Sort by
map
All filters (1)

30 Holiday apartments & homes for a holiday with pool in San Gimignano & surrounding area

House Capannina
House Capannina
House Capannina
House Capannina
House Capannina
House Capannina
House Capannina
House Capannina
House Capannina
House Capannina
House Capannina
House Capannina
House Capannina
House Capannina
House Capannina
Cedri

House Capannina

4 guests
70 m2
2 bedrooms

A detached house with pool in the heart of Tuscany -Volterra

from 135 / night
5.0
prices from 135€ per night
View
LA CAMBRUNA
LA CAMBRUNA
LA CAMBRUNA
LA CAMBRUNA
LA CAMBRUNA
LA CAMBRUNA
LA CAMBRUNA
LA CAMBRUNA
LA CAMBRUNA
LA CAMBRUNA
LA CAMBRUNA
LA CAMBRUNA
LA CAMBRUNA
LA CAMBRUNA
LA CAMBRUNA
Casole d'Elsa

LA CAMBRUNA

4 guests
130 m2
2 bedrooms
from 232 / night
5.0
prices from 232€ per night
View
PEPERONCINO
PEPERONCINO
PEPERONCINO
PEPERONCINO
PEPERONCINO
PEPERONCINO
PEPERONCINO
PEPERONCINO
PEPERONCINO
PEPERONCINO
PEPERONCINO
PEPERONCINO
PEPERONCINO
PEPERONCINO
PEPERONCINO
Casole d'Elsa

PEPERONCINO

4 guests
85 m2
2 bedrooms

Charming cottages with private pool in Siena area

from 125 / night
4.7
prices from 125€ per night
View
10%
VILLA CAMILLA
VILLA CAMILLA
VILLA CAMILLA
VILLA CAMILLA
VILLA CAMILLA
VILLA CAMILLA
VILLA CAMILLA
VILLA CAMILLA
VILLA CAMILLA
VILLA CAMILLA
VILLA CAMILLA
VILLA CAMILLA
VILLA CAMILLA
VILLA CAMILLA
VILLA CAMILLA
Casole d'Elsa

VILLA CAMILLA

5 guests
110 m2
2 bedrooms (+1)

Cozy renovated farmhouse surrounded by a large garden, completely enclosed and provided with a private 5 x 10 large swimming pool

10% Promotion 05/02/2026 - 05/16/2026

from 130 / night
prices from 130€ per night
View
10%
PANORAMIC HOUSE
PANORAMIC HOUSE
PANORAMIC HOUSE
PANORAMIC HOUSE
PANORAMIC HOUSE
PANORAMIC HOUSE
PANORAMIC HOUSE
PANORAMIC HOUSE
PANORAMIC HOUSE
PANORAMIC HOUSE
PANORAMIC HOUSE
PANORAMIC HOUSE
PANORAMIC HOUSE
PANORAMIC HOUSE
PANORAMIC HOUSE
Casole d'Elsa

PANORAMIC HOUSE

4 guests
100 m2
2 bedrooms

The property is a lovingly renovated Tuscany cottage with private pool and garden for al fresco dining, ideal for families and couples seeking relaxation

10% Promotion 05/02/2026 - 05/22/2026

from 155 / night
prices from 155€ per night
View
THE CHAMPION
THE CHAMPION
THE CHAMPION
THE CHAMPION
THE CHAMPION
THE CHAMPION
THE CHAMPION
THE CHAMPION
THE CHAMPION
THE CHAMPION
THE CHAMPION
THE CHAMPION
THE CHAMPION
THE CHAMPION
THE CHAMPION
Casole d'Elsa

THE CHAMPION

12 guests
350 m2
6 bedrooms

Hilltop Tuscan Villa located between Siena and Pisa, stunning views, geogeous pool and garden, sleeps 12

from 243 / night
3.8
prices from 243€ per night
View
10%
Holiday home relaxing holiday Volterra - San Gimignano
Holiday home relaxing holiday Volterra - San Gimignano
Holiday home relaxing holiday Volterra - San Gimignano
Holiday home relaxing holiday Volterra - San Gimignano
Holiday home relaxing holiday Volterra - San Gimignano
Holiday home relaxing holiday Volterra - San Gimignano
Holiday home relaxing holiday Volterra - San Gimignano
Holiday home relaxing holiday Volterra - San Gimignano
Holiday home relaxing holiday Volterra - San Gimignano
Holiday home relaxing holiday Volterra - San Gimignano
Holiday home relaxing holiday Volterra - San Gimignano
Holiday home relaxing holiday Volterra - San Gimignano
Holiday home relaxing holiday Volterra - San Gimignano
Holiday home relaxing holiday Volterra - San Gimignano
Holiday home relaxing holiday Volterra - San Gimignano
Volterra - San Gimignano

