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96 Holiday apartments & homes for a holiday with your dog in Siena & surrounding area

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
Top advertisement
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

12%
Villa Alari
Villa Alari
Villa Alari
Villa Alari
Villa Alari
Villa Alari
Villa Alari
Villa Alari
Villa Alari
Villa Alari
Villa Alari
Villa Alari
Villa Alari
Villa Alari
Villa Alari
Top advertisement
Cetona

Villa Alari

14 guests
450 m2
5 bedrooms

Villa for 14 people with private pool and hot tub. Located on a 40-hectare farmstead, with vineyards, olive groves, and private forest.

-12% discount 04/21/2025 - 04/30/2025

Free cancellation
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

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 - 05/30/2025

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

10%
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

-10% discount 04/20/2025 - 05/17/2025

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

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

10%
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

-10% discount 04/05/2025 - 06/20/2025

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
2 reviews

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
15%
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

-15% discount 04/01/2025 - 05/31/2025

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).

Raffaele
Raffaele
Raffaele
Raffaele
Raffaele
Raffaele
Raffaele
Raffaele
Raffaele
Raffaele
Raffaele
Raffaele
Raffaele
Raffaele
Raffaele
Chianciano Terme

Raffaele

10 guests
160 m2
4 bedrooms

It is located only 13 km from Montepulciano. You will find a Coop supermarket, tennis courts, banks, petrol stations, restaurants and the post office within 6-7 km from the house.

Villa San Pierino
Villa San Pierino
Villa San Pierino
Villa San Pierino
Villa San Pierino
Villa San Pierino
Villa San Pierino
Villa San Pierino
Villa San Pierino
Villa San Pierino
Villa San Pierino
Villa San Pierino
Villa San Pierino
Villa San Pierino
Top advertisement
Radicondoli

Villa San Pierino

6 guests
100 m2
3 bedrooms

Holiday home San Pierino in Tuscany near Siena, 100m² for up to 6 people, quiet, panoramic location.

Free cancellation
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
Top advertisement
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

20%
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
90 m2
2 bedrooms

up to -20% discount 03/29/2025 - 04/23/2025

Belvilla by OYO Nando
Belvilla by OYO Nando
Belvilla by OYO Nando
Belvilla by OYO Nando
Belvilla by OYO Nando
Belvilla by OYO Nando
Belvilla by OYO Nando
Belvilla by OYO Nando
Belvilla by OYO Nando
Belvilla by OYO Nando
Belvilla by OYO Nando
Belvilla by OYO Nando
Belvilla by OYO Nando
Belvilla by OYO Nando
Belvilla by OYO Nando
Asciano
Belvilla by OYO Nando
5 guests
80 m2
2 bedrooms
3 reviews

Ground floor: (open kitchen(toaster, cooker(4 ring stoves, gas), espresso machine, oven, fridge-freezer), Living/diningroom(single sofa bed, TV, fireplace)

Free cancellation
Belvilla by OYO Garbo
Belvilla by OYO Garbo
Belvilla by OYO Garbo
Belvilla by OYO Garbo
Belvilla by OYO Garbo
Belvilla by OYO Garbo
Belvilla by OYO Garbo
Belvilla by OYO Garbo
Belvilla by OYO Garbo
Belvilla by OYO Garbo
Belvilla by OYO Garbo
Belvilla by OYO Garbo
Belvilla by OYO Garbo
Belvilla by OYO Garbo
Belvilla by OYO Garbo
Asciano
Belvilla by OYO Garbo
6 guests
80 m2
3 bedrooms
1 review

Ground floor: (Living room(TV, fireplace, seating area), Large kitchen(dining table, toaster, cooker(4 ring stoves, gas)

Free cancellation
Belvilla by OYO La Verbena
Belvilla by OYO La Verbena
Belvilla by OYO La Verbena
Belvilla by OYO La Verbena
Belvilla by OYO La Verbena
Belvilla by OYO La Verbena
Belvilla by OYO La Verbena
Belvilla by OYO La Verbena
Belvilla by OYO La Verbena
Belvilla by OYO La Verbena
Belvilla by OYO La Verbena
Belvilla by OYO La Verbena
Belvilla by OYO La Verbena
Belvilla by OYO La Verbena
Belvilla by OYO La Verbena
Montalcino
Belvilla by OYO La Verbena
6 guests
100 m2
2 bedrooms
5 reviews

On the 1st floor: (Living room(TV, fireplace), open kitchen, bedroom(single bed, double bed), bedroom(single bed, bunk bed), bathroom(shower, washbasin, toilet, bidet))

Free cancellation
Belvilla by Oyo Casa Tiglio
Belvilla by Oyo Casa Tiglio
Belvilla by Oyo Casa Tiglio
Belvilla by Oyo Casa Tiglio
Belvilla by Oyo Casa Tiglio
Belvilla by Oyo Casa Tiglio
Belvilla by Oyo Casa Tiglio
Belvilla by Oyo Casa Tiglio
Belvilla by Oyo Casa Tiglio
Belvilla by Oyo Casa Tiglio
Belvilla by Oyo Casa Tiglio
Belvilla by Oyo Casa Tiglio
Belvilla by Oyo Casa Tiglio
Belvilla by Oyo Casa Tiglio
Belvilla by Oyo Casa Tiglio
Castiglione d'Orcia
Belvilla by Oyo Casa Tiglio
8 guests
120 m2
4 bedrooms
6 reviews

