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Siena Area Vacation Rental Accommodations - Page 1 of 20

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SPECIAL OFFER! 10% discount for autumn October 4 - November 7

Sovicille Old charming and characteristic farm house with Pool - 10 km from Siena

  • 5 BR/4 BA Farmhouse (sleeps 10)
    $1,120 - $2,672/wk
    per property, rural, garden, pool, pets considered

Castellina in Chianti Spectacular Apartments on 16th Century Tuscan Estate between Siena & Florence - Casa Pineta

  • 4 BR/4 BA Farmhouse (sleeps 12)
    $359/nt
    $2,514 - $3,175/wk
    per property, rural, village, garden, pool, pets considered

Castellina in Chianti Spectacular Apartments on 16th Century Tuscan Estate between Siena & Florence - Cosy studio 'Il Rifugio'

  • 1 BR/1 BA Apartment (sleeps 3)
    $101/nt
    $675/wk
    per property, rural, village, garden, pool, pets considered

Chiusi South Tuscany Rental: charming Villa (up to 9) and Annex (up to 3)

  • 5 BR/3 BA Villa (sleeps 12)
    $230 - $350/nt
    $1,600 - $2,400/wk
    per property, lake, rural, accept credit card, washing machine, internet access

Siena Beautiful country house, centrally located in the Chianti Classico region, pool - Capanna

  • 2 BR House (sleeps 4)
    $575 - $1,580/wk
    per property, rural, garden, pool

Murlo Beautiful Tuscany villa with swimming pool inside, an attractive landscape - Murlo

  • 1 BR Apartment (sleeps 3)
    $108 - $158/nt
    $532 - $1,006/wk
    per property, rural, garden, pool, pets considered

Murlo Beautiful Tuscany villa with swimming pool inside, an attractive landscape - Palazzina

  • 3 BR Apartment (sleeps 6)
    $144 - $273/nt
    $934 - $1,796/wk
    per property, rural, garden, pool, pets considered

Murlo Beautiful Tuscany villa with swimming pool inside, an attractive landscape - dipendenza

  • 4 BR/1 BA Villa (sleeps 10)
    $287 - $488/nt
    $1,939 - $3,232/wk
    per property, rural, garden, pool, golf

Murlo Beautiful Tuscany villa with swimming pool inside, an attractive landscape - Suite apartment

  • 1 BR Cottage (sleeps 4)
    $115 - $187/nt
    $704 - $1,221/wk
    per property, rural, air-conditioning, garden, pool

Radicondoli Come and enjoy the authentic Tuscan country life in stunning settings - La Galera

  • 3 BR/2 BA, 1 half bath House (sleeps 5)
    $215/nt
    $1,149/wk
    per property, rural, village
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Radicondoli Come and enjoy the authentic Tuscan country life in stunning settings - 'Il Noce della Fonte'

  • 2 BR/2 BA Apartment (sleeps 4)
    $259/nt
    $1,264/wk
    per property, rural, village

Radicofani Luxury Tuscan farmhouse with pool and magnificent views

  • 5 BR/3 BA Farmhouse (sleeps 8)
    $3,258 - $5,068/wk
    per property, rural, garden, pool, pets not allowed

Radicondoli Come and enjoy the authentic Tuscan country life in stunning settings - 'Il Susino della Fonte'

  • 1 BR/1 BA Apartment (sleeps 2)
    $144/nt
    $718/wk
    per property, rural, village, garden

Siena Beautiful country house, centrally located in the Chianti Classico region, pool - Annesso

  • 1 BR Chateau / Country House (sleeps 2)
    $259 - $503/wk
    per property, rural, garden, pool

Sarteano A magnificent farmhouse in Val d'Orcia, Tuscany

  • 5 BR/6 BA Farmhouse (sleeps 10)
    $4,310 - $6,177/wk
    per property, rural, village, garden, pool, pets not allowed

San Casciano dei Bagni A Charming and Luxurious Country Villa at the Border of Tuscany, Umbria & Lazio

  • 5 BR/4 BA, 1 half bath Villa (sleeps 10)
    $3,300 - $5,800/wk
    per property, rural, swimming pool, washing machine, tennis

Monteriggioni Exclusive holiday house Tuscany, Charming cottage Tuscany, maison de charme

