50 Best Siena Apartments on Holiday Lettings - Villas

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Costalpino
10 properties
Isola d'Arbia
6 properties
Val di Merse
6 properties
Caprera
5 properties

Siena

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4,299 Vacation rentals

(5) Excellent 

18

Apartment rental in Siena with shared pool

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 95 mi
  • Swimming pool
  • Child friendly
Podere Incrociati rises in the heart of Montagnola Senese, just 15 km/9 miles far from Siena and 75 km/47,5 miles far from Florence, among the greenery of age-old oaks, holm-oaks and chestnut-trees. Thanks to its high position (500 mt./1640 ft. above sea level) you will …see more

from $111 / night

$737 - $1,351 / week

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from $111 / night

(1) Excellent 

22

Siena Vacation apartment rental

Province of Siena / Siena

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Nearest beach 80 mi
  • Child friendly
  • Car not necessary
Prestigious house in the medieval heart of Siena. A beautiful house in the center of Siena, where to be pampered in the beauty of a unique city. Step into a historical building in Siena - a short walk from Piazza del Campo - and treat yourself to your holiday in a charm …see more

from $221 / night

$1,548 / week

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Responds fast!
avg. 2 hours 55 minutes

from $221 / night

22

Vacation farmhouse with shared pool in Isola d'Arbia

Siena / Isola d'Arbia

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
Podere Vesta is a small hamlet consisting of 4 adjacent buildings, where are located the apartments and common areas. For nature lovers, look out every window offers an incomparable view, by the landscapes of the Val d'Orcia, the Crete Senesi glimpse of Siena to the vie …see more

from $155 / night

$576 / week

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Responds fast!
avg. 3 hours 12 minutes

from $155 / night

(12) Excellent 

17

Siena Vacation home rental

Province of Siena / Siena

2 3 3 nights min

  • 2 bedrooms
  • Sleeps 3
  • 3 nights min
  • Nearest beach 95 mi
  • Child friendly
  • Pet friendly
The "Stalla di San Lazzero", adorable country house a few steps from Siena center, is the perfect starting point to discover Tuscany! The house is spacious with high ceilings, large windows, a lovely garden and a beautiful view of the countryside. One large queen sized …see more

from $105 / night

$731 / week

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from $105 / night

(1) Very Good 

19

Vacation apartment in Isola d'Arbia

Siena / Isola d'Arbia

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Pet friendly
Delicious partment placed in a texturized vintage building protected by the Italian cultural heritage, situated in a medieval village, a few minutes from the center città.Restrutturato in rustic style, with a strong romantic note. The apartment consists of two bedrooms, …see more

from $62 / night

$369 / week

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Responds fast!
avg. 2 hours 54 minutes

from $62 / night

14

Vacation villa with swimming pool in Siena

Province of Siena / Siena

5 9 Min stay varies

  • 5 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Large living room with sitting area and fireplace. Kitchen with dining area. 5 bedrooms: 1 with two single beds. 3 with a double bed. 1 with double singolo.In total 3 Full Bathrooms: 2 bathrooms with shower and toilet, a bathroom with Jacuzzi tub and toilet. Washing mac …see more

from $197 / night

$1,376 / week

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from $197 / night

(8) Excellent 

56

Vacation guest house in Siena

Province of Siena / Siena

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 60 mi
  • Child friendly
  • Air conditioning
One of the original, charming and elegant garden pavilions, situated within the garden of Villa di Geggiano, has recently been renovated into two luxury suites which have now been opened to guests for reservation. The Pavilion has a total capacity of 4 persons but it …see more

from $553 / night

$3,378 / week

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from $553 / night

(7) Excellent 

Certificate of Excellence

30

Vacation guest house in Siena

Province of Siena / Siena

2 4 6 nights min

  • 2 bedrooms
  • Sleeps 4
  • 6 nights min
  • Nearest beach 100 mi
  • Child friendly
  • Private garden
★My Cozy Country House is part of a hamlet about 20km from Siena and central to Chianti, San Gimignano, Florence, Montalcino&Montepulciano. It's located in a forest on top of a hill in the heart of Tuscany. Peaceful and quiet area. Patio&Garden. Perfect for hiking&bikin …see more

