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Holiday home rentals in Siena

Find and book unique holiday home rentals on Airbnb

Top-rated holiday home rentals in Siena

Guests agree: these holiday home rentals are highly rated for location, cleanliness and more.

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Holiday home in Poggibonsi

4.91 out of 5 average rating, 43 reviews

Il Casale di Villore, Poggibonsi, Siena, Tuscany , Cardisco Apt.

Thanks to a careful restructuring, the Casale di Villorehas remained intact over time. The interior design and rustic exterior combine in perfect harmony with the surrounding countryside. Looking from the windows of the old tower it is clear how the panorama is as it was in the past and the spirit of "old" Tuscanyis still there waiting for it to be rediscovered by anyone who spends a holiday period at the Casale. The village is divided into six apartments of different sizes but can also be rented as a private villa in its entirety.If rented separately, each apartment will have its own entrance, bedrooms, bathrooms, and private kitchen and customers will only share the outdoor spaces, including the swimming pool, with the other guests. While, rented as a villa, customers will have the opportunity to enjoy the entire property privately and fully enjoy a holiday of relaxation and total independence. In this case the Sangioveto, Prugnolo, Cardisco and Morellino apartments will be unified with each other (with internal doors) and the entire farmhouse can accommodate up to 16 people. All the apartments, and therefore the villa, have been furnished with great care by the owner, combining the old family furniture with original pieces of modern furniture. Cardisco, casually furnished in comfortable Tuscan style, is located on the first floor of the villa complex. The apartment includes two double bedrooms, with beds in wrought iron, a bathroom with shower, kitchen and living room. Spacious garden (more than 3000 s. meters) at disposal for all the guests with tables, chairs and a BBQ.

8–15 Nov

$187 SGD per night

Guest favourite

Holiday home in Florence

4.89 out of 5 average rating, 633 reviews

charming studio ponte vecchio/ lift

Quite and luminous studio to sleep 2, located on the left side of the river arno, only at 30 yards/meters from ponte vecchio. The studio is on the third floor with lift and has a living room with parquet floor and a real double sized bed, bathroom with shower and fully equipped kitchenette. the double glaze window is overlooking the main street and the bathroom window has mosquito net . it is also provided of air conditioning/heating, Wi-Fi connection and tv wall mount for all your conforts.

28 Jan – 4 Feb

$162 SGD per night

Guest favourite

Holiday home in Sovicille

4.8 out of 5 average rating, 20 reviews

Holiday house Claudia / 10 min from Siena

The apartment is in a renovated farmhouse, surrounded by the Sienese countryside, just 12 km from Siena, and in the vicinity of other cultural sites such as Monteriggioni, San Gimignano and San Galgano. The entrance and the kitchen are for the exclusive service of the apartment, a large garden , free parking spaces and Wi-Fi. The apartment has heating and a fireplace . Upon reservation, we offer the opportunity to have a cook at home who prepares you lunch or dinner with a menu of your choice.

21–28 Jul

$175 SGD per night

Guest favourite

Holiday home in Poggibonsi

4.95 out of 5 average rating, 110 reviews

Vittoria Chianti Vacations 🍇🍷

Vittoria Chianti Vacations is the ideal solution for those seeking peace and tranquility in the heart of Chianti, close to all comforts. Typical Tuscan farmhouse halfway between Florence and Siena, is located in a strategic position to quickly reach Florence, Siena, San Gimignano, Monteriggioni, Volterra and the Chianti hills. Siena Eye Laser Clinic 2 min. Private parking, two bedrooms, equipped kitchen, private bathroom, Wi-Fi, private garden, barbecue, a wonderful view of the Chianti hills.

4–11 Jan

$153 SGD per night

Holiday home in Impruneta

4.87 out of 5 average rating, 190 reviews

Lovely house with fabulous view....

Typical Tuscan farmhouse with splendid views of the Chianti, suitable for 2 people. The house is furnished in Tuscan style being a former barn, has been recently renovated and is 70 square meters. Double bedroom with bathroom, large living room with sofa and nice mezzanine, kitchen equipped with stove, refrigerator, etc. Customers are requested to come by car. If you want the heating is paid and according to consumption and can only be switched on from the period established by the region.

8–15 Dec

$127 SGD per night

Guest favourite

Holiday home in Florence

4.96 out of 5 average rating, 339 reviews

Breathtaking view from romantic nest in citycenter

Unique and charming attic in the middle of historic center with amazing breathtaking view on the city center. Perfect for a romantic stay in the heart of Florence. Fully windowed on 3/4 walls. Completely renewed with modern design furniture. Powerful A/C, fast wi-fi, fully equipped kitchen. Going downstairs you will immediately be absorbed in the most beautiful area of city center. Attention! Only for young-soul people: 5th FLOOR, NO LIFT, last 2 flights of stairs in a narrow spiral stair.

