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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 Momi

Tuscany , Italy

Villa | Bedroom 1 | Sleeps 2

12m private swimming pool
Stunning views across rolling hills
Walking distance to restaurant
Radda in Chianti 5-minute drive

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

Accommodation Only

Villa

Prices
from

$714pp

Total price $1,428

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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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Villa Forconi

Umbria , Italy

Villa | Bedrooms 3 | Sleeps 6

12-metre private pool
Far-reaching views
Very spacious
Private and secluded

Prices are per person, based on 2 sharing for 7 nights
on Saturday 2 May 2026

Accommodation Only

Villa

Prices
from

$1,312pp

Total price $2,623

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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

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

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Villa Mille Desideri

Tuscany , Italy

Villa | Bedrooms 6 | Sleeps 11

Peaceful and secluded
Ideal for 2 families
14m private swimming pool
Table tennis, table football, boules, football goals

Prices are per person, based on 2 sharing for 7 nights
on Saturday 2 May 2026

Accommodation Only

Villa

Prices
from

$1,708pp

Total price $3,415

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Colto dei Pallanti

Tuscany , Italy

Villa | Bedrooms 3 | Sleeps 6

In the heart of Chianti
Stunning panoramic views
Heated, gated 12m private pool
Spa area with sauna and Jacuzzi

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

Accommodation Only

Villa

Prices
from

$1,789pp

Total price $3,577

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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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Casa al Colle

Tuscany , Italy

Villa | Bedrooms 5 | Sleeps 10

Spectacular hillside location
Fantastic cook available
Ideal for a group/two families
Pizza oven

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

Accommodation Only

Villa

Prices
from

$1,876pp

Total price $3,751

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 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

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

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Villa Vita

Umbria , Italy

Villa | Bedrooms 3 | Sleeps 2-6

State-of-the-art design
Stunning roof-top living area
Heated 12m swimming pool
Pool-side gym room

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

Accommodation Only

Villa

Prices
from

$2,180pp

Total price $4,359

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

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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-perfect villa 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
‘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
Our stay was also infused with his thoughtful brand of hospitality, matched with that of the experienced tour operator (Simpson Travel). Author: Claire Irvin, The Times

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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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