Certificate of Excellence

from $74 / night

$492 - $725 / week

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avg. 2 hours 28 minutes

from $74 / night

(8) Excellent 

24

Farmhouse rental in Caprera

Siena / Caprera

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 100 mi
  • Child friendly
  • Air conditioning
A stylish apartment close to Siena ancient city walls, still surrounded by olive groves and fields; ideal for visitors looking for a quite lodge. The farmhouse is part of a unique Liberty village built by Garibaldi's doctor in 1880. Local shops are at walking distance. …see more

from $197 / night

$1,228 - $1,695 / week

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from $197 / night

(8) Excellent 

Certificate of Excellence

31

Vacation villa in Costalpino

Siena / Costalpino

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Private garden
This beautifully renovated rustic villa is only 10 minutes' drive from the heart of Siena. Built in the 1500's, Belvedere (beautiful view) is situated on a remote hilltop with breathtaking views of the Tuscan countryside with vineyards and olive trees in the immediate v …see more

Certificate of Excellence

from $277 / night

$1,965 / week

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Responds fast!
avg. 3 hours 45 minutes

from $277 / night

(4) Excellent 

39

Vacation villa with swimming pool in Siena

Province of Siena / Siena

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
Key points: large apartment (140 m2) in a farmhouse renovated with taste and attention to details. Terrace and independent entrance into the courtyard of the property, large pool with view and garden-park with olive grove. Fully equipped kitchen, comfortable living room …see more

from $191 / night

$1,081 - $2,837 / week

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from $191 / night

(1) Very Good 

24

Apartment rental in Sant Andrea a Montecchio with shared pool

Siena / Sant Andrea a Montecchio

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 80 mi
  • Swimming pool
  • Child friendly
In the countryside around Siena, a short walk from the historic center of Siena, is the holiday home Oliveta The typical Tuscan farmhouse, completely renovated, divided into apartments. You enter through an automatic gate, directly to the shaded parking de Olive grove, …see more

from $86 / night

$639 - $676 / week

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Responds fast!
avg. 1 hour 56 minutes

from $86 / night

(1) Excellent 

18

Siena Vacation townhouse rental

Province of Siena / Siena

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
Recently renovated, centrally located apartment with private entrance. We are in the heart of Siena, in the heart of the historical centre, in the territory of Contrada Capitana (flagship) of the wave, 150 mt from piazza IL CAMPO, at 300 metres from the DUOMO Cathedral …see more

from $80 / night

$492 / week

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from $80 / night

(1) Excellent 

49

Siena Vacation villa rental

Province of Siena / Siena

6 10 7 nights min

  • 6 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
This beautiful villa in Siena with Pool&SPA and air conditioning is situated on the hills with a breathtaking view over the vineyards up to Siena. An ideal accommodation for all those seeking peace and quiet but also a perfect point of departure for visiting the beauti …see more

from $430 / night

$2,764 - $5,220 / week

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from $430 / night

(48) Excellent 

95

Vacation villa in Siena

Province of Siena / Siena

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
OUR LAST MINUTE SPECIAL OFFER : - BEST RATES ON MAY! - OVER 30% DISCOUNT ON WEEKLY RATES ALL YEAR!! - OUR RATES ARE PROUNDLY ALL INCLUDED....no extra expenses,no final cleanings, no damage deposit, city tax included, the rate you see it's what you will pay! ALL PROPERT …see more

from $492 / night

$2,211 - $6,141 / week

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Responds fast!
avg. 3 hours 38 minutes