1–8 Nov

$406 SGD per night

Guest favourite

Holiday home in Barberino Tavarnelle (Fi)

5.0 out of 5 average rating, 58 reviews

Chianti Craft House Badia a Passignano

Ancient house in the historic village of Badia a Passignano, completely and finely restored in 2022. The house is located exactly in the center of the village of Badia a Passignano, overlooking the abbey castle and the Chianti vineyards. The house consists of 2 bedrooms air-conditioned: 1 double bedroom with service bathroom and 1 with 2 single beds and the possibility of a third with sofa chair; a full bathroom with shower, a full kitchen with washing machine and dishwasher, dining area

22–29 Nov

$254 SGD per night

Guest favourite

Holiday home in Porto

4.96 out of 5 average rating, 105 reviews

La Dimora del Lago - Lake views Tuscany and Umbria

Recently and authentically restored in a small rural hamlet, located halfway between Florence and Rome and Montepulciano and Cortona in the tranquil countryside overlooking tiny Lake Chiusi - less than 2 hours drive by Autostrada or train from Florence or Rome. Forged from a 500-year-old watchtower, an authentic country house - tranquil and relaxing, it also has an excellent internet connection and Netflix. PLEASE NOTE - €75 CLEANING AND TOURIST TAX TO PAY IN CASH ONCE HERE. .

12–19 Apr

$206 SGD per night

Guest favourite

Holiday home in Casole d'Elsa (SI)

4.92 out of 5 average rating, 175 reviews

Off the beaten path Tuscan Farmhouse, great views

Away from it all in the heart of Tuscany, Agriturismo Timignano is a beautiful farmhouse surrounded by stunning unspoilt countryside. Perfect for couples and older families to relax, recharge or work remotely, the apartment has a private entrance and garden with outdoor seating area and a private rooftop balcony - stunning views, fantastic sunsets and big night skies. There are two other independent apartments on the olive farm that share the pool and private parking.

15–22 Nov

$196 SGD per night

Guest favourite

Holiday home in Cortona

4.95 out of 5 average rating, 202 reviews

La casina sulle Mura (with garden and spa jacuzzi)

La Casina è situata nella parte alta di Cortona, nella zona denominata "il Poggio". Si puo' giungere in auto fino al suo ingresso. Il Centro citta' e' raggiungibile a piedi in pochi minuti, percorrendo strade e vicoli caratteristici. Gode di una splendida vista su Cortona e la Valdichiana. E' facile parcheggiare nelle vicinanze. Gli ospiti che giungono in treno in una delle stazioni vicine, su richiesta, possono essere prelevati e accompagnati a destinazione.

21–28 Nov

$153 SGD per night

Guest favourite

Holiday home in Siena

4.88 out of 5 average rating, 16 reviews

The Pearl among Olives

The pearl among olive trees was an ancient hut, now completely renovated, which was part of an ancient farm. It is located in a private property right in front of the old city walls and is completely independent. It has a private residence and free parking. It is in a privileged location, surrounded by greenery. You can enjoy relaxation and tranquility, immersed in the countryside among olive trees, and at the same time walk to the city center in 10 min.

22–29 Jan

$170 SGD per night

Guest favourite

Holiday home in Dimezzano

4.88 out of 5 average rating, 264 reviews

Authentic StoneHouse & ViewPool

Authentic, quiet and cozy entire Stonehouse situated in a medieval small village, with stunning view pool on the top of the garden overlooking hills and vineyards, wide garden, many resting areas, stone-bbq and Pizza oven. Few Km away from Greve in Chianti, about 30 minutes from Florence and Arezzo, 45 minutes from the horse-ride city of Siena. Typical tuscany restaurant and wineries within 5 minutes by car.

15–22 Feb

$211 SGD per night

Holiday rentals for every style

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Popular amenities for holiday home rentals in Siena

Free parking on premises

Air conditioning

Family-friendly holiday home rentals

Guest favourite

Holiday home in Florence

4.82 out of 5 average rating, 755 reviews

Visitflorentiapartment - Borgo La Croce Suite

30 Jul – 6 Aug

$161 SGD per night

Guest favourite

Holiday home in San Casciano in Val di Pesa

4.83 out of 5 average rating, 201 reviews

lovely farm- apartment (Fox)

3–10 Nov

$177 SGD per night

Guest favourite

Holiday home in Pistoia

4.89 out of 5 average rating, 106 reviews

CountryAl, Stay in the green at my house.

