13 results found

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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Simply Simpson

The simple things in life often give the greatest pleasure and we believe our Simply Simpson Collection offers the chance to experience a more authentic taste of local living in some of the most idyllic locations in the Mediterranean. Take time to discover our comfortable, no-frills accommodation and join us on the road less travelled.
Simply Simpson

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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 27 September 2025

Accommodation Only

Villa

Prices
from

$980pp

Total price $1,960

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Reserve now for 2026 with a fully refundable deposit of $700

Use our Advanced Registration service to secure your 2026 holiday with a deposit of $700, fully refundable when prices are published

Reserve Now

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Villa Ddò

Puglia , Italy

Villa | Bedrooms 3 | Sleeps 6

Fully air-conditioned
Private 12m swimming pool
Walking distance to facilities of neighbouring Relais
10min drive to Cisternino

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

Accommodation Only

Villa

Prices
from

$1,297pp

Total price $2,593

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Reserve now for 2026 with a fully refundable deposit of $700

Use our Advanced Registration service to secure your 2026 holiday with a deposit of $700, fully refundable when prices are published

Reserve Now

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Tenuta Fonte

Puglia , Italy

Villa | Bedrooms 4 | Sleeps 8

Ideal configuration for 2 families
Very private
Short drive to Ostuni, Cisternino, Rosamarina, Villanova
Beach 8min drive

Prices are per person, based on 2 sharing for 7 nights
on Saturday 4 October 2025

Accommodation Only

Villa

Prices
from

$1,610pp

Total price $3,220

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Reserve now for 2026 with a fully refundable deposit of $700

Use our Advanced Registration service to secure your 2026 holiday with a deposit of $700, fully refundable when prices are published

Reserve Now

Simpson Signature

Discover our top-rated, most luxurious villas, with exceptional service to match.
Simpson Signature

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Masseria Specchia

Puglia , Italy

Villa | Bedrooms 4 | Sleeps 8

Simpson Signature villa
Understated luxury
Huge grounds
Set in beautiful Salento

Prices are per person, based on 2 sharing for 7 nights
on Saturday 4 October 2025

Accommodation Only

Villa

Prices
from

$2,030pp

Total price $4,060

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Reserve now for 2026 with a fully refundable deposit of $700

Use our Advanced Registration service to secure your 2026 holiday with a deposit of $700, fully refundable when prices are published

Reserve Now

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Trullo Iana

Puglia , Italy

Villa | Bedrooms 3 | Sleeps 6

Charming converted trullo house
Extensive outdoor space
Summer kitchen
Ideal for couples

Prices are per person, based on 2 sharing for 7 nights
on Saturday 13 September 2025

Accommodation Only

Villa

Prices
from

$2,293pp

Total price $4,585

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Reserve now for 2026 with a fully refundable deposit of $700

Use our Advanced Registration service to secure your 2026 holiday with a deposit of $700, fully refundable when prices are published

Reserve Now

Simpson Signature

Discover our top-rated, most luxurious villas, with exceptional service to match.
Simpson Signature

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Villa Mea

Puglia , Italy

Villa | Bedrooms 6 | Sleeps 12

Simpson Signature villa
Historically significant building
Superb 18m heatable pool
Pool house with full kitchen & fitness room

Prices are per person, based on 2 sharing for 7 nights
on Saturday 20 September 2025

Accommodation Only

Villa

Prices
from

$5,537pp

Total price $11,073

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Reserve now for 2026 with a fully refundable deposit of $700

Use our Advanced Registration service to secure your 2026 holiday with a deposit of $700, fully refundable when prices are published

Reserve Now

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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 per person, based on 2 sharing for 7 nights
on Saturday 4 October 2025

Accommodation Only

Villa

Prices
from

$1,684pp

Total price $3,367

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Reserve now for 2026 with a fully refundable deposit of $700

Use our Advanced Registration service to secure your 2026 holiday with a deposit of $700, fully refundable when prices are published

Reserve Now

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Villa Favorita

Puglia , Italy

Villa | Bedrooms 3 | Sleeps 8

Elegant historic villa
15m heated swimming pool
Exceptional outdoor area
Table tennis and table football

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

Accommodation Only

Villa

Prices
from

$2,055pp

Total price $4,109

View details

Reserve now for 2026 with a fully refundable deposit of $700

Use our Advanced Registration service to secure your 2026 holiday with a deposit of $700, fully refundable when prices are published

Reserve Now

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