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Luxury rentals in Province of Siena

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Top-rated luxury vacation rentals in Province of Siena

Guests agree: these stays are highly rated for location, cleanliness, and more.

Luxe
Villa in Montalcino
Villa La Palazzetta
Wake up early to catch the morning sun as it hits the mist in Val d’Orcia, turning the entire valley gold. You’ll have quite the view from this 5-acre hilltop villa 7-minute’s walk from Montalcino’s center. When the mist settles, set out to explore the property’s private vineyard and olive grove. Then, walk into town for breakfast. And, make sure to pick up some Brunello di Montalcino for later.  Lovingly-restored, this 1600’s farmhouse has been updated with a state of the kitchen, in-floor heating and cooling, and the highest-end electronics and appliances. Staying true to its roots, Villa La Palazetta also boasts a private cantina and wine cellar, wood-burning pizza oven, and rustic fire pit. Dine outside amongst the mountain views. After dinner, issue a challenge on the night-lit bocce court.  Make that home-cooked meal extra-special and get the concierge to book an in-house Italian cooking lesson. The professional kitchen is the perfect place to learn how to hand-make pasta and combine fresh local produce. When the party inevitably moves to the terrace, cool off in the swimming pool, or sample the finest local wines around the alfresco dining set.  Rather dine out? Walk into Montalcino and wander within their historic city walls, where high-quality restaurants, bakeries, and gelato shops line the streets. Take a day trip to Siena and explore the museums, galleries, and churches of the ancient Renaissance city. And, wine tours of the World-famous Brunelle Vineyards are a great way to see all the different areas and landscapes of Val d’Orcia. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary : King size bed, Ensuite bathroom with stand-alone rain shower and bathtub, Safe • Bedroom 2: King size bed, Ensuite bathroom with stand-alone rain shower    • Bedroom 3: 2 Twin size beds, Ensuite bathroom with stand-alone rain shower, Safe • Bedroom 4: Double size bed, Ensuite bathroom with stand-alone rain shower, Safe   OUTDOOR FEATURES • Pergola  STAFF & SERVICES Included • Firewood for outside pizza oven  • Welcome gift • More under “What this place offers” below Extra cost (advance notice may be required): • Activities and excursions • Wine tasting  • Babysitting • Cooking classes  • More under “Add-on services” below
Feb 6 – 13, Professional Host
€ 3,064 per night
Luxe
Villa in Chiusdino
Quercia
Step outside each morning to feel the warm, fresh breeze as you stroll through fruit gardens and forests of oak at this traditional farmhouse estate in the heart of Tuscany. Embark on day trips to nearby villages, vineyards, and the famous Abbey of San Galgano. Return home for an afternoon swim, a delicious alfresco dinner, and a night of incredible Italian wine by the fireplace. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM Main House • Bedroom 1 - Primary: King size bed, Ensuite bathroom with shower/bathtub combo, Bidet • Bedroom 2: King size bed, Ensuite bathroom with stand-alone rain shower, Bidet, Balcony • Bedroom 3: 2 Twin size beds (can be converted to a king), Day bed, Ensuite bathroom with stand-alone rain & steam shower, Bidet House 2 • Bedroom 4: King size bed, Ensuite bathroom with shower/bathtub combo, Bidet, Walk-in closet, Sofa, Desk • Bedroom 5: King size bed, Shared access to hallway bathroom, shower/bathtub combo, Dual vanity, Bidet, Desk • Bedroom 6: 2 Twin size beds (can be converted to a king), Ensuite bathroom with stand-alone rain & steam shower, Bidet, Walk-in closet, Desk • Bedroom 7: 2 Twin size beds (can be converted to a king), Ensuite bathroom with stand-alone rain shower, Bidet, Walk-in closet OUTDOOR FEATURES • Outdoor living space STAFF & SERVICES Included: • Linen change - twice per week • Concierge service Extra Cost (advance notice may be required): • Activities and excursions • Additional housekeeping
Oct 14 – 21, Professional Host
€ 2,759 per night
Luxe
Villa in Volterra
Villa Finesterra
Preserving the historical character of the structure through an innovative approach: the design of Villa Volterra has been curated with the intention of creating the right balance between rustic and modern, tradition and design. The beating heart of the property is the living area, which is adorned by a panoramic glass wall with a spectacular view of the swimming pool that creates a seamless bridge to the garden.
Sep 21 – 28, Professional Host
€ 1,387 per night

Popular amenities for Province of Siena luxury vacation rentals

Other great luxury vacation rentals in Province of Siena

Luxe
Villa in Gaiole
Villa Rietine
Dec 21 – 28, Professional Host
€ 1,372 per night
Luxe
Villa in Sarteano
Villa Conti Galgani
Jul 27 – Aug 3, Professional Host
€ 2,691 per night
Luxe
Villa in San Martino a Bocena
Tenuta Pomona
Apr 27 – May 4, Professional Host
€ 562 per night
Luxe
Villa in Radicofani
Villa Poggio Fibbia
Jul 27 – Aug 3, Individual Host
€ 1,800 per night
Luxe
Villa in Montepulciano
Villa Benefizio
Aug 22 – 29, Professional Host
€ 3,390 per night
Luxe
Villa in Radicondoli
Villa Mugnello
Jan 17 – 24, Individual Host
€ 2,000 per night
Luxe
Villa in Tocchi
Villa Ferraia
Jan 29 – Feb 5, Professional Host
€ 4,583 per night
Luxe
Villa in Gaiole in Chianti
Le Pratola
Jan 24 – 31, Professional Host
€ 2,350 per night
Luxe
Villa in Sovicille
Villa Cetinale
Jan 29 – Feb 5, Professional Host
€ 4,500 per night
Luxe
Villa in Monteroni D'arbia
San Gerolamo
Feb 15 – 22, Professional Host
€ 5,304 per night
Luxe
Villa in Buonconvento
Villa Il Poggino
Feb 1 – 8, Professional Host
€ 3,000 per night
Luxe
Villa in Ribolla
Villa Marchesa
Nov 16 – 23, Professional Host
€ 2,340 per night

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Siena
  5. Luxury rentals