  • 3 BR/1 BA House (sleeps 5)
    $575 - $833/wk
    per property, rural, town, garden, pets considered, golf

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

  • 5 BR/4 BA, 1 half bath Villa (sleeps 10)
    $3,088 - $5,243/wk
    per property, rural, village, garden, pool, pets not allowed

Siena Beautiful country house, centrally located in the Chianti Classico region, pool - Casa Principale - Lower Apartment

  • 2 BR/1 BA Farmhouse (sleeps 4)
    $402 - $934/wk
    per property, rural, garden, pool

Montalcino Stay in the Wine Country of Tuscany—Day Trip to Siena, Florence, Pisa and Rome

  • Studio/1 BA Apartment (sleeps 2)
    $850/wk
    per property, village, accept credit card, linens provided, satellite or cable
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Castellina in Chianti Spectacular Apartments on 16th Century Tuscan Estate between Siena & Florence - Lofty apartment 'La Bellavista'

  • 1 BR/1 BA Apartment (sleeps 4)
    $129/nt
    $819/wk
    per property, rural, village, garden, pool, pets considered

Castellina in Chianti Spectacular Apartments on 16th Century Tuscan Estate between Siena & Florence - Economical 2BR apartment 'La Tana'

  • 2 BR/1 BA Apartment (sleeps 5)
    $962 - $1,135/wk
    per property, rural, village, garden, pool, pets considered

Castellina in Chianti Spectacular Apartments on 16th Century Tuscan Estate between Siena & Florence - romant. 2BR cottage 'La Capannina'

  • 2 BR/1 BA, 1 half bath Farmhouse (sleeps 6)
    $244 - $302/nt
    $1,508 - $1,796/wk
    per property, rural, village, garden, pool, pets considered

Gaiole in Chianti Charming 15th Century Tuscan Stone VIlla in the Heart of Chianti Region

  • 5 BR/5 BA Villa (sleeps 10)
    $2,500 - $4,500/wk
    per property, rural, village, swimming pool, washing machine, internet access

Siena Beautiful country house, centrally located in the Chianti Classico region, pool - Casa Principale - Upstairs Apartment

  • 3 BR House (sleeps 8)
    $1,077 - $1,796/wk
    per property, rural, garden, pool

Gaiole in Chianti Podere Lucignano Secondo - Charming Villa in Chianti - Tuscany - “La Mangiatoia”

  • 2 BR/1 BA Villa (sleeps 4)
    $246 - $307/nt
    $1,724 - $2,155/wk
    per property, rural, garden, pets not allowed, golf

Gaiole in Chianti Podere Lucignano Secondo - Charming Villa in Chianti - Tuscany - “Le Logge”

  • 3 BR/3 BA Villa (sleeps 6)
    $276 - $359/nt
    $1,939 - $2,514/wk
    per property, rural, garden, pets not allowed, golf

Radicondoli Charming House in the heart of Tuscany

  • 3 BR/2 BA House (sleeps 6)
    $600 - $1,000/wk
    per property, river, village, washing machine, pets considered, tennis

Casole d'Elsa Charming accommodation in villa with pool near Siena

  • 2 BR/2 BA Apartment (sleeps 5)
    $65 - $120/nt
    $670 - $890/wk
    per property, resort, village, accept credit card, swimming pool, pets considered

Gaiole in Chianti Chianti Villas surrounded by olive groves and Vineyards with pool - Eolo

  • 3 BR/3 BA Villa (sleeps 6)
    $1,077 - $1,688/wk
    per property, rural, village, pool, pets considered
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Gaiole in Chianti Chianti Villas surrounded by olive groves and Vineyards with pool - Scorpione

  • 1 BR/1 BA Villa (sleeps 3)
    $575 - $998/wk
    per property, rural, village, air-conditioning, garden, pool

Gaiole in Chianti Chianti Villas surrounded by olive groves and Vineyards with pool - Taglialegna

  • 1 BR/1 BA Villa (sleeps 4)
    $575 - $804/wk
    per property, rural, village, garden, pool, pets considered

Gaiole in Chianti Chianti Villas surrounded by olive groves and Vineyards with pool - Melograno

