The trick to finding the perfect Italian holiday villa

Nick Trend
·11-min read
Tuscany - Getty
Tuscany - Getty

That dreamy view from the terrace, over the pool to the hills in the heat haze beyond. Those warm, wine-infused evenings lulled by the cicadas. All the pleasures of your own home without the day-to-day stresses – and in the most idyllic of settings. Two weeks when shopping becomes a joy not a chore, when breakfast lasts all morning and then merges into lunch, and when it doesn’t really matter if you go sightseeing in the afternoon or just read a book by the pool. In fact, when nothing really matters except enjoying the moment.

Those, for me, are the pleasures of a villa holiday. And there is nowhere better to enjoy such an escape than in Italy. So we have surveyed the top 20 agents and operators and reported back on what is on offer this summer, whether you are looking for a classic farmhouse in Chianti, a masseria in Puglia or a remote cottage in Sicily.

The good news is that prices have remained relatively stable over the past year, as owners, many of whom lost out heavily in 2020, have been nervous that hikes might suppress demand. For example, To Tuscany, the largest specialist in the area, says that all its prices are unchanged for 2021. However, at least for peak season, availability may become an issue if you delay booking for too long.

Some operators (Oliver’s Travels, for example) say they have fewer properties on their books because some owners have withdrawn from the market. A few have done so due to concerns over Covid-19 safety, others for financial reasons and some because they have given up doing holiday lets and moved to their second homes on a permanent basis – having appreciated them more when they moved in to escape the city in 2020. There is also an issue with large numbers of holidays being held over from last year. For example, CV Villas says 60 per cent of its 2020 bookings have been rebooked for 2021, Vintage Travel cites 50 per cent, while Just Sicily and Sardinia says its figure is 75 per cent.

Many of these are likely to be in the first part of the summer, however – from May to July. As operator Scott Williams points out, August and September were less affected by cancellations and postponements because most holidays took place, and Italy was only removed from the travel corridor list in mid-October.

Prices quoted here are for the whole villa per week, rental only unless stated otherwise, and are the base prices for the season – usually in May. August prices are substantially higher.

Best for Puglia, Sicily and Sardinia

Beautiful Sicily - getty
Beautiful Sicily - getty

The Thinking Traveller

Launched in Sicily in 2002, this company is still one of the biggest specialists on the island with exclusive access to more than 90 varied properties, from tiny escapist retreats to fully serviced villas. It also offers over 40 rentals in Puglia, including masseria farmsteads and trulli in Valle d’Itria and Salento.

Top pick: TerraMia, sleeping six, is a contemporary villa in the south of Sicily overlooking the Vendicari nature reserve.

From €4,720 (£4,200);

Solo Sicily

Offers a good selection of 70 villas spread throughout the island, including a price-conscious, budget category with either pools or easy access to beaches. The website goes the extra mile to provide ideas and inspiration.

Top pick: New to Solo Sicily’s books is La Balata, sleeping eight, a stylish, modern villa with a pool in Cefalù, boasting contemporary furnishings and sea views.

From €3,400;

Simpson Travel

Its portfolio of nearly 30 villas includes many in Puglia, where properties range from tiny trulli to seven-bedroom manor houses. Tuscany and Umbria also feature. Families are well-catered for, too, with a “Simpson Kids” option including complimentary infant packs and garden games for children.

Top pick: Villa Favorita, sleeping eight, near Monopoli has a poolside kitchen and antique furnishing.

From £2,500;

Long Travel

Long Travel has around 30 villas and self-catering apartments at agritourism and hotel resorts in Puglia, Sicily and Sardinia.

Top pick: Trullo Madia, sleeping four, is a stone-built hideaway near Cisternino in Puglia, overlooking a wooded valley with private pool and gardens planted with pomegranate and olive trees.

From £937 with car hire;

Freelance Holidays

This Mediterranean island specialist has 22 villas in Sicily – modern, mainly three-bedroom properties in scenic locations on the east and south-east coast, plus a handful in the north-west.

Top pick: Corte Moscata, sleeping six, is a modern villa in south-eastern Sicily’s Noto Valley close to the baroque towns of Modica and Ragusa-Ibla with grassy gardens planted with olive and carob trees.