from $492 / night

15

Siena Vacation farmhouse rental

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 83 mi
  • Swimming pool
  • Child friendly
Very nice farmhouse of the end of 1700 (already surveyed in the first land register of the Grand Duchy of Tuscany in 1812) consists of two apartments with independent entrance and well separated, "La Loggia" and "the oven". Furthermore, the apartment's oven is divided o …see more

from $117 / night

$602 - $1,253 / week

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Responds fast!
avg. 2 hours 34 minutes

from $117 / night

39

Siena Vacation apartment rental

Province of Siena / Siena

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Pet friendly
The apartment consists of a bedroom, a living room with kitchenette, a bedroom with twin beds, a bathroom with bidet and toilet and a bathroom with separate shower. The apartment has a washing machine.The apartment is located on the first floor of one wing of the Manor …see more

from $105 / night

$492 / week

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from $105 / night

(8) Excellent 

25

Apartment rental in Siena

Province of Siena / Siena

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 100 mi
  • Child friendly
' The Senesina '. Charming apartment situated in the beautiful Tuscan countryside just 4 km from Siena and 8 km from Monteriggioni. strategic point to quickly reach cities rich in art and beauty which Florence Volterra San Gimignano and Chianti "La Senesina"-Enchanting …see more

from $99 / night

$614 - $848 / week

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from $99 / night

(1) Excellent 

24

Vacation apartment in Val di Merse

Siena / Val di Merse

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 70 mi
  • Child friendly
The antique spaces have been reinvigorated, made more comfortable and personalized whilst using traditional local materials, rough stone, terra cotta, wrought iron, wood. There are six complete and elegant, well-appointed apartments, complete with stylish fitted bathroo …see more

from $369 / night

$2,457 - $2,948 / week

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Responds fast!
avg. 2 hours 49 minutes

from $369 / night

(2) Excellent 

22

Caprera Vacation apartment rental

Siena / Caprera

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Nearest beach 100 mi
  • Child friendly
  • Air conditioning
Caprera is an elegant village in Liberty Style built at the end of 19th Century. The place has retained its original charm, still offers all modern comforts and facilities; Ideally located for visiting Siena and its countryside, the Chianti area, the 'crete senesi' and …see more

from $99 / night

$614 - $676 / week

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from $99 / night

(2) Excellent 

16

Vacation townhouse in Siena

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Ask about pets
The apartment is on the third floor of the building with elevator Giorgi. Has two large bedrooms, one double and one with two single beds can be joined in a king size bed, two bathrooms, one with shower the other with bathtub, equipped kitchen and living area and a lar …see more

from $455 / night

$3,009 - $18,421 / week

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from $455 / night

20

Vacation farmhouse rental

Province of Siena / Siena

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Child friendly
  • Ask about pets
  • Private garden
Ancient barn situated right outside Siena city center (only 3,5 km away). This property has been recently restored and turned into a modern and bright accommodation ideal for a couple or a family of 4 people. Outside guests can enjoy use of a large, well-groomed garden …see more

from $132 / night

$921 - $1,086 / week

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from $132 / night

(12) Very Good 

16

Apartment rental in Siena

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 105 mi
  • Swimming pool
  • Car not necessary
This very stylish 430-square-foot apartment a few minutes walk from Piazza del Campo. You will not need anymore to walk up 66 steps to access this apartment,because now there is a new elevator to lift you on two amazing terraces and their spectacular views. The main l …see more

from $123 / night

$1,118 - $1,376 / week

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Responds fast!
avg. 2 hours 49 minutes

from $123 / night

87

Vacation villa with swimming pool in Siena

Province of Siena / Siena

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
OUR LAST MINUTE SPECIAL OFFER : - BEST RATES ON MAY! - OVER 30% DISCOUNT ON WEEKLY RATES ALL YEAR!! - OUR RATES ARE PROUNDLY ALL INCLUDED....no extra expenses,no final cleanings, no damage deposit, city tax included, the rate you see it's what you will pay! ALL PROPERT …see more

from $430 / night

$2,579 - $7,123 / week

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Responds fast!
avg. 3 hours 38 minutes

