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Villas with private pools (65 properties found)

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A selection of our villas in Tuscany with private pools.


villa tuscany private pool

Morre, Todi

Casa Carina

The house and its upper terrace fit snugly against the rising hillside.

Sleeps: 4

An idyllic retreat for a couple or a small family, this stone house sits atop a wooded Umbrian hillside with sweeping views. With outdoor eating areas on two levels, a small panoramic pool and charming interiors, the house is perfect place to 'get away from it all'. And yet it is well placed to discover the medieval cities of Todi, Orvieto and Perugia or take in the lakeside delights of Lake Corbara.

Rates to be confirmed View property Check availability

Umbertide, Umbria

Il Borgo

The houses in the Borgo include: a cottage for 2 at the top overlooking the pool, a studio apartment for 2 in the middle with the open loggia, and the large farmhouse to the left with from for 8 on the top two floors and 4 on the ground level.  The owner

Sleeps: 16 (Multiple properties at this location)

For a family reunion, a workshop or a shared holiday of friends, Il Borgo is the ideal location. With spaces for everyone to dine together, inside and out, and accommodations distant enough to allow a bit of private space, this beautifully tended estate is an excellent base for discovering the treasures of Umbria. Having nurtured its 20 year restoration, the owner is a wonderful font of information on how to make this a holiday of a lifetime.

Rates to be confirmed View property Check availability

Castiglion Fiorentino


The pleasure of having a portico just outside the kitchen is having breakfast overlooking the garden in any weather.

Sleeps: 8

Set in the wide Chiana valley, this newly renovated stone house is designed with family holidays in mind. With a large fenced garden and pool, bunk bedroom and an extra children's dining area, younger guests will be delighted. Yet panoramic living and dining areas inside and out and a modern kitchen that invites an Italian cooking lesson mean adults will also feel well placed for relaxing days at home as well as excursions that put Florence, Cortona and Arezzo at hand.

7 nights from £2327.00 / €2449.00 / $2988.00 View property Check availability

Pancole, San Gimignano


The Francigena  pool at the back of the house has spots both for sunning and for enjoying the view from under the arched loggia.

Sleeps: 10

The perfect size for a family on holiday or a group of friends, this villa and its pool is off an ancient pilgrim's trail on a wine estate near San Gimignano. With five ensuite bedrooms, air-conditioning and the estate restaurant a pleasant walk away, this is a fine base from which to explore the medieval cities that dot the nearby landscape.

7 nights from £2356.00 / €2480.00 / $3026.00 View property Check availability

Pancole, San Gimignano


The wide facade of Pellegrino hints at the space one will find inside the front door.

Sleeps: 15

This generous family home on a large wine and olive oil estate sits off the famous Via Francigena, the ancient route from France to Rome. With accommodations for up to 15, and places inside and out to get together, it is a wonderful place for family reunions or relaxed holiday workshops. With an estate restaurant in walking distance and the famous medieval towers of San Gimignano nearby, it is an excellent base for touring or a retreat from a faster pace.

7 nights from £3135.00 / €3300.00 / $4026.00 View property Check availability

Montisi, Siena


The pleasure of staying in this village home is the wide panorama which waits at the end of the garden patio.

Sleeps: 6 to 8

This beautifully restored home sitting in the middle of a Tuscan hilltop village just about has it all - the convenience of shops and restaurants outside the front door, restful bedrooms and sitting rooms with panoramic views spread on four floors and an outdoor dining pergola, and refreshing plunge pool on a garden terrace with a stunning countryside panorama.

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Carmignano, Prato

Il Convento

The view from the dining pergola takes in the long facade of the historic convent.

Sleeps: 14

In the hills in which the Medici built their grand country villas, this former convent offers spacious bedroom suites and numerous gathering places to members of a family reunion, a workshop or couples on holiday together. With an in-house bar, billiards table and air-conditioning, it has all of the comforts and more, yet is in easy reach of fascinating Medieval and Renaissance sites.

