Sort by
map
All filters (1)

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

15%
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.

Free cancellation

15% Promotion 11/16/2026 - 03/24/2027

from 585 / night
prices from 586€ per night
View
5%
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
1 bedroom (+1)

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 100 / night
5.0
prices from 100€ per night
View
5%
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

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

Sustainable

5% Early-Bird 11/01/2027 - 04/28/2028

from 90 / night
5.0
prices from 90€ per night
View
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% Promotion 06/06/2026 - 06/13/2026

from 238 / night
prices from 238€ per night
View
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 127 / night
prices from 128€ per night
View
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)

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

from 140 / night
4.7
prices from 140€ per night
View
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

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

from 158 / night
4.4
prices from 158€ per night
View
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

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

from 130 / night
5.0
prices from 130€ per night
View
Virgilius
Virgilius
Virgilius
Virgilius
Virgilius
Virgilius
Virgilius
Virgilius
Virgilius
Virgilius
Virgilius
Virgilius
Virgilius
Virgilius
Virgilius
Radicondoli

Virgilius

6 guests
90 m2
3 bedrooms

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

from 155 / night
3.3
prices from 155€ per night
View
Casa Murlo
Casa Murlo
Casa Murlo
Casa Murlo
Casa Murlo
Casa Murlo
Casa Murlo
Casa Murlo
Casa Murlo
Casa Murlo
Casa Murlo
Casa Murlo
Casa Murlo
Casa Murlo
Casa Murlo
Torrita di Siena

Casa Murlo

4 guests
75 m2
1 bedroom (+1)

House in a farmhouse in the Tuscan countryside, with private garden, located in a panoramic position

Free cancellation
from 90 / night
5.0
prices from 90€ per night
View
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

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 244 / night
5.0
prices from 244€ per night
View
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.

from 316 / night
prices from 316€ per night
View
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
prices from 205€ per night
View
Tranquil Stay in Montepulciano
Tranquil Stay in Montepulciano
Tranquil Stay in Montepulciano
Tranquil Stay in Montepulciano
Tranquil Stay in Montepulciano
Tranquil Stay in Montepulciano
Tranquil Stay in Montepulciano
Tranquil Stay in Montepulciano
Tranquil Stay in Montepulciano
Tranquil Stay in Montepulciano
Tranquil Stay in Montepulciano
Tranquil Stay in Montepulciano
Tranquil Stay in Montepulciano
Tranquil Stay in Montepulciano
Tranquil Stay in Montepulciano
Siena
Tranquil Stay in Montepulciano
4 guests
50 m2
2 bedrooms

Ground floor: (Large kitchen(TV, coffee machine(filter), oven, dishwasher, fridge, high chair)

Free cancellation
from 51 / night
4.1
prices from 52€ per night
View
Villa in Tuscany with Wine Tours & Pools
Villa in Tuscany with Wine Tours & Pools
Villa in Tuscany with Wine Tours & Pools
Villa in Tuscany with Wine Tours & Pools
Villa in Tuscany with Wine Tours & Pools
Villa in Tuscany with Wine Tours & Pools
Villa in Tuscany with Wine Tours & Pools
Villa in Tuscany with Wine Tours & Pools
Villa in Tuscany with Wine Tours & Pools
Villa in Tuscany with Wine Tours & Pools
Villa in Tuscany with Wine Tours & Pools
Villa in Tuscany with Wine Tours & Pools
Villa in Tuscany with Wine Tours & Pools
Villa in Tuscany with Wine Tours & Pools
Villa in Tuscany with Wine Tours & Pools
Siena
Villa in Tuscany with Wine Tours & Pools
10 guests
140 m2
5 bedrooms

On the 1st floor: (Living room(fireplace), Living room, open kitchen(fridge-freezer), open kitchen, bedroom(2x single bed), bedroom(double bed), bedroom(2x single bed)

