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Siena Area Vacation Rentals: Luxury(75)

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1 2 3
Chic contemporary Tuscan villa complete with private spa facilities in
    4 Bedrooms,
  • 3 Bathrooms, 
  • 2 Half Baths
    • , Sleeps 8
  • Viewed

Chic contemporary Tuscan villa complete with private spa facilities in

4 Bedrooms,
  • 3 Bathrooms, 
  • 2 Half Baths
    • , Sleeps 8
    1. Val d'Elsa - Siena  >
    2. Radicondoli Villa
    #486557

    C$3,201 - C$3,601
    per week (C$)
    7 night Minimum Stay
    CLUB MONTECCHIO - Home from Home in Tuscany- 2 Luxury rental homes, large pool - Il Prato
      2 Bedrooms,
    • 2 Bathrooms
      • , Sleeps 4
    • Viewed

    CLUB MONTECCHIO - Home from Home in Tuscany- 2 Luxury rental homes, large pool - Il Prato

    2 Bedrooms,
  • 2 Bathrooms
    • , Sleeps 4
    1. Chianti Senese  >
    2. Castelnuovo Berardenga Villa
    #95620

    C$220 - C$433
    per night (C$)
    4 - 7 night Minimum Stay
    Special Offer
    Free House Wine Throughout Stay (April 19 - December 31)
    CLUB MONTECCHIO - Home from Home in Tuscany- 2 Luxury rental homes, large pool - L'Oliveto
      3 Bedrooms,
    • 3 Bathrooms
      • , Sleeps 6
    • Viewed

    CLUB MONTECCHIO - Home from Home in Tuscany- 2 Luxury rental homes, large pool - L'Oliveto

    3 Bedrooms,
  • 3 Bathrooms
    • , Sleeps 6
    1. Chianti Senese  >
    2. Castelnuovo Berardenga Villa
    #95620

    C$367 - C$487
    per night (C$)
    5 - 7 night Minimum Stay

    Charming country apartment with stunning views*Pool*BBQ - IL CASTAGNO
      2 Bedrooms,
    • 1 Bathroom
      • , Sleeps 4
    • Viewed

    Charming country apartment with stunning views*Pool*BBQ - IL CASTAGNO

    2 Bedrooms,
  • 1 Bathroom
    • , Sleeps 4
    1. Val di Chiana  >
    2. Sarteano Apartment
    #894849

    C$667 - C$800
    per week (C$)
    3 - 7 night Minimum Stay
    Charming tranquil Tuscan villa set in the exclusive Villa Arceno Chianti estate
      2 Bedrooms,
    • 2 Bathrooms
      • , Sleeps 4
    • Viewed

    Charming tranquil Tuscan villa set in the exclusive Villa Arceno Chianti estate

    2 Bedrooms,
  • 2 Bathrooms
    • , Sleeps 4
    1. Chianti Senese  >
    2. Castelnuovo Berardenga Apartment
    #433025

    C$1,600 - C$1,867
    per week (C$)
    7 night Minimum Stay
    A vacation to remember in the Chianti area between Florence and Siena - Granaio
      2 Bedrooms,
    • 1 Bathroom
      • , Sleeps 5
    • Viewed

    A vacation to remember in the Chianti area between Florence and Siena - Granaio

    2 Bedrooms,
  • 1 Bathroom
    • , Sleeps 5
    1. Val d'Elsa - Siena  >
    2. Poggibonsi Villa
    #83171

    C$253
    per night (C$)
    3 - 7 night Minimum Stay
    Chianti Luxury Country Homes with pool in olive grove
      2 Bedrooms,
    • 2 Bathrooms
      • , Sleeps 4
    • Viewed

    Chianti Luxury Country Homes with pool in olive grove

    2 Bedrooms,
  • 2 Bathrooms
    • , Sleeps 4
    1. Chianti Senese  >
    2. Castelnuovo Berardenga Barn
    #90235

    C$867 - C$1,894
    per week (C$)
    7 night Minimum Stay
    La Casina Toscana, Your holiday in Tuscany
      3 Bedrooms,
    • 2 Bathrooms
      • , Sleeps 6
    • Viewed

