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Villas with pool to sleep 20 to 25 people

Villas to sleep 20 to 25 people with private pool in Italy.

Big villas for large groups of family and friends!

For this size of group there are two solutions. Either pick a large independent villa or a MULTIPLE-UNIT property where you take all the accommodation. (N.B. In some cases the owner may live on-site).

Multiple-unit properties – e.g. farmhouse complexes divided into apartments with pool and good on-site facilities – are particularly suitable for very large groups whose members need privacy as well as time spent together.

Tip: Always look at villas slightly bigger than you need as well as those that fit your party size exactly – you may find prices are lower, as each villa is priced individually.

Need help to choose the right property for your large group? More tips here.

Let’s talk and plan your perfect large villa holiday…


Aerial view of Santa Flora

Santa Flora grounds

SANTA FLORA, near Capolona, Tuscany.

Walk to small town of Capolona with shops, restaurants and railway station (700m).

A beautiful property near the River Arno.

Santa Flora can sleep from 18 – 35 people in up to 15 bedrooms.

100% exclusivity for your group guaranteed.

Comprises an ancient 12th century tower with 4 bedrooms, and a central core with 5 bedrooms, a kitchen and a dining room. Up to 6 extra bedrooms + 5 extra beds can be made available for your group on request.

 Air conditioning.

Jacuzzi, fitness centre, table tennis.


The large communal areas are perfect to organize family meals and reunion dinners.

Chef service on request.

From Santa Flora you can easily reach the main Tuscan cities (Arezzo, Florence, Siena) and characteristic villages in Valdichiana, Orcia Valley and Chianti.

Arezzo is reachable by train through a local connection from Capolona.
From Arezzo there are daily connections to Florence and Rome.

SANTA FLORA –  ask us here for a price for your size of group.


Villa Sorbaiano sleep 20 private pool

Villa Sorbaiano  near Montecatini Val di Cecina (food shops, restaurants, pizzerias, bars, bank, post office) 1.5 km. Private pool. Sleeps 20 in 10 bedrooms.  Large terraced dining area for al fresco meals. Rental prices from Euro 3658 per week.


Villa La Quiete private pool sleeps 20 tuscany

Villa La Quiete near Civitella in Valdichiana, Tuscany. Private pool. 8 bedrooms. Sleeps 20. Large garden, play-ground for children, table tennis, small football pitch, bicycle hire. Barbecue and free wifi .  Rental prices from Euro 2625 per week.


Borgo Usciano sleeps 20

Borgo Usciano sleeps 20  infinity pool

Borgo di Usciano, near Arezzo, Tuscany. Ancient stone hamlet in a panoramic position. Sleeps 20 in 10 bedrooms. Beautiful private infinity pool. The property comprises a farmhouse + 2 stone cottages. Barbecue. Free wifi. On request, the owner can organize tastings in the villa with typical Tuscan products, and tours of the area by mountain bike with guides. Rental price from euro 2835 per week.


Villa Il Palazzo private pool cortona sleeps 20

Villa Il Palazzo, near Cortona, Tuscany. Private pool. Table-tennis. Mountain bikes.  MULTIPLE-UNIT PROPERTY. Sleeps 20 in 9 bedrooms. There are 6 independent units, each with own cooking facilities. Plus a large living-dining room with kitchen and sitting area in the basement, big enough for everyone to eat together. Ideal for large family groups.  Gazebo and pergola equipped for outdoor meals. Rental price from Euro 2835 per week.  


La Pineta sleeps 20 private pool private tennis court tuscany

La Pineta: house / private pool / private tennis court

Private tennis court at La Pineta

LA PINETA , Sleeps 20 in 9 bedrooms / 8 bathrooms. Private villa. Ideal for groups of family and friends. Only 3 km from the beaches of Lake Trasimeno (reachable on foot or by bicycle)

Only 3 km from the small town of Castiglione del Lago, with shops, restaurants and services of all kinds. 

Private pool. Private tennis court. Table tennis. Shady garden with pine trees.

At the back of the house a big gazebo with table, chairs and BBQ, perfect for preparing delicious dinners in the open air.

