The Best Luxury Villas & Handpicked Private Rentals

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Tuscany, Italy

Rosewood Castiglion del Bosco Villa Alba
Sweeping gardens

Centuries-old site

Private pool

Price per night from (ex tax) $7,479.83

Why book with us?

Best-price guarantee

Found your stay for less elsewhere? We'll match the price and give you a £50 voucher.

Free Smith Extras on arrival

From a bottle of champagne, to a spa treatment or a cookery class, you’ll get a little extra thank you with every booking

Here for you 24/7

Personal service from Smith24, our in-house travel specialists, 1 800 464 2040

Anonymously reviewed

Every hotel is reviewed by undercover tastemakers (and their partners)
Smith Extra
A wine-tasting tour for all villa guests
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Tuscany, Italy

Rosewood Castiglion del Bosco Villa Chiusa
Historic former police station

Classic Tuscan style

Bloom-packed private gardens

Price per night from (ex tax) $10,892.84

Why book with us?

Best-price guarantee

Found your stay for less elsewhere? We'll match the price and give you a £50 voucher.

Free Smith Extras on arrival

From a bottle of champagne, to a spa treatment or a cookery class, you’ll get a little extra thank you with every booking

Here for you 24/7

Personal service from Smith24, our in-house travel specialists, 1 800 464 2040

Anonymously reviewed

Every hotel is reviewed by undercover tastemakers (and their partners)
Smith Extra
A wine-tasting tour for all villa guests
View villa
Health & safety New safety measures are in place at this hotel. Read more here
Tuscany, Italy

Borgo Pignano Maisonnette Il Granaio
Rustic and romantic

Fantastic for families

Blissful bucolic setting

Price per night from (ex tax) $1,073.61

Why book with us?

Best-price guarantee

Found your stay for less elsewhere? We'll match the price and give you a £50 voucher.

Free Smith Extras on arrival

From a bottle of champagne, to a spa treatment or a cookery class, you’ll get a little extra thank you with every booking

Here for you 24/7

Personal service from Smith24, our in-house travel specialists, 1 800 464 2040

Anonymously reviewed

Every hotel is reviewed by undercover tastemakers (and their partners)
Smith Extra
A bottle of organic wine and a small selection of Pignano Organic products in your room on arrival
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Health & safety New safety measures are in place at this hotel. Read more here
Tuscany, Italy

Borgo Pignano Maisonnette La Piccionaia
Remote, rural setting

Views of Volterra

Traditional and Tuscan

Price per night from (ex tax) $966.25

Why book with us?

Best-price guarantee

Found your stay for less elsewhere? We'll match the price and give you a £50 voucher.

Free Smith Extras on arrival

From a bottle of champagne, to a spa treatment or a cookery class, you’ll get a little extra thank you with every booking

Here for you 24/7

Personal service from Smith24, our in-house travel specialists, 1 800 464 2040

Anonymously reviewed

Every hotel is reviewed by undercover tastemakers (and their partners)
Smith Extra
A bottle of organic wine and a small selection of Pignano Organic products in your room on arrival
View villa
Health & safety New safety measures are in place at this hotel. Read more here
Tuscany, Italy

Borgo Pignano Cottage Casa del Lago
Rustic glamour

Organic farm

Plenty of activities

Price per night from (ex tax) $858.88

Why book with us?

Best-price guarantee

Found your stay for less elsewhere? We'll match the price and give you a £50 voucher.

Free Smith Extras on arrival

From a bottle of champagne, to a spa treatment or a cookery class, you’ll get a little extra thank you with every booking

Here for you 24/7

Personal service from Smith24, our in-house travel specialists, 1 800 464 2040

Anonymously reviewed

Every hotel is reviewed by undercover tastemakers (and their partners)
Smith Extra
A bottle of organic wine and a small selection of Pignano Organic products in your room on arrival
View villa
Health & safety New safety measures are in place at this hotel. Read more here
Tuscany, Italy

Borgo Pignano Maisonnette Il Pozzo
Family friendly

Traditionally Tuscan

Verdant views

Price per night from (ex tax) $1,073.61

Why book with us?

Best-price guarantee

Found your stay for less elsewhere? We'll match the price and give you a £50 voucher.

Free Smith Extras on arrival

From a bottle of champagne, to a spa treatment or a cookery class, you’ll get a little extra thank you with every booking

Here for you 24/7

Personal service from Smith24, our in-house travel specialists, 1 800 464 2040

Anonymously reviewed

Every hotel is reviewed by undercover tastemakers (and their partners)
Smith Extra
A bottle of organic wine and a small selection of Pignano Organic products in your room on arrival
View villa
Health & safety New safety measures are in place at this hotel. Read more here
Tuscany, Italy

Borgo Santo Pietro Casa dell'Unicorno
Hidden in the grounds

Twice-daily housekeeping

Private garden

Price per night from (ex tax) $1,927.13

Why book with us?

Best-price guarantee

Found your stay for less elsewhere? We'll match the price and give you a £50 voucher.

Free Smith Extras on arrival

From a bottle of champagne, to a spa treatment or a cookery class, you’ll get a little extra thank you with every booking

Here for you 24/7

Personal service from Smith24, our in-house travel specialists, 1 800 464 2040

Anonymously reviewed

Every hotel is reviewed by undercover tastemakers (and their partners)
Smith Extra
A bottle of spumante classic method from a vineyard in Trentino; and guests' choice of an assortment of hand-made chocolates made by the in-hou… more
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Tuscany, Italy

Monteverdi Villa Amiata
A private garden

Val d’Orcia views

Peace and quiet

Price per night from (ex tax) $2,898.75

Why book with us?

Best-price guarantee

Found your stay for less elsewhere? We'll match the price and give you a £50 voucher.

Free Smith Extras on arrival

From a bottle of champagne, to a spa treatment or a cookery class, you’ll get a little extra thank you with every booking

Here for you 24/7

Personal service from Smith24, our in-house travel specialists, 1 800 464 2040

Anonymously reviewed

Every hotel is reviewed by undercover tastemakers (and their partners)
Smith Extra
Welcome reception including a glass of prosecco and selection of local cheeses and meats.
View villa
Tuscany, Italy

Monteverdi Villa San Pietro
Goodie-stocked kitchen

Hand-made furnishings

Refined rusticity

Price per night from (ex tax) $1,986.18

Why book with us?

Best-price guarantee

Found your stay for less elsewhere? We'll match the price and give you a £50 voucher.

Free Smith Extras on arrival

From a bottle of champagne, to a spa treatment or a cookery class, you’ll get a little extra thank you with every booking

Here for you 24/7

Personal service from Smith24, our in-house travel specialists, 1 800 464 2040

Anonymously reviewed

Every hotel is reviewed by undercover tastemakers (and their partners)
Smith Extra
Welcome reception including a glass of prosecco and selection of local cheeses and meats.
View villa
Tuscany, Italy

Monteverdi Villa Muri Antichi
Peace and quiet

Stylish interiors

Friendly staff

Price per night from (ex tax) $4,723.88

Why book with us?

Best-price guarantee

Found your stay for less elsewhere? We'll match the price and give you a £50 voucher.

Free Smith Extras on arrival

From a bottle of champagne, to a spa treatment or a cookery class, you’ll get a little extra thank you with every booking

Here for you 24/7

Personal service from Smith24, our in-house travel specialists, 1 800 464 2040

Anonymously reviewed

Every hotel is reviewed by undercover tastemakers (and their partners)
Smith Extra
Welcome reception including a glass of prosecco and selection of local cheeses and meats.
View villa