    La Casina Toscana, Your holiday in Tuscany

    3 Bedrooms,
  • 2 Bathrooms
    • , Sleeps 6
    1. Val di Chiana  >
    2. Montepulciano Chateau / Country House
    #436049vb

    C$107 - C$153
    per night (C$)
    3 - 6 night Minimum Stay
    Deluxe stone villa with pool, hot tub, pool table, wifi, wine cellar, fitness
      8 Bedrooms,
    • 1 Bathroom
      • , Sleeps 16
    • Viewed

    Deluxe stone villa with pool, hot tub, pool table, wifi, wine cellar, fitness

    8 Bedrooms,
  • 1 Bathroom
    • , Sleeps 16
    1. Val d'Orcia - Amiata  >
    2. Pienza Villa
    #750321

    C$9,336 - C$12,003
    per week (C$)
    7 night Minimum Stay
    Luxory Villa close to San Casciano dei Bagni. Siena
      9 Bedrooms,
    • 10 Bathrooms
      • , Sleeps 20
    • Viewed

    Luxory Villa close to San Casciano dei Bagni. Siena

    9 Bedrooms,
  • 10 Bathrooms
    • , Sleeps 20
    1. Val di Chiana  >
    2. San Casciano dei Bagni Villa
    #1091650

    C$2,654 - C$5,855
    per week (C$)
    7 night Minimum Stay
    U.S. Homeowner ~ Private Home near Siena, Lovely Location in Tuscany~
      4 Bedrooms,
    • 2 Bathrooms, 
    • 1 Half Bath
      • , Sleeps 7
    • Viewed

    U.S. Homeowner ~ Private Home near Siena, Lovely Location in Tuscany~

    4 Bedrooms,
  • 2 Bathrooms, 
  • 1 Half Bath
    • , Sleeps 7
    1. Chianti Senese  >
    2. Castelnuovo Berardenga Farmhouse
    #412266vb

    Villa Gimigano
      9 Bedrooms,
    • 4 Bathrooms
      • , Sleeps 20
    • Viewed

    Villa Gimigano

    9 Bedrooms,
  • 4 Bathrooms
    • , Sleeps 20
    1. Siena Area  >
    2. Siena Villa
    #1071966

    C$3,471 - C$7,574
    per night (C$)
    2 night Minimum Stay
    Style, Charm, Amazing Views, Eco-pool, Wifi, Unbeatable Price
      3 Bedrooms,
    • 3 Bathrooms
      • , Sleeps 6
    • Viewed

    Style, Charm, Amazing Views, Eco-pool, Wifi, Unbeatable Price

    3 Bedrooms,
  • 3 Bathrooms
    • , Sleeps 6
    1. Siena Area  >
    2. Siena Chateau / Country House
    #462950vb

    C$1,734
    per week (C$)
    7 night Minimum Stay
    The Hills of Dreams- San Casciano Dei Bagni
      6 Bedrooms,
    • 4 Bathrooms, 
    • 1 Half Bath
      • , Sleeps 12
    • Viewed

    The Hills of Dreams- San Casciano Dei Bagni

    6 Bedrooms,
  • 4 Bathrooms, 
  • 1 Half Bath
    • , Sleeps 12
    1. Val di Chiana  >
    2. San Casciano dei Bagni Villa
    #86772

    C$4,001 - C$6,002
    per week (C$)
    7 night Minimum Stay
    Charming villa with pool near San Gimignano. An oasis of peace
      3 Bedrooms,
    • 2 Bathrooms
      • , Sleeps 8
    • Viewed

