Discover luxury villas with swimming pools in Italy

Tuscany, Italy

Locanda Rossa Superior Apartment
Triplex family apartment

Idyllic countryside location

Three pools and spa on-site

Price per night from (ex tax)$326.94

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 the hotel’s extra-virgin olive oil, and a 50 per cent discount on extra beds for kids
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Tuscany, Italy

Borgo Pignano Maisonnette La Piccionaia
Remote, rural setting

Views of Volterra

Traditional and Tuscan

Price per night from (ex tax)$731.41

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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Tuscany, Italy

Borgo Pignano Maisonnette Il Pozzo
Family friendly

Traditionally Tuscan

Verdant views

Price per night from (ex tax)$828.94

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
Tuscany, Italy

Borgo Pignano Maisonnette Il Granaio
Rustic and romantic

Fantastic for families

Blissful bucolic setting

Price per night from (ex tax)$975.21

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
Tuscany, Italy

Borgo Pignano Cottage Casa del Lago
Rustic glamour

Organic farm

Plenty of activities

Price per night from (ex tax)$1,316.54

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
Tuscany, Italy

Rosewood Castiglion del Bosco Villa Alba
Sweeping gardens

Centuries-old site

Private pool

Price per night from (ex tax)$6,256.01

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
Tuscany, Italy

Rosewood Castiglion del Bosco Villa Castello
Large gardens

Historic site

Val d’Orcia views

Price per night from (ex tax)$6,677.30

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
Tuscany, Italy

Rosewood Castiglion del Bosco Villa Casa del Fiume
Traditional Tuscan style

Private pool and tennis court

Set on a World Heritage Site

Price per night from (ex tax)$7,176.61

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 wine-tasting tour for all villa guests
View villa
Tuscany, Italy

Rosewood Castiglion del Bosco Villa Oliviera
Private infinity pool

Postcard-perfect views

Authentic Tuscan style

Price per night from (ex tax)$7,784.17

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
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)$9,069.51

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