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  • Destinations

    Destinations

    France

    France

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

    Mallorca

    Mallorca

    • Pollensa & Puerto Pollensa

    Greece

    Greece

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

    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
    Family villas
  • Hotels

    Hotels

    Simpson Hotels
    Partner hotels
    Family hotels
    Beachfront hotels
    Adult-only hotels
    Romantic hotels for two
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    Car-free hotels
  • 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 Greece
    • Special Interest Holidays

    Family holidays

    Family holidays

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

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    • Simpson Exclusive
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    More inspiration

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Luxury villa holidays in Puglia

From the elegance of Villa Favorita, the former home of the Baron of Monopoli, to charming Trullo Rosalinda, one of the traditional trulli houses transformed, each of our carefully chosen villas in Puglia has its own unique character. Together, they create a collection with simplicity and style, that combines tradition and contemporary innovation in equal measures.

Our luxury villa holidays in Puglia offer an inspiring choice of accommodation for families as well as couples travelling together and we’ve chosen locations that give everyone something to celebrate, whether you’re an avid foodie, a devotee of history or fond of sea and sandy beaches.

Choose a family home near Alberobello and its UNESCO-listed trulli village in the lovely Valle d’Itria, or go further south to Lecce, the Salento’s Baroque masterpiece – either way, our luxury villas put you within easy reach of Puglia’s most absorbing attractions and you’re never too far from the coast. Although with private swimming pools and spacious gardens, some with their own olive groves, staying at home is always a great option, for a villa holiday that puts quality time with the ones you love at the top of the itinerary.

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Casa Rosanna

Puglia , Italy

Villa | Bedroom 1 | Sleeps 2

  • Romantic hideaway
  • Beautiful sea views
  • Private and stylish
  • Charming Valle d'Itria location

Prices are per person, based on 2 sharing for 7 nights
on Saturday 3 May 2025

Accommodation Only
Villa
Prices
from
£595pp
Total price £1,190
View details
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Villa Ddò

Puglia , Italy

Villa | Bedrooms 3 | Sleeps 6

  • Striking contemporary villa
  • Tranquil rural setting overlooking vineyards
  • Walking distance to facilities of neighbouring Relais
  • Easy access to Cisternino and Valle d'Itria

Prices are per person, based on 2 sharing for 7 nights
on Saturday 3 May 2025

Accommodation Only
Villa
Prices
from
£855pp
Total price £1,710
View details
Go to property page

Tenuta Fonte

Puglia , Italy

Villa | Bedrooms 4 | Sleeps 8

  • Ideal configuration for 2 families
  • 3 hours of housekeeping included 6 days pw
  • Huge grounds
  • Very private

Prices are per person, based on 2 sharing for 7 nights
on Saturday 3 May 2025

Accommodation Only
Villa
Prices
from
£1,145pp
Total price £2,290
View details
Go to property page

Trullo Ashi

Puglia , Italy

Villa | Bedrooms 5 | Sleeps 9

  • Beautiful high-spec villa
  • Spacious gardens with charming views
  • Large heated swimming pool
  • Outdoor kitchen with pizza oven

Prices are per person, based on 2 sharing for 7 nights
on Saturday 3 May 2025

Accommodation Only
Villa
Prices
from
£1,145pp
Total price £2,290
View details
Simpson Exclusive

The most luxurious of our villas include a dedicated pre-departure booking service to arrange all the indulgent essentials before you travel, from private chefs to spa treatments – and while you’re away, your personal Concierge will be on hand to add the finishing touches.
Simpson Exclusive

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Masseria Specchia

Puglia , Italy

Villa | Bedrooms 4 | Sleeps 8

  • Stunning Simpson Exclusive
  • Understated luxury
  • Huge grounds
  • Set in beautiful Salento

Prices are per person, based on 2 sharing for 7 nights
on Saturday 3 May 2025

Accommodation Only
Villa
Prices
from
£1,395pp
Total price £2,790
View details
Simpson Secrets

Our search for exceptional villas occasionally leads us along the road less travelled to find hidden gems just too lovely to leave behind. Aimed at the adventurous at heart, each Simpson Secret offers a unique take on what a holiday off the beaten track can be.
Simpson Secrets

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Simpson Secret – Puglia

Puglia , Italy

Villa | Bedrooms 2 | Sleeps 4

  • Stunning nature reserve location
  • Comfortable country villa
  • Unique natural rock pool
  • Walking distance to beach

Prices are per person, based on 2 sharing for 7 nights
on Saturday 11 October 2025

Accommodation Only
Villa
Prices
from
£811pp
Total price £1,621
View details
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Villa Favorita

Puglia , Italy

Villa | Bedrooms 3 | Sleeps 8

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

Prices are per person, based on 2 sharing for 7 nights
on Saturday 11 October 2025

Accommodation Only
Villa
Prices
from
£1,715pp
Total price £3,430
View details
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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 per person, based on 2 sharing for 7 nights
on Saturday 11 October 2025

Accommodation Only
Villa
Prices
from
£1,805pp
Total price £3,610
View details
Simpson Exclusive

The most luxurious of our villas include a dedicated pre-departure booking service to arrange all the indulgent essentials before you travel, from private chefs to spa treatments – and while you’re away, your personal Concierge will be on hand to add the finishing touches.
Simpson Exclusive

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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 per person, based on 2 sharing for 7 nights
on Saturday 27 September 2025

Accommodation Only
Villa
Prices
from
£5,550pp
Total price £11,100
View details
Go to property page

Trullo Raffaella

Puglia , Italy

Villa | Bedrooms 3 | Sleeps 5

  • Enchanting trulli house
  • Valle d’Itria location
  • Flexible accommodation
  • Private garden
Reserve now for 2025 with a fully refundable deposit of £500

Use our Advanced Registration service to secure your 2025 holiday with a deposit of £500, fully refundable when prices are published

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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 - Telegraph 2018
  • Award - Baby 2019
  • Award - Conde Naste Traveller 2020
  • Award - Conde Naste Traveller 2021
  • Award - Conde Naste Traveller 2022
  •  Silver British travel awards 2021/22
  • Runner up Telegraph travel awards 2023

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Holiday ideas

  • Holidays in Corsica
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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.

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