Free cancellation
from 159 / night
4.3
prices from 159€ per night
View
Holiday flat family holiday Asciano
Holiday flat family holiday Asciano
Holiday flat family holiday Asciano
Holiday flat family holiday Asciano
Holiday flat family holiday Asciano
Holiday flat family holiday Asciano
Holiday flat family holiday Asciano
Holiday flat family holiday Asciano
Holiday flat family holiday Asciano
Holiday flat family holiday Asciano
Holiday flat family holiday Asciano
Holiday flat family holiday Asciano
Holiday flat family holiday Asciano
Holiday flat family holiday Asciano
Holiday flat family holiday Asciano
Asciano
Holiday flat family holiday Asciano
6 guests
80 m2
3 bedrooms
from 85 / night
4.4
prices from 86€ per night
View
Farmhouse in Tuscany with Pool & Scenic Views
Farmhouse in Tuscany with Pool & Scenic Views
Farmhouse in Tuscany with Pool & Scenic Views
Farmhouse in Tuscany with Pool & Scenic Views
Farmhouse in Tuscany with Pool & Scenic Views
Farmhouse in Tuscany with Pool & Scenic Views
Farmhouse in Tuscany with Pool & Scenic Views
Farmhouse in Tuscany with Pool & Scenic Views
Farmhouse in Tuscany with Pool & Scenic Views
Farmhouse in Tuscany with Pool & Scenic Views
Farmhouse in Tuscany with Pool & Scenic Views
Farmhouse in Tuscany with Pool & Scenic Views
Farmhouse in Tuscany with Pool & Scenic Views
Farmhouse in Tuscany with Pool & Scenic Views
Farmhouse in Tuscany with Pool & Scenic Views
Asciano
Farmhouse in Tuscany with Pool & Scenic Views
4 guests
55 m2
1 bedroom

Ground floor: (Living room(single sofa bed, TV(satellite)), open kitchen(hob, coffee machine, oven, dishwasher, fridge-freezer, washbasin), bedroom(double bed)

Free cancellation
from 49 / night
4.5
prices from 50€ per night
View
Sunny Apartment with Pool
Sunny Apartment with Pool
Sunny Apartment with Pool
Sunny Apartment with Pool
Sunny Apartment with Pool
Sunny Apartment with Pool
Sunny Apartment with Pool
Sunny Apartment with Pool
Sunny Apartment with Pool
Sunny Apartment with Pool
Sunny Apartment with Pool
Sunny Apartment with Pool
Sunny Apartment with Pool
Sunny Apartment with Pool
Sunny Apartment with Pool
Siena
Sunny Apartment with Pool
3 guests
37 m2
1 bedroom

Ground floor: (Living room(single sofa bed, TV), open kitchen, bedroom(double bed), bathroom(shower, washbasin, toilet, bidet)) terrace(private), garden(shared with other guests)

Free cancellation
from 104 / night
prices from 104€ per night
View
Authentic pool house
Authentic pool house
Authentic pool house
Authentic pool house
Authentic pool house
Authentic pool house
Authentic pool house
Authentic pool house
Authentic pool house
Authentic pool house
Authentic pool house
Authentic pool house
Authentic pool house
Authentic pool house
Authentic pool house
Pienza
Authentic pool house
6 guests
110 m2
2 bedrooms

On the 1st floor: (Large kitchen(TV, fireplace, oven, freezer, heating), bedroom(single sofa bed, double bed), bedroom(single bed, double bed)

Free cancellation
from 35 / night
4.2
prices from 35€ per night
View
Holiday home relaxing holiday Radicofani
Holiday home relaxing holiday Radicofani
Holiday home relaxing holiday Radicofani
Holiday home relaxing holiday Radicofani
Holiday home relaxing holiday Radicofani
Holiday home relaxing holiday Radicofani
Holiday home relaxing holiday Radicofani
Holiday home relaxing holiday Radicofani
Holiday home relaxing holiday Radicofani
Holiday home relaxing holiday Radicofani
Holiday home relaxing holiday Radicofani
Holiday home relaxing holiday Radicofani
Holiday home relaxing holiday Radicofani
Holiday home relaxing holiday Radicofani
Holiday home relaxing holiday Radicofani
Radicofani
Holiday home relaxing holiday Radicofani
8 guests
160 m2
3 bedrooms
from 169 / night
5.0
prices from 170€ per night
View
Scenic Tuscan Farmhouse
Scenic Tuscan Farmhouse
Scenic Tuscan Farmhouse
Scenic Tuscan Farmhouse
Scenic Tuscan Farmhouse
Scenic Tuscan Farmhouse
Scenic Tuscan Farmhouse
Scenic Tuscan Farmhouse
Scenic Tuscan Farmhouse
Scenic Tuscan Farmhouse
Scenic Tuscan Farmhouse
Scenic Tuscan Farmhouse
Scenic Tuscan Farmhouse
Scenic Tuscan Farmhouse
Scenic Tuscan Farmhouse
Castiglione d'Orcia
Scenic Tuscan Farmhouse
8 guests
120 m2
4 bedrooms

