Luxury rentals in Siena

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Top-rated luxury vacation rentals in Siena

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Luxe

Villa in Radicofani

5 out of 5 average rating, 11 reviews

Villa Poggio Fibbia

Steep yourself in Tuscan history, culture and cuisine at Villa Poggio Fibbia. This beautifully renovated farmhouse is just a half-mile from the fortress at Radicofani, in a medieval village that garnered mentions in both Dante’s Divine Comedy and Boccaccio’s Decameron. Today, this vacation rental features a lovingly curated mix of traditional and modern decor and five bedrooms—the perfect Val d’Orcia escape for groups of up to ten friends or family members. Look out over the hills of Tuscany or up to the fortress tower from outdoor living areas with an infinity pool, loungers and a barbecue. During the hottest parts of the day, retreat to the shade of the al-fresco sitting and dining areas; in the evenings, relax inside by the flat-screen TVs, Wi-Fi and fireplace. Though it still has the architectural charm of the region’s traditional homes, Villa Poggio Fibbia is a modern masterpiece inside. Its beamed ceilings and stone floors are juxtaposed with sleek furnishings in the living and dining rooms, as well as playful details like orange fabric or a trompe-l’oeil wall painting. The fully equipped kitchen is equally stylish and functional, too. This luxury property has two bedrooms with king beds, a primary bedroom with a double bed, and one bedroom with two twin beds. The fifth bedroom, ideal for families on holiday with children, has a French queen bed and a twin bed. All five bedrooms have private en-suite bathrooms. Spend your stay simply enjoying the villa or exploring the area. It’s well worth the climb to the Radicofani fortress for both the views and the history, not to mention the 15-minute walk to the nearest village, where you can stop for a drink in one of the bars or sit down to a honeymoon-worthy dinner in one of the restaurants. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: Double size bed, Walk-in closet, Ensuite bathroom with stand-alone shower with chromotherapy & bathtub with hand-held shower • Bedroom 2: French Queen bed, 1 twine size bed, Ensuite bathroom with stand-alone shower with chromotherapy • Bedroom 3: King size bed, Ensuite bathroom with combo shower/bathtub, Balcony • Bedroom 4: 2 Twin size bed (can be converted into a double bed), Ensuite bathroom with stand-alone shower with chromotherapy • Bedroom 5: King size bed, Ensuite bathroom with combo shower/bathtub FEATURES & AMENITIES • Alarm system OUTDOOR FEATURES • Lounge area STAFF & SERVICES Included: • One four course dinner or one cooking class included in the price. The specific day to be agreed • Linen change - every Saturday • Light housekeeping - every Wednesday (2 hrs per day) • Towel change - every Wednesday and Saturday • Air conditioning consumption • Heating consumption At Extra Cost – advance notice may be required: •Chef and cooking classes •Van with driver for airport transfer or any other need • Activities and excursions • Additional housekeeping (40 euros/hour) (Advance notice required)

Luxe

Villa in Sarteano

4.82 out of 5 average rating, 11 reviews

Villa Conti Galgani

Located in the heart of the Tuscan countryside, between Florence and Rome, just 70km from Siena, Villa Conti Galgani is a charming estate, immersed in 65 hectares of hilly countryside, among olive groves and gardens. The villa has 7 suites, each characterized by an individual style, inspired by the rich history of the estate. Conti Galgani is the perfect place for those who want to spend a relaxing holiday in the Tuscan countryside, equipped with an outdoor swimming pool, a gym, an indoor hydro-massage pool and a billiard room. Handcrafted furniture and a modern eye for color breathe new life into this 16th-century former convent set between Tuscany’s Val di Chiana and Val d’Orcia. Olive groves and a lawn surround the outdoor pool and for-the-picking vegetable garden, and inside there’s a second pool and a games room. It’s 20 kilometers to Renaissance architecture in Pienza and hot springs in San Casciano dei Bagni. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone rain shower, Dual vanity, Bidet, Television, Countryside view • Bedroom 2: King size bed, Ensuite bathroom with stand-alone rain shower, Bidet, Air extractor, Countryside view • Bedroom 3: King size bed, Ensuite bathroom with stand-alone rain shower & bathtub, Dual vanity, Bidet, Countryside view • Bedroom 4: Queen size bed, Ensuite bathroom with stand-alone rain shower, Bidet • Bedroom 5: 2 Twin size beds, Ensuite bathroom with stand-alone rain shower, Bidet, Air extractor, Television • Bedroom 6: King size bed, Day bed, Ensuite bathroom with stand-alone rain shower & bathtub, Bidet, Air extractor, Television, Mountain view • Bedroom 7: Queen size bed, Ensuite bathroom with stand-alone rain shower, Bidet STAFF & SERVICES Extra Cost (advance notice may be required): • Activities and excursions

