Luxury family holidays in Italy

La Madonnina

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 4 sharing for 7 nights
on Saturday 11 October 2025

Accommodation Only

Villa

Prices
from

$409pp

Total price $1,634

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Villa Donatella

Umbria , Italy

Villa | Bedrooms 5 | Sleeps 6-9

A secluded, relaxing retreat
14m private swimming pool
All bedrooms air-conditioned
Close to Perugia and Assisi

Prices are per person, based on 4 sharing for 7 nights
on Saturday 27 September 2025

Accommodation Only

Villa

Prices
from

$760pp

Total price $3,038

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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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Trulli Gianpaolo

Villa | Bedrooms 3 | Sleeps 5

Enchanting trulli house
Val d’Itria location
Picturesque garden
Private pool

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

Accommodation Only

Villa

Prices
from

$842pp

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

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Villa Favorita

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 4 sharing for 7 nights
on Saturday 11 October 2025

Accommodation Only

Villa

Prices
from

$1,027pp

Total price $4,109

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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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La Perla del Mare

Villa | Bedrooms 2 | Sleeps 4

Two-bedroom apartment
Stunning sea views
Direct access to the sea
Private Mediterranean garden and terrace

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

Accommodation Only

Villa

Prices
from

$1,295pp

Total price $5,180

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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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Villa Montelopio

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 4 sharing for 7 nights
on Saturday 4 October 2025

Accommodation Only

Villa

Prices
from

$1,311pp

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

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Villa Rosa

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 4 sharing for 7 nights
on Saturday 6 September 2025

Accommodation Only

Villa

Prices
from

$1,827pp

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

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Trulli Rosalinda

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 per person, based on 4 sharing for 7 nights
on Saturday 5 July 2025

Accommodation Only

Villa

Prices
from

$2,937pp

Total price $11,746

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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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Villa Da Vinci

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 4 sharing for 7 nights
on Saturday 27 September 2025

Accommodation Only

Villa

Prices
from

$3,049pp

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

La Tenuta