Skip to content

Luxury villas, boutique Simpson Hotels and unforgettable holidays

  • My Wishlist (0)

    Use the + WISHLIST button to collect your holiday ideas, then share with friend or make an enquiry.

  • My Account

Enquire or call +44 (0) 208 392 5858

Simpson Travel logo

+44 (0) 208 392 5858 We are open today until 6pm

Menu

  • Destinations

    Destinations

    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

    Turkey

    Turkey

    • Akyaka
    • Bozburun Peninsula
    • Islamlar & Uzumlu
    • Kalkan
    • Kaş

    Italy

    Italy

    • Tuscany
    • Umbria
    • Puglia

    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

  • Hotels

    Hotels

    • Simpson Hotels
    • Partner hotels
    • Family hotels
    • Beachfront hotels
    • Adult-only hotels
    • Romantic hotels for two
    • Hotels with childcare
    • Car-free hotels

    Back

  • Holiday inspiration

    Holiday inspiration

    Holiday Types

    Holiday Types

    • Couples holidays
    • Beach holidays
    • Large group holidays
    • Car-free holidays
    • Twin Centre holidays
    • 10-night holidays
    • Countryside holidays
    • Honeymoons
    • Babymoons
    • Walking Holidays in Crete
    • Special Interest Holidays
    • Experiences and Activities

    Family Holidays

    Family Holidays

    • Holidays with childcare
    • Easter holidays
    • Half-term holidays
    • Multi-gen holidays

    Collections

    Collections

    • Simpson Exclusive
    • Simpson Secrets
    • Simpson Hotels
    • Simply Simpson
    • Simpson Kids
    • Simpson Bespoke

    Our Blog

    Our Blog

    • Where to go
    • What to do
    • What's new
    • Views and reviews
    • Family travel
    • 2023 holidays
    • Give the gift of travel
  • About us

    About us

    • Why Simpson Travel?
    • Travel arrangements
    • Advance Registration
    • Our heritage
    • Awards
    • Reviews
    • Loyalty Club
    • Our Destination Specialists
    • Giving back
    • Our blog
    • Our digital brochure
    • Our Partners
    • Responsible Tourism

    Back

  • Covid-19

    Covid-19

    • Simpson Safe

    Back

  • Contact us

    Contact us

    • Sign up to emails
    • Gift Vouchers
    • Press & PR
    • Property owners
    • Simpson Travel App
    • FAQs

    Back

  • Late availability
  • Search

    Search by property or destination…

    In this section...

    • Villas and apartments
    • Hotels
    2 adults 0 children 0 infants

    Select your preferred departure airport

    Inactive airports indicate no flights available to selected destination

    Loading...

    2 adults 0 children 0 infants

    Select your preferred departure airport

    Inactive airports indicate no flights available to selected destination

    Loading...

    SearchBlock.mustache file to be converted

    Close
  • My Account
  • Wishlist
  • en USD ()

30 search results found

SearchResultsSummaryText.mustache file to be converted

Filters

Main search criteria

Clear search criteria

Loading...

SearchBlockSeoLandingPage.mustache file to be converted

Filter your results

Facilities

Holiday types

Collections

Close

Luxury villa holidays in Italy

Italy may be a place we’ve seen before, in photographs, paintings, at the cinema: those ancient villages and rolling hills are timeless and unforgettable – but to experience it, first hand, from the comfort of your own luxury villa is to really appreciate what la dolce vita is really all about.

Couples and families return to this irresistible destination year after year – the good food, excellent wines and centuries of art and culture converging to create a backdrop for the sweetest of experiences and the most inspiring of luxury villa holidays.

Which luxury villa will suit you best?

From Tuscany to Umbria and Lazio, from a 10th-century fortress to sprawling estates or romantic hideaways for two, there’s a villa that is your perfect fit – a luxury villa with a private pool that gives you privacy plus a location that puts you within easy reach of some of Italy’s best attractions. Whether you want to be near the masterpieces of Florence and surrounded by the vineyards of Chianti or near Liguria’s Italian Riviera, our villas offer our guests a chance to experience the true magic of Italy.  

Be our guest

We chose our luxury villas not only for their superb locations but also for the quality of care and attention our guests receive when they stay there. Villa owners and experienced property managers welcome you with open arms, often bringing vegetables from the garden and home-cooked goodies to treat you. And if you want to know the best restaurant, the loveliest walks or the most welcoming child-friendly attractions, they’re the ones to talk to. Or they’ll just leave you to enjoy your luxury villa holiday, undisturbed and with a myriad of pleasurable pursuits to fill your days.

+ Show more

  • List view
  • Map view

Go to property page

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

Accommodation Only

  • Villa

Prices
from

$1,395pp Total price $2,789
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

Close
More information about advance registrations
Reserve Now
Go to property page

Trulli Gianpaolo

Puglia, Italy

Villa | Bedrooms 3 | Sleeps 5

  • Enchanting trulli house
  • Val d’Itria location
  • Picturesque garden
  • Private pool

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

Accommodation Only

  • Villa

Prices
from

$1,398pp Total price $2,795
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

Close
More information about advance registrations
Reserve Now
Go to property page

Le Guardie

Tuscany, Italy

Villa | Bedroom 1 | Sleeps 2

  • Charming renovated villa
  • Stylish interiors
  • 20min walk to central Florence
  • Flexible stays available

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

Accommodation Only

  • Villa

Prices
from

$1,463pp Total price $2,925
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

Close
More information about advance registrations
Reserve Now
Go to property page