7 nights from £5150.00 / €5421.00 / $6614.00 View property Check availability

Rignano sull'Arno

Villa Colombaia

While it is possible to enter the villa on the ground floor, the beautiful dual stairway also leads to a formal entrance on the first floor.

Sleeps: 12

This carefully restored country villa in the Arno valley, belonging to the same aristocratic family for centuries, offers its guests the gentle authenticity of earlier times. Ideal for a family reunion or a holidaying group of friends who are happy to explore the pleasures of relaxed country living, happily with all services only a kilometre away.

7 nights from £3288.00 / €3461.00 / $4222.00 View property Check availability

San Casciano dei Bagni


A very spacious main room with dining and living accommodation greets Aceronina guests who enter through wide double doors.

Sleeps: 6

With long panoramas from its pool and dining loggia, this spacious first floor apartment is a charming spot for a family or couples on holiday together. Set on an agricultural estate producing its own wine and olive oil, the property is in easy reach of historic spa and medieval market towns scattered in the hills of the stunning Val d'Orcia south of Siena.

7 nights from £760.00 / €800.00 / $976.00 View property Check availability

San Casciano dei Bagni

Villa Frescollina

Easy entry to the villa's panoramic pool makes a daily swim possible for guests of all ages.

Sleeps: 11

With sweeping views of the valley below, this villa, beautifully refashioned from watchtower and farmhouse origins, along with its gracious guest cottage provide spacious accommodations for a large family gathering or a group of friends. Its position in the Chiana valley puts ancient spas, medieval market towns and cities perched on towering ridges but a short drive away.

7 nights from £2470.00 / €2600.00 / $3172.00 View property Check availability

Radda in Chianti


Poolside cocktails and castle-studded views are certainly reasons to head down the terraced garden to its lowest level.

Sleeps: 9

This lovely villa, with accommodations on the ground and first floors, provides spacious and stylish living for a group of friends or a large family interested in exploring the famous vine-strewn hillsides outside Radda in Chianti. Beautifully planted terraced gardens lead down to a pool whose views take in the neighbouring castle that has been standing for 1,000 years, yet good roads have you off to the medieval villages between Florence and Siena which host events throughout a lively summer.

7 nights from £2565.00 / €2700.00 / $3294.00 View property Check availability

Radda in Chianti


The generous proportions of the living room reflect the open-hearted hospitality of Docciole.

Sleeps: 14

In walking distance to Radda in Chianti, Docciole is a great base for a large family holiday or a group of friends wishing to explore the famous Chianti hills. Set on large grounds with green vistas, the lovingly restored stone farmhouse has four independent bedroom suites on the ground floor and three bedrooms on the top floor along with a living room and kitchen of soaring proportions.

7 nights from £2432.00 / €2560.00 / $3123.00 View property Check availability

San Casciano Val di Pesa, Chianti

La Caserotta

La Caserotta houses all of its guests in the two large structures facing each other - a converted olive mill and stone barn.

Sleeps: 22 (Multiple properties at this location)

La Caserotta offers ample and elegant accommodation for a large family reunion or a special event set in the Tuscan countryside. With five spacious apartments providing room for up to 22 guests, this hamlet has individual outdoor areas as well as wide terraces where a group can dine or party. Located just south of Florence and an easy drive from the famed villages of the Chianti, this is the perfect spot for celebration or simply savoring the best Tuscany has to offer.

Rates to be confirmed View property Check availability

Trevinano, San Casciano dei Bagni

Villa San Rocco

Morning sun warms the earthern-hued stones of Villa San Rocco and makes it a good day to step out into the sun.

Sleeps: 9

A stone farmhouse, beautifully restored and with pools, furnished terraces and sweeping views of wooded hillsides and a village perched on a tufa cliff, Villa San Rocco has become a villa with a taste of luxury. With generous room for a family reunion or holidaying friends, it offers several places for the group to be together, but comfortable corners in which to retreat. It is well-positioned for easy reach of historic spa towns, medieval hilltop villages, protected parklands and cities that fill guidebooks.

