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227 Holiday apartments & homes for a holiday with pool in the Arezzo region

15%
Villa Loft Borgo Syrah
Villa Loft Borgo Syrah
Villa Loft Borgo Syrah
Villa Loft Borgo Syrah
Villa Loft Borgo Syrah
Villa Loft Borgo Syrah
Villa Loft Borgo Syrah
Villa Loft Borgo Syrah
Villa Loft Borgo Syrah
Villa Loft Borgo Syrah
Villa Loft Borgo Syrah
Villa Loft Borgo Syrah
Villa Loft Borgo Syrah
Villa Loft Borgo Syrah
Villa Loft Borgo Syrah
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Mercatale di Cortona

Villa Loft Borgo Syrah

6 guests
174 m2
3 bedrooms

Villa Loft in Borgo Syrah | Pool, spa & private garden with views of the Tuscan hills

Free cancellation

15% Last-Minute 06/12/2026 - 06/19/2026

from 177 / night
5.0
prices from 177€ per night
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14%
Casa Rossa
Casa Rossa
Casa Rossa
Casa Rossa
Casa Rossa
Casa Rossa
Casa Rossa
Casa Rossa
Casa Rossa
Casa Rossa
Casa Rossa
Casa Rossa
Casa Rossa
Casa Rossa
Casa Rossa
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Foiano della Chiana

Casa Rossa

6 guests
180 m2
2 bedrooms (+1)

Red House in Gervasella: 180 m², 3 rooms, max. 6 persons.

14% Last-Minute 06/13/2026 - 06/26/2026

from 292 / night
prices from 293€ per night
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Ferienhaus mit eigenem Pool
Ferienhaus mit eigenem Pool
Ferienhaus mit eigenem Pool
Ferienhaus mit eigenem Pool
Ferienhaus mit eigenem Pool
Ferienhaus mit eigenem Pool
Ferienhaus mit eigenem Pool
Ferienhaus mit eigenem Pool
Ferienhaus mit eigenem Pool
Ferienhaus mit eigenem Pool
Ferienhaus mit eigenem Pool
Ferienhaus mit eigenem Pool
Ferienhaus mit eigenem Pool
Ferienhaus mit eigenem Pool
Ferienhaus mit eigenem Pool
Castiglion Fiorentino

Ferienhaus mit eigenem Pool

9 guests
180 m2
5 bedrooms

Holiday home in Castiglion Fiorentino for a maximum of 9 people (8+1) with private pool in panoramic position, barbecue, pizza oven, parking spaces

Free cancellation
from 148 / night
4.6
prices from 149€ per night
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VILLA SIMPATIA
VILLA SIMPATIA
VILLA SIMPATIA
VILLA SIMPATIA
VILLA SIMPATIA
VILLA SIMPATIA
VILLA SIMPATIA
VILLA SIMPATIA
VILLA SIMPATIA
VILLA SIMPATIA
VILLA SIMPATIA
VILLA SIMPATIA
VILLA SIMPATIA
VILLA SIMPATIA
VILLA SIMPATIA
Bibbiena

VILLA SIMPATIA

21 guests
450 m2
9 bedrooms

Luxury Villa up to 21 people in panoramic position private heated swimming pool & extensive park in Tuscany

from 710 / night
prices from 710€ per night
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Two Birds one Room-La Villa ARTE del Lupo
Two Birds one Room-La Villa ARTE del Lupo
Two Birds one Room-La Villa ARTE del Lupo
Two Birds one Room-La Villa ARTE del Lupo
Two Birds one Room-La Villa ARTE del Lupo
Two Birds one Room-La Villa ARTE del Lupo
Two Birds one Room-La Villa ARTE del Lupo
Two Birds one Room-La Villa ARTE del Lupo
Two Birds one Room-La Villa ARTE del Lupo
Two Birds one Room-La Villa ARTE del Lupo
Two Birds one Room-La Villa ARTE del Lupo
Two Birds one Room-La Villa ARTE del Lupo
Two Birds one Room-La Villa ARTE del Lupo
Two Birds one Room-La Villa ARTE del Lupo
Two Birds one Room-La Villa ARTE del Lupo
Subbiano

