sixteen in the main villa, twenty with the Poggiarello cottage.
Countryside Classic16
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.
Countryside Classic17
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…
Wellness Estate18
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.
Countryside Classic19
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 Classic20
Villa delle SorelleVal d'Orcia · 12 guests · 6 bedrooms
From €14,150 / week
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 Classic21
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 Classic22
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 Classic23
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 Estate24
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…
Historic Estate25
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.
Restored Borgo26
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.
Countryside Classic27
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.
Restored Borgo28
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.
Countryside Classic29
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 Classic30
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 Classic31
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.
Choosing the right villa
Most are twenty-five minutes to an hour away, in Chianti to the north or the Crete Senesi and Val d'Orcia to the south. Park at the Santa Caterina garage, ride the escalators up, and you are beside the Duomo before the coaches.
Choose the base, then plan the journey
If golf is part of the week, our golf courses and villa guide compares Royal Golf La Bagnaia with an estate stay at Castiglion del Bosco. Rosewood villa guests have exclusive course access; staying elsewhere near Siena does not provide that benefit.
For a villa near Siena, compare the journey from the individual property to the part of the city you want to visit. Time to the edge of town is different from time to park and reach a museum or restaurant. Ask about the access road, parking and the return journey if an evening out is part of your plans.
Use the Tuscany map and driving-distance guide to place the area within your wider itinerary. Check the airport comparison against the actual villa and your flight times, rather than choosing an airport from the city name alone.
For a family or group, make a second shortlist based on life at the villa: room distribution, en-suite bathrooms, indoor dining and the nearest useful shops. A good city base should also work on the days when everyone wants to stay at the villa.
North of Siena or south
The choice sets the character of the week. North means Chianti: vineyards, wine estates, and Florence also within reach. South means the Crete Senesi and the Val d'Orcia: emptier, more cinematic, and the drive to Florence becomes a commitment rather than an outing. Both put Siena itself within an hour, and several of our Castiglion del Bosco villas sit about forty minutes south of the walls.
Getting into the city
Siena's entire centre is a ZTL, so the rule is absolute: do not drive inside the walls. The Santa Caterina garage below the west walls connects to the Duomo level by public escalators, which removes the only genuinely hard part of arriving. The train is the wrong tool here, ninety minutes from Florence with a change; from a villa the car is right.
Frequently asked
- How many villas do you have near Siena?
- 31: Casa Lilia (sleeps 8), Casale Olivaio (sleeps 10), Tenuta Belvedere Estate (sleeps 26), Villa Elle (sleeps 24), Villa Il Cellese (sleeps 19), Villa Castellaro (sleeps 13), Villa Agresto (sleeps 12), Casa dell'Erta (sleeps 14), Casale Gherardi (sleeps 18), Villa Casa del Fiume (sleeps 8), Borgo delle Vigne (sleeps 22), Tenuta La Barricaia (sleeps 26) and 19 more.
- Which villas near Siena have a private pool?
- 28 of 31: Casa Lilia (Its own fenced saltwater pool (9 × 4 m, 1.3 m deep) in a private…); Casale Olivaio (Private salt-chlorinated pool (about 12 × 6 m, up to 1.6 m deep) with…); Tenuta Belvedere Estate (Private panoramic saltwater pool with whirlpool, plus an indoor…); Villa Elle (private pool, 16 m); Villa Il Cellese (Two pools: a long outdoor pool looking over the vineyards to…); Villa Castellaro (Private pool (15 × 7 m, 1.2–1.4 m deep) in the olive grove, heatable…); Villa Agresto (heated private pool and outdoor Jacuzzi); Casa dell'Erta (Private fenced infinity pool (11 × 4 m, 1.4 m deep, chlorine-free)…); Casale Gherardi (infinity pool overlooking the olive grove); Villa Casa del Fiume (heated private pool, with a pool house), and 18 more. Tell us your dates and we will confirm which are free.
- When are the pools open near Siena?
- Most villa pools in Tuscany open from May to late September; heated pools usually extend the season from April into October. 17 of the villas here list a heated pool (Villa Il Cellese, Villa Castellaro, Villa Agresto, Villa Casa del Fiume, Borgo delle Vigne, Tenuta La Barricaia and 11 more); heating can carry an extra charge, so we confirm it for your dates. Opening dates are set by each villa. In high season villas rent Saturday to Saturday.
- Which villas near Siena suit large groups?
- 16 sleep 12 or more: Tenuta Belvedere Estate (sleeps 26, 13 bedrooms), Tenuta La Barricaia (sleeps 26, 13 bedrooms), Villa Elle (sleeps 24, 12 bedrooms), Borgo delle Vigne (sleeps 22, 9 bedrooms), Solare del Chianti (sleeps 20, 10 bedrooms), Villa Il Cellese (sleeps 19, 10 bedrooms), Casale Gherardi (sleeps 18, 9 bedrooms), Villa Erbavoglio (sleeps 18, 9 bedrooms) and 8 more. For a celebration, ask about seated dining for the whole group and whether outside guests are allowed.
- How much does a villa near Siena cost?
- Starting rates run from about €4,000 a week (Casa Pernicella, sleeps 6) to about €112,000 a week (Villa Biondi, sleeps 10). Rates rise in July and August and fall in spring and autumn; each villa page shows its rates by season, and we confirm the exact price for your dates.
- How far are your villas from Siena?
- Between twenty-five minutes and an hour. The Crete Senesi begin a short drive east of the walls; the Castiglion del Bosco estate is about forty minutes south; the southern Chianti villages are half an hour north.
- Where do you park in Siena?
- The Santa Caterina garage below the west walls, which has public escalators up into the city beside the Duomo, or San Francesco on the north side. Never inside the walls: the ZTL is camera-enforced.
- Is a villa near Siena good for seeing the rest of Tuscany?
- Yes, it is arguably the most central base in the region. Florence is around an hour from the northern properties, the Val d'Orcia towns are twenty to forty minutes from the southern ones, and San Gimignano is about forty-five minutes west.
See also
Tell us the dates, the numbers and what the week is for. , usually within a working day.