    Charming villa with pool near San Gimignano. An oasis of peace

    3 Bedrooms,
  • 2 Bathrooms
    • , Sleeps 8
    1. Val d'Elsa - Siena  >
    2. San Gimignano Villa
    #830535

    C$2,001 - C$3,668
    per week (C$)
    7 night Minimum Stay
    'Crazy-Gorgeous' Home in Chianti ~ Private Estate Property
      4 Bedrooms,
    • 2 Bathrooms, 
    • 1 Half Bath
      • , Sleeps 7
    • Viewed

    'Crazy-Gorgeous' Home in Chianti ~ Private Estate Property

    4 Bedrooms,
  • 2 Bathrooms, 
  • 1 Half Bath
    • , Sleeps 7
    1. Chianti Senese  >
    2. Castelnuovo Berardenga House
    #1028606

    C$560 - C$613
    per night (C$)
    3 night Minimum Stay
    Antique villa with top-quality equipment and private pool near San Gimignano
      7 Bedrooms,
    • 7 Bathrooms, 
    • 1 Half Bath
      • , Sleeps 14
    • Viewed

    Antique villa with top-quality equipment and private pool near San Gimignano

    7 Bedrooms,
  • 7 Bathrooms, 
  • 1 Half Bath
    • , Sleeps 14
    1. Val d'Elsa - Siena  >
    2. San Gimignano Villa
    #529352

    C$7,069 - C$8,402
    per week (C$)
    7 night Minimum Stay
    Villa Masseto- beautiful independent restored villa private pool /tennis court
      5 Bedrooms,
    • 4 Bathrooms, 
    • 1 Half Bath
      • , Sleeps 10
    • Viewed

    Villa Masseto- beautiful independent restored villa private pool /tennis court

    5 Bedrooms,
  • 4 Bathrooms, 
  • 1 Half Bath
    • , Sleeps 10
    1. Chianti Senese  >
    2. Castellina in Chianti Villa
    #6809

    C$3,268 - C$5,068
    per week (C$)
    7 night Minimum Stay
    Tradtional Style Townhouse with shared pool and cycles - Casacorvo Maggiore
      3 Bedrooms,
    • 2 Bathrooms
      • , Sleeps 8
    • Viewed

    Tradtional Style Townhouse with shared pool and cycles - Casacorvo Maggiore

    3 Bedrooms,
  • 2 Bathrooms
    • , Sleeps 8
    1. Chianti Senese  >
    2. Gaiole in Chianti Apartment
    #489852

    C$289 - C$390
    per night (C$)
    4 - 5 night Minimum Stay
    Spectacular 5 Bedroom Villa With Pool In Siena, Tuscany
      5 Bedrooms, Sleeps 10
    • Viewed

    Spectacular 5 Bedroom Villa With Pool In Siena, Tuscany

    5 Bedrooms, Sleeps 10
    1. Siena Area  >
    2. Siena Villa
    #1095146

    C$9,360
    per week (C$)
    7 night Minimum Stay
    Stunning Country Villa with Saline Pool and Spa facility
      3 Bedrooms,
    • 2 Bathrooms
      • , Sleeps 6
    • Viewed

    Stunning Country Villa with Saline Pool and Spa facility

    3 Bedrooms,
  • 2 Bathrooms
    • , Sleeps 6
    1. Val d'Elsa - Siena  >
    2. Radicondoli Villa
    #258864

    C$567 - C$800
    per night (C$)
    3 - 146 night Minimum Stay
    Tuscany, Chianti, luxury villa, pool, park
      5 Bedrooms,
    • 5 Bathrooms
      • , Sleeps 11
    • Viewed

    Tuscany, Chianti, luxury villa, pool, park

    5 Bedrooms,
  • 5 Bathrooms
    • , Sleeps 11
    1. Chianti Senese  >
    2. Gaiole in Chianti Villa
    #405660

    C$5,188 - C$5,722
    per week (C$)
    7 night Minimum Stay
    Beautiful Typical Chianti Farmhouse With Pool
      3 Bedrooms,
    • 3 Bathrooms
      • , Sleeps 6
    • Viewed

    Beautiful Typical Chianti Farmhouse With Pool

    3 Bedrooms,
  • 3 Bathrooms
    • , Sleeps 6
    1. Chianti Senese  >
    2. Gaiole in Chianti Estate
    #453013vb

    C$200
    per night (C$)
    3 night Minimum Stay
    Great House, Great Garden, Great Location !!!
      4 Bedrooms,
    • 4 Bathrooms
      • , Sleeps 8
    • Viewed

    Great House, Great Garden, Great Location !!!

