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109 Holiday apartments & homes for a holiday with pool in Siena & surrounding area

13%
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

13% Promotion 06/06/2026 - 06/13/2026

from 238 / night
prices from 238€ per night
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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

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 200 / night
4.9
prices from 200€ per night
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15%
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)

15% Promotion 06/05/2026 - 06/06/2026

from 575 / night
prices from 575€ per night
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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
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
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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
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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
prices from 180€ per night
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10%
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

10% Last-Minute 06/05/2026 - 06/12/2026

from 90 / night
5.0
prices from 90€ per night
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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
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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
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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 108 / night
prices from 108€ per night
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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
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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 130 / night
prices from 130€ per night
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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
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
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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
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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 108 / night
prices from 108€ per night
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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

from 378 / night
prices from 378€ per night
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Palazzo a Merse
Palazzo a Merse
Palazzo a Merse
Palazzo a Merse
Palazzo a Merse
Palazzo a Merse
Palazzo a Merse
Palazzo a Merse
Palazzo a Merse
Palazzo a Merse
Palazzo a Merse
Palazzo a Merse
Palazzo a Merse
Palazzo a Merse
Palazzo a Merse
Sovicille

Palazzo a Merse

4 guests
80 m2
2 bedrooms

Holiday home for a relaxing vacation Sovicille: 80 m², 2 rooms, for up to 4 people in Tuscany.

Free cancellation

Sustainable

from 120 / night
prices from 120€ per night
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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
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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 391 / night
prices from 391€ per night
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A Spacious Retreat for Ten
A Spacious Retreat for Ten
A Spacious Retreat for Ten
A Spacious Retreat for Ten
A Spacious Retreat for Ten
A Spacious Retreat for Ten
A Spacious Retreat for Ten
A Spacious Retreat for Ten
A Spacious Retreat for Ten
A Spacious Retreat for Ten
A Spacious Retreat for Ten
A Spacious Retreat for Ten
A Spacious Retreat for Ten
A Spacious Retreat for Ten
A Spacious Retreat for Ten
Siena
A Spacious Retreat for Ten
10 guests
150 m2
3 bedrooms

On the 1st floor: (open kitchen(hob, electric kettle, boiling water tap, coffee machine, fridge, insect screens, Juicer)

Free cancellation
from 125 / night
4.2
prices from 125€ per night
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Farmhouse in Val d'Orcia Charm
Farmhouse in Val d'Orcia Charm
Farmhouse in Val d'Orcia Charm
Farmhouse in Val d'Orcia Charm
Farmhouse in Val d'Orcia Charm
Farmhouse in Val d'Orcia Charm
Farmhouse in Val d'Orcia Charm
Farmhouse in Val d'Orcia Charm
Farmhouse in Val d'Orcia Charm
Farmhouse in Val d'Orcia Charm
Farmhouse in Val d'Orcia Charm
Farmhouse in Val d'Orcia Charm
Farmhouse in Val d'Orcia Charm
Farmhouse in Val d'Orcia Charm
Farmhouse in Val d'Orcia Charm
Castiglione d'Orcia
Farmhouse in Val d'Orcia Charm
4 guests
55 m2
2 bedrooms

Ground floor: (Living room(seating area), Large kitchen(dining table, oven), bathroom(shower, washbasin, toilet, bidet)) On the 1st floor: (bedroom(double bed or 2 single beds)

Free cancellation
from 99 / night
4.5
prices from 99€ per night
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Belvilla by OYO Fiore
Belvilla by OYO Fiore
Belvilla by OYO Fiore
Belvilla by OYO Fiore
Belvilla by OYO Fiore
Belvilla by OYO Fiore
Belvilla by OYO Fiore
Belvilla by OYO Fiore
Belvilla by OYO Fiore
Belvilla by OYO Fiore
Belvilla by OYO Fiore
Belvilla by OYO Fiore
Belvilla by OYO Fiore
Belvilla by OYO Fiore
Belvilla by OYO Fiore
Montepulciano
Belvilla by OYO Fiore
9 guests
175 m2
4 bedrooms

Ground floor: (Living room(TV(satellite)), open kitchen(oven, microwave, dishwasher, fridge-freezer), bedroom(single bed, double bed)

Free cancellation
from 195 / night
4.5
prices from 195€ per night
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Belvilla by OYO Casa del Re
Belvilla by OYO Casa del Re
Belvilla by OYO Casa del Re
Belvilla by OYO Casa del Re
Belvilla by OYO Casa del Re
Belvilla by OYO Casa del Re
Belvilla by OYO Casa del Re
Belvilla by OYO Casa del Re
Belvilla by OYO Casa del Re
Belvilla by OYO Casa del Re
Belvilla by OYO Casa del Re
Belvilla by OYO Casa del Re
Belvilla by OYO Casa del Re
Belvilla by OYO Casa del Re
Belvilla by OYO Casa del Re
Siena
Belvilla by OYO Casa del Re
11 guests
300 m2
6 bedrooms

Ground floor: (Living room(TV, fireplace), dining room, open kitchen(cooker(4 ring stoves, gas), oven, microwave, dishwasher, fridge-freezer), toilet, air conditioning)

Free cancellation
from 359 / night
4.7
prices from 359€ per night
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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 161 / night
4.5
prices from 161€ per night
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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
4 guests
50 m2
1 bedroom
from 83 / night
4.3
prices from 84€ per night
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Guest reviews of our holiday apartments in Siena & surrounding area

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
4.0

Verified guest from Tourist-paradise.com

Lovely typical Tuscan holiday home

COLOMBAIA

Montecastelli Pisano

View German

Lovely typical Tuscan holiday home

The house is located in an absolutely quiet location. The beautiful Tuscan countryside is easily accessible. It is a 40-minute drive to the sea. Great private pool. Excursions to Siena and Volterra are doable in 45-60 minutes and worthwhile. Beach tip: Dog beach near Cecina. (There were hardly any dogs when we were there. It is a free beach, nicely located.) The house had everything you needed. Sufficient cutlery, etc. Definitely recommended.


from 140€ night

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