Holiday home relaxing holiday Volterra - San Gimignano

4 guests
80 m2
2 bedrooms

10% Promotion 05/16/2026 - 05/23/2026

from 126 / night
5.0
prices from 126€ per night
View
Fico Nero
Fico Nero
Fico Nero
Fico Nero
Fico Nero
Fico Nero
Fico Nero
Fico Nero
Fico Nero
Fico Nero
Fico Nero
Fico Nero
Fico Nero
Fico Nero
Fico Nero
San Gimignano

Fico Nero

11 guests
250 m2
5 bedrooms
from 242 / night
prices from 242€ per night
View
Casa Ecologica
Casa Ecologica
Casa Ecologica
Casa Ecologica
Casa Ecologica
Casa Ecologica
Casa Ecologica
Casa Ecologica
Casa Ecologica
Casa Ecologica
Casa Ecologica
Casa Ecologica
Casa Ecologica
Casa Ecologica
Casa Ecologica
Casole d'Elsa

Casa Ecologica

2 guests
50 m2
1 bedroom

Charming eco-house for 2 people on a farm near Casole d'Elsa - Swimming pool - Pure nature

Very sustainable

from 140 / night
prices from 140€ per night
View
Holiday home relaxing holiday San Gimignano
Holiday home relaxing holiday San Gimignano
Holiday home relaxing holiday San Gimignano
Holiday home relaxing holiday San Gimignano
Holiday home relaxing holiday San Gimignano
Holiday home relaxing holiday San Gimignano
Holiday home relaxing holiday San Gimignano
Holiday home relaxing holiday San Gimignano
Holiday home relaxing holiday San Gimignano
Holiday home relaxing holiday San Gimignano
Holiday home relaxing holiday San Gimignano
Holiday home relaxing holiday San Gimignano
Holiday home relaxing holiday San Gimignano
Holiday home relaxing holiday San Gimignano
Holiday home relaxing holiday San Gimignano
San Gimignano

Holiday home relaxing holiday San Gimignano

4 guests
70 m2
1 bedroom
from 202 / night
5.0
prices from 203€ per night
View
NICE SUN
NICE SUN
NICE SUN
NICE SUN
NICE SUN
NICE SUN
NICE SUN
NICE SUN
NICE SUN
NICE SUN
NICE SUN
NICE SUN
NICE SUN
NICE SUN
NICE SUN
Casole d'Elsa

NICE SUN

5 guests
120 m2
2 bedrooms

Cozy cottage with shared swimming pool situated on the green, panoramic hills at 1.5 km from the hilltop town of Casole d'Elsa.

from 121 / night
prices from 122€ per night
View
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Barberino Val d'Elsa
Holiday Home in Montecarelli with Pool
6 guests
91 m2
2 bedrooms

Ground floor: (Large kitchen(double sofa bed, TV(digital, International television channels, No Dutch television channels), coffee machine(filter)

Free cancellation
from 70 / night
4.1
prices from 70€ per night
View
Tuscan Escape for Families
Tuscan Escape for Families
Tuscan Escape for Families
Tuscan Escape for Families
Tuscan Escape for Families
Tuscan Escape for Families
Tuscan Escape for Families
Tuscan Escape for Families
Tuscan Escape for Families
Tuscan Escape for Families
Tuscan Escape for Families
Tuscan Escape for Families
Tuscan Escape for Families
Tuscan Escape for Families
Tuscan Escape for Families
Casole d'Elsa
Tuscan Escape for Families
12 guests
172 m2
4 bedrooms

Ground floor: (open kitchen(hob(4 ring stoves, gas), boiling water tap, hood, coffee machine, oven, microwave, fridge), open kitchen(hob(4 ring stoves, gas)

Free cancellation
from 142 / night
4.3
prices from 142€ per night
View
Holiday Home in Tuscany with Vineyard Views
Holiday Home in Tuscany with Vineyard Views
Holiday Home in Tuscany with Vineyard Views
Holiday Home in Tuscany with Vineyard Views
Holiday Home in Tuscany with Vineyard Views
Holiday Home in Tuscany with Vineyard Views
Holiday Home in Tuscany with Vineyard Views
Holiday Home in Tuscany with Vineyard Views
Holiday Home in Tuscany with Vineyard Views
Holiday Home in Tuscany with Vineyard Views
Holiday Home in Tuscany with Vineyard Views
Holiday Home in Tuscany with Vineyard Views
Holiday Home in Tuscany with Vineyard Views
Holiday Home in Tuscany with Vineyard Views
Holiday Home in Tuscany with Vineyard Views
Barberino Val d'Elsa
Holiday Home in Tuscany with Vineyard Views
5 guests
65 m2
2 bedrooms

