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Villas for large groups in Italy

It could be for a birthday or anniversary, or just a gathering of friends and family on holiday. Whatever the occasion, if your choice of venue matters, we’d love to help. Simpson Travel handpicks the best large villas in Italy – a collection of beautiful places to share with the ones who matter most.

Our large villas cover every conceivable variation on the simple theme that more is definitely more when it comes to a luxury holiday in Italy with those closest to you. Generous gardens and sprawling estates await, with rural farmhouses and contemporary stone villas. While each one is unique, they all exude quality and style – and allow large groups to celebrate together in surroundings that reflect true Italian flair.

In a country that is famous for its love of family gatherings, generously proportioned villas are in abundant supply, but we’ve spent many weeks searching for the very best, including the most popular areas of Tuscany and its stunning Chianti region – a wonderful place to be when it comes to stocking up on excellent wines...

But wherever you decide to bring everyone together, we’ve ensured you’ll have plenty of room, with generous communal spaces, well-equipped kitchens or even the potential of a private chef service to create a truly memorable holiday for six, eight or even 14 of your favourite people.     

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Casa al Colle

Tuscany, Italy

Villa | Bedrooms 5 | Sleeps 10

  • Elevated, spacious retreat
  • Stunning panoramic views
  • Comfortable interiors
  • Simpson family extras available

Prices are based on 2 sharing for 7 nights on Saturday 8 October 2022

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  • Villa

Prices
from

$972pp Total price $1,944
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Reserve now for 2023 with a fully refundable deposit of $650

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Villa Aurora

Puglia, Italy

Villa | Bedrooms 4 | Sleeps 8

  • Stylish and contemporary villa
  • Delightful countryside views
  • Shaded balcony for al fresco dining
  • Bar/restaurant 15-minute walk

Prices are based on 2 sharing for 7 nights on Saturday 8 October 2022

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  • Villa

Prices
from

$1,395pp Total price $2,789
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Reserve now for 2023 with a fully refundable deposit of $650

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Trulli Rosalinda

Puglia, Italy

Villa | Bedrooms 5 | Sleeps 10

  • Beautifully restored trulli
  • Ideal for families and multi-generational groups
  • Expansive lawned grounds
  • Peaceful setting amongst the olive groves

Prices are based on 2 sharing for 7 nights on Saturday 15 October 2022

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  • Villa

Prices
from

$1,976pp Total price $3,952
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Reserve now for 2023 with a fully refundable deposit of $650

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Masseria Borgo San Benedetto

Puglia, Italy

Villa | Bedrooms 4 | Sleeps 8

  • Imposing 18th century masseria
  • Spacious elegant interiors
  • Walled garden with pool
  • 5-minute drive to Conversano

Prices are based on 2 sharing for 7 nights on Saturday 15 October 2022

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  • Villa

Prices
from

$2,048pp Total price $4,095
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Reserve now for 2023 with a fully refundable deposit of $650

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Villa Montelopio

Tuscany, Italy

Villa | Bedrooms 5 | Sleeps 10

  • Elegant villa in hilltop village
  • Stunning panoramic views
  • Elegant and spacious interiors
  • Castiglioncello beach 52km/1hr drive

Prices are based on 2 sharing for 7 nights on Saturday 15 October 2022

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  • Villa

Prices
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$2,113pp Total price $4,225
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Reserve now for 2023 with a fully refundable deposit of $650

Use our Advanced Registration service to secure your 2023 holiday with a deposit of $650, fully refundable when prices are published

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Villa Rosa

Tuscany, Italy

Villa | Bedrooms 4 | Sleeps 8

  • Historic 19th century building
  • Extensive private grounds
  • 16-metre swimming pool
  • Tower lounge with beautiful views

Prices are based on 2 sharing for 7 nights on Saturday 15 October 2022

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  • Villa

Prices
from

$2,210pp Total price $4,420
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Reserve now for 2023 with a fully refundable deposit of $650

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Villa Da Vinci

Tuscany, Italy

Villa | Bedrooms 6 | Sleeps 12

  • Exceptional manor house
  • Spacious and comfortable
  • Set in the heart of Chianti
  • Outstanding views

Prices are based on 2 sharing for 7 nights on Saturday 8 October 2022

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  • Villa

Prices
from

$2,968pp Total price $5,935
View details
Reserve now for 2023 with a fully refundable deposit of $650

Use our Advanced Registration service to secure your 2023 holiday with a deposit of $650, fully refundable when prices are published

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When only the best will do...