Two Birds one Room-La Villa ARTE del Lupo

2 guests
60 m2
1 bedroom
Free cancellation
from 280 / night
prices from 280€ per night
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BORGO SERENO
BORGO SERENO
BORGO SERENO
BORGO SERENO
BORGO SERENO
BORGO SERENO
BORGO SERENO
BORGO SERENO
BORGO SERENO
BORGO SERENO
BORGO SERENO
BORGO SERENO
BORGO SERENO
BORGO SERENO
BORGO SERENO
Poppi

BORGO SERENO

27 guests
448 m2
12 bedrooms
from 554 / night
prices from 554€ per night
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50%
TUSCANY HOUSE WITH POOL
TUSCANY HOUSE WITH POOL
TUSCANY HOUSE WITH POOL
TUSCANY HOUSE WITH POOL
TUSCANY HOUSE WITH POOL
TUSCANY HOUSE WITH POOL
TUSCANY HOUSE WITH POOL
TUSCANY HOUSE WITH POOL
TUSCANY HOUSE WITH POOL
TUSCANY HOUSE WITH POOL
TUSCANY HOUSE WITH POOL
TUSCANY HOUSE WITH POOL
TUSCANY HOUSE WITH POOL
TUSCANY HOUSE WITH POOL
TUSCANY HOUSE WITH POOL
Cortona

TUSCANY HOUSE WITH POOL

6 guests
135 m2
3 bedrooms

HOUSE WITH PRIVATE SWIMMING POOL, LARGE ENCLOSED GARDEN, BARBECUE, INTERNET WI-FI, SMART TV.

50% Promotion 06/13/2026 - 06/20/2026

from 143 / night
prices from 143€ per night
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Colonica Valentina (8+3 beds)
Colonica Valentina (8+3 beds)
Colonica Valentina (8+3 beds)
Colonica Valentina (8+3 beds)
Colonica Valentina (8+3 beds)
Colonica Valentina (8+3 beds)
Colonica Valentina (8+3 beds)
Colonica Valentina (8+3 beds)
Colonica Valentina (8+3 beds)
Colonica Valentina (8+3 beds)
Colonica Valentina (8+3 beds)
Colonica Valentina (8+3 beds)
Colonica Valentina (8+3 beds)
Colonica Valentina (8+3 beds)
Colonica Valentina (8+3 beds)
Arezzo

Colonica Valentina (8+3 beds)

11 guests
400 m2
4 bedrooms

Detached country house in a panoramic position, 400 m² living space, 40 acres of land, 4 bedrooms and 3 bathrooms, WIFI, air conditioning, private pool, parking

from 457 / night
5.0
prices from 457€ per night
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Casa Ippocastani
Casa Ippocastani
Casa Ippocastani
Casa Ippocastani
Casa Ippocastani
Casa Ippocastani
Casa Ippocastani
Casa Ippocastani
Casa Ippocastani
Casa Ippocastani
Casa Ippocastani
Casa Ippocastani
Casa Ippocastani
Casa Ippocastani
Casa Ippocastani
Bibbiena

Casa Ippocastani

4 guests
80 m2
2 bedrooms

Old stone house on a typical Tuscan farm with horses and swimming pool, with 2 bedrooms, 2 bathrooms, central heating, private garden part with outdoor seating

from 77 / night
prices from 77€ per night
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casa fantone
casa fantone
casa fantone
casa fantone
casa fantone
casa fantone
casa fantone
casa fantone
casa fantone
casa fantone
casa fantone
casa fantone
casa fantone
casa fantone
casa fantone
Top advertisement
Poppi

casa fantone

12 guests
300 m2
5 bedrooms

Charming Tuscan villa with private pool, breathtaking view and wide fenced garden.

