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House holiday rentals in Siena

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Top-rated house rentals in Siena

Guests agree: These houses are highly rated for location, cleanliness and more.

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Home in Sarteano

4.94 out of 5 average rating, 97 reviews

Wonderful Cozy House in Tuscany with AC and Patio

House is located in the Valdichiana Region of Tuscany.. Villa has been renovated and updated with comfortable furniture. House has Air-conditioning, WIFI, beautiful LR, Kitchen, Bathroom, and bedroom.. It has its own private entrance and private patio with dining table, chairs, and a comfortable seating area There are two houses on this property. One is the small house we rent to guests and the other is another villa that my husband and I live in. The house is a few feet from the rental house.

Guest favourite

Home in Cortona

4.9 out of 5 average rating, 79 reviews

Cortona historical centre. Great views and WiFi

Charming apartment on the top floor of a Tuscan mansion house with traditional floor and exposed timber beams. The apartment is located in the heart of Cortona and it has triple exposure, so it is flooded with light and it boasts a stunning view over the valley and the Trasimene lake. Self check-in available. PARKING on the street is available. NO AIR CONDITIONING! This is an environmentally friendly choice. I welcome guests of all backgrounds, faiths, genders, ages and sexual orientations

Home in Pratolino

5 out of 5 average rating, 5 reviews

casa nat 20mins from Florence

Casa di Nat offers a unique experience immersed in nature but a few minutes from the center of Florence, a unique vacation for those who want to relax and have fun with friends and family, suitable for adults and children, with its outdoor space it will be possible to involve everyone in lunches or dinners, with barbecues and deck chairs, the covered porch will allow you to eat outdoors even in the colder months, to facilitate travel there is free parking on the street and bus stop nearby.

Guest favourite

Home in San Casciano in Val di pesa

4.83 out of 5 average rating, 86 reviews

Tuscan Villa Featured Conde Nast Best Villas Italy

Step under archways into a home where the original wood ceilings and tiled floors showcase Tuscan style. Enjoy delicious meals on the terrace with sweeping views of Tuscany, winters curled up in front of a huge fire place or relaxing on warm summer days by the pool. Savour the best of Tuscan food and wine with cooking classes with a Michelin chef, master classes in wine and visits to local artisan cheese and wine makers. Listed by Condé Nast as one of the most beautiful villas in Italy.

Home in Cortona

5 out of 5 average rating, 11 reviews

Casa delle Rose

Charming Independent House with stunning balcony in the Heart of Cortona; Stunning Balcony View: Enjoy your morning coffee or unwind with a glass of wine as you soak in the enchanting sights of the city. 2 Double Bedrooms: Experience comfort and tranquility in a beautifully appointed master bedroom. 2 Bathrooms: Enjoy the convenience of well-equipped bathrooms, designed for your utmost comfort. Wi-Fi: Stay connected with high-speed internet access, ensuring you can effortlessly share

Guest favourite

Home in Prato

4.98 out of 5 average rating, 125 reviews

Tofanello Orange Luxury and Modern Comfort with Outdoor Pool

Escape to the rolling hills of Umbria in this updated farmhouse (90 m2 over 2 floors) that retains its original charm. The home features classic beamed vaulted ceilings, original stone finishes, an indoor wood-burning fireplace, private entrance and a private garden terrace. The pool has a large sun lounge area. If your favourite dates aren't available anymore take a look at our turquoise apartment, there might still be availability. Turquoise: https://www.airbnb.com/rooms/plus/9430389

Guest favourite

Home in Terranuova Bracciolini

4.96 out of 5 average rating, 24 reviews

Casa Canto alla Luna Pool WiFi Orto & Garden

In the center of a small historic village, surrounded by nature and hills. From here, right in front of our houses, the peasants once passed by singing the May song, thus welcoming the arrival of spring. Our vegetable garden is located just above the ancient village, here every season works its magic, we grow the plants and vegetables that we use to prepare the dishes for our cooking classes. Welcome, warmth and comfort are the ingredients of our hospitality.

Guest favourite

Home in Castelmuzio

4.97 out of 5 average rating, 32 reviews

Casa Ora d"Oro - Panoramic Views

Our villa is nestled in the rolling hills of Tuscany, located in the Val d’Orcia and Crete Senesi region. Located in the Borgo, “Podere Pascianella,” this quiet villa is perched up on a hilltop overlooking Montisi and within walking distance of the medieval village of Castelmuzio. This villa offers stunning and panoramic views of the Tuscan countryside, including the UNESCO World Heritage site of Val d’Orcia, which provides picturesque sunrises and sunsets.