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Villa Petraia

Tuscany, Italy

Villa | Bedrooms 5 | Sleeps 10

  • Simpson Exclusive
  • Classic Tuscan views
  • Elegant décor
  • Swimming pool

Prices are based on 2 sharing for 7 nights on Saturday 1 October 2022

Accommodation Only

  • Villa

Prices
from

$5,142pp Total price $10,283
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Reserve now for 2023 with a fully refundable deposit of $650

Use our Advanced Registration service to secure your 2023 holiday with a deposit of $650, fully refundable when prices are published

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Simpson Exclusive

When only the best will do...


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La Tenuta

Puglia, Italy

Villa | Bedrooms 9 | Sleeps 18

  • Simpson Exclusive
  • Stylish villa set in 5 hectares
  • Superb 13-metre pool
  • Versatile layout

Prices are based on 2 sharing for 7 nights on Saturday 15 October 2022

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  • Villa

Prices
from

$6,312pp Total price $12,623
View details
Reserve now for 2023 with a fully refundable deposit of $650

Use our Advanced Registration service to secure your 2023 holiday with a deposit of $650, fully refundable when prices are published

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Villa Romantica

Tuscany, Italy

Villa | Bedrooms 6 | Sleeps 12

  • Beautiful stone farmhouse
  • Spacious and comfortable
  • Daily maid service
  • Yoga and Pilates studio
Reserve now for 2023 with a fully refundable deposit of $650

Use our Advanced Registration service to secure your 2023 holiday with a deposit of $650, fully refundable when prices are published

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Reviews

Simpson Travel in the media

  • ‘[Simpson Travel] specialise in the sort of magical, unspoilt destinations my family loves’ Author: The Telegraph

  • ‘So how did we find the near-perfection that was Villa Cabanellas in Mallorca? The first step was to approach… Simpson Travel… we needed expertise, not just blinding choice.’ Author: Sunday Times Travel Magazine, The Villas Handbook

  • ‘The Simpson Travel check-in at Heathrow’s Terminal 5 was seamless.’ Author: Family Traveller, Katy Hill

  • ‘Where Simpson [Exclusive] really excels is in its first-hand knowledge of properties and destinations’ Author: House & Garden

  • ‘Simpson [Exclusive] delivers holidays that combine sunshine, five-star luxury and friendly service’ Author: House & Garden

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Travel advice

For up-to-date advice and information on travel from the UK, including passports, visas and health and safety, please visit the Foreign Commonwealth & Development Office website or call 020 7008 1500. For travel from countries outside the UK, please visit your corresponding government website.

The air holidays and flights shown are ATOL protected by the Civil Aviation Authority. Our ATOL number is ATOL 5858. ATOL protection extends primarily to customers who book and pay in the United Kingdom. Find out more about ATOL. Simpson Travel is the trading name of Far & Wide Ltd.

Copyright © 2022 Simpson Travel

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  • Destinations

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    France

    France

    • Provence
    • The Dordogne & South West
    • Vendée
    • Aquitaine Coast
    • Ile de Ré

    Mallorca

    Mallorca

    • Fornalutx & Sóller
    • Pollença & Puerto Pollença

    Greece

    Greece

    • Corfu
    • Crete
    • Ithaca
    • Kefalonia
    • Lefkada
    • Meganissi
    • Paxos
    • Sivota
    • Zakynthos

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    Turkey

    • Akyaka
    • Bozburun Peninsula
    • Islamlar & Uzumlu
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    • Kaş

    Italy

    Italy

    • Tuscany
    • Umbria
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    Corsica

    Corsica

    • Calvi & The Balagne
    • Porto Vecchio & Bonifacio
    • The Valinco
  • Villas

    Villas

    • Villas with childcare
    • Luxury villas
    • Off the beaten track villas
    • Car-free villas
    • Large group villas
    • Villas together
    • Romantic villas for two
    • Family Favourite villas
    • Teen-friendly villas
    • Beachfront villas
    • Villas with heated pools
    • Villas near the beach
    • Villas near a restaurant

    Back

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    Back

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    Holiday Types

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    • Couples holidays
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