7 nights from £2646.00 / €2786.00 / $3399.00 View property Check availability

Piazze, Cetona

Villa Vista Lunga

Though the panoramic pool at Villa Vista Lunga sits at a lower level to the house it is not far to go for a swim.

Sleeps: 10

Carefully restored to preserve its country heritage, Villa Vista Lunga is special place in which to spend a holiday. With generous space for up to 10 guests, it offers bedroom suites in which to retreat and various areas in which to come together, including a panoramic pool. Nearby medieval villages and history spa towns provide the chance to slip into Tuscan life, while the villa itself encourages one to relax into 'la bella vita'.

7 nights from £2918.00 / €3071.00 / $3747.00 View property Check availability

Piazze, Cetona


Whether from the french doors to the lower bedrooms or the upper level dining room the stroll to the pool is a short one.

Sleeps: 8

Set in a generous clearing on a wooded hillside, Radura is a charming farmhouse that follows the lay of the land, thus giving all of its floors access to the garden. With four ensuite bedrooms it is the perfect size for a family or a group of friends on holiday. Well situated between the medieval town of Cetona and San Casciano dei Bagni, historically famous for its thermal waters, it is an excellent base for exploration, but a comfortable place to savor the views.

7 nights from £2538.00 / €2671.00 / $3259.00 View property Check availability

Celle sul Rigo, San Casciano dei Bagni


Only a few steps separate the sweet Cellevista cottage from its refreshing private pool.

Sleeps: 4

Whether for a small family or a couple wanting a relaxing romantic retreat, Cellevista is ideally situated. The panoramic view from the front portico is all countryside, with the property's pool set in a generous lawn, yet a short walk of 100 m. has guests in the heart of the ancient village of Celle sul Rigo where there are small shops and restaurants. Nearby is the attractive town of San Casciano dei Bagni, whose history is entwined with its famous hot springs and elegant spa, yet this is only the beginning. Roads through a beautiful landscape easily deliver one to medieval towns their guidebooks will praise.

Rates to be confirmed View property Check availability

Piazze, San Casciano dei Bagni

Villa Veduta

The dual staircases at the front of the villa lead directly to the sleeping quarters on the upper floor.

Sleeps: 10

This restored country house, spacious enough for a family reunion, makes the most of its panoramic position on the slopes of Monte Cetona. With furnished patios and pergolas and a swimming pool dressed with sun beds and umbrellas, it is excellent for guests who enjoy outdoor living. Yet its air-conditioned bedrooms and comfortable interiors ensure similar ease once inside. Well placed for quick access to medieval spa towns, stately gardens and a motorway that delivers you to sites that fill guide books.

7 nights from £3325.00 / €3500.00 / $4270.00 View property Check availability

Cetona, Sarteano

Dama di Campagna

Dama di Campagna is a charming Tuscan farmhouse only 2 km from the nearest village.

Sleeps: 6

Near the medieval town of Cetona, this charming stone house is a perfect location for a small family or couples on holiday. Carefully restored and furnished with warmth and good taste, it offers a pool set in a fenced garden and pergolas and porticos dressed for outdoor dining. Drives through the rolling landscape lead to nearby and varied destinations: ancient spa towns, historic gardens holding summer concerts, a Pope's ideal Renaissance city, outlet shopping or a motorway entrance that has you in Tuscan and Umbrian capitals for a relaxing day out.

Rates to be confirmed View property Check availability

Resina, Perugia

Casa del Cambio

A favorite gathering place for summertime guests is at the shaded patio, furnished for meals al fresco.

Sleeps: 10 to 11

In the midst of the green hills of Umbria, this carefully restored farmhouse gives ample space for a family reunion or gathering of friends. With a panoramic pool, five en-suite bedrooms and generous areas for indoor or outdoor dining, Casa del Cambio is an excellent base from which to explore the hill towns this region is famous for - Perugia, Assisi, Todi, Spoleto, Gubbio, and still be home in time to light the BBQ.

7 nights from £1974.00 / €2078.00 / $2535.00 View property Check availability