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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

View details

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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

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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

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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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La Madonnina

Tuscany , Italy

Villa | Bedrooms 1-2 | Sleeps 2-4

Two delightful 2-bedroom apartments, one studio cottage
Stunning views
Beautiful gardens
Cook service available

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

Accommodation Only

Villa

Prices
from

$691pp

Total price $1,381

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Le Guardie

Tuscany , Italy

Villa | Bedroom 1 | Sleeps 2

Charming renovated cottage, perfect for couples
Designer interiors
Hot tub
Fully air-conditioned

Prices are per person, based on 2 sharing for 7 nights
on Saturday 27 September 2025

Accommodation Only

Villa

Prices
from

$1,197pp

Total price $2,394

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Villa Montelopio

Tuscany , Italy

Villa | Bedrooms 5 | Sleeps 10

Elegant villa in hilltop village
Multiple terraces with panoramic views
12m private swimming pool
Chef service available

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

Accommodation Only

Villa

Prices
from

$2,622pp

Total price $5,243

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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 Rosa

Tuscany , Italy

Villa | Bedrooms 4 | Sleeps 8

Ideal for families
Extensive private grounds
16-metre fenced swimming pool
Breakfast and pizza delivery service

Prices are per person, based on 2 sharing for 7 nights
on Saturday 6 September 2025

Accommodation Only

Villa

Prices
from

$3,654pp

Total price $7,307

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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 Da Vinci

Tuscany , Italy

Villa | Bedrooms 6 | Sleeps 13

16m private pool
Breath-taking panoramic views
Stunning guest cottage
Set in the heart of Chianti

Prices are per person, based on 2 sharing for 7 nights
on Saturday 27 September 2025

Accommodation Only

Villa

Prices
from

$6,098pp

Total price $12,196

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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Villa Petraia

Tuscany , Italy

Villa | Bedrooms 5 | Sleeps 10

Simpson Signature villa
Classic Tuscan views
Elegant décor
Heated swimming pool

Prices are per person, based on 2 sharing for 7 nights
on Saturday 27 September 2025

Accommodation Only

Villa

Prices
from

$8,246pp

Total price $16,492

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] 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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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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