Photo Gallery 


Views from Villa Casavecchia sleeps 20

Villa Casavecchia  MULTIPLE – UNIT property. Villa with private pool for 20 people, between Arezzo and Florence, Tuscany. 9 bedrooms, 6 bathrooms. Villa Casavecchia is a stone farmhouse divided into three comfortable apartments, furnished with care. Beautiful completely-fenced swimming pool (5x10m – depth 1,20m) in the natural terrace which overlooks the Arno valley. Barbecue, a wood burning oven, children’s playground, a laundry room. Rental prices from Euro 1770 per week. 


Annarita, sleep 20, private pool, tuscany Annarita, near Pratovecchio, Tuscany. 8 bedrooms, 6 bathrooms. Independent villa. Private pool. Sleeps 20. Rental prices from Euro 1308 per week.

Check prices, availability and book Annarita here.


Villa Lorenzo sleep 20 private pool

Villa Lorenzo, near Anghiari, Tuscany. 9 bedrooms + 1 connecting room with a bunk bed, 7 bathrooms. Independent villa. Private pool. Sleeps 20. Rental prices from Euro 1908 per week. Bar and restaurant in walking distance.

Check prices, availability and book Villa Lorenzo here.


Villa gubbio umbria sleeps 20Villa Gubbio, near Gubbio, Umbria. 10 bedrooms, 12 bathrooms. Independent villa. Private pool. Sleeps 20. Air conditioning. Rental prices from Euro 4949 per week.  Check prices, availability and book Villa Gubbio here.



Villa I Gigli di Bolsena, sleeps 22

I Gigli di Bolsena, near Montefiascone / Lake Bolsena, Lazio. Private pool. 10 bedrooms. Sleeps up to 22. Air conditioning. Big ground floor dining room (35 m2), and a patio, where everyone can eat together.  Rental prices from Euro 2630 per week. Check prices, availability and book I Gigli di Bolsena here


Villa Lorenza sleeps 22 private pool + children's pool

Villa Lorenza, near Palaia (Pisa area), Tuscany. Independent villa. Private pool + children’s pool. 10 bedrooms. 10 bathrooms. Sleeps 22. Rental prices from Euro 3706 per week. Check, price, availability and book Villa Lorenza.


Villa Le Capanne private pool sleeps 22 tuscany

Villa Le Capanne, near Volterra, Tuscany. Independent villa. Private pool. 9 bedrooms. 10 bathrooms. Air conditioning. Sleeps 22. Rental prices from Euro 5555 per week. Check price, availability and book Villa Le Capanne.


Villa fabbri private pool sleeps 22 tuscany

Villa Fabbri, near Bucine, Tuscany. Luxury independent villa. 10 bedrooms, 9 bathrooms. Private pool. Air conditioning. Sleeps 22. Rental prices from Euro 6060 per week. Check price, availability and book Villa Fabbri.


TO SLEEP 23   To be advised



Villa Le ferrette private pool sleeps 24

 Ville Le Ferrette, near Montecatini (less than 2km away), in Tuscany. Independent villa with private pool. 11 bedrooms, 13 bathrooms. Set on a 10 hectare hilltop estate surrounded by olive trees, gardens, orchard, and forest with paths for exploring.  Panoramic views. Rental prices from Euro 3390 to Euro 5935 per week. Availability.  Prices.  Book.


Villa felciai sleep 24 private pool tuscany

Villa Felciai, near Bucine, Tuscany. Farmhouse with private pool. 11 bedrooms, 11 bathrooms. Views over the surrounding landscape with vineyards and olive groves. Ideal for family reunions / weddings.  Rental prices from Euro 6500 to Euro 7000 per week.  Availability.  Prices.   Book. 


Villa Petrognano tuscany

Villa Petrognano, near Barberino Val d’Elsa, Tuscany. (Comprises 2 Units: An independent villa sleeping 16 plus an outbuilding sleeping an additional 8 people). 12 bedrooms, 12 bathrooms. Rental prices from Euro 8657 per week + outbuilding rental.

Check prices, availability and book Villa Petrognano here


Still can’t find what you’re looking for? Don’t give up on us just yet !

This is just a small selection. Search here for more villas .

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Villas with pool sleeping 26, 27, 28, 29 or 30 people

Villas with pool sleeping over 30 people

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Villas with pool sleeping 15 or 16 people

Villas with pool sleeping 17, 18 or 19 people

Let’s talk and plan your perfect large villa holiday

+44 (0)1603 812212 

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