from $430 / night

(4) Excellent 

30

Vacation apartment in Siena

Province of Siena / Siena

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 60 mi
  • Child friendly
  • Car not necessary
Treat yourself with a special holiday. Admire a spectacular, unique panorama from a flat that was built not just at the heart of Siena but also on its highest spot. You will be able to see the whole of Siena and all of its surroundings up to Mount Amiata or …see more

from $102 / night

$578 - $887 / week

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from $102 / night

(19) Very Good 

Certificate of Excellence

27

Vacation apartment in Sant Andrea a Montecchio

Siena / Sant Andrea a Montecchio

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 120 mi
  • Child friendly
  • Car not necessary
Located in the quiet countryside 5 km south of the beautiful medieval city of Siena, the Sant'Andrea apartment is part of a fully restored 15th century monastery.Only 5 minutes from the superstrada linking Siena to Florence and the Grosseto beaches, this residence is an …see more

Certificate of Excellence

from $86 / night

$492 - $737 / week

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from $86 / night

(5) Very Good 

42

Siena Vacation apartment rental

Province of Siena / Siena

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Pet friendly
Apartment with bedroom, living room with kitchenette, three bedded room, bathroom with bidet, toilet, shower and washing machine.The apartment is located on the second floor of a wing of villa Certano holding. The Tenuta di Certano includes the Manor House with its eleg …see more

from $123 / night

$614 / week

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from $123 / night

24

Monastero Vacation farmhouse rental

Siena / Monastero

1 4 5 nights min

  • 1 bedroom
  • Sleeps 4
  • 5 nights min
  • Nearest beach 100 mi
  • Child friendly
  • Ask about pets
A stylish loft made from a converted stable and a cellar in a countryside village close to Siena, surrounded by olive groves and fields; ideal for visitors looking for a quite and romantic lodge. The farmhouse is part of a unique Liberty village built by Garibaldi's doc …see more

from $123 / night

$737 - $860 / week

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from $123 / night

(1) Excellent 

12

Siena Vacation villa rental

Province of Siena / Siena

3 5 2 nights min

  • 3 bedrooms
  • Sleeps 5
  • 2 nights min
  • Private garden
The ' Stable ' is located on the first floor of a building that was once used as a stables and barn and is separated from the central block of Manor House di Certano, forming with his position inside the square of the village. From the entrance on the ground floor, furn …see more

from $185 / night

$1,204 / week

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from $185 / night

(7) Excellent 

Certificate of Excellence

14

Vacation home in Siena

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 70 mi
  • Child friendly
  • Ask about pets
This bright and modern apartment totally renovated by just one year, is situated in the charming historic centre of Siena.The apartment is part of a palace complex with other apartments and is located on the ground floor and consists of two floors. The apartment is s …see more

Certificate of Excellence

from $117 / night

$799 / week

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Responds fast!
avg. 2 hours 11 minutes

from $117 / night

(30) Excellent 

Certificate of Excellence

18

Vacation apartment in Siena

Province of Siena / Siena

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Car not necessary
Historic Residence Palazzo Bichi Ruspoli is situated on the main street, in the heart of Siena. The entrance is from the ancient tower, one of the three buildings wich the palace is composed. The house is on the third floor with elevator and has a stunning view on the c …see more

Certificate of Excellence

from $147 / night

$1,007 - $2,911 / week

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Responds fast!
avg. 3 hours 9 minutes

from $147 / night

(2) Excellent 

43

Vacation villa rental

Siena / Val di Merse

6 11 7 nights min

  • 6 bedrooms
  • Sleeps 11
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
7000 sqm, hills, quiet swimming pool, close to the village, 6 bedrooms, 4 bathrooms, all comfortIdilliaca hillside villa with pool, unique complex (200 sqm), near Siena (10 km). Old farm dating back to 1280 already. Refurbished in a rustic style (hand-baked bricks, beam …see more