From £1,615;

The pool at Corte Moscata
The pool at Corte Moscata

Sardinian Places

The company has 19 villas scattered across Sardinia, predominantly in the Costa Smeralda and north-east corner, plus a few in the Alghero region and two in the south. Most properties are secluded with private pools, but its premium collection singles out the best.

Top pick: Villa Asfodeli, sleeping five, is a three-bedroom, hillside villa between Arzachena and Palau with sea views from the pool terrace.

From £495 per person, including flights and car hire;

Just Sicily

Its villas are mainly in Sicily’s south-east corner, and most have private pools. Sister company Just Sardinia ( has a smaller portfolio in the island’s north and some hotel villas.

Top pick: Villa Dimora di Circe, sleeping four, is a recently renovated Sicilian beach house on the sea front near Ispica with a plunge pool and pergola.

From £2,510;

Best for Luxury

Abercrombie & Kent

From stylish, family-sized country retreats to grand palazzi and converted convents, A&K has more than 260 properties throughout the Italian regions.

Top pick: Casa Porpora, sleeping eight, is one of the comopany’s more affordable properties. It’s a chic seaside villa in Praiano, on the Amalfi Coast, with a rooftop sun terrace and a cactus garden.

From €10,900;

Red Savannah

While the main areas of focus are Tuscany and Umbria, its 104-strong portfolio of beachside, lakeside and rural villas also features Lake Como, the Amalfi Coast and Puglia, with property numbers set to increase for 2021.

Top pick: Villa Della Vetta, sleeping 14, offers spectacular views of Lake Como and has an infinity pool.

From £19,970;

SJ Villas

Its carefully curated collection of villas are mainly in Tuscany and Umbria.

Top pick: Masseria Lamacoppa is an imposing 17th-century farmhouse in Puglia, sleeping 12, set in more than 70 acres of garden planted with lemon trees and olive groves.

From €40,000;

17th-century farmhouse, Masseria Lamacoppa
17th-century farmhouse, Masseria Lamacoppa

Scott Williams

For groups ranging from six to 18, its 21-strong portfolio includes manor houses, farmsteads and contemporary retreats across Umbria, Tuscany, Puglia, Sardinia, Sicily and Favignana, with prices made available “on request”.

Top pick: The Light House is a sleek modern villa, sleeping six, near Cala Azzurra beach on Favignana.

From €2,900;

Best for Tuscany

To Tuscany

With 600-plus villas on its books, from one to 12 bedrooms, this is the operator for the lesser-known areas of Grosseto and Maremma, the coastal areas of Lucca and Viareggio, rural Val d’Orcia, as well as honeypot areas around Siena and Florence. To Tuscany also arranges cooking and wine-tasting sessions. Top pick: Macia Viva, sleeping four, is a stone-built villa near Castellina looking out on hills and vineyards.

From £2,151;

Invitation to Tuscany

Its collection of around 150 mid-range properties is curated by owner Daniel Wrightson, whose mother started the company in the 1970s. Particularly strong in the areas around Arezzo.

Top pick: Fienile, sleeping 10, is a tranquil villa in the Chianti hills with a poolside terrace and long views over the surrounding countryside, a 10-minute drive from Siena.

From €3,150;

Bridgewater’s Idyllic Italy

Founded in 1973, Bridgewater has traditionally focused on the Tuscan coast and Lucca. Its portfolio includes a small selection in Amalfi, Sicily and the northern lakes Como and Maggiore.

Top pick: Villa di Colle, sleeping nine, is a family-friendly option nine miles from Lucca and close to the Versilia coast. A sister property next door, Villa Grappolina, can host a further six people.

From £2,370;

Tuscany Now & More

With 30 years under its belt and more than 130 villas on its books, this company focuses on atmospheric, rural properties in Tuscany and Umbria, many with in-house staff and chefs.

Top pick: Sul Coccomorlo, sleeping eight, is a stone-built hideaway on a hillside, a short drive to San Gimignano, with a large pool house and loggia.

