50 Best Siena Apartments on Holiday Lettings - Villas

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338 Vacation rentals

(28) 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 $179 / night

$1170 - $2641 / week

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from $179 / 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

$312 / week

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Responds fast!
avg. 1 hour 25 minutes

from $45 / night

(4) 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 $102 / night

$674 - $1236 / week

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from $102 / 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

$809 - $1280 / week

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from $135 / night

20

Vacation villa rental

Province of Siena / Siena

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 70 mi
  • Swimming pool
  • Child friendly
Elegant villa on the hills of Siena of 170 square meters with garden and pool, furnished with fine furniture. Towering over the city, surrounded by greenery, in absolute peace and privacy, a few steps from the center, close to services pubblici.La villa on one floor wit …see more

from $145 / night

$1014 / week

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Responds fast!
avg. 2 hours 44 minutes

from $145 / 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 $278 / night

$1783 - $2173 / week

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Responds fast!
avg. 3 hours 2 minutes

from $278 / 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 $121 / night

$527 - $1439 / week

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from $121 / night

(1) Very Good 

39

Vacation apartment rental

Province of Siena / Siena

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Child friendly
  • Ask about pets
Apartment of approximately 70 m2, on the ground floor of an ancient building in the historical centre of Siena, just a few metres from the Accademia Chigiana and behind Piazza del Campo. Composed of living room, kitchen, bathroom, spacious bedroom with a double bed and …see more

Pricing unknown

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Pricing unknown

(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

$764 - $1078 / week

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from $124 / night

(1) Very Good 

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

$765 / week

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from $110 / 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

$433 - $1069 / week

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from $99 / 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 $102 / night

$539 - $1067 / week

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Responds fast!
avg. 2 hours 19 minutes

from $102 / night

(3) Excellent 

22

Villa rental in Siena with swimming pool

Province of Siena / Siena

9 18 Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • 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) …see more

from $446 / night

$2563 - $4457 / week

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from $446 / 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 $502 / night

$3064 / week

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from $502 / 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 $618 / night

$3369 - $5615 / week

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from $618 / 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 $416 / night

$2471 - $2695 / week

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Responds fast!
avg. 2 hours 34 minutes

from $416 / 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 $145 / night

$1248 / week

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from $145 / 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

$899 - $1123 / week

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from $135 / night

(2) 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 $102 / night

$674 - $989 / week

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from $102 / night

40

Penthouse rental in Siena

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
The place is unique for the panorama you can enjoy : you have a 360° view all over the main monuments and palaces of the city and the surrounding country. Moreover it' s located in the hearth of historical center (1 minute walking both from Piazza del Campo and Piazza d …see more

from $169 / night

$899 - $1123 / week

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Responds fast!
avg. 2 hours 36 minutes

from $169 / night

18

Siena Vacation villa rental

Province of Siena / Siena

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
An eighteenth century Tuscan farmhouse in a delightful little valley along the historic Via Francigena, surrounded by 14 hectares of privately owned vines, olive trees and woods that ensure utter privacy and tranquillity – this is Bellavalle, just 3.5 kilometres from th …see more

from $1108 / night

$4492 - $7748 / week

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from $1108 / night

(2) Excellent 

16

Vacation townhouse in Siena

Province of Siena / Siena

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • 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 $416 / night

$2639 - $11790 / week

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from $416 / night

(37) 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 $54 / night

$337 - $556 / week

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from $54 / night

(2) Very Good 

23

Townhouse rental in Siena

Province of Siena / Siena

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Ask about pets
  • Private garden
The apartment, located on the ground floor, is located within a wonderful Tuscan farmhouse from the early '900, completely renovated, immersed in the green countryside, situated in the locality Costafabbri. The historic center of Siena is a 10-minute drive. Given the lo …see more

from $101 / night

$702 / week

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from $101 / night

(18) Very Good 

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

from $78 / night

$446 - $669 / week

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Responds fast!
avg. 3 hours 11 minutes

from $78 / night

17

Vacation apartment in Siena

Province of Siena / Siena

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Private garden
L'appartamento relais garden 6 è uno splendido appartamento con giardino nel centro di Siena a pochi metri da piazza del Campo all'interno delle mura. Le sue principali caratteristiche sono le volte in mattoncini tipici senesi ed il giardino . L'appartamento è compos …see more

from $132 / night

$920 / week

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from $132 / 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