Luxe

Villa in Radicofani

Beautiful modern villa with pool in Val D'Orcia

Nestled into the rolling hillside of Tuscany, this luxurious farmhouse enjoys sweeping views decorated with emerald lawns, lush gardens, and mature trees. With 17 beds, this spacious estate is perfect for large gatherings. Spend your days shooting pool, swimming, and playing tennis on the grass court. Inside, gorgeous architecture and high-end finishings await. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary:Double size bed, Ensuite bathroom with stand-alone shower • Bedroom 2: Double size bed, Ensuite bathroom with stand-alone shower & bathtub • Bedroom 3: Double size bed, Ensuite bathroom with stand-alone shower & bathtub • Bedroom 4: Double size bed, Ensuite bathroom with stand-alone shower & bathtub • Bedroom 5: 2 Twin size beds (can be converted to a double bed ) Ensuite bathroom with stand-alone shower • Bedroom 6: 2 Twin size beds (can be converted to a double bed , Ensuite bathroom with stand-alone shower • Bedroom 7: Double size bed, Ensuite bathroom with stand-alone shower • Bedroom 8: Double size bed, Ensuite bathroom with stand-alone shower • Bedroom 9: Double size bed, Ensuite bathroom with stand-alone shower FEATURES & AMENITIES • Home theater STAFF & SERVICES Extra Cost (advance notice may be required): • Activities and excursions

Luxe

Villa in San Quirico d'Orcia

Tenuta Val D’Orcia

EXCLUSIVE VAL D’ORCIA Perched on a hilltop with breathtaking views over the Val d’Orcia, this extraordinary luxury villa—featured in the renowned interior design magazine AD (Architectural Digest)—is the perfect blend of tradition and modernity. Nestled in one of Tuscany’s most iconic areas, known for its rolling hills and postcard-perfect landscapes, the property offers an exclusive retreat for those seeking privacy, relaxation, and an authentic experience in a refined, one-of-a-kind setting.

Luxe

Villa in Radda in Chianti

4.89 out of 5 average rating, 18 reviews

Villa Montemaggio

This booking is a chance to stay in a real Tuscan Farmhouse that is situated inside an actual vineyard. Its a private property of the owners of the estate, completely refurbished to give every possible comfort but still live in the middle of nature. The setting is absolutely breathtaking amongst the rolling tuscan hills, far away from the noise of the concrete jungle and busy streets. Here the only noise you will hear is the chirping of the birds or faraway hum of the tractor in the fields.

Luxe

Villa in Cetona

5 out of 5 average rating, 25 reviews

Luxury Villa Tuscany

An exclusive estate set on 30 private acres of vineyards and olive groves—ideal for luxury travelers and families seeking serenity and style. The villa combines designer Italian furnishings, curated contemporary art, and timeless antiques. Recently transformed into a private residence, it offers five-star comfort with new premium bedding, linens, and kitchenware. Services are designed to meet the highest standards, including cleaning and options to add private cook or chef.

Luxe

Villa in Montepulciano

5 out of 5 average rating, 7 reviews

Villa Benefizio

Villa Benefizio offers a charming, elegant, and exclusive retreat 3 km from Montepulciano's historic center. Guests can relax or work in six stylish rooms with modern facilities and panoramic views. The villa, built around an 18th-century Renaissance guard tower, features a restored structure integrated with modern furnishings. Products from the farm are used in the Villa’s restaurants. Wi-Fi and satellite TV are available in each room.

Luxe

Villa in Volterra

5 out of 5 average rating, 8 reviews

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.

Luxe

Villa in San Gimignano

5 out of 5 average rating, 4 reviews

Villa Sarah Tenuta Melograni

Villa Sarah enjoys spectacular views of the famous towers of San Gimignano. A large garden surrounds the entire structure and also the four-sided infinity pool with spa whirlpool, made with valuable stone of Cardoso, renowned local stone. Next to the swimming pool is a big dependance with large panoramic terrace, equipped outdoor kitchen, bbq, bar area, relaxation area and a large table to enjoy outdoor dining.