1. Photo of Rosewood Castiglion del Bosco Villa Sant’Anna

    Tuscany, Italy

    Rosewood Castiglion del Bosco Villa Sant’Anna

    • Private pool and tennis court
    • Large gardens
    • Furnished pool house
    Sleeps up to
    9

    Chosen dates areUnavailable

    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 availability
  2. Photo of Rosewood Castiglion del Bosco Villa Stabbi

    Tuscany, Italy

    Rosewood Castiglion del Bosco Villa Stabbi

    • Private infinity pool
    • Val d’Orcia views
    • Styled by the Ferragamo family
    Sleeps up to
    9

    Chosen dates areUnavailable

    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 availability
  3. Photo of Rosewood Castiglion del Bosco Villa Alba

    Tuscany, Italy

    Rosewood Castiglion del Bosco Villa Alba

    • Sweeping gardens
    • Centuries-old site
    • Private pool
    Sleeps up to
    6

    Chosen dates areUnavailable

    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 availability
  4. Photo of Rosewood Castiglion del Bosco Villa Biondi

    Tuscany, Italy

    Rosewood Castiglion del Bosco Villa Biondi

    • Ferragamo-styled decor
    • Rosewood hotel facilities
    • Set on a World Heritage Site
    Sleeps up to
    10

    Chosen dates areUnavailable

    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 availability
  5. Photo of Rosewood Castiglion del Bosco Villa Castello

    Tuscany, Italy

    Rosewood Castiglion del Bosco Villa Castello

    • Large gardens
    • Historic site
    • Val d’Orcia views
    Sleeps up to
    6

    Chosen dates areUnavailable

    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 availability
  6. Photo of Rosewood Castiglion del Bosco Villa Casa del Fiume

    Tuscany, Italy

    Rosewood Castiglion del Bosco Villa Casa del Fiume

    • Traditional Tuscan style
    • Private pool and tennis court
    • Set on a World Heritage Site
    Sleeps up to
    8

    Chosen dates areUnavailable

    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 availability
  7. Photo of Rosewood Castiglion del Bosco Villa Chiusa

    Tuscany, Italy

    Rosewood Castiglion del Bosco Villa Chiusa

    • Historic former police station
    • Classic Tuscan style
    • Bloom-packed private gardens
    Sleeps up to
    8

    Chosen dates areUnavailable

    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 availability
  8. Photo of Locanda Rossa Superior Apartment

    Tuscany, Italy

    Locanda Rossa Superior Apartment

    • Triplex family apartment
    • Idyllic countryside location
    • Three pools and spa on-site
    Sleeps up to
    6

    Chosen dates areUnavailable

    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
    View availability
  9. Photo of Amanzoe Four-Bedroom Villa

    East Peloponnese, Greece

    Amanzoe Four-Bedroom Villa

    • Aegean views
    • Cool contemporary design
    • Seclusion and space
    Sleeps up to
    8

    Chosen dates areUnavailable

    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

    One 60-minute massage per person at the Aman Spa
    View availability
  10. Photo of Daios Cove Two-Bedroom Family Villa with Private Pool

    Crete, Greece

    Daios Cove Two-Bedroom Family Villa with Private Pool

    • Very family-friendly
    • Private saltwater pool
    • Kids club and resort access
    Sleeps up to
    4

    Chosen dates areUnavailable

    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 champagne and a spa treat; for five-night stays, four crèche sessions or two hours' babysitting; for seven-night stays, free kids' … more
    View availability
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