50 Best Siena Apartments on Holiday Lettings - Villas

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Costalpino
9 properties
Isola d'Arbia
7 properties
Caprera
6 properties
Val di Merse
6 properties

Siena

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3,989 Vacation rentals

(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 $375 / night

$2,496 - $2,995 / week

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from $375 / night

(7) 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 $74 / night

$500 - $814 / week

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Responds fast!
avg. 2 hours 34 minutes

from $74 / 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 $194 / night

$1,098 - $3,095 / week

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from $194 / 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 $500 / night

$2,870 - $4,992 / week

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from $500 / 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 $63 / night

$375 / week

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Responds fast!
avg. 2 hours 54 minutes

from $63 / 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 $130 / night

$481 / week

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Responds fast!
avg. 3 hours 12 minutes

from $130 / night

15

Vacation apartment with shared pool in Siena

Province of Siena / Siena

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 110 mi
  • Swimming pool
  • Child friendly
Apartment consists of living room and bedroom open space, kitchen, bathroom with shower with curtain and legna.Riscaldamento natural gas stove. Mosquito nets. Private garden with table, chairs and umbrella. Adjacent to the apartment a wonderful swimming pool with gazebo …see more

from $75 / night

$524 - $787 / week

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from $75 / 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 $368 / night

$1,560 - $3,307 / week

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Responds fast!
avg. 3 hours 46 minutes

from $368 / 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 $437 / night

$2,621 - $7,238 / week

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Responds fast!
avg. 3 hours 53 minutes

from $437 / 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 $158 / night

$586 / week

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Responds fast!
avg. 3 hours 12 minutes

from $158 / night

(29) 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 $163 / night

$1,024 - $2,958 / week

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Responds fast!
avg. 3 hours 7 minutes

from $163 / night

(4) Excellent 

20

Siena Vacation townhouse accommodation

Province of Siena / Siena

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Swimming pool
  • Private garden
Apartment of 50 sqm, is part of an old building renovated, beautifully decorated in style. Perched atop a hill, offers from all Windows a beautiful skyline of Siena, the view of the castle of Leonina, of the famous "Site transitoire ' and all Crete Senesi. Swimming pool …see more

from $86 / night

$599 / week

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from $86 / night

(19) Very Good 

Certificate of Excellence

40

Vacation cottage in Siena

Province of Siena / Siena

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 65 mi
  • Air conditioning
Totally renewed ancient tuscan house with air conditioning and radiant panel heating system. The cottage is located in a natural reserve however it is just 2 km from the closest village with all facilities: supermarket, banks, gas stations, pharmacy. Siena is 15 minutes …see more

Certificate of Excellence

from $119 / night

$830 / week

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Responds fast!
avg. 2 hours 43 minutes

from $119 / 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 $562 / night

$3,432 / week

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from $562 / 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 $437 / night

$2,496 - $2,758 / week

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Responds fast!
avg. 1 hour 50 minutes

from $437 / night

(9) 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 $113 / night

$599 - $1,410 / week

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Responds fast!
avg. 2 hours 34 minutes

from $113 / night

10

Siena Vacation apartment rental

Province of Siena / Siena

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
It is a basement with two bedrooms and a bathroom. The room is in the basement, has no window but a ventilation system for air exchange. The room can be delivered with a double bed or, on request, with two single beds. It is quite spacious and, if needed and requested, …see more

from $44 / night

$300 / week

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from $44 / 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 $188 / night

$1,223 / week

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from $188 / night

(1) Excellent 

22

Vacation apartment in Val di Merse

Siena / Val di Merse

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 70 mi
  • Child friendly
The antique spaces of the apartment have been reinvigorated, made more comfortable and personalized whilst using traditional local materials, rough stone, terracotta, wrought iron, wood. Giotto is one of six complete and elegant, well-appointed apartments, comple …see more

from $88 / night

$562 - $749 / week

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from $88 / 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 $119 / night

