A pool is nice. But with Villas in Tuscany with private pools, the part that matters is everything around it. A good photo can hide a lot. Privacy, layout, shade, and whether you’ll actually want to stay put count more.
I learned that the annoying way: one place had a lovely view and absolutely nowhere comfortable to sit after 5 p.m. Pretty can wear off by dinner. For a real Tuscany countryside vacation, the stay does a lot of the work.
So this list is basically a filter. Not every country villa with pool is worth the rate. These are the ones that feel right on the ground too, not just in photos.
Il Borro private villas – Villas in Tuscany with Private Pool
At Il Borro, these Villas in Tuscany with Private Pools range from a garden house among Merlot vines to a converted watermill by the woods.
The appeal is real privacy with estate perks: wine, farm-to-table dining, spa time, and a true Tuscany Countryside Vacation feel.
Castelfalfi Villas in Tuscany with Private Pool
Castelfalfi stands out for Villas in Tuscany with Private Pool thanks to its restored medieval borgo feel and 2,700 acres of vineyards, olive groves, and rolling hills.
Its villas and converted farmhouses bring real privacy, while hotel dining, wine tastings, and spa time keep this Italian holiday accommodation from feeling too remote.
Rustico del Chiasso Villas in Tuscany with Private Pool
Rustico del Chiasso earns its spot among Villas in Tuscany with Private Pool with a four-bedroom layout, saltwater pool, big lawn, patio, and barbecue near Lucca.
In Capannori, it feels like a Country Villa With Pool with real breathing room: quiet, green, and handy for Lucca, Pisa, and Florence.
Sunset Hill Villas in Tuscany with Private Pool
Sunset Hill fits Villas in Tuscany with Private Pool if you want rolling-hill views over polished-glam vibes. In Castelfiorentino, it pairs a pool with a view with a terrace, garden, and barbecue-ready outdoor setup.
This four-bedroom stay works well for a Tuscany road trip or Italian Holiday Accommodation near Florence, without feeling stuck in the city. The setting is quiet, roomy, and refreshingly unfussy.
Villa Cicogna Villas in Tuscany with Private Pool
Villa Cicogna makes Villas in Tuscany with Private Pool feel grounded, not glossy: a historic palazzo in Cicogna with broad hill views, a big terrace, and a private pool.
It suits a Tuscany road trip nicely, since Arezzo is about 30 minutes away and Florence is around an hour, while the village shop and restaurant stay walkable.
Villa Briciola Villas in Tuscany with Private Pool
Villa Briciola fits Villas in Tuscany with Private Pool for travelers who want a polished pool terrace, mountain backdrop, and a calm base near Capannori.
This Vacation Rental Villa With Pool keeps things easy with three bedrooms, outdoor space, and access to Lucca, Pisa, and day-trip country roads.
Podere Mencoini Villas in Tuscany with Private Pool
Podere Mencoini suits Villas in Tuscany with a private pool, terraces, and olive-green privacy near Scrofiano.
This Country Villa With Pool sits among olive trees and woodland, yet stays handy for Tuscany day trips. Quiet, but not marooned.
Villa Giardino Lucca Villas in Tuscany with Private Pool
Villa Giardino Lucca fits Villas in Tuscany with a private pool, mountain views, and a leafy garden just outside Lucca.
It works well as a Vacation Rental Villa With Pool for travelers who want countryside calm without giving up easy access to town.
Villa Il Cesto Villas in Tuscany with Private Pool
Villa Il Cesto belongs on a list of villas in Tuscany with Private Pool list for its secluded Lucolena setting in Greve in Chianti, with a garden, terrace, barbecue, and wooded hill views.
This Vacation Rental Villa With Pool has five bedrooms and enough space for a group, yet the mood is more quiet-country escape than showy estate.
Casa all’Erta Villas in Tuscany with Private Pool
Casa all’Erta earns its place among Villas in Tuscany with Private Pool with Chianti vineyard views, an infinity pool, and a restored farmhouse setting on the San Polo in Rosso estate.
A smart pick for a Tuscany Countryside Vacation, it also adds a sauna and Turkish bath—useful when pool weather decides to get moody.
Villa Matilde Villas in Tuscany with Private Pool
Villa Matilde stands out for Villas in Tuscany with a private pool with its stone farmhouse setting in Sant’Andrea di Compito, south of Lucca, plus cypress-framed views and a private pool.
This Country Villa With Pool sleeps six in three bedrooms, making it a smart Tuscany road trip base that feels rural without being marooned.
Casa di Campagna Pianelli Villas in Tuscany with Private Pool
Casa di Campagna Pianelli fits Villas in Tuscany with Private Pool with Valdarno hill views, a garden, and an elegant hillside pool near Pergine Valdarno.
A strong pick for a Tuscany road trip, it’s walkable to the village and well placed for Arezzo, Chianti, Siena, and Cortona.