12–19 Apr

$96 SGD per night

Guest favourite

Holiday home in Florence

4.83 out of 5 average rating, 289 reviews

La Gabbia del Grillo <Anna Maria> (A-04)

3–10 Aug

$455 SGD per night

Holiday home in Florence

4.9 out of 5 average rating, 278 reviews

Ciardo-Cozy house in the heart of Florence

12–19 Oct

$375 SGD per night

Guest favourite

Holiday home in Cortona

4.88 out of 5 average rating, 240 reviews

Wonderful Casa Idilio Cortona

15–22 Jan

$80 SGD per night

Guest favourite

Holiday home in Sesto Fiorentino (FI)

4.86 out of 5 average rating, 259 reviews

Pretty Apt in Tuscan style Firenze Sesto Fioreno

18–25 Oct

$149 SGD per night

Guest favourite

Holiday home in Montespertoli

4.95 out of 5 average rating, 127 reviews

Tuscan Orchard

8–15 Sep

$205 SGD per night

Holiday home rentals with a patio

Guest favourite

Holiday home in Bagno a Ripoli

4.87 out of 5 average rating, 124 reviews

I Rosai apartment on the Florentine hills

20–27 Dec

$130 SGD per night

Guest favourite

Holiday home in Rosennano

5.0 out of 5 average rating, 32 reviews

HOUSE ABOVE THE CHIANTI. WITH GARDEN AND POOL

11–18 Mar

$248 SGD per night

Guest favourite

Holiday home in Lucca

5.0 out of 5 average rating, 16 reviews

Penthouse with terrace and panoramic view of the city

6–13 Nov

$273 SGD per night

Guest favourite

Holiday home in Cantagallina

5.0 out of 5 average rating, 27 reviews

Il Gelsomino, apartment between Tuscany and Umbria

8–15 Oct

$196 SGD per night

Guest favourite

Holiday home in Chianni

5.0 out of 5 average rating, 25 reviews

Casa Serena - one bedroom with parking and garden

4–11 Apr

$132 SGD per night

Guest favourite

Holiday home in Greve in Chianti

4.9 out of 5 average rating, 30 reviews

Casa Canaiolo with mini-pool in the centre of Greve

31 Oct – 7 Nov

$310 SGD per night

Guest favourite

Holiday home in Poggibonsi

5.0 out of 5 average rating, 25 reviews

Ellerone 20, an ancient barn in Chianti

9–16 Apr

$269 SGD per night

Guest favourite

Holiday home in Orvieto

5.0 out of 5 average rating, 56 reviews

Casa Isla, near Orvieto, amazing views + pool

25 Oct – 1 Nov

$186 SGD per night

Holiday home rentals with a washing machine and dryer

Guest favourite

Holiday home in Florence

4.92 out of 5 average rating, 190 reviews

Melarancio Residence

3–10 Nov

$324 SGD per night

Guest favourite

Holiday home in Florence

4.95 out of 5 average rating, 133 reviews

TOSCANELLA LOFTED ROOM MADREPERLA

5–12 Oct

$275 SGD per night

Guest favourite

Holiday home in Pistoia

4.99 out of 5 average rating, 111 reviews

Podere Shower Vacation Rental

26 Nov – 3 Dec

$306 SGD per night

Guest favourite

Holiday home in Poggibonsi

5.0 out of 5 average rating, 11 reviews

App.Cavallo - Megognano,2/A

1–8 Dec

$204 SGD per night

Guest favourite

Holiday home in Serravalle Pistoiese

5.0 out of 5 average rating, 32 reviews

La Terrazza @ Casa d'Olival - Stunning sunsets

25 Jun – 2 Jul

$377 SGD per night

Guest favourite

Holiday home in Passignano sul Trasimeno

5.0 out of 5 average rating, 5 reviews

Antico Casale Tiravento - Apartment with balcony

18–25 Sep

$163 SGD per night

Guest favourite

Holiday home in Lucca

4.73 out of 5 average rating, 131 reviews

Apartment in Lucca Walls

5–12 Aug

$170 SGD per night

Guest favourite

Holiday home in Chianciano Terme

4.93 out of 5 average rating, 57 reviews

Cottage in Val d'Orcia, Jacuzzi, Hot tub with view

29 Nov – 6 Dec

$307 SGD per night

Destinations to explore