$612 - $1,360 / week

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Responds fast!
avg. 2 hours 34 minutes

from $119 / 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 $88 / night

$961 - $1,398 / week

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Responds fast!
avg. 2 hours 53 minutes

from $88 / night

(2) Excellent 

17

Vacation apartment rental

Province of Siena / Siena

2 7 1 night min

  • 2 bedrooms
  • Sleeps 7
  • 1 night min
  • Child friendly
  • Pet friendly
Senio on roofs is the perfect place to fully experience the smells, the life and the happy chatter of one of the most beautiful and famous city in the world. Staying very close to Piazza del Campo, our guests will be involved in the contrada's life, a unique experience …see more

from $150 / night

$1,049 / week

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from $150 / night

(8) Very Good 

16

Siena Vacation farmhouse rental

Province of Siena / Siena

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 83 mi
  • Swimming pool
  • Child friendly
Very nice farmhouse of the end of 1700 (already surveyed in the first cadastre 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 on two …see more

from $131 / night

$699 - $1,535 / week

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Responds fast!
avg. 2 hours 34 minutes

from $131 / night

(7) 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 $90 / night

$749 - $1,186 / week

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Responds fast!
avg. 3 hours 30 minutes

from $90 / 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 $200 / night

$1,248 - $1,722 / week

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from $200 / 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 $113 / night

$712 - $861 / week

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from $113 / 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 $75 / night

$437 - $749 / week

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from $75 / night

(6) Very Good 

24

Vacation apartment rental

Siena / Val di Merse

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • 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. A large fireplace in the living This elegant, well-appointed apartment is complete with st …see more

from $250 / night

$1,373 - $1,747 / week

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from $250 / night

10

Vacation apartment in Siena

Province of Siena / Siena

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly
It is a studio composed of a living room, a kitchenette and a bathroom. The room is in the loft, with double bed. From the bedroom you go to a walk-in closet. The room can be delivered, on request, with two single beds. In the living room instead there is a sofa bed. Th …see more

from $69 / night

$437 / week

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from $69 / night

20

Vacation apartment in Siena

Province of Siena / Siena

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Nearest beach 100 mi
  • Child friendly
  • Air conditioning
Nice studio of 40 square meters located in a typical Tuscan country house recently renovated. The farmhouse, surrounded by olive trees, is located in a quiet but well served and not isolated, in the hills around Siena. The city center is about 3km. L 'apartment has a se …see more

from $100 / night

$874 / week

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from $100 / night

(3) 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 $113 / night

$787 / week

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from $113 / night

14

Apartment rental in Siena

Province of Siena / Siena

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Pet friendly
It is a basement with two bedrooms and a bathroom. The room is located in the basement, however with two windows (without light) for changing the air. The room can be delivered with a double bed or, on request, with two single beds. It is quite spacious and, whenever ne …see more

from $50 / night

$312 / week

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from $50 / 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 $88 / night

$437 / week

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from $88 / 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 $188 / night

$999 - $1,248 / week

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Responds fast!
avg. 1 hour 50 minutes

from $188 / night

(1) Excellent 

56

Vacation apartment rental

Province of Siena / Siena

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Fully refurbished apartment 6 km from Siena in a former convent dating back to 1200 with inner courtyard, in the hills living room with sofa bed and TV, full kitchen with dishwasher, large bathroom with shower, utility room with washing machine, and 2 double bedrooms, s …see more

from $100 / night

$699 / week

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from $100 / night

(4) Excellent 

26

Vacation apartment rental

Province of Siena / Siena

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Nearest beach 80 mi
  • Swimming pool
  • Child friendly
The apartment (80m2) is on two floors. The entrance is on the ground floor through a glassdoor. The main room include a living area with a double sofa bed, a fully equipped kitchen and dining table, all renewed on January 2014. The bathroom is equipped with shower cabin …see more

from $98 / night

$687 - $1,348 / week

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from $98 / night

12

Siena Vacation apartment rental

Province of Siena / Siena

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Pet friendly
The apartment is located only 500 meters from Piazza del Campo and is located in a lovely building surrounded by greenery and tranquility. And 'double bedroom, lounge with kitchenette and bathroom, and is equipped with all the comforts (TV, wi-fi, washing machine, dishw …see more

from $100 / night

$633 / week

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from $100 / 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 $106 / night

$743 / week

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from $106 / 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 $200 / night

$1,398 / week

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from $200 / 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 $150 / night

$936 - $1,248 / week

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from $150 / night