Vacation Rentals & Apartments in Siena

Close

Enter dates for more accurate prices

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more

3,962 apartments

(5) Excellent 

44

Villa Caprera, Siena Farmhouse. Suite Il Tinaio

Province of Siena / Siena

Siena villa

1 4 5 nights min

  • 1 bedroom
  • sleeps 4
  • 5 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$121

Price per night from

$121

(8) Excellent 

40

Monterzi 4

Province of Siena / Siena

Siena villa

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Ask about children
  • Ask about pets

Price per night from

$145

Price per night from

$145

21

One Bedroom Villa at Castello di Montalto in Chianti

Province of Siena / Siena

Siena villa

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

Price per night from

$127

Price per night from

$127

32

La Pergola 6 + 2

Province of Siena / Siena

Siena villa

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Ask about children
  • Ask about pets

Price per night from

$217

Price per night from

$217

(1) Excellent 

17

2 Bedrooms Apartment (Ambrosia)

Province of Siena / Siena

Siena apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$62

Price per night from

$62

(2) Excellent 

32

Sferracavalli 4

Province of Siena / Siena

Siena villa

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Ask about children
  • Pet Friendly

Price per night from

$196

Price per night from

$196

(3) Excellent 

57

Independent villa with private pool in Siena countryside - 3 bedrooms

Province of Siena / Siena

Siena villa

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Nearest beach 156 mi
  • Swimming pool
  • Pet Friendly

Price per night from

$333

Responds fast!
avg. 1 hour 45 minutes

Price per night from

$333

(1) Very Good 

39

Podere Madonna di Mezzo 6

Province of Siena / Siena

Siena villa

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Nearest beach 120 mi
  • Ask about children
  • Ask about pets

Price per night from

$267

Price per night from

$267

(1) Excellent 

17

2 Bedrooms Apartment (Belladonna)

Province of Siena / Siena

Siena apartment

2 8 min stay varies

  • 2 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Pet Friendly

Price per night from

$62

Price per night from

$62

(1) Excellent 

25

Villa with Pool and Jacuzzi private Deal 2019

Province of Siena / Siena

Siena villa

2 7 7 nights min

  • 2 bedrooms
  • sleeps 7
  • 7 nights min
  • Nearest beach 45 mi
  • Swimming pool
  • Child Friendly

Price per night from

$112

Responds fast!
avg. 40 minutes

Price per night from

$112

(2) Very Good 

31

Abbadia di Siena

Province of Siena / Siena

Siena house

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$253

Price per night from

$253

(8) Excellent 

27

La Senesina , enchanting apartment near Siena

Province of Siena / Siena

Siena apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly

Price per night from

$111

Price per night from

$111

(68) Excellent 

34

Tuscany Villa with pool - Villa le Capanne holday in private villas

Province of Siena / Siena

Siena villa

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Nearest beach 60 mi
  • Swimming pool
  • Child Friendly
“Fantastic Hosts for this unique countryside Villa” Our trip to Italy still fresh in our minds so we wanted to write to tell others about our lovely experience at Villa le Capanne. We stayed with another couple for one week, make trips to Florence, Vol
…see more

Price per night from

$107

Responds fast!
avg. 1 hour 21 minutes

Price per night from

$107

(1) Excellent 

30

SOURCE GAIA - 3bd with Piazza del Campo view

Province of Siena / Siena

Siena apartment

2 3 min stay varies

  • 2 bedrooms
  • sleeps 3
  • min stay varies
  • Ask about children
  • Air conditioning

Price per night from

$106

Price per night from

$106

15

Cino Apartment A

Province of Siena / Siena

Siena studio

Studio 2 4 nights min

  • Studio
  • sleeps 2
  • 4 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

Price per night from

$85

Responds fast!
avg. 2 hours 51 minutes

Price per night from

$85

28

La Pergola 4 + 2

Province of Siena / Siena

Siena villa

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Ask about children
  • Ask about pets

Price per night from

$190

Price per night from

$190

(12) Excellent 

33

Siena San Fabiano climatized villa with outdoor heated pool

Province of Siena / Siena

Siena villa

6 21 min stay varies

  • 6 bedrooms
  • sleeps 21
  • min stay varies
  • Nearest beach 113 mi
  • Swimming pool
  • Child Friendly
“The Best Place to Celebrate your Birthday with Friends” Coming back to "San Fabiano" is like coming back to friends. If you wish to forget all your day-by-day problems, come to stay at this place. Located in the middle of the farm fields. Sit under t
…see more

Price per night from

$803

Responds fast!
avg. 3 hours 11 minutes

Price per night from

$803

(3) Very Good 

19

Castello di Montalto - 3 Bedroom Villa in Chianti

Province of Siena / Siena

Siena villa

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Ask about pets

Price per night from

$278

Price per night from

$278

(4) Very Good 

63

Santo Stefano 10

Province of Siena / Siena

Siena villa

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Nearest beach 95 mi
  • Ask about children
  • Ask about pets
“Nice for our family group of 10” We rented Villa Santo Stefano from Emma Villas for a week in July (2013). It was as advertised, which was wonderful. The structure is well restored, and the grounds well cared for. The family acting as the local manage
…see more

Price per night from

$482

Price per night from

$482

(11) Excellent 

38

Villa Caprera, Siena Farmhouse. Casa Borgianni.