  • 2 BR/2 BA Villa (sleeps 4)
    $790 - $1,362/wk
    per property, rural, village, garden, pool, pets considered

Gaiole in Chianti Chianti Villas surrounded by olive groves and Vineyards with pool - La Stella

  • 2 BR/2 BA Villa (sleeps 4)
    $790 - $1,362/wk
    per property, rural, village, garden, pool, pets considered

Sovicille Charming and romantic Villa in the countryside near Siena

  • 4 BR/4 BA Villa (sleeps 10)
    $1,867 - $3,160/wk
    per property, rural, village, garden, pool, pets not allowed

Gaiole in Chianti Magnificent villa in the heart of the Chianti region, Tuscany - Panorama

  • 1 BR/1 BA Apartment (sleeps 3)
    $550 - $968/wk
    per property, village, pool, pets considered

Gaiole in Chianti Magnificent villa in the heart of the Chianti region, Tuscany - La Contessina

  • 1 BR/1 BA Villa (sleeps 4)
    $586 - $1,428/wk
    per property, village, garden, pool, pets considered

Gaiole in Chianti Magnificent villa in the heart of the Chianti region, Tuscany - La Taverna

  • 2 BR/2 BA Villa (sleeps 4)
    $1,173 - $2,353/wk
    per property, village, garden, pool, pets considered

Siena Agriturismo Il Lucherino - Charming medieval built near Siena- - Sirlad

  • 1 BR/1 BA Apartment (sleeps 4)
    $115 - $129/nt
    $718 - $790/wk
    per property, rural, village, garden, pool, pets considered

Siena Agriturismo Il Lucherino - Charming medieval built near Siena- - Ribot

  • 1 BR/1 BA Apartment (sleeps 4)
    $115 - $129/nt
    $718 - $790/wk
    per property, rural, village, garden, pool, pets considered
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Siena Agriturismo Il Lucherino - Charming medieval built near Siena- - Nearco

  • 2 BR/1 BA Apartment (sleeps 6)
    $201 - $230/nt
    $934 - $1,077/wk
    per property, rural, village, garden, pool, pets considered

Siena Agriturismo Il Lucherino - Charming medieval built near Siena- - Panezio

  • 2 BR/1 BA Apartment (sleeps 4)
    $201 - $230/nt
    $934 - $1,077/wk
    per property, rural, village, garden, pool, pets considered

Siena Agriturismo Il Lucherino - Charming medieval built near Siena- - Varenne

  • 1 BR/1 BA Apartment (sleeps 4)
    $115 - $129/nt
    $718 - $790/wk
    per property, rural, village, garden, pool, pets considered

Gaiole in Chianti Villa LisiDor - Authentic Cottage with Private Pool and Tennis Court

  • 3 BR/2 BA, 1 half bath Villa (sleeps 8)
    $3,070 - $4,775/wk
    per property, rural, swimming pool, washing machine, tennis, tennis court

Torrita di Siena Unique Tuscan Castle Apartment with Wondrous views

  • 2 BR/2 BA Apartment (sleeps 4)
    $2,050/wk
    per property, rural, village, washing machine, internet access, stereo system

Chiusi Charming Tuscany Villa in Siena Area For Max 10 People

  • 5 BR/3 BA Villa (sleeps 10)
    $2,225 - $3,700/wk
    per property, rural, village, swimming pool, air-conditioning, washing machine

Gaiole in Chianti Magnificent villa in the heart of the Chianti region, Tuscany - L'Oliveta

  • 2 BR/1 BA Villa (sleeps 4)
    $575 - $1,580/wk
    per property, village, air-conditioning, garden, pool

Gaiole in Chianti Magnificent villa in the heart of the Chianti region, Tuscany - La Vigna

  • 2 BR/1 BA Villa (sleeps 4)
    $575 - $1,580/wk
    per property, village, garden, pool, pets considered

Montepulciano Large Apartment Beautifully Restored in Historical Sarteano, Tuscany

  • 2 BR/1 BA Apartment (sleeps 6) town, village, accept credit card, swimming pool, internet access

Radicondoli Come and enjoy the authentic Tuscan country life in stunning settings - 'Podere la Fonte'

  • 6 BR/5 BA Chateau / Country House (sleeps 12) rural, village, garden, pets not allowed
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