Ground floor: (Large kitchen(hob, hood, coffee machine, oven, fridge, washbasin, Juicer), Living/diningroom(single sofa bed, dining table), bedroom(double bed)

Free cancellation
from 62 / night
4.5
prices from 63€ per night
View
Holiday flat family holiday Casole d'Elsa
Holiday flat family holiday Casole d'Elsa
Holiday flat family holiday Casole d'Elsa
Holiday flat family holiday Casole d'Elsa
Holiday flat family holiday Casole d'Elsa
Holiday flat family holiday Casole d'Elsa
Holiday flat family holiday Casole d'Elsa
Holiday flat family holiday Casole d'Elsa
Holiday flat family holiday Casole d'Elsa
Holiday flat family holiday Casole d'Elsa
Holiday flat family holiday Casole d'Elsa
Holiday flat family holiday Casole d'Elsa
Holiday flat family holiday Casole d'Elsa
Holiday flat family holiday Casole d'Elsa
Holiday flat family holiday Casole d'Elsa
Casole d'Elsa
Holiday flat family holiday Casole d'Elsa
6 guests
55 m2
2 bedrooms
from 82 / night
prices from 82€ per night
View
Villa La Bruscola Comfortable holiday...
Villa La Bruscola Comfortable holiday...
Villa La Bruscola Comfortable holiday...
Villa La Bruscola Comfortable holiday...
Villa La Bruscola Comfortable holiday...
Villa La Bruscola Comfortable holiday...
Villa La Bruscola Comfortable holiday...
Villa La Bruscola Comfortable holiday...
Villa La Bruscola Comfortable holiday...
Villa La Bruscola Comfortable holiday...
Villa La Bruscola Comfortable holiday...
Villa La Bruscola Comfortable holiday...
Villa La Bruscola Comfortable holiday...
Villa La Bruscola Comfortable holiday...
Villa La Bruscola Comfortable holiday...
Barberino Val d'Elsa
Villa La Bruscola Comfortable holiday...
9 guests
500 m2
5 bedrooms
Free cancellation
from 367 / night
prices from 368€ per night
View
Holiday flat family holiday Casole d'Elsa
Holiday flat family holiday Casole d'Elsa
Holiday flat family holiday Casole d'Elsa
Holiday flat family holiday Casole d'Elsa
Holiday flat family holiday Casole d'Elsa
Holiday flat family holiday Casole d'Elsa
Holiday flat family holiday Casole d'Elsa
Holiday flat family holiday Casole d'Elsa
Holiday flat family holiday Casole d'Elsa
Holiday flat family holiday Casole d'Elsa
Holiday flat family holiday Casole d'Elsa
Holiday flat family holiday Casole d'Elsa
Holiday flat family holiday Casole d'Elsa
Holiday flat family holiday Casole d'Elsa
Holiday flat family holiday Casole d'Elsa
Casole d'Elsa
Holiday flat family holiday Casole d'Elsa
4 guests
42 m2
1 bedroom
from 68 / night
4.6
prices from 69€ per night
View
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Barberino Val d'Elsa
Holiday Home in Montecarelli with Pool
4 guests
67 m2
1 bedroom

Ground floor: (Living room(double sofa bed, TV(International television channels, No Dutch television channels), high chair), Kitchen(coffee machine(filter)

Free cancellation
from 55 / night
4.3
prices from 55€ per night
View
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Barberino Val d'Elsa
Holiday Home in Montecarelli with Pool
6 guests
105 m2
2 bedrooms

Ground floor: (Large kitchen(double sofa bed, TV(digital, international television channels, no dutch television channels), coffee machine(filter)

Free cancellation
from 57 / night
4.3
prices from 58€ per night
View
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Barberino Val d'Elsa
Holiday Home in Montecarelli with Pool
6 guests
120 m2
2 bedrooms

Ground floor: (Large kitchen(double sofa bed, TV(digital, international television channels, no dutch television channels), fireplace, coffee machine(filter)

Free cancellation
from 71 / night
4.3
prices from 72€ per night
View
Cozy Stay with Scenic Views
Cozy Stay with Scenic Views
Cozy Stay with Scenic Views
Cozy Stay with Scenic Views
Cozy Stay with Scenic Views
Cozy Stay with Scenic Views
Cozy Stay with Scenic Views
Cozy Stay with Scenic Views
Cozy Stay with Scenic Views
Cozy Stay with Scenic Views
Cozy Stay with Scenic Views
Cozy Stay with Scenic Views
Cozy Stay with Scenic Views
Cozy Stay with Scenic Views
Cozy Stay with Scenic Views
Casole d'Elsa
Cozy Stay with Scenic Views
2 guests
37 m2
1 bedroom