Province of Siena / Siena

Siena villa

3 6 5 nights min

  • 3 bedrooms
  • sleeps 6
  • 5 nights min
  • Child Friendly
  • Pet Friendly
“heavenly” A beautifully appointed home, with mercifully two batherooms, tastefully decorated with all that you need. The kitchen is a dream - everything you need. Lovely crockery, not bottom-of-the-range, and the bed linen also of excellent quality. E
…see more

Price per night from

$213

Price per night from

$213

(5) Excellent 

42

Gated Luxury Estate "LaChiusa" Prime Chianti Classico! Exquisite Privacy & Views

Province of Siena / Siena

Siena farmhouse

4 6 4 nights min

  • 4 bedrooms
  • sleeps 6
  • 4 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$919

Responds fast!
avg. 2 hours 3 minutes

Price per night from

$919

27

SIENA ROMANTIC

Province of Siena / Siena

Siena apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Ask about children
  • Air conditioning
  • Ask about pets

Price per night from

$106

Price per night from

$106

19

THE WAVE – 8bd with terrace behind Piazza del Campo

Province of Siena / Siena

Siena apartment

2 8 min stay varies

  • 2 bedrooms
  • sleeps 8
  • min stay varies
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$106

Price per night from

$106

(11) Excellent 

Certificate of Excellence

20

Luxurious Vacation Rental at Palazzo Cinotti in Si

Province of Siena / Siena

Siena apartment

3 5 min stay varies

  • 3 bedrooms
  • sleeps 5
  • min stay varies
  • Nearest beach 89 mi
  • Child Friendly
  • Car not necessary

Certificate of Excellence

Price per night from

$333

Price per night from

$333

(3) Excellent 

16

Palazzo Cinotti Suite Giulio

Province of Siena / Siena

Siena apartment

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Nearest beach 80 mi
  • Ask about children
  • Car not necessary

Price per night from

$219

Price per night from

$219

(1) Excellent 

24

IL TOLOMEI central in the middle of main street

Province of Siena / Siena

Siena apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Ask about children
  • Air conditioning

Price per night from

$106

Price per night from

$106

(4) Excellent 

20

Siena Romantic Escape

Province of Siena / Siena

Siena apartment

2 3 2 nights min

  • 2 bedrooms
  • sleeps 3
  • 2 nights min
  • Nearest beach 81 mi
  • Child Friendly
  • Car not necessary

Price per night from

$150

Price per night from

$150

11

Palio 2 - Charming Cosy Studio in Siena Center

Province of Siena / Siena

Siena studio

Studio 2 7 nights min

  • Studio
  • sleeps 2
  • 7 nights min
  • Suitable for children age 5+
  • Air conditioning

Price per night from

$82

Price per night from

$82

51

Piandisette 8

Province of Siena / Siena

Siena villa

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Ask about children
  • Ask about pets

Price per night from

$229

Price per night from

$229

(1) Excellent 

26

MODERN SAN FRANCESCO

Province of Siena / Siena

Siena apartment

2 8 min stay varies

  • 2 bedrooms
  • sleeps 8
  • min stay varies
  • Ask about children
  • Air conditioning
  • Ask about pets

Price per night from

$106

Price per night from

$106

(1) Excellent 

24

Live Siena from the very top

Province of Siena / Siena

Siena apartment

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$96

Price per night from

$96

(6) Excellent 

157

Private Villa,Pool, Hot tub,A/C,WiFi,5BR,15km from Siena

Province of Siena / Siena

Siena villa

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Nearest beach 113 mi
  • Swimming pool
  • Child Friendly

Price per night from

$459

Price per night from

$459

50

Piandisette 10+1

Province of Siena / Siena

Siena villa

5 11 7 nights min

  • 5 bedrooms
  • sleeps 11
  • 7 nights min
  • Ask about children
  • Ask about pets

Price per night from

$241

Price per night from

$241

(2) Excellent 

73

Podere Bellaria 14

Province of Siena / Siena

Siena villa

7 14 7 nights min

  • 7 bedrooms
  • sleeps 14
  • 7 nights min
  • Ask about children
  • Pet Friendly

Price per night from

$524

Price per night from

$524

About Siena

Siena is a classic 13th century Italian village in the hills of the Tuscan countryside. Its wealthy golden era took place between 1200 and 1300 AD and much of its art and architecture still bears the signature of this medieval period. For centuries, travelers have been coming to Siena for its beauty and history, its unusual piazza, its religious pilgrimage sites, and its famous summer horse races that take place in the market square. Visitors also come here to experience the romance of Tuscany. While you're here, wander the curious side streets, rest your feet beside ornate fountains, and stroll the galleries of Siena's fascinating art museums. Don't miss the gothic town hall building, and make sure you also find time to explore the hills and vineyards beyond the village center.

Here are some suggested things to do and see on your visit to Siena:

  • Take a culinary and winery tour: There are several tours available in Siena that can take visitors from one Tuscan vineyard to another and offer culinary sampling from some of Siena's world-class restaurants. This is a wonderful opportunity to take in the legendary countryside and experience the delicious traditions of this region.
  • Take a Tuscan cooking class: Immerse yourself in Tuscany's culinary traditions by taking a cooking class. Many available courses are taught by accomplished Italian chefs.
  • Visit the Siena Cathedral: Many visitors consider this the most beautiful religious site in Italy. Observe the classic Gothic architecture and intricate carvings of the exterior.
  • See the Piazza del Campo: As the heart of Siena, this is an excellent starting point for a walking tour of the city. If you visit during July and August, the square will be alive with noise and excitement surrounding the Palio horse races that take place here.
  • Visit the Torre del Mangia: For breathtaking views of the city and surrounding landscape, climb the Tower of Mangia. Constructed in 1325, the tower rises up about 290 feet.
  • Explore the National Archeological Museum of Siena: This building itself is a destination. Originally constructed as a pilgrim's hostel, it has been a hospital since the 10th century.

No matter what time of year you plan to arrive here, you'll have no trouble finding a vacation rental that meets your needs. In the heart of the village, within reach of the town square, you can book a condo or apartment in what may be a 13th century structure. You can also easily rent a beautiful Tuscan villa with views of the city or the rolling inland hills.