Free cancellation
from 205 / night
5.0
prices from 205€ per night
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Casale Cortona
Casale Cortona
Casale Cortona
Casale Cortona
Casale Cortona
Casale Cortona
Casale Cortona
Casale Cortona
Casale Cortona
Casale Cortona
Casale Cortona
Casale Cortona
Casale Cortona
Casale Cortona
Casale Cortona
Cortona

Casale Cortona

24 guests
780 m2
12 bedrooms

Beautiful country estate in Cortona for larger groups (up to 29 people), large fenced garden with pool (7x14m), table tennis, small football field, pool table, WIFI

from 780 / night
prices from 781€ per night
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Countryhouse for 22 pax with pool
Countryhouse for 22 pax with pool
Countryhouse for 22 pax with pool
Countryhouse for 22 pax with pool
Countryhouse for 22 pax with pool
Countryhouse for 22 pax with pool
Countryhouse for 22 pax with pool
Countryhouse for 22 pax with pool
Countryhouse for 22 pax with pool
Countryhouse for 22 pax with pool
Countryhouse for 22 pax with pool
Countryhouse for 22 pax with pool
Countryhouse for 22 pax with pool
Countryhouse for 22 pax with pool
Countryhouse for 22 pax with pool
Marciano della Chiana

Countryhouse for 22 pax with pool

23 guests
420 m2
9 bedrooms

Detached elegant country house with cottage in Val di Chiana, panoramic position, 20,000m² garden, private pool, fireplace, WIFI, DVD / CD player, satellite TV, grill, playground (swing u slide)

from 471 / night
prices from 471€ per night
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Villa and pool for sole use
Villa and pool for sole use
Villa and pool for sole use
Villa and pool for sole use
Villa and pool for sole use
Villa and pool for sole use
Villa and pool for sole use
Villa and pool for sole use
Villa and pool for sole use
Villa and pool for sole use
Villa and pool for sole use
Villa and pool for sole use
Villa and pool for sole use
Villa and pool for sole use
Villa and pool for sole use
Lucignano

Villa and pool for sole use

13 guests
220 m2
6 bedrooms

Detached Tuscan Villa in Lucignano near Arezzo, sole use, panoramic, air conditioning, large garden, barbecue, private pool, parking, fireplace, satellite TV, WIFI, accessible

from 285 / night
prices from 286€ per night
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Villa with heatable pool (10+4beds)
Villa with heatable pool (10+4beds)
Villa with heatable pool (10+4beds)
Villa with heatable pool (10+4beds)
Villa with heatable pool (10+4beds)
Villa with heatable pool (10+4beds)
Villa with heatable pool (10+4beds)
Villa with heatable pool (10+4beds)
Villa with heatable pool (10+4beds)
Villa with heatable pool (10+4beds)
Villa with heatable pool (10+4beds)
Villa with heatable pool (10+4beds)
Villa with heatable pool (10+4beds)
Villa with heatable pool (10+4beds)
Villa with heatable pool (10+4beds)
Bucine

Villa with heatable pool (10+4beds)

14 guests
350 m2
5 bedrooms

Detached luxury villa, big garden, private pool, jacuzzi/children's wading pool, sauna, outside kitchen with large pizza oven and barbecue device, AC, sat-TV, WIFI, Sonos, Polo 1km

from 546 / night
prices from 546€ per night
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Farm for 15 persons with pool
Farm for 15 persons with pool
Farm for 15 persons with pool
Farm for 15 persons with pool
Farm for 15 persons with pool
Farm for 15 persons with pool
Farm for 15 persons with pool
Farm for 15 persons with pool
Farm for 15 persons with pool
Farm for 15 persons with pool
Farm for 15 persons with pool
Farm for 15 persons with pool
Farm for 15 persons with pool
Farm for 15 persons with pool
Farm for 15 persons with pool
Montevarchi

Farm for 15 persons with pool

15 guests
280 m2
7 bedrooms

Typical Tuscan property, absolute view, panoramic view, 5000 m² garden, large pool, jacuzzi, air conditioning, table tennis, fireplace, DVD / CD player, satellite TV, WIFI, barbecue

from 427 / night
prices from 427€ per night
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Villa Elisabetta
Villa Elisabetta
Villa Elisabetta
Villa Elisabetta
Villa Elisabetta
Villa Elisabetta
Villa Elisabetta
Villa Elisabetta
Villa Elisabetta
Villa Elisabetta
Villa Elisabetta
Villa Elisabetta
Villa Elisabetta
Villa Elisabetta
Villa Elisabetta
Caprese Michelangelo

Villa Elisabetta

23 guests
300 m2
10 bedrooms

Spacious villa with pool in Tuscany, in the Valtiberina countryside, close to wonderful historic villages.