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
from 151 / night
4.5
prices from 151€ per night
View
Elegant Villa in Tuscany
Elegant Villa in Tuscany
Elegant Villa in Tuscany
Elegant Villa in Tuscany
Elegant Villa in Tuscany
Elegant Villa in Tuscany
Elegant Villa in Tuscany
Elegant Villa in Tuscany
Elegant Villa in Tuscany
Elegant Villa in Tuscany
Elegant Villa in Tuscany
Elegant Villa in Tuscany
Elegant Villa in Tuscany
Elegant Villa in Tuscany
Elegant Villa in Tuscany
Siena
Elegant Villa in Tuscany
8 guests
180 m2
4 bedrooms

Ground floor: (Kitchen(cooker(4 ring stoves), oven, dishwasher, fridge-freezer, washing machine)) On the 1st floor: (Living room(TV(satellite), fireplace, DVD player)

Free cancellation
from 160 / night
4.2
prices from 160€ per night
View
Belvilla by OYO Il Melograno
Belvilla by OYO Il Melograno
Belvilla by OYO Il Melograno
Belvilla by OYO Il Melograno
Belvilla by OYO Il Melograno
Belvilla by OYO Il Melograno
Belvilla by OYO Il Melograno
Belvilla by OYO Il Melograno
Belvilla by OYO Il Melograno
Belvilla by OYO Il Melograno
Belvilla by OYO Il Melograno
Belvilla by OYO Il Melograno
Belvilla by OYO Il Melograno
Belvilla by OYO Il Melograno
Belvilla by OYO Il Melograno
Siena
Belvilla by OYO Il Melograno
4 guests
40 m2
1 bedroom

On the 1st floor: (Large kitchen(hob, microwave, fridge, washbasin), Living/diningroom(double sofa bed, TV, dining table), bedroom(double bed)

Free cancellation
from 58 / night
4.0
prices from 59€ per night
View
Rustic Escape with Pool
Rustic Escape with Pool
Rustic Escape with Pool
Rustic Escape with Pool
Rustic Escape with Pool
Rustic Escape with Pool
Rustic Escape with Pool
Rustic Escape with Pool
Rustic Escape with Pool
Rustic Escape with Pool
Rustic Escape with Pool
Rustic Escape with Pool
Rustic Escape with Pool
Rustic Escape with Pool
Rustic Escape with Pool
Siena
Rustic Escape with Pool
6 guests
80 m2
3 bedrooms

Ground floor: (Living room(TV, seating area), open kitchen(dining table, coffee machine, oven), bedroom(double bed), bedroom(double bed), bedroom(2x single bed)

Free cancellation
from 69 / night
4.5
prices from 70€ per night
View
Peaceful Pienza Garden Escape
Peaceful Pienza Garden Escape
Peaceful Pienza Garden Escape
Peaceful Pienza Garden Escape
Peaceful Pienza Garden Escape
Peaceful Pienza Garden Escape
Peaceful Pienza Garden Escape
Peaceful Pienza Garden Escape
Peaceful Pienza Garden Escape
Peaceful Pienza Garden Escape
Peaceful Pienza Garden Escape
Peaceful Pienza Garden Escape
Peaceful Pienza Garden Escape
Peaceful Pienza Garden Escape
Peaceful Pienza Garden Escape
Pienza
Peaceful Pienza Garden Escape
3 guests
40 m2
1 bedroom

Ground floor: (Large kitchen(TV, oven, freezer, heating), bedroom(single bed, bunk bed), bathroom(shower, washbasin, toilet, bidet)) terrace(private)

Free cancellation
from 18 / night
4.2
prices from 18€ per night
View

Guest reviews of our holiday apartments in Siena & surrounding area

5.0

Holiday home relaxing holiday Siena

Siena

View German

The holiday home is perfect for an unforgettable holiday. The owner Michele is very friendly, looks after his guests perfectly and gives lots of tips for things to do in the area if required. The house and grounds are very clean and well maintained. The equipment is excellent and leaves nothing to be desired. Our family enjoyed every minute in this oasis.


from 160€ night
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 130€ night
4.4

Verified guest from Tourist-paradise.com

Vacation in Tuscany

Private holiday home with pool (7 + 1)

San Giovanni d'Asso

View German

Vacation in Tuscany

Lovingly furnished house with its own pool (the highlight!)
Pure relaxation for stressed people with a great view of the surroundings. Delicious honey can be purchased next door.
The owners are super nice and caring. All questions were answered immediately, generally always a listening ear!
We were happy to be guests here - we really liked it.
Tip -> an off-road vehicle is advantageous.


from 158€ night

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

Rent out now on Ferienhausmiete.de

Are you still looking for the right holidaymakers for your holiday home or apartment?