from $137 / night

$958 - $2,641 / week

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from $137 / night

(1) Excellent 

12

Apartment rental in Siena

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning
Green apartment is located at ground floor and easily accessible, perfect for a family. It consists of a fully equipped kitchen where a folding sofa bed for two guests is provided, a bedroom with a double bed, a bathroom with shower, toilet, hairdryer, washing machin …see more

from $68 / night

$473 / week

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from $68 / night

(6) Excellent 

22

Vacation villa rental

Province of Siena / Siena

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
La villa (5 posti letto ) è situata nella campagna di Siena a circa 15 minuti a piedi dalla famosa 'Piazza del Campo' di Siena. Si trova in cima ad una collina, corredata di piscina e campo da tennis, offre splendidi panorami sulla città e sulla campagna circostante. È …see more

from $363 / night

$1,535 - $3,255 / week

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from $363 / night

(1) Very Good 

28

Vacation home in Siena

Province of Siena / Siena

2 4 6 nights min

  • 2 bedrooms
  • Sleeps 4
  • 6 nights min
  • Nearest beach 100 mi
  • Child friendly
  • Private garden
★My Cozy Country House is part of a hamlet about 20km from Siena and central to Chianti, San Gimignano, Florence, Montalcino&Montepulciano. It's located in a forest on top of a hill in the heart of Tuscany. Peaceful and quiet area. Patio&Garden. Perfect for hiking&bikin …see more

from $74 / night

$492 - $725 / week

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Responds fast!
avg. 2 hours 28 minutes

from $74 / night

(8) Excellent 

17

Apartment rental in Siena

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
House Contrada is a 50sq.m apartment of a building of 1400, in a historic district of Siena, with a historical and natural constraint of 1926. From Via Salicotto it is the 1s floor, but the house looks out on the second floor of Via Porta Giustizia , from which you can …see more

from $89 / night

$737 - $1,167 / week

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Responds fast!
avg. 3 hours 43 minutes

from $89 / night

29

Siena Vacation home rental

Province of Siena / Siena

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 115 mi
  • Swimming pool
  • Child friendly
House (120 m2) in an elegant Residence in typical Tuscan style, with nice pool attached. Entrance and terrace with loggia and garden independent. The nearest village is Villa a Sesta (600 meters, even walkable) with two restaurants and a bar. At 7 km there's the town of …see more

from $121 / night

$848 - $1,413 / week

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from $121 / night

(5) Excellent 

51

Vacation cottage in Siena

Province of Siena / Siena

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 100 mi
  • Child friendly
  • Pet friendly
On the ground floor of an old Tuscan stone house built in 1911, in the area of Montagnola, we offer a large apartment of 2260ft², with traditional furniture and fittings, with 3 bedrooms, 8 beds, 2 bathrooms, a large living room with fireplace and a large kitchen. On tw …see more

from $62 / night

$430 / week

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Responds fast!
avg. 1 hour 6 minutes

from $62 / night

21

Isola d'Arbia Vacation farmhouse rental

Siena / Isola d'Arbia

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly
Between Chianti and Val d'Orcia, just minutes from Siena, in the beautiful landscape of the Crete Senesi Podere Vesta offers its guests the typical hospitality of Tuscany. Relaxing, quiet and nature surround to a holiday to regenerate body and mind. the apartment consis …see more

from $128 / night

$473 / week

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Responds fast!
avg. 3 hours 12 minutes

from $128 / night

49

Vacation farmhouse rental

Province of Siena / Siena

6 10 2 nights min

  • 6 bedrooms
  • Sleeps 10
  • 2 nights min
  • Nearest beach 70 mi
  • Child friendly
  • Pet friendly
This beautiful farmhouse in the Tuscan style is part of the estate of Certano and represents the ideal place for a quiet and relaxing holiday in the countryside, a stone's throw from Siena. The building enjoys a panoramic view over the surrounding vineyards and olive g …see more

from $271 / night

$1,535 / week

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from $271 / night