Free cancellation
from 345 / night
prices from 346€ per night
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Casa Valle
Casa Valle
Casa Valle
Casa Valle
Casa Valle
Casa Valle
Casa Valle
Casa Valle
Casa Valle
Casa Valle
Casa Valle
Casa Valle
Casa Valle
Casa Valle
Casa Valle
Bucine

Casa Valle

12 guests
200 m2
5 bedrooms (+1)

Casa Valle (2 houses) in a quiet, idyllic secluded location with a stream, 200 m², 12 people, 5 bedrooms, private pool. Great starting point for excursions. Nearest place approx. 3 km.

from 114 / night
prices from 114€ per night
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VILLA NICOLE
VILLA NICOLE
VILLA NICOLE
VILLA NICOLE
VILLA NICOLE
VILLA NICOLE
VILLA NICOLE
VILLA NICOLE
VILLA NICOLE
VILLA NICOLE
VILLA NICOLE
VILLA NICOLE
VILLA NICOLE
VILLA NICOLE
VILLA NICOLE
Arezzo

VILLA NICOLE

15 guests
200 m2
6 bedrooms

Stunning villa with infinity pool in Tuscany, near Arezzo, surrounded by beautiful historic towns.

Free cancellation
from 258 / night
prices from 258€ per night
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Casa Carsignano
Casa Carsignano
Casa Carsignano
Casa Carsignano
Casa Carsignano
Casa Carsignano
Casa Carsignano
Casa Carsignano
Casa Carsignano
Casa Carsignano
Casa Carsignano
Casa Carsignano
Casa Carsignano
Casa Carsignano
Casa Carsignano
Mercatale di Cortona

Casa Carsignano

8 guests
185 m2
4 bedrooms

Holiday home Casa Carsignano in Mercatale di Cortona, Tuscany, 185 sqm for 8 people, 6 rooms.

Free cancellation
from 150 / night
prices from 150€ per night
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Holiday home relaxing holiday Arezzo
Holiday home relaxing holiday Arezzo
Holiday home relaxing holiday Arezzo
Holiday home relaxing holiday Arezzo
Holiday home relaxing holiday Arezzo
Holiday home relaxing holiday Arezzo
Holiday home relaxing holiday Arezzo
Holiday home relaxing holiday Arezzo
Holiday home relaxing holiday Arezzo
Holiday home relaxing holiday Arezzo
Holiday home relaxing holiday Arezzo
Holiday home relaxing holiday Arezzo
Holiday home relaxing holiday Arezzo
Holiday home relaxing holiday Arezzo
Holiday home relaxing holiday Arezzo
Arezzo

Holiday home relaxing holiday Arezzo

20 guests
350 m2
8 bedrooms

It is an old stone farmhouse located in Valdichiana, just 15 km from Arezzo which can accommodate 20 people.

Free cancellation
from 805 / night
prices from 806€ per night
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Sasso Villa
Sasso Villa
Sasso Villa
Sasso Villa
Sasso Villa
Sasso Villa
Sasso Villa
Sasso Villa
Sasso Villa
Sasso Villa
Sasso Villa
Sasso Villa
Sasso Villa
Sasso Villa
Sasso Villa
Lucignano

Sasso Villa

9 guests
250 m2
5 bedrooms

Situated among the hills of Tuscany, only 1,5 km from the medieval town of Lucignano, between Siena and Arezzo.

