50 Best Siena Apartments on Holiday Lettings - Villas

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Val di Merse
9 properties
Caprera
7 properties
Isola d'Arbia
5 properties

Siena

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357 Vacation rentals

(27) 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 $180 / night

$1177 - $2556 / week

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from $180 / night

(1) Very Good 

19

Vacation apartment in Isola d'Arbia

Siena / Isola d'Arbia

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • 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 $45 / night

$314 / week

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from $45 / night

(35) Excellent 

24

Apartment rental in Val di Merse

Siena / Val di Merse

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 60 mi
  • Child friendly
  • Pet friendly
LAST MINUTE OFFER IN MAY AND JUNE 2017 ! The property dates back to the 14th century and for generations has been part of the property Santini, once farmers. The apartments were once stables for livestock. It has now been restored by the Santini family with much love a …see more

from $57 / night

$359 - $555 / week

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from $57 / night

22

Vacation farmhouse with shared pool in Isola d'Arbia

Siena / Isola d'Arbia

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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 $120 / night

$526 - $1436 / week

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from $120 / night

10

Siena Vacation home rental

Province of Siena / Siena

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Private garden
truly unique property - Enjoy your home away from home. Consisting of approximately 180 mq2, connected to Piazza del Campo in a few minutes (10) of the beautiful promenade along the Medici Fortress getting in front of the Basilica of San Domenico. Around the house there …see more

from $110 / night

$769 / week

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from $110 / night

(2) Excellent 

39

Vacation villa with swimming pool in Siena

Province of Siena / Siena

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • 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 $189 / night

$1323 - $2914 / week

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from $189 / night

36

Vacation villa in Siena

Province of Siena / Siena

11 22 Min stay varies

  • 11 bedrooms
  • Sleeps 22
  • 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 $617 / night

$3363 - $5604 / week

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from $617 / night

20

Vacation farmhouse rental

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • 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 $108 / night

$750 - $898 / week

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from $108 / night

(3) Excellent 

32

Siena Vacation condo rental

Province of Siena / Siena

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Car not necessary
L 'apartment is on the third floor in a residence d' era of the late '700, in the heart of the historic center of Siena. L 'apartment, about 80 meters, is characterized by beautiful frescoed ceilings and antique beams. With lift, it consists of a 'large living room, din …see more

from $135 / night

$807 - $1278 / week

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from $135 / night

(1) 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 $96 / night

$673 - $987 / week

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from $96 / night

(2) Excellent 

19

Vacation apartment in Siena

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 95 mi
  • Child friendly
  • Air conditioning
The apartment overlooks the beautiful Piazza del Campo , with a light coming from the three main windows and invades the entire house is unique about every hour of the day . The apartment has just been renovated and furnished with designer pieces and equipped with every …see more

from $415 / night

$2466 - $2690 / week

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from $415 / night

(8) Very Good 

22

Condo rental in Siena

Province of Siena / Siena

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Pet friendly
L 'apartment is located on the first floor in a historic residence. E 'consists of a spacious living room, a well equipped kitchen, double bedroom and a bathroom with shower. Both rooms are light and airy with very characteristic beamed ceilings and enjoy a splendid pan …see more

from $107 / night

$650 / week

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from $107 / night

(7) 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 $505 / night

$3082 / week

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from $505 / night

(4) Excellent 

16

Vacation apartment with swimming pool in Siena

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • 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 register of the lands of Tuscany Grand Duchy in 1812) consists of two apartments with independent entrance and well separated, "La Loggia" and "the oven". Furthermore, the apartment's oven is divided …see more

from $96 / night

$516 - $1065 / week

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from $96 / night

(3) 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 $101 / night

$673 - $1233 / week

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from $101 / night

(4) 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 $331 / night

$1401 - $2970 / week

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from $331 / night

24

Vacation farmhouse in Siena

Province of Siena / Siena

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
APARTMENTS AND HOLIDAY HOUSES IN SIENA IN TUSCANY Villa Agostoli is a residential complex of apartments for holidays in Siena in Tuscany. The holiday houses of Villa Agostoli are located in the countryside right outside Siena and they are so close to the city …see more

from $152 / night

$1060 / week

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from $152 / night

(8) Very Good 

16

Apartment rental in Siena

Province of Siena / Siena

1 4 5 nights min

  • 1 bedroom
  • Sleeps 4
  • 5 nights min
  • 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 $146 / night

$1256 / week

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from $146 / night

(43) Excellent 

39

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
SPECIAL DISCOUNT 2017 30% OFF for the available weeks March-April-May 15% OFF for the available weeks July and August -------------------------------------------------------------------------------------------------------- JUST RELAX...... YOUR VACATION IN TUSCANY BEG …see more

from $313 / night

$2018 - $4707 / week

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from $313 / night

(2) Excellent 

24

Vacation villa with swimming pool in Siena

Province of Siena / Siena

6 10 7 nights min

  • 6 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This beautiful villa in Siena with private Spa-Wellness Center room 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 beau …see more

from $257 / night

$1794 - $4481 / week

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from $257 / night

(5) Very Good 

15

Vacation apartment in Siena

Province of Siena / Siena

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Car not necessary
  • Air conditioning
Apartment on two floors situated in the Centre of Siena, St. Francis Basilica area. Excellent for visiting the numerous churches of the city, rich in history and culture; accommodation in the days of the Palio di Siena, the event more attractive to visitors. For individ …see more

from $67 / night

$449 - $731 / week

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from $67 / night

(1) 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 $90 / night

$561 - $617 / week

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from $90 / night

(5) Very Good 

14

Vacation apartment in Siena

Province of Siena / Siena

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
A pretty apartment situated in a land of only 2 storey roof, in the historic centre of Siena. Very bright and comfortable, while being in the Center, (very quiet), it can be reached with a short walk from a restricted traffic zone, where there is a free parking and a co …see more

