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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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La Lamia

Puglia, Italy

Villa | Bedroom 1 | Sleeps 2

  • Romantic hideaway
  • Wonderful countryside views
  • Peaceful setting in Valle d'Itria
  • Cisternino 5min drive

Prices are based on 2 sharing for 7 nights on Saturday 14 October 2023

Accommodation Only

  • Villa

Prices
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$594pp Total price $1,188
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Reserve now for 2024 with a fully refundable deposit of $625

Use our Advanced Registration service to secure your 2024 holiday with a deposit of $625, fully refundable when prices are published

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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 based on 2 sharing for 7 nights on Saturday 14 October 2023

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Prices
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$657pp Total price $1,313
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Reserve now for 2024 with a fully refundable deposit of $625

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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 6 May 2023

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Prices
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$841pp Total price $1,682
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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 14 October 2023

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$1,272pp Total price $2,544
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Tenuta Fonte

Puglia, Italy

Villa | Bedrooms 4 | Sleeps 8

  • Elegantly understated
  • Huge grounds
  • Very private
  • Close to Ostuni

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

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  • Villa

Prices
from

$1,344pp Total price $2,688
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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 6 May 2023

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  • Villa

Prices
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$1,407pp Total price $2,813
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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 7 October 2023

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  • Villa

Prices
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$1,463pp Total price $2,925
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Reserve now for 2024 with a fully refundable deposit of $625

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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 7 October 2023

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  • Villa

Prices
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$1,494pp Total price $2,988
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Reserve now for 2024 with a fully refundable deposit of $625

Use our Advanced Registration service to secure your 2024 holiday with a deposit of $625, fully refundable when prices are published

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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

  • Understated luxury
  • Huge grounds
  • Beaches 5min drive
  • Lecce 5km

Prices are based on 2 sharing for 7 nights on Saturday 14 October 2023

Accommodation Only

  • Villa

Prices
from

$1,507pp Total price $3,013
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Reserve now for 2024 with a fully refundable deposit of $625

Use our Advanced Registration service to secure your 2024 holiday with a deposit of $625, fully refundable when prices are published

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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 6 May 2023

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  • Villa

Prices
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$1,900pp Total price $3,800
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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

Awards

  •  Silver British travel awards 2017
  • 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

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Holiday ideas

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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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    • Provence
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  • Villas

    Villas

    • Villas with childcare
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    • 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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  • Holiday inspiration

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    Holiday Types

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    • Couples holidays
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    • Honeymoons
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