    4 Bedrooms,
  • 4 Bathrooms
    • , Sleeps 8
    1. Val di Chiana  >
    2. Cetona Farmhouse
    #300649vb

    C$6,142
    per week (C$)
    7 night Minimum Stay
    detached house with private pool Wi Fi, panoramic view, gym
      3 Bedrooms,
    • 3 Bathrooms
      • , Sleeps 6
    • Viewed

    detached house with private pool Wi Fi, panoramic view, gym

    3 Bedrooms,
  • 3 Bathrooms
    • , Sleeps 6
    1. Chianti Senese  >
    2. Gaiole in Chianti
    #871286

    C$400 - C$667
    per night (C$)
    3 night Minimum Stay
    Lovely Tuscan villa, pool, superb views, cleaning, cooking available
      5 Bedrooms,
    • 3 Bathrooms
      • , Sleeps 8
    • Viewed

    Lovely Tuscan villa, pool, superb views, cleaning, cooking available

    5 Bedrooms,
  • 3 Bathrooms
    • , Sleeps 8
    1. Val d'Orcia - Amiata  >
    2. Radicofani Villa
    #15714

    C$2,654 - C$5,152
    per week (C$)
    7 night Minimum Stay
    Il CIPRESSO HIDEAWAY Apartment with wonderful views and pool
      1 Bedrooms,
    • 1 Bathroom
      • , Sleeps 2
    • Viewed

    Il CIPRESSO HIDEAWAY Apartment with wonderful views and pool

    1 Bedrooms,
  • 1 Bathroom
    • , Sleeps 2
    1. Val di Chiana  >
    2. Sarteano Apartment
    #895389

    C$600 - C$734
    per week (C$)
    5 night Minimum Stay
    Special Offer
    BOOK NOW TO SAVE 15% ON YOUR HOLIDAYS (June 22 - November 1)
    Luxury Tuscan villa, heated pool, superb views, underfloor cooling
      5 Bedrooms,
    • 5 Bathrooms, 
    • 1 Half Bath
      • , Sleeps 10
    • Viewed

    Luxury Tuscan villa, heated pool, superb views, underfloor cooling

    5 Bedrooms,
  • 5 Bathrooms, 
  • 1 Half Bath
    • , Sleeps 10
    1. Val d'Orcia - Amiata  >
    2. Pienza Villa
    #860747

    C$3,903 - C$7,650
    per week (C$)
    7 night Minimum Stay
    A Magical Country House near Montalcino, Siena
      8 Bedrooms, Sleeps 17
    • Viewed

    A Magical Country House near Montalcino, Siena

    8 Bedrooms, Sleeps 17
    1. Val d'Orcia - Amiata  >
    2. Montalcino Villa
    #70004

    C$3,895 - C$7,728
    per week (C$)
    7 night Minimum Stay
    Special Offer
    Special Offer on Remaining Weeks! (June 1 - July 27)
    Beautiful house on Chianti hilltop with exceptional views.
      4 Bedrooms,
    • 4 Bathrooms, 
    • 1 Half Bath
      • , Sleeps 8
    • Viewed

    Beautiful house on Chianti hilltop with exceptional views.

    4 Bedrooms,
  • 4 Bathrooms, 
  • 1 Half Bath
    • , Sleeps 8
    1. Chianti Senese  >
    2. Castellina in Chianti Farmhouse
    #13754

    C$1,405 - C$3,747
    per week (C$)
    7 night Minimum Stay
    1 2 3
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