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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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Trullo Raffaella

Puglia, Italy

Villa | Bedrooms 3 | Sleeps 5

  • Enchanting trulli house
  • Valle d’Itria location
  • Flexible accommodation
  • Private garden

Prices are based on 2 sharing for 7 nights on Saturday 1 May 2021

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  • Villa

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$799pp Total price $1,598
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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 16 October 2021

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$1,017pp Total price $2,034
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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 1 May 2021

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$1,090pp Total price $2,179
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Villa Flavia

Puglia, Italy

Villa | Bedrooms 4 | Sleeps 6

  • Spacious contemporary villa
  • Panoramic sea view
  • Large lawned garden
  • Polignano a Mare beach 10-minute drive

Prices are based on 2 sharing for 7 nights on Saturday 16 October 2021

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$1,308pp Total price $2,615
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Villa Rudy

Puglia, Italy

Villa | Bedrooms 4 | Sleeps 8

  • Spacious family villa
  • Generous entertaining space
  • Outdoor kitchen
  • Private heated swimming pool

Prices are based on 2 sharing for 7 nights on Saturday 1 May 2021

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$1,591pp Total price $3,182
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Villa Aia

Puglia, Italy

Villa | Bedrooms 4 | Sleeps 8

  • Stylish contemporary villa
  • Beautiful countryside views
  • Peaceful and secluded
  • Media room

Prices are based on 2 sharing for 7 nights on Saturday 16 October 2021

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  • Villa

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$1,755pp Total price $3,509
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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 based on 2 sharing for 7 nights on Saturday 1 May 2021

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$976pp Total price $1,952
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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 May 2021

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  • Suite

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$1,671pp Total price $3,341
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Villa Polignano

Puglia, Italy

Villa | Bedrooms 3 | Sleeps 6

  • Delightful versatile villa
  • Attractive gardens
  • Superb 16-metre pool
  • Stylish garden annexe

Prices are based on 2 sharing for 7 nights on Saturday 9 October 2021

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$1,716pp Total price $3,431
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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 based on 2 sharing for 7 nights on Saturday 1 May 2021

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  • Villa

Prices
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$1,730pp Total price $3,459
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Simpson Travel in the press

  • ‘[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 from the Foreign Office

For up-to-date advice and information on travelling abroad, including passports, visas and health and safety, please visit the Foreign Commonwealth & Development Office website or call 020 7008 1500.

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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  • Destinations

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    France

    France

    • Côte d'Azur
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    • Vendée
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    • Ile de Ré

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    • Romantic villas for two
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  • Holiday inspiration

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    Holiday Types

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    • Couples holidays
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    • 10-night holidays
    • Countryside holidays
    • Honeymoons
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    Family Holidays

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    • Holidays with childcare
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    Collections

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    Be Inspired

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