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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 15 October 2022

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  • Villa

Prices
from

$920pp Total price $1,840
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Reserve now for 2023 with a fully refundable deposit of $650

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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 15 October 2022

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  • Villa

Prices
from

$1,323pp Total price $2,646
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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
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$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 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

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  • Villa

Prices
from

$1,398pp Total price $2,795
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Reserve now for 2023 with a fully refundable deposit of $650

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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 27 August 2022

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  • Villa

Prices
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$1,658pp Total price $3,315
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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 15 October 2022

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  • Villa

Prices
from

$1,681pp Total price $3,362
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Reserve now for 2023 with a fully refundable deposit of $650

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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 October 2022

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  • Suite

Prices
from

$1,957pp Total price $3,913
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Reserve now for 2023 with a fully refundable deposit of $650

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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 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

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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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

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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

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

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  • ‘[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

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  • ‘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.

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  • Destinations

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    • Provence
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  • Villas

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    • Villas with childcare
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    • 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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