$955 - $1112 / week

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from $169 / night

24

Vacation b&b in Siena

Province of Siena / Siena

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 100 mi
  • Child friendly
  • Car not necessary
Historical, notified to fine arts superintendence, completely restored, very central (10 metres from Piazza del Campo, 15 from Piazza del Duomo) apartment, consisting of: 1) under floor: 1 triple room with bathroom, 1 single and 1 double room sharing bathroom, kitche …see more

from $393 / night

$2246 - $2482 / week

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Responds fast!
avg. 2 hours 36 minutes

from $393 / 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

$433 / week

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Responds fast!
avg. 3 hours 0 minutes

from $62 / night

(1) Excellent 

18

Vacation apartment in Siena

Province of Siena / Siena

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Child friendly
  • Air conditioning
If you are going to stay in Siena and would also like to visit the marvelous surrounding places, this charming little apartment is the best basis point for you: in the heart of the city centre and, at the same time, few steps away from the bus station * ** Please, read …see more

from $102 / night

$618 - $854 / week

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from $102 / night

20

Vacation farmhouse in Siena

Province of Siena / Siena

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Suitable for children age 5+
  • Ask about pets
The Farmhouse Malafrasca is located just outside the historic centre of Siena, at the beginning of the road of Chianti in a strategic position for a lot of tours to dicover the tuscan countryside and its medieval villages and at the mean time very close to the historic …see more

Pricing unknown

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Responds fast!
avg. 3 hours 24 minutes

Pricing unknown

12

Vacation bungalow in Iesa

Siena / Iesa

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden
L'alloggio è indipendente composto da letto matrimoniale, armadio guardaroba, tavolo da pranzo e piccolo frigorifero. Incluso nel prezzo ci sono le lenzuola e una semlice ma gustosa colazione (offriamo acqua tè caffè fette biscottate marmellate fatte in casa, frutta). L …see more

from $57 / night

$337 / week

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from $57 / night

(2) Excellent 

27

Apartment rental in Siena

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 96 mi
  • Suitable for children age 5+
  • Car not necessary
This cosy two bedroom apartment is located in the historic city center of Siena (inside the city walls) approximately 300 meters distant from „Piazza del Campo“. The apartment is on the third floor of a small typical, ancient Sienese town house built in the 16th cent …see more

from $90 / night

$569 - $931 / week

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from $90 / night

(1) Excellent 

11

Vacation apartment accommodation

Province of Siena / Siena

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning
Located on the hills of central Tuscany, at only 2 km from the walls of Siena, this charming holiday accommodation in Tuscany has been totally restored into 7 comfortable self-catering apartments with high quality furniture. All the holiday apartments have independent …see more

from $78 / night

$491 - $613 / week

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Responds fast!
avg. 3 hours 14 minutes

from $78 / night

(3) Excellent 

12

Farmhouse rental in Val di Merse

Siena / Val di Merse

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly
OFFER IN JUNE and JULY !!! The property PODERE SORTOIANO dates back to the 14th century and for generations has been part of the property Santini, once farmers. The apartments, as well as the "hut" were once stables for livestock. It has now been restored by the Santi …see more

from $45 / night

$292 - $495 / week

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from $45 / night

22

Vacation villa in Siena

Province of Siena / Siena

5 13 2 nights min

  • 5 bedrooms
  • Sleeps 13
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Located between Florence and Siena in Chianti, Villa Gaiole's private hilltop position provides 360 degree panoramic views of the breathtaking Tuscan countryside. Set around an expansive central courtyard with barbeque area, this luxury villa rental provides visitors wi …see more

from $3519 / night

$11729 - $14815 / week

Inquire View

from $3519 / night

(1) Excellent 

21

Vacation apartment in Siena

Province of Siena / Siena

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Car not necessary
  • Air conditioning
Delizioso appartamento situato poco fuori le mura di Siena, di fronte alle antiche Fonti di San Carlo. Appena finemente ristrutturato è composto da ampia camera matrimoniale, camera doppia, soggiorno/cucina e bagno. Corredato di vano lavanderia con lavatrice. Gode di gi …see more

from $90 / night

$558 - $869 / week

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Responds fast!
avg. 3 hours 12 minutes

from $90 / 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 $107 / night

$551 - $1280 / week

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Responds fast!
avg. 2 hours 19 minutes

from $107 / 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 $56 / night

$390 / week

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Responds fast!
avg. 3 hours 59 minutes

from $56 / night

(1) Very Good 

15

Vacation apartment in Siena

Province of Siena / Siena

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden
In Siena - Completely renovated, large terrace (loggia) opening over the Sienese countryside. 3 minutes from the historic city center. Very light and quiet. Splendid Panorama of Tuscan hillsides. Garden and private parking space. Three large double bedrooms and two tile …see more

from $203 / night

$1067 / week

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from $203 / night

1