On the 1st floor: (open kitchen(hob(4 ring stoves, gas), hood, coffee machine, oven, fridge), Living/diningroom(TV(satellite), dining table), bedroom(double bed)

Free cancellation
from 43 / night
4.3
prices from 44€ per night
View
Holiday flat family holiday Casole d'Elsa
Holiday flat family holiday Casole d'Elsa
Holiday flat family holiday Casole d'Elsa
Holiday flat family holiday Casole d'Elsa
Holiday flat family holiday Casole d'Elsa
Holiday flat family holiday Casole d'Elsa
Holiday flat family holiday Casole d'Elsa
Holiday flat family holiday Casole d'Elsa
Holiday flat family holiday Casole d'Elsa
Holiday flat family holiday Casole d'Elsa
Holiday flat family holiday Casole d'Elsa
Holiday flat family holiday Casole d'Elsa
Holiday flat family holiday Casole d'Elsa
Holiday flat family holiday Casole d'Elsa
Holiday flat family holiday Casole d'Elsa
Casole d'Elsa
Holiday flat family holiday Casole d'Elsa
6 guests
55 m2
2 bedrooms
from 82 / night
prices from 82€ per night
View
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Barberino Val d'Elsa
Holiday Home in Montecarelli with Pool
6 guests
85 m2
2 bedrooms

Ground floor: (Living room(double sofa bed, TV(digital, International television channels, No Dutch television channels), high chair), Kitchen(coffee machine(filter)

Free cancellation
from 66 / night
4.3
prices from 66€ per night
View
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Holiday Home in Montecarelli with Pool
Barberino Val d'Elsa
Holiday Home in Montecarelli with Pool
6 guests
100 m2
2 bedrooms

Ground floor: (Living room(double sofa bed, TV(digital, international television channels, no dutch television channels), dining table, high chair)

Free cancellation
from 135 / night
4.2
prices from 136€ per night
View
Cottage in Chianti with Pool & Vineyard Views
Cottage in Chianti with Pool & Vineyard Views
Cottage in Chianti with Pool & Vineyard Views
Cottage in Chianti with Pool & Vineyard Views
Cottage in Chianti with Pool & Vineyard Views
Cottage in Chianti with Pool & Vineyard Views
Cottage in Chianti with Pool & Vineyard Views
Cottage in Chianti with Pool & Vineyard Views
Cottage in Chianti with Pool & Vineyard Views
Cottage in Chianti with Pool & Vineyard Views
Cottage in Chianti with Pool & Vineyard Views
Cottage in Chianti with Pool & Vineyard Views
Cottage in Chianti with Pool & Vineyard Views
Cottage in Chianti with Pool & Vineyard Views
Cottage in Chianti with Pool & Vineyard Views
Barberino Val d'Elsa
Cottage in Chianti with Pool & Vineyard Views
4 guests
75 m2
2 bedrooms

Ground floor: (dining room, Large kitchen(dining table, hob, hood, coffee machine, oven, fridge-freezer, washbasin, Juicer), bedroom(double bed), bedroom(single bed, single bed)

Free cancellation
from 67 / night
4.5
prices from 68€ per night
View

Guest reviews of our holiday apartments in San Gimignano & surrounding area

4.4

Holiday Home in Chianti with Pool & Garden

Barberino Val d'Elsa

View Spanish

We had a lovely stay in this vacation home in San Donato in Poggio. The pool was a hit with the kids, and the garden provided a perfect place to relax while we watched them. I highly recommend it!


from 68€ night
4.8

Verified guest from Tourist-paradise.com

Pure relaxation

LA CAMBRUNA

Casole d'Elsa

View German

Pure relaxation

La Cambruna is really a beautiful little house in the countryside.
If you want to enjoy your vacation in peace, I can only recommend this house. The only downside is that the access to the house is somewhat bumpy with a 2km long gravel road. However, this did not cause us any problems. I would not recommend it for a sports car. The only drawback was that the air conditioning in the bedrooms worked poorly or not at all. Ainoa, our host, was right there with fans and an air conditioning technician and helped us further.
All in all, a wonderfully relaxing vacation! We would come back!


from 232€ night
5.0

Verified guest from Tourist-paradise.com

A great holiday in San Gimignano

Holiday home relaxing holiday San Gimignano

San Gimignano

View German

A great holiday in San Gimignano

We already stayed in your holiday home a month ago
We really enjoyed the place, the surroundings and your hospitality.
The boys had a fantastic time, also in the pool.
Thank you again and we wish you all the best!

Barend and Gerrianne
Joas and Levy
Stay July/August 2022


from 203€ night

Popular regions and locations for your holiday homes with pool in San Gimignano & surrounding area

Rent out now on Ferienhausmiete.de

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