List your home
Apply filters
£ to

41 Holiday homes in Certaldo

Reset search

Show results on map

Also consider

Coastal Cottages
222 properties
Sardinia
478 properties
Tuscany
3,181 properties
Lake Garda Area
103 properties
Lake Como Area
494 properties
Sicily
634 properties
Rome
2,497 properties
Florence
982 properties
Venice, Veneto
497 properties
Trapani
481 properties
Amalfi Coast
452 properties
Lucca
439 properties
Cortona
411 properties
Palermo
411 properties
Sorrento, Campania
351 properties
Cefalu
315 properties
San Gimignano
289 properties
Taormina
274 properties
Greve in Chianti
262 properties
Massa Lubrense
245 properties

Filters applied: Balcony or terrace (41)

To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more
41 Results  |  
23 Photos

Apartment | 1 Bedroom | sleeps 4

2 Nights min stay

Add to shortlist

from £58 /night

£402 - £582 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Confortable apartment with pool and private terrace on the top of a hill in the Chianti region, between Pisa, Siena, San Gimignano and Florence. A place where to relax and strategical departing point for visiting, the Tuscan citie. Massage on demande Horse riding Wine tasting Cooking class At 6 Km Certaldo Restauants. Lake  …see more

11 Photos

Farmhouse | 3 Bedrooms | sleeps 8

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £162 /night

£1129 - £1522 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
A villa immersed in the peace of the Chianti countryside with breathtaking panorama, spectacular sunsets, private garden and parking and all the conforts of a modern agriturism. Taking day trips or relaxing by the pool, you and your family will instantly feel at home. Easy to reach,paved roads.Shops and markets at few minutes by car. Dinners, oil tasting and cooking classes.  …see more

24 Photos

Villa | 9 Bedrooms | sleeps 18

7 Nights min stay

Add to shortlist

from £289 /night

£2017 - £5242 / week

View

Key info:

  • Nearest beach 75 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
If you require superior accommodation with an unmistakable touch of class, this fully refurbished, early 19th century, two-storey villa will not disappoint you.  …see more

Featured properties

12 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £145 /night

£1009 - £1105 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Villa della Torre is a large, historic estate halfway between Florence and Siena (22 miles each), perched on a hilltop amidst a lush green countryside.  …see more

11 Photos

Apartment | 1 Bedroom | sleeps 2

7 Nights min stay

Add to shortlist

from £125 /night

£871 - £1009 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Villa della Torre is a large, historic estate halfway between Florence and Siena (22 miles each), perched on a hilltop amidst a lush green countryside.  …see more

12 Photos

Villa | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £149 /night

£1041 - £1121 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
The elegant farmstead Villa Olivo is located in the most coveted region of central Tuscany.  …see more

13 Photos

Apartment | 1 Bedroom | sleeps 3

7 Nights min stay

Add to shortlist

from £138 /night

£960 - £1041 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Villa della Torre is a large, historic estate halfway between Florence and Siena (22 miles each), perched on a hilltop amidst a lush green countryside.  …see more

21 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £98 /night

£686 - £839 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Casale Elsa is a perfect starting point to explore Tuscany: situated in the heart of Chianti, the major attractions of the region can easily be reached.  …see more

23 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £98 /night

£686 - £839 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Casale Elsa is a perfect starting point to explore Tuscany: situated in the heart of Chianti, the major attractions of the region can easily be reached  …see more

22 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £103 /night

£718 - £880 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Casale Elsa is a perfect starting point to explore Tuscany: situated in the heart of Chianti, the major attractions of the region can easily be reached.  …see more

14 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £145 /night

£1009 - £1105 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
Villa della Torre is a large, historic estate halfway between Florence and Siena (22 miles each), perched on a hilltop amidst a lush green countryside.  …see more

21 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £98 /night

£686 - £839 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
Casale Elsa is a perfect starting point to explore Tuscany: situated in the heart of Chianti, the major attractions of the region can easily be reached  …see more

21 Photos

Farmhouse | 4 Bedrooms | sleeps 9

7 Nights min stay

Add to shortlist

from £483 /night

£3380 - £4428 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Il Podere is a beautiful farmhouse located halfway between Florence and Siena, in the heart of the Chianti Hills.  …see more

9 Photos

Apartment | 1 Bedroom | sleeps 2

7 Nights min stay

Add to shortlist

from £92 /night

£638 - £718 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Villa della Torre is a large, historic estate halfway between Florence and Siena (22 miles each), perched on a hilltop amidst a lush green countryside.  …see more

11 Photos

Villa | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £149 /night

£1041 - £1121 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
The elegant farmstead Villa Olivo is located in the most coveted region of central Tuscany.  …see more

23 Photos

Farmhouse | 3 Bedrooms | sleeps 6

7 Nights min stay

Add to shortlist

from £333 /night

£2331 - £2412 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
This elegant farmstead is located in the most coveted region of central Tuscany.  …see more

9 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £125 /night

£871 - £1009 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Villa della Torre is a large, historic estate halfway between Florence and Siena (22 miles each), perched on a hilltop amidst a lush green countryside  …see more

11 Photos

Villa | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £149 /night

£1041 - £1121 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
The elegant farmstead Villa Olivo is located in the most coveted region of central Tuscany.  …see more

11 Photos

Apartment | 1 Bedroom | sleeps 2

7 Nights min stay

Add to shortlist

from £92 /night

£638 - £718 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Villa della Torre is a large, historic estate halfway between Florence and Siena (22 miles each), perched on a hilltop amidst a lush green countryside.  …see more

7 Photos

Villa | 3 Bedrooms | sleeps 6

Short stays welcome

Add to shortlist

from £202 /night

£1412 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Tuscan Villa with amazing tuscan views  …see more

8 Photos

Villa | 1 Bedroom | sleeps 4

7 Nights min stay

Add to shortlist

from £58 /night

£406 - £626 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
Attractive holiday house for 4 persons, with swimming pool , in Chianti  …see more

23 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £56 /night

£386 - £1002 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
The apartments are located in the heart of the Chianti area, near San Gimignano, a small Tuscan village within the municipality of Capezzano which stands at the top of a hill - a breathtaking landscape. The ancient houses of the village, with a splendid view of San G...  …see more

23 Photos

House | 1 Bedroom | sleeps 2

7 Nights min stay

Add to shortlist

from £50 /night

£348 - £773 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
The apartments and rooms are located in the heart of the Chianti area, near San Gimignano, a small Tuscan village within the municipality of Capezzano which stands at the top of a hill - a breathtaking landscape. The ancient houses of the village, with a splendid vie...  …see more

18 Photos

Apartment | 1 Bedroom | sleeps 3

7 Nights min stay

Add to shortlist

from £45 /night

£310 - £350 / week

View

Key info:

  • Great for children of all ages
  • Car not necessary
  • Pets welcome
Apartment for 3 persons in San Gimignano  …see more

24 Photos

House | 1