from 538 / night
prices from 539€ per night
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Holiday home relaxing holiday Arezzo
Holiday home relaxing holiday Arezzo
Holiday home relaxing holiday Arezzo
Holiday home relaxing holiday Arezzo
Holiday home relaxing holiday Arezzo
Holiday home relaxing holiday Arezzo
Holiday home relaxing holiday Arezzo
Holiday home relaxing holiday Arezzo
Holiday home relaxing holiday Arezzo
Holiday home relaxing holiday Arezzo
Holiday home relaxing holiday Arezzo
Holiday home relaxing holiday Arezzo
Holiday home relaxing holiday Arezzo
Holiday home relaxing holiday Arezzo
Holiday home relaxing holiday Arezzo
Arezzo
Holiday home relaxing holiday Arezzo
12 guests
250 m2
6 bedrooms
Free cancellation
from 640 / night
prices from 640€ per night
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Bucine Hideaway with Pool
Bucine Hideaway with Pool
Bucine Hideaway with Pool
Bucine Hideaway with Pool
Bucine Hideaway with Pool
Bucine Hideaway with Pool
Bucine Hideaway with Pool
Bucine Hideaway with Pool
Bucine Hideaway with Pool
Bucine Hideaway with Pool
Bucine Hideaway with Pool
Bucine Hideaway with Pool
Bucine Hideaway with Pool
Bucine Hideaway with Pool
Bucine Hideaway with Pool
Arezzo
Bucine Hideaway with Pool
3 guests
40 m2
1 bedroom

Ground floor: (Living room(single sofa bed, seating area), Large kitchen(TV, cooker, microwave), bedroom(double bed), bathroom(shower, washbasin, toilet, bidet))

Free cancellation
from 52 / night
4.6
prices from 53€ per night
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Villa in Tuscany with Pool and Valley Views
Villa in Tuscany with Pool and Valley Views
Villa in Tuscany with Pool and Valley Views
Villa in Tuscany with Pool and Valley Views
Villa in Tuscany with Pool and Valley Views
Villa in Tuscany with Pool and Valley Views
Villa in Tuscany with Pool and Valley Views
Villa in Tuscany with Pool and Valley Views
Villa in Tuscany with Pool and Valley Views
Villa in Tuscany with Pool and Valley Views
Villa in Tuscany with Pool and Valley Views
Villa in Tuscany with Pool and Valley Views
Villa in Tuscany with Pool and Valley Views
Villa in Tuscany with Pool and Valley Views
Villa in Tuscany with Pool and Valley Views
Castiglion Fiorentino
Villa in Tuscany with Pool and Valley Views
8 guests
250 m2
4 bedrooms

Ground floor: (Living room(TV(satellite), fireplace), dining room(dining table), Kitchen(oven, dishwasher, fridge), bathroom(shower, washbasin, toilet, bidet))

Free cancellation
from 509 / night
4.2
prices from 509€ per night
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Villa with Pool and Wine Country Charm
Villa with Pool and Wine Country Charm
Villa with Pool and Wine Country Charm
Villa with Pool and Wine Country Charm
Villa with Pool and Wine Country Charm
Villa with Pool and Wine Country Charm
Villa with Pool and Wine Country Charm
Villa with Pool and Wine Country Charm
Villa with Pool and Wine Country Charm
Villa with Pool and Wine Country Charm
Villa with Pool and Wine Country Charm
Villa with Pool and Wine Country Charm
Villa with Pool and Wine Country Charm
Villa with Pool and Wine Country Charm
Villa with Pool and Wine Country Charm
Arezzo
Villa with Pool and Wine Country Charm
10 guests
280 m2
5 bedrooms

Ground floor: (Living room(TV(satellite)), dining room(fireplace), open kitchen(wood cooker, coffee machine(filter), coffee machine(espresso), coffee machine(pads)

Free cancellation
from 308 / night
4.4
prices from 309€ per night
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Guest reviews of our holiday apartments in the Arezzo region

5.0

Verified guest from Tourist-paradise.com

Fantastic?

casa fantone

Poppi

View German

Fantastic?

We, nine adults and a dog, spent a dreamlike week here. The house is very spacious, the kitchen is well equipped. We cooked, baked, grilled, and nothing was missing. Breakfast on the loggia with an incredible view. The bathrooms, the pool, everything is well-maintained and clean. And finally played table tennis again. The garden is huge, the hammocks are wonderful. Poppi and Bibienna are easily accessible. Florence is a day trip. Anyone who wants to relax and enjoy nature is in the right place here.


from 205€ night
5.0

Holiday home relaxing holiday Capolona

Capolona

Booking was "simple" and I entered my payment info, but then got an email saying unless I wire money to a bank in Germany my booking would be canceled-this is unacceptable in every way. Email communications were entirely in German, not sure how we are expected me to understand, especially since the email was from "HomeAway" and not VRBO, the site where I booked the apartment.


from 198€ night

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