Ground floor: (hallway, Living room(fireplace, seating area), dining room(dining table), Kitchen(oven, dishwasher), bedroom(double bed or 2 single beds), bedroom(2x single bed)

Free cancellation
Farmhouse in Arbia Asciano with pool
Farmhouse in Arbia Asciano with pool
Farmhouse in Arbia Asciano with pool
Farmhouse in Arbia Asciano with pool
Farmhouse in Arbia Asciano with pool
Farmhouse in Arbia Asciano with pool
Farmhouse in Arbia Asciano with pool
Farmhouse in Arbia Asciano with pool
Farmhouse in Arbia Asciano with pool
Farmhouse in Arbia Asciano with pool
Farmhouse in Arbia Asciano with pool
Farmhouse in Arbia Asciano with pool
Farmhouse in Arbia Asciano with pool
Farmhouse in Arbia Asciano with pool
Farmhouse in Arbia Asciano with pool
Siena
Farmhouse in Arbia Asciano with pool
8 guests
100 m2
4 bedrooms
6 reviews

On the 1st floor: (Living room(fireplace), Large kitchen(hob, cooker, hood, espresso machine, oven, microwave, fridge-freezer), bedroom(double bed), bedroom(2x single bed)

Free cancellation
Belvilla by OYO Ginestra2
Belvilla by OYO Ginestra2
Belvilla by OYO Ginestra2
Belvilla by OYO Ginestra2
Belvilla by OYO Ginestra2
Belvilla by OYO Ginestra2
Belvilla by OYO Ginestra2
Belvilla by OYO Ginestra2
Belvilla by OYO Ginestra2
Belvilla by OYO Ginestra2
Belvilla by OYO Ginestra2
Belvilla by OYO Ginestra2
Belvilla by OYO Ginestra2
Belvilla by OYO Ginestra2
Belvilla by OYO Ginestra2
Siena
Belvilla by OYO Ginestra2
4 guests
45 m2
1 bedroom
1 review

Ground floor: (open kitchen(hob, electric kettle, boiling water tap, cooker, hood, coffee machine, fridge-freezer), Living/diningroom(single bed, single sofa bed, dining table)

Free cancellation
Belvilla by OYO Villa Valardegna
Belvilla by OYO Villa Valardegna
Belvilla by OYO Villa Valardegna
Belvilla by OYO Villa Valardegna
Belvilla by OYO Villa Valardegna
Belvilla by OYO Villa Valardegna
Belvilla by OYO Villa Valardegna
Belvilla by OYO Villa Valardegna
Belvilla by OYO Villa Valardegna
Belvilla by OYO Villa Valardegna
Belvilla by OYO Villa Valardegna
Belvilla by OYO Villa Valardegna
Belvilla by OYO Villa Valardegna
Belvilla by OYO Villa Valardegna
Belvilla by OYO Villa Valardegna
Montepulciano
Belvilla by OYO Villa Valardegna
15 guests
550 m2
7 bedrooms
4 reviews

Ground floor: (bedroom(2x single bed), Bedroom with bathroom(double bed, Bubble bath, washbasin, toilet, bidet)

Free cancellation
5%
Holiday flat family holiday Siena
Holiday flat family holiday Siena
Holiday flat family holiday Siena
Holiday flat family holiday Siena
Holiday flat family holiday Siena
Holiday flat family holiday Siena
Holiday flat family holiday Siena
Holiday flat family holiday Siena
Holiday flat family holiday Siena
Holiday flat family holiday Siena
Holiday flat family holiday Siena
Holiday flat family holiday Siena
Holiday flat family holiday Siena
Holiday flat family holiday Siena
Holiday flat family holiday Siena
Siena
Holiday flat family holiday Siena
6 guests
85 m2
2 bedrooms

up to -5% discount 03/25/2025 - 09/29/2025

Holiday flat family holiday Siena
Holiday flat family holiday Siena
Holiday flat family holiday Siena
Holiday flat family holiday Siena
Holiday flat family holiday Siena
Holiday flat family holiday Siena
Holiday flat family holiday Siena
Holiday flat family holiday Siena
Holiday flat family holiday Siena
Holiday flat family holiday Siena
Holiday flat family holiday Siena
Siena
Holiday flat family holiday Siena
10 guests
120 m2
4 bedrooms
Free cancellation

Guest Reviews of Vacation Rentals in Siena & surrounding area

These accommodations are rated the best by vacationers

4.1

Belvilla by OYO Chiaraquattro

Siena

View Dutch

Nice (small) house with pool. Clean bathroom and pool. Small downside was only 1 set of sheets towels per person and cutlery was still dirty. But definitely worth it and a good price / quality ratio. With outdoor shower, ventilation in the rooms, ...


from 43€ night
4.3

Belvilla by OYO Tinaia

Siena

View Spanish

A lovely place for a family vacation! The proximity to Siena allowed us to enjoy the city without feeling too crowded. The local attractions were just a short drive away.


from 191€ night
4.4

Verified guest from Tourist-paradise.com

Top location

Private holiday home with pool (7 + 1)

San Giovanni d'Asso

View German

Top location

We have been to Tuscany for the 4th time now, this house is what we have always been looking for, beautiful location and tranquility, simply fantastic. We have recovered very well and will definitely come back. Our dogs also felt very comfortable.


from 158€ night

Popular regions and locations for your Dog friendly holidays in Siena & surrounding area

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