Home in Cerretti

4.86 out of 5 average rating, 7 reviews

Guest House Podere Cerbaie,in the heart of Tuscany

The Guest house Podere Cerbaie is near to the cities' s art, the beach and thermal place. Here the countryside is amazing and full of beautiful views. In the little Town of Cerretti there are a supermarket with local food and a Bar where you can drink something and eat Pizza like a local inhabitant. The house is perfect for families or couples. Here you can relax and enjoy drinking a glass of Red Wine looking at the beautiful views.

Guest favourite

Home in Certaldo (Fi)

4.87 out of 5 average rating, 60 reviews

Paluffo Torre House

This is the antic tower of the villa and it is built on three levels and features a private garden and a marvellous view of the Chianti hills and San Gimignano. • Ground-floor: living room with a fireplace, bathroom and dining room with kitchen. • First floor: double bedroom with private bathroom and studio with sofa bed. • Second floor: 2 double bedrooms with bathroom.

Guest favourite

Home in Chianni

4.89 out of 5 average rating, 45 reviews

Three bedroom historical house with the best views

Newly renovated and furnished Tuscan home in Chianni, Italy. There are two units, an upstairs apartment with a chef's kitchen, two bedrooms, a bathroom, a dining hall, and living room. The studio unit below has a bedroom, kitchenette and full bathroom. Guests receive a welcome package with a bottle of wine, water, and a free wine-tasting ticket at Castelvecchio.

Holiday rentals for every style

Get the amount of space that is right for you

Villas

Luxurious estates for the ultimate escape

Apartments

Convenient locations with everyday essentials

Hotels

Stylish accommodation and amenities

Popular amenities for Siena house rentals

Free parking on premises

Air conditioning

House rentals with a pool

Home in Montespertoli

4.84 out of 5 average rating, 69 reviews

Holiday immersed in the Tuscan countryside 'Canaiolo'

Guest favourite

Home in Firenze

5 out of 5 average rating, 8 reviews

La Torretta Luxury Private Pool

Home in Poppi

4.75 out of 5 average rating, 4 reviews

Villa for 22 people w/private pool

Home in Caccialupi

5 out of 5 average rating, 4 reviews

Country house with pool

Guest favourite

Home in Pistoia

5 out of 5 average rating, 8 reviews

Countryside Cottage with Pool "Il Melograno"

Guest favourite

Home in Lecchi in Chianti

4.96 out of 5 average rating, 135 reviews

Casa di Lyndall - Entire house with exclusive pool

Guest favourite

Home in Campagnatico

5 out of 5 average rating, 5 reviews

Beautiful bright villa with view/ Casa Luca

Guest favourite

Home in Casanova

4.89 out of 5 average rating, 36 reviews

Casa Liliana

Weekly house rentals

Guest favourite

Home in Palazzone

4.92 out of 5 average rating, 36 reviews

Logge Vecchie, a Tuscan holiday

Home in Matraia

4.78 out of 5 average rating, 9 reviews

The stone dwelling

Guest favourite

Home in Greve in Chianti

4.88 out of 5 average rating, 113 reviews

La Meridiana in Montefioralle

Guest favourite

Home in Asciano

4.96 out of 5 average rating, 45 reviews

Tuscan farmhouse near Siena + Cortona, heated pool

Guest favourite

Home in Montebenichi

4.87 out of 5 average rating, 15 reviews

Colombaio di Montebenichi

Guest favourite

Home in Impruneta

4.84 out of 5 average rating, 68 reviews

Independent house with private pool and garden

Guest favourite

Home in Castiglione del lago

5 out of 5 average rating, 24 reviews

Bliss out in Historic Farmhouse on Organic Wine Estate with Tennis and Pool

Home in Montaione

5 out of 5 average rating, 5 reviews

Farmhouse in Tuscany - Il Glicine

Private house rentals

Home in Civitella in Val di Chiana

4.77 out of 5 average rating, 35 reviews

Casa Guardiano - Tuscan countryside house

Home in Siena

4.78 out of 5 average rating, 782 reviews

Little heaven on the hills

Guest favourite

Home in San Martino

4.95 out of 5 average rating, 197 reviews

Casa Bada - Barn

Home in Radda in Chianti SI

5 out of 5 average rating, 9 reviews

Le Bonatte by Interhome

Home in Campiglia Marittima

4.75 out of 5 average rating, 4 reviews

Villa delle Stelle by Interhome

Guest favourite

Home in Castiglion Fiorentino

5 out of 5 average rating, 16 reviews

Volpe by Interhome

Guest favourite

Home in Torricchio

5 out of 5 average rating, 17 reviews

Dependance Petri - with Jacuzzi

Guest favourite

Home in Roccastrada

4.92 out of 5 average rating, 13 reviews

Casa la Selvolina by Interhome

Quick stats about house rentals in Siena

Total rentals
110 properties
Total number of reviews
7.2K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
50 properties have a dedicated workspace

Destinations to explore