Sul Coccomorlo
Sul Coccomorlo


Around 70 properties offer plenty of choice for groups of friends or extended families looking for houses sleeping up to 20, mainly in northern Tuscany, along the coast or in the Chianti region.

Top pick: Villa Rignana, sleeps 11, is a part 13th-century house with original features and antique furnishing near Panzano in Chianti. Facilities include a private pool, an astro-turf tennis court and a billiards room. The terraced gardens are surrounded by vineyards and olive groves.

From £5,581;

Best for affordable, countrywide choice

Oliver’s Travels

This company has the largest selection, with more than 600 properties. Most are concentrated in Tuscany, Puglia and Sicily, but there are also mid-sized villas in the Liguria and Veneto regions. New on the books is Piedmont, where villas are centred in the Langhe winelands.

Top pick: Villa Meraviglia, sleeping eight, has a pool on the shores of Lake Maggiore in Lombardy.

From £6,128 including welcome hamper on arrival;

CV Villas

Strong on characterful family-sized properties in sought-after locations, CV has 200-plus villas located across Tuscany, Puglia, Sicily, Umbria and Lazio, Campania and the Amalfi Coast.

Top pick: Il Palazzeddu, sleeping six, is a farmhouse with a cottage garden on Sardinia’s north-east tip.

From £2,828;

Ilios Travel

This small, specialist company has been around since the late 1970s and has built up a collection of around 100 villas. Although central Italy and regions of Tuscany, Umbria and Marche remain the focus, the portfolio is also strong in Puglia, Sicily and Sardinia.

Top pick: Poggio della Fornace, sleeping eight, with a fenced pool near Orvieto in Umbria, is a good choice for families with children.

From £1,895;

James Villas

Erring towards purpose-built villas rather than older converted farmhouses, the portfolio of some 100 properties is strong on affordable family-sized places, many with tennis courts and pools, in less visited corners.

Top pick: Villa Luisa, sleeps eight, is a modern villa suiting active families in Le Marche with a pool and floodlit tennis court.

From £3,336;

Vintage Travel

This long-standing Mediterranean-wide specialist has built up a small selection of more than 20 competitively priced villas in Italy, located mainly in Tuscany, Umbria and Lazio, plus five near Cefalu. All have private pools and offer from one to six bedrooms.

Top pick: La Gioia, sleeping six, is a one-storey villa built of local “tufa” with travertine terraces overlooking Lake Bolsena in Lazio.

From £1,068;

Competitively priced La Gioia
Competitively priced La Gioia

Landmark Trust

You won’t find pools, but you will find plenty of atmosphere and outstanding architecture at the Landmark’s selection of six standout properties. Smallest are two apartments sleeping four in a Renaissance villa near Padua, while a 16th-century Palladian Villa in Vicenza sleeps 16 (see villas for groups, right).

Top pick: Sant’Antonio, sleeping 12, is a former monastery in terraced gardens near Rome, with ancient walls dating back to 60BC.

From £646 for a three-night weekend;

Little and Large

Three great villas for couples…

La Casa dei Mandorli, sleeping two, is a hillside bolt-hole in Chianti with distant views of Siena’s city towers and an infinity pool. From £1,365. Simpson Travel (

La Sabinetta is a newly renovated, stone-built hideaway sleeping two, in private gardens with a pool in the Sabine Hills just outside Rome. From £2,113. CV Villas (

Il Ciocchetto, shaded by pines and oaks near Lucca, sleeps two with a pool, dining terrace and open-plan living area. From £788. Vintage Travel (

… and three for groups

Villa Saraceno, a 16th-century Palladian villa in Vicenza, sleeps up to 16 guests. From £930 for a three-night weekend. The Landmark Trust (

Villa Artistica, a stylishly renovated collection of five trulli and farm buildings near Ostuni in Puglia, can be booked as a whole to sleep up to 20. From £14,360 including breakfast. Oliver’s Travels (

Tesoro, sleeping 12, is a traditional Umbrian farmhouse with a soft play room and fenced garden near Città della Pieve. From €4,655. Scott Williams (

Overseas holidays are currently subject to restrictions.