from $62 / night

$432 / week

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from $62 / night

18

Vacation apartment in Siena

Province of Siena / Siena

1 5 Min stay varies

  • 1 bedroom
  • Sleeps 5
  • Min stay varies
  • Nearest beach 85 mi
  • Child friendly
  • Car not necessary
Brown apartment is a typical Tuscan house and features a private fully equipped garden. Located at the first floor, completely restored, it consists of a bedroom with double bed and a bathroom with shower, toilet, hairdryer. A flight of stairs leads to the living area …see more

from $68 / night

$471 / week

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from $68 / night

(5) Excellent 

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

from $107 / night

$729 / week

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from $107 / night

(5) Excellent 

23

Vacation apartment in Val di Merse

Siena / Val di Merse

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 70 mi
  • Child friendly
The antique apartment have been reinvigorated, made more comfortable and personalized whilst using traditional local materials, rough stone, terracotta, wrought iron, wood. This elegant, well-appointed apartment is complete with stylish fitted bathroom and kitche …see more

from $135 / night

$897 - $1121 / week

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from $135 / night

9

Siena Vacation apartment rental

Province of Siena / Siena

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Child friendly
  • Ask about pets
Fattoria Il Poderaccio is an organic farm five miles from Siena, extends 32 hectares of hilly terrain at the edge of Chianti, produces three types of red wine: Chianti Riserva DOCG "2011" Keekorok, Chianti Colli Senesi DOCG and the "Brunaccio" IGT rosso Toscano, Extra V …see more

from $79 / night

$505 / week

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from $79 / night

(6) Excellent 

Certificate of Excellence

31

Vacation villa in Costalpino

Siena / Costalpino

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • 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 $280 / night

$1794 - $2186 / week

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from $280 / night

(4) Excellent 

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 $113 / night

$561 / week

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from $113 / night

(1) Very Good 

16

Vacation apartment in Siena

Province of Siena / Siena

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Pet friendly
GRANAINO apartment called is on the second floor in one wing of the villa in the Tenuta di Certano. It has a double bedroom, a living room with two sofa beds, a kitchen and a bathroom. From the room and the living room has a beautiful view on the roof garden of the vi …see more

from $78 / night

$389 / week

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from $78 / night

(2) Excellent 

11

Siena Vacation apartment rental

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning
A spacious and luminous two roomed unit (55sqm) in Siena. The apartment is situated on the 1st floor of my historical palace (a splendid aristocratic Villa from the first part of the C17th - just 1.6 km from the pedestrian historical centre of Siena) and can accommodat …see more

from $146 / night

$897 - $1009 / week

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from $146 / night

24

Apartment rental in Siena with shared pool

Province of Siena / Siena

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
APARTMENTS AND HOLIDAY HOUSES IN SIENA IN TUSCANY Villa Agostoli is a residential complex of apartments for holidays in Siena in Tuscany. The holiday houses of Villa Agostoli are located in the countryside right outside Siena and they are so close to the city tha …see more

from $113 / night

$785 / week

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from $113 / night

(3) Very Good 

34

Vacation cottage in Siena

Province of Siena / Siena

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Independent 2 family cottage located in the outskirts of Siena in an olive tree grove at 1km from: newsstand, coffee shop, food market, hair dresser, pastry shop, butcher, pizza restaurant, discount market, gas station, free parking lot, bus stops to down town, train s …see more

from $169 / night

$1121 - $1513 / week

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from $169 / night

(4) Excellent 

22

Condo rental in Siena

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
Located on the third floor with elevator, the apartment and 'consists of a' living room with kitchenette and double sofa bed open plan, twin bedroom plus a bathroom with shower.The rooms are bright and airy with ceilings beamed. The apartment is less than 50 meters from …see more

from $124 / night

$763 - $1076 / week

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from $124 / 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 $96 / night

$449 / week

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from $96 / night

(2) Very Good 

35

Home rental in Siena

Province of Siena / Siena

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 110 mi
  • Child friendly
  • Air conditioning
Costaberci's name is compounded by two sienese words: '' costs '', which means hill, and '' Grab '' which mean scream. This remarkable name comes from the historical battle of Montaperti, which occurred in 1260, where there have been a struggle the Ghibellines, lead by …see more

from $169 / night

$953 - $1110 / week

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from $169 / night

21

Isola d'Arbia Vacation farmhouse rental

Siena / Isola d'Arbia

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • 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 $99 / night

$432 - $1067 / week

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from $99 / night

(4) Very Good 

7

Siena Vacation b&b rental

Province of Siena / Siena

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Air conditioning
The apartment consists of bedroom, living room with kitchenette and bathroom. Is located in Via del Costone 2, just a few steps from the Duomo and Piazza del Campo, on the ground floor with independent entrance. The kitchen is fully equipped with wi-fi and bed linen, ba …see more

from $67 / night

$463 / week

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from $67 / night

29

Siena Vacation apartment rental

Province of Siena / Siena

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
APARTMENTS AND HOLIDAY HOUSES IN SIENA IN TUSCANY Villa Agostoli is a residential complex of apartments for holidays in Siena in Tuscany. The holiday houses of Villa Agostoli are located in the countryside right outside Siena and they are so close to the city tha …see more

from $152 / night

$1060 / week

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from $152 / night

12

Vacation apartment in Costalpino

Siena / Costalpino

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden
Located 6 km from Porta San Marco gate in Siena, Villa Sant’Andrea is housed in a 18th-century villa with private garden and offers elegant accommodation with free Wi-Fi. Free on-site parking is provided. A bus stop, 150 m away, has links to Siena centre. Siena Station …see more

from $79 / night

$505 / week

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from $79 / night

1