Villa Mille Desideri

Tuscany, Italy

Villa | Bedrooms 6 | Sleeps 11

  • Beautifully positioned villa
  • Breathtaking views
  • Comfortable and welcoming
  • Simpson family extras available

Prices are based on 2 sharing for 7 nights on Saturday 6 May 2023

Accommodation Only

  • Villa

Prices
from

$1,528pp Total price $3,055
View details
Go to property page

Colto dei Pallanti

Tuscany, Italy

Villa | Bedrooms 3 | Sleeps 6

  • Beautifully restored farm house
  • Stunning panoramic views
  • Heated pool
  • Spa area with sauna and Jacuzzi

Prices are based on 2 sharing for 7 nights on Saturday 7 October 2023

Accommodation Only

  • Villa

Prices
from

$1,648pp Total price $3,296
View details
Go to property page

La Perla del Mare

Puglia, Italy

Villa | Bedrooms 2 | Sleeps 4

  • Two-bedroom suite
  • Stunning sea views
  • Direct access to the sea
  • Private garden and terrace

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

Accommodation Only

  • Suite

Prices
from

$1,957pp Total price $3,913
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

Close
More information about advance registrations
Reserve Now
Go to property page

Villa Favorita

Puglia, Italy

Villa | Bedrooms 3 | Sleeps 8

  • Elegant historic villa
  • Spacious and comfortable
  • Heated swimming pool
  • Exceptional outdoor area

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

Accommodation Only

  • Villa

Prices
from

$1,976pp Total price $3,952
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

Close
More information about advance registrations
Reserve Now
Go to property page

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

Accommodation Only

  • Villa

Prices
from

$1,976pp Total price $3,952
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

Close
More information about advance registrations
Reserve Now
Go to property page

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

Accommodation Only

  • Villa

Prices
from

$2,048pp Total price $4,095
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

Close
More information about advance registrations
Reserve Now
Go to property page

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 8 October 2022

Accommodation Only

  • Villa

Prices
from

$2,113pp Total price $4,225
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

Close
More information about advance registrations
Reserve Now

SearchResults.mustache file to be converted

  • Previousious
  • 1
  • 2
  • 3
  • Next

SearchPager.mustache file to be converted

Why travel with us..?

Talk to one of our experts

Talk to one of our experts
CONTACT US

A brand you can trust

A brand you can trust

See what others say about us

See what others say about us
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

Awards

  • Award - Conde Naste Traveller
  • Award - Telegraph
  • Award - Baby

Keep in touch

Sign up to receive our latest news and exclusive offers, direct to your inbox.

Back to top

Quick links

Get in touch

  • Facebook
  • Twitter
  • Pinterest
  • Instagram
  • YouTube
  • Careers
  • Contact us
  • Press & PR
  • Travel Agents
  • Special Assistance

Useful links

  • Why Simpson Travel?
  • Brochure request
  • Booking Conditions
  • Terms & Conditions
  • FAQs
  • Coronavirus
  • Responsible Tourism
  • Privacy notice
  • Cookie policy
  • Sitemap
  • Site Terms
  • Legal Disclosure

Holiday ideas

  • Holidays in Corsica
  • Villas in Corsica
  • Holidays in France
  • Villas in France
  • Holidays in Greece
  • Villas in Greece
  • Holidays in Italy
  • Villas in Italy
  • Holidays in Mallorca
  • Villas in Mallorca
  • Holidays in Turkey
  • Villas in Turkey

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

  • British Airways Appointed Operator
  • ABTA Number W5698
  • ATOL Number 5858
  • Show menu
  • Search
  • +44 (0) 208 392 5858

Menu

  • Destinations

    Destinations

    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

    Turkey

    Turkey

    • Akyaka
    • Bozburun Peninsula
    • Islamlar & Uzumlu
    • Kalkan
    • Kaş

    Italy

    Italy

    • Tuscany
    • Umbria
    • Puglia

    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

  • Hotels

    Hotels

    • Simpson Hotels
    • Partner hotels
    • Family hotels
    • Beachfront hotels
    • Adult-only hotels
    • Romantic hotels for two
    • Hotels with childcare
    • Car-free hotels

    Back

  • Holiday inspiration

    Holiday inspiration

    Holiday Types

    Holiday Types

    • Couples holidays
    • Beach holidays
    • Large group holidays
    • Car-free holidays
    • Twin Centre holidays
    • 10-night holidays
    • Countryside holidays
    • Honeymoons
    • Babymoons
    • Walking Holidays in Crete
    • Special Interest Holidays
    • Experiences and Activities

    Family Holidays

    Family Holidays

    • Holidays with childcare
    • Easter holidays
    • Half-term holidays
    • Multi-gen holidays

    Collections

    Collections

    • Simpson Exclusive
    • Simpson Secrets
    • Simpson Hotels
    • Simply Simpson
    • Simpson Kids
    • Simpson Bespoke

    Our Blog

    Our Blog

    • Where to go
    • What to do
    • What's new
    • Views and reviews
    • Family travel
    • 2023 holidays
    • Give the gift of travel
  • About us

    About us

    • Why Simpson Travel?
    • Travel arrangements
    • Advance Registration
    • Our heritage
    • Awards
    • Reviews
    • Loyalty Club
    • Our Destination Specialists
    • Giving back
    • Our blog
    • Our digital brochure
    • Our Partners
    • Responsible Tourism

    Back

  • Covid-19

    Covid-19

    • Simpson Safe

    Back

  • Contact us

    Contact us

    • Sign up to emails
    • Gift Vouchers
    • Press & PR
    • Property owners
    • Simpson Travel App
    • FAQs

    Back

  • Late availability
  • My Account
  • Wishlist

Back

Close