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Holiday apartments and houses in Siena & surrounding area

157 offers for your holiday in Siena & surrounding area

Villa Renata Tuscany
Villa Renata Tuscany
Villa Renata Tuscany
Villa Renata Tuscany
Villa Renata Tuscany
Villa Renata Tuscany
Villa Renata Tuscany
Villa Renata Tuscany
Villa Renata Tuscany
Villa Renata Tuscany
Villa Renata Tuscany
Villa Renata Tuscany
Villa Renata Tuscany
Villa Renata Tuscany
Villa Renata Tuscany
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Monticiano

Villa Renata Tuscany

7 guests
170 m2
3 bedrooms

Villa Renata Toscana: 170 m², 7 guests, 3 bedrooms, 2 bathrooms, large open space living room, dining area and kitchen, equipped patio, swimming pool and private garden use - Monticiano

Free cancellation
from 368 / night
San Lorenzo a Montalbano
San Lorenzo a Montalbano
San Lorenzo a Montalbano
San Lorenzo a Montalbano
San Lorenzo a Montalbano
San Lorenzo a Montalbano
San Lorenzo a Montalbano
San Lorenzo a Montalbano
San Lorenzo a Montalbano
San Lorenzo a Montalbano
San Lorenzo a Montalbano
San Lorenzo a Montalbano
San Lorenzo a Montalbano
San Lorenzo a Montalbano
San Lorenzo a Montalbano
Radicondoli

San Lorenzo a Montalbano

10 guests
550 m2
5 bedrooms

San Lorenzo a Montalbano: A Timeless Tuscan Retreat

from 855 / night
Ancient tower with private pool 5+1
Ancient tower with private pool 5+1
Ancient tower with private pool 5+1
Ancient tower with private pool 5+1
Ancient tower with private pool 5+1
Ancient tower with private pool 5+1
Ancient tower with private pool 5+1
Ancient tower with private pool 5+1
Ancient tower with private pool 5+1
Ancient tower with private pool 5+1
Ancient tower with private pool 5+1
Ancient tower with private pool 5+1
Ancient tower with private pool 5+1
Ancient tower with private pool 5+1
Ancient tower with private pool 5+1
Gaiole in Chianti

Ancient tower with private pool 5+1

6 guests
120 m2
3 bedrooms
25 reviews

Ancient tower for 5 to 6 persons in a medieval castle near Siena in Chianti, panoramic views, 3 bedrooms, 2 bathrooms, garden, pool, air conditioning, fireplace, satellite TV, WIFI

from 285 / night
Casa della Tessitrice
Casa della Tessitrice
Casa della Tessitrice
Casa della Tessitrice
Casa della Tessitrice
Casa della Tessitrice
Casa della Tessitrice
Casa della Tessitrice
Casa della Tessitrice
Casa della Tessitrice
Casa della Tessitrice
Casa della Tessitrice
Casa della Tessitrice
Casa della Tessitrice
Casa della Tessitrice
Belforte

Casa della Tessitrice

5 guests
80 m2
2 bedrooms (+1)

Romantic cottage with private pool and garden.

from 180 / night
10%
MADONNA
MADONNA
MADONNA
MADONNA
MADONNA
MADONNA
MADONNA
MADONNA
MADONNA
MADONNA
MADONNA
MADONNA
MADONNA
MADONNA
MADONNA
Radicondoli

MADONNA

12 guests
240 m2
5 bedrooms (+1)

Situated on the edge of a park, just 5 minutes walk to the medieval hilltop village of Radicondoli, the property enjoys an exceptional view

-10% discount 03/29/2025 - 04/25/2025

from 207 / night
Private holiday home with pool (7 + 1)
Private holiday home with pool (7 + 1)
Private holiday home with pool (7 + 1)
Private holiday home with pool (7 + 1)
Private holiday home with pool (7 + 1)
Private holiday home with pool (7 + 1)
Private holiday home with pool (7 + 1)
Private holiday home with pool (7 + 1)
Private holiday home with pool (7 + 1)
Private holiday home with pool (7 + 1)
Private holiday home with pool (7 + 1)
Private holiday home with pool (7 + 1)
Private holiday home with pool (7 + 1)
Private holiday home with pool (7 + 1)
Private holiday home with pool (7 + 1)
San Giovanni d'Asso

Private holiday home with pool (7 + 1)

8 guests
100 m2
4 bedrooms
3 reviews

Rustic stone house in the Crete Senesi in a panoramic position, fenced garden with private pool, barbecue, fireplace, satTV, covered parking

from 215 / night
Virgilius
Virgilius
Virgilius
Virgilius
Virgilius
Virgilius
Virgilius
Virgilius
Virgilius
Virgilius
Virgilius
Virgilius
Virgilius
Virgilius
Virgilius
Radicondoli

Virgilius

6 guests
90 m2
3 bedrooms
1 review

Tuscany villa with stunning views, private pool, five minutes walk to the village

from 155 / night
Apartment - LA CAPANNA with pool
Apartment - LA CAPANNA with pool
Apartment - LA CAPANNA with pool
Apartment - LA CAPANNA with pool
Apartment - LA CAPANNA with pool
Apartment - LA CAPANNA with pool
Apartment - LA CAPANNA with pool
Apartment - LA CAPANNA with pool
Apartment - LA CAPANNA with pool
Apartment - LA CAPANNA with pool
Apartment - LA CAPANNA with pool
Apartment - LA CAPANNA with pool
Apartment - LA CAPANNA with pool
Apartment - LA CAPANNA with pool
Apartment - LA CAPANNA with pool
Radicondoli

Apartment - LA CAPANNA with pool

4 guests
55 m2
1 bedroom
2 reviews

The CAPANNA was a hayloft, where the farmers of the tuscan countryside were putting the grain back, it has been completely restructured.

Sustainable

from 80 / night
Farmhouse with private pool 8+2beds
Farmhouse with private pool 8+2beds
Farmhouse with private pool 8+2beds
Farmhouse with private pool 8+2beds
Farmhouse with private pool 8+2beds
Farmhouse with private pool 8+2beds
Farmhouse with private pool 8+2beds
Farmhouse with private pool 8+2beds
Farmhouse with private pool 8+2beds
Farmhouse with private pool 8+2beds
Farmhouse with private pool 8+2beds
Farmhouse with private pool 8+2beds
Farmhouse with private pool 8+2beds
Farmhouse with private pool 8+2beds
Farmhouse with private pool 8+2beds
Pienza

Farmhouse with private pool 8+2beds

10 guests
150 m2
4 bedrooms
3 reviews

Rustic country house in the province of Siena, panoramic location, 500 m² garden, 150 m² living space, 4 bedrooms, 4 bathrooms, pool, WIFI, satellite TV, fireplace, bicycles

from 392 / night
Near Siena (6 km), in Chianti
Near Siena (6 km), in Chianti
Near Siena (6 km), in Chianti
Near Siena (6 km), in Chianti
Near Siena (6 km), in Chianti
Near Siena (6 km), in Chianti
Near Siena (6 km), in Chianti
Near Siena (6 km), in Chianti
Near Siena (6 km), in Chianti
Near Siena (6 km), in Chianti
Near Siena (6 km), in Chianti
Near Siena (6 km), in Chianti
Near Siena (6 km), in Chianti
Near Siena (6 km), in Chianti
Near Siena (6 km), in Chianti
Siena

Near Siena (6 km), in Chianti

7 guests
140 m2
3 bedrooms
3 reviews

Independent apartment in splendid 18th century mansion with typical Sienese architecture. Swimming pool and terrace, Wi-fi, A/C

Free cancellation
from 250 / night
Farmhouse with pool for 17 persons
Farmhouse with pool for 17 persons
Farmhouse with pool for 17 persons
Farmhouse with pool for 17 persons
Farmhouse with pool for 17 persons
Farmhouse with pool for 17 persons
Farmhouse with pool for 17 persons
Farmhouse with pool for 17 persons
Farmhouse with pool for 17 persons
Farmhouse with pool for 17 persons
Farmhouse with pool for 17 persons
Farmhouse with pool for 17 persons
Farmhouse with pool for 17 persons
Farmhouse with pool for 17 persons
Farmhouse with pool for 17 persons
Val d'Orcia

Farmhouse with pool for 17 persons

17 guests
400 m2
6 bedrooms

Charming country house in Val d'Orcia (Siena), 6500 m² garden with pool and playground, barbecue, pizza oven, table tennis, satellite TV, WIFI, bicycles

from 714 / night
Spinobianco
Spinobianco
Spinobianco
Spinobianco
Spinobianco
Spinobianco
Spinobianco
Spinobianco
Spinobianco
Spinobianco
Spinobianco
Spinobianco
Spinobianco
Spinobianco
Spinobianco
Chianciano Terme

Spinobianco

10 guests
160 m2
4 bedrooms (+1)

Charming Villa With Pool In Montepulciano Area

from 286 / night
CASA ROSANNA
CASA ROSANNA
CASA ROSANNA
CASA ROSANNA
CASA ROSANNA
CASA ROSANNA
CASA ROSANNA
CASA ROSANNA
CASA ROSANNA
CASA ROSANNA
CASA ROSANNA
CASA ROSANNA
CASA ROSANNA
CASA ROSANNA
CASA ROSANNA
Radicondoli

CASA ROSANNA

8 guests
120 m2
3 bedrooms (+1)

Charming tuscany villa with private pool and garden

from 110 / night
CASAVICO
CASAVICO
CASAVICO
CASAVICO
CASAVICO
CASAVICO
CASAVICO
CASAVICO
CASAVICO
CASAVICO
CASAVICO
CASAVICO
CASAVICO
CASAVICO
CASAVICO
Colle di Val d'Elsa

CASAVICO

5 guests
95 m2
3 bedrooms
1 review

Beautiful cottage with private pool ideal for spending a relaxing holiday in Tuscany

from 117 / night
Metina
Metina
Metina
Metina
Metina
Metina
Metina
Metina
Metina
Metina
Metina
Metina
Metina
Metina
Metina
Montepulciano

Metina

5 guests
110 m2
2 bedrooms

Spacious 2 floors apt for 5 people with amazing view. Garden, swimming pool, Wifi, barbecue Perfect for visiting Tuscany and Umbria. 6 km from Montepulciano and 2 km from shops.

Free cancellation
from 140 / night
Gaiole 2 with private swimming lake
Gaiole 2 with private swimming lake
Gaiole 2 with private swimming lake
Gaiole 2 with private swimming lake
Gaiole 2 with private swimming lake
Gaiole 2 with private swimming lake
Gaiole 2 with private swimming lake
Gaiole 2 with private swimming lake
Gaiole 2 with private swimming lake
Gaiole 2 with private swimming lake
Gaiole 2 with private swimming lake
Gaiole 2 with private swimming lake
Gaiole 2 with private swimming lake
Gaiole 2 with private swimming lake
Gaiole 2 with private swimming lake
Gaiole in Chianti

Gaiole 2 with private swimming lake

8 guests
115 m2
3 bedrooms

Lovingly restored holiday home for 6-8 people with private swimming lake in former farmhouse, located in the heart of the Chianti Classico area!

from 250 / night
Villa Montebello
Villa Montebello
Villa Montebello
Villa Montebello
Villa Montebello
Villa Montebello
Villa Montebello
Villa Montebello
Villa Montebello
Villa Montebello
Villa Montebello
Villa Montebello
Villa Montebello
Villa Montebello
Villa Montebello
Montalcinello

Villa Montebello

18 guests
800 m2
8 bedrooms (+1)
from 575 / night
10%
VILLA DORA
VILLA DORA
VILLA DORA
VILLA DORA
VILLA DORA
VILLA DORA
VILLA DORA
VILLA DORA
VILLA DORA
VILLA DORA
VILLA DORA
VILLA DORA
VILLA DORA
VILLA DORA
VILLA DORA
Montalcinello

VILLA DORA

13 guests
400 m2
8 bedrooms

Elegant and refined pool Villa in medieval village in Tuscany

-10% discount 04/26/2025 - 09/26/2025

from 261 / night
COLOMBAIA
COLOMBAIA
COLOMBAIA
COLOMBAIA
COLOMBAIA
COLOMBAIA
COLOMBAIA
COLOMBAIA
COLOMBAIA
COLOMBAIA
COLOMBAIA
COLOMBAIA
COLOMBAIA
COLOMBAIA
COLOMBAIA
Montecastelli Pisano

COLOMBAIA

8 guests
120 m2
3 bedrooms (+3)
3 reviews

Typical Tuscan country farmhouse converted into a perfect holiday house for families or groups of friends

from 135 / night
Apartment LA CASINA with pool
Apartment LA CASINA with pool
Apartment LA CASINA with pool
Apartment LA CASINA with pool
Apartment LA CASINA with pool
Apartment LA CASINA with pool
Apartment LA CASINA with pool
Apartment LA CASINA with pool
Apartment LA CASINA with pool
Apartment LA CASINA with pool
Apartment LA CASINA with pool
Apartment LA CASINA with pool
Apartment LA CASINA with pool
Apartment LA CASINA with pool
Apartment LA CASINA with pool
Radicondoli

Apartment LA CASINA with pool

4 guests
65 m2
2 bedrooms
1 review

The apartment LA CASINA is part of an ancient farmhouse immersed in the green of the Tuscan hills and in the center of a wildlife reserve.

Free cancellation

Sustainable

from 95 / night
Holiday home relaxing holiday Gaiole in Chianti
Holiday home relaxing holiday Gaiole in Chianti
Holiday home relaxing holiday Gaiole in Chianti
Holiday home relaxing holiday Gaiole in Chianti
Holiday home relaxing holiday Gaiole in Chianti
Holiday home relaxing holiday Gaiole in Chianti
Holiday home relaxing holiday Gaiole in Chianti
Holiday home relaxing holiday Gaiole in Chianti
Holiday home relaxing holiday Gaiole in Chianti
Holiday home relaxing holiday Gaiole in Chianti
Holiday home relaxing holiday Gaiole in Chianti
Holiday home relaxing holiday Gaiole in Chianti
Holiday home relaxing holiday Gaiole in Chianti
Gaiole in Chianti

Holiday home relaxing holiday Gaiole in Chianti

6 guests
65 m2
2 bedrooms

This typical stone farm is located on the Chianti hills bewteen Siena (17 Km) and Gaiola in Chainti (12 Km).

from 205 / night
HUT OF SILVIA
HUT OF SILVIA
HUT OF SILVIA
HUT OF SILVIA
HUT OF SILVIA
HUT OF SILVIA
HUT OF SILVIA
HUT OF SILVIA
HUT OF SILVIA
HUT OF SILVIA
HUT OF SILVIA
HUT OF SILVIA
HUT OF SILVIA
HUT OF SILVIA
HUT OF SILVIA
Colle di Val d'Elsa

HUT OF SILVIA

4 guests
50 m2
1 bedroom (+1)

La Capanna di Silvia is located in a panoramic and strategic location, within easy reach of the most beautiful towns and villages in Tuscany

from 113 / night
Girasole
Girasole
Girasole
Girasole
Girasole
Girasole
Girasole
Girasole
Girasole
Girasole
Girasole
Girasole
Girasole
Girasole
Girasole
Monteriggioni

Girasole

4 guests
100 m2
2 bedrooms
from 162 / night
Holiday home relaxing holiday Siena
Holiday home relaxing holiday Siena
Holiday home relaxing holiday Siena
Holiday home relaxing holiday Siena
Holiday home relaxing holiday Siena
Holiday home relaxing holiday Siena
Holiday home relaxing holiday Siena
Holiday home relaxing holiday Siena
Holiday home relaxing holiday Siena
Holiday home relaxing holiday Siena
Holiday home relaxing holiday Siena
Holiday home relaxing holiday Siena
Holiday home relaxing holiday Siena
Holiday home relaxing holiday Siena
Holiday home relaxing holiday Siena
Siena

Holiday home relaxing holiday Siena

4 guests
50 m2
2 bedrooms
from 100 / night
PANORAMIC APARTMENT
PANORAMIC APARTMENT
PANORAMIC APARTMENT
PANORAMIC APARTMENT
PANORAMIC APARTMENT
PANORAMIC APARTMENT
PANORAMIC APARTMENT
PANORAMIC APARTMENT
PANORAMIC APARTMENT
PANORAMIC APARTMENT
PANORAMIC APARTMENT
PANORAMIC APARTMENT
Radicondoli

PANORAMIC APARTMENT

4 guests
50 m2
1 bedroom (+1)

Flat in the ancient village of Radicondoli in Tuscany, 50m², 1 room, sleeps 4.

Free cancellation

Very sustainable

from 80 / night

Guest Reviews of Vacation Rentals in Siena & surrounding area

These accommodations are rated the best by vacationers

October 2024

Tobias F. from Langenfeld(Rheinland)

5.0

Verified guest from Tourist-paradise.com

Relaxing vacation in the heart of Tuscany

CASAVICO

Colle di Val d'Elsa

View German

Relaxing vacation in the heart of Tuscany

Hello everyone.

We felt very comfortable during the week at Pietro and Erika's.

The house is in a secluded location and is only surrounded by a few farmsteads. The entire property is fenced, making it dog-friendly.

However, it should be mentioned that Boscona is situated in the middle of a hunting area, and we heard distinct gunshots on some evenings. This may be a consideration for owners of anxious pets.

Otherwise, the house is well-equipped. We used the pool; the pool robot needs to be turned on by the tenants once in the evening.

The water temperature and water pressure in the sanitary facilities were good.

There are a total of 3 rooms for up to 5 people. It can be a bit cramped for taller individuals on the upper floor, as the ceilings are relatively low.

The kitchen is well-equipped, with a dishwasher and washing machine available.

The location of the house allows for excursions into the heart of Tuscany, St. Gimignano, Siena, Volterra can be reached within 30 minutes. Florence or the beach of Marina di Bibona takes 60-90 minutes.

In nearby Cole Val D'elsa, you can find supermarkets, restaurants, and opportunities for nature excursions (waterfall).

The check-in and check-out process was straightforward and familiar. Once again, great praise to Erika for the very good and prompt correspondence via WhatsApp.

We can only recommend this beautiful house, which offers an exceptional price-performance ratio.

The best travel time in terms of climate is September. In summer, there are indeed many mosquitoes.

We would love to come back!

Best regards, Felina, Nala, Tobias


from 117€ night

May 2021

Nathalie H. from D-55263 Wackernheim

5.0

Verified guest from Tourist-paradise.com

Holiday May 2021

Ancient tower with private pool 5+1

Gaiole in Chianti

View German

Holiday May 2021

The holiday home has a wonderful quiet location with a great big pool.
From the pool you have a fantastic view of the Tuscan countryside.
The landlord is very attentive and the house is very clean and tastefully restored.


from 286€ night

October 2017

Markus Z. from Magdeburg

5.0

Verified guest from Tourist-paradise.com

Beautiful holiday house in Chianti

Ancient tower with private pool 5+1

Gaiole in Chianti

View German

Beautiful holiday house in Chianti

- very beautiful panoramic view
- beautiful holiday home with very good facilities in a quiet location (very clean)
- recommended restaurant in town
- many excursion possibilities nearby (central location)
- very suitable for cycling / motorcycling


from 286€ night

Vacation ideas for your holiday home vacation in Siena & surrounding area

Dog friendly holidays in Siena & surrounding area

Dog friendly holidays in Siena & surrounding area

holiday homes with pool in Siena & surrounding area

holiday homes with pool in Siena & surrounding area

beach holiday in Siena & surrounding area

beach holiday in Siena & surrounding area

sightseeing, city tours in Siena & surrounding area

sightseeing, city tours in Siena & surrounding area

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157 dreamy accommodations in the most beautiful places Siena & vicinity

Other popular regions for your holiday in Siena & surrounding area

Information about holiday homes & apartments in Siena & surrounding area

Helpful Information

Available vacation rentals
157 offers
Possible discounts
up to 20%
Min. price per night
from 54 €
Popular amenities
dog friendly vacation, TV, Wifi, garden and swimming pool
Pets allowed
99 offers
Accommodations with pool
133 offers

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