Vacation Rentals & Apartments in Siena

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144 apartments

Villa with Pool and Jacuzzi private Deal 2024

Siena villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 7

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Price per night from

$124

Castello di Montalto - 3 Bedroom Villa in Chianti

Siena villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$408

PALAZZO GIORGI Suite in Piazza del Campo, Siena

Siena apartment

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 4

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$456

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Price per night from

$1,541

Beautiful tuscan Villa not far from Siena 14+2pax

Siena villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 16

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Price per night from

$1,110

Tuscan/Siena Villa 22 pax Fenced Pool, Hot tub, WiFi,A/C, Outdoorkitchen

Siena villa

  • 11 bedrooms
  • 11 bathrooms
  • sleeps 22

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Price per night from

$1,134

“Perfect in every way!!!” What can I say….???We have already decided to book this Villa for next year…..one week is not enough, we will be back Villa "Le Caggia" was the setting for a fabulous vacation with our family. The location was perfect as we could take a number of day trips to explore Tuscany, from Florence(one hour driving) to Siena(20 minutes) and many other lovely towns in the Chianti or in the Orcia valley Waking up in the morning to see the fields spread below us was absolutely incredible, the Villa is spacious, very clean and decorated with care in every detail. A huge garden with a beautiful swimmingpool where you can relax while sipping a good Chianti wine, always cherished by the magical breeze(it is a Le Caggia trademark that you can only find here) ever-present and pleasant. Last but not least, Fabio e Jacopo were terrific hosts, always helping us, have made our stay more enjoyable and memorable…. Absolutely do not miss their welcome dinner and their cooking class….I already used their recipes to prepare a dinner and I have delighted all my friends, friends that will be with us for the second time at Le Caggia Absolutely the perfect place for those who want to enjoy Tuscany.

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Price per night from

$1,541

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Price per night from

$284

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Price per night from

$1,541

Cozy apartment in the heart of Siena

Siena apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$198

Charming apartment ideal for couple

Siena apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$93

Very nice apartment close to center of Siena

Siena apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$122

Lady Camollia Apartment

Siena apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$308

Great rentals within 20 miles that match your search

3 San Gimignano Luxury Leonardo Country House Il Castro

Pancole apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$369

4 San Gimignano Luxury Michelangelo Country House Il Castro

San Gimignano apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$615

5 San Gimignano Luxury Donatello Country House Il Castro

Pancole apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$369

San Gimignano Luxury Raffaello Country House Il Castro

San Gimignano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$369

Villa Prenzano, luxury villa, private pool, breathtaking views, sleeps 12.

Greve in Chianti villa

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 12

Responds fast! avg. 3 hours 49 minutes

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Price per night from

$1,217

Podere Bellaria 18+2, Emma Villas

Asciano villa

  • 9 bedrooms
  • 11 bathrooms
  • sleeps 20

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Price per night from

$1,113

Torre Vecchia Country House

Barberino Tavarnellle villa

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 10

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Price per night from

$884

Casa BD in Gaiole - 150 m² apartment with a view & travel guide - sleeps 8

Gaiole in Chianti villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$185

Stylish Luxury Loft Sleeps 4 San Gimignano Tuscany

San Gimignano apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

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Price per night from

$163

Casa Vacanze San Pierino - Il Pozzo

Monteroni d'Arbia apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 3

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Price per night from

$197

Tranquil Tuscan Barn Getaway in the Heart of Chianti

Greve in Chianti house

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

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Price per night from

$148

Stylish Tuscan Retreat in Lamole, Greve in Chianti

Greve in Chianti house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 8

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Price per night from

$234

Villa San Nazario 18+2, Emma Villas

Asciano villa

  • 9 bedrooms
  • 11 bathrooms
  • sleeps 20

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Price per night from

$1,664

Siena Entire Tuscan Property 20P Private pool A/C Hottub wifi OutdoorKitchen

Sovicille villa

  • 8 bedrooms
  • 7 bathrooms
  • sleeps 20

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Price per night from

$982

Casa Del Grifone , maison de vacance en Toscane

Casole d'Elsa house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 14

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Price per night from

$569

Anita , Holiday Home With Pool, Wifi, Colle Di Val D'elsa, Toscana

Mensanello villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$126

Nilde - Holiday Home With Pool, Wifi, Colle Di Val D'elsa, Toscana - Nilde

Mensanello villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$126

Anilde, Holiday Home With Pool, Wifi, Colle Di Val D'elsa , Tuscany

Mensanello villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$250

Nice appartement for 2 ppl. with shared pool at Trequanda

Trequanda studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 50 minutes

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Price per night from

$199

Villa Rinaldi 6

Toiano villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$355

Scandelaia 12, Emma Villas

Castelnuovo Berardenga villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

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Price per night from

$2,063

Mulino nel Chianti 10, Emma Villas

Gaiole in Chianti villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$682

Country House Girasole Crete Senesi Vakantie Huis

Asciano apartment

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$514

Pieve di Campoli by Vacavilla

Barberino Tavarnelle villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$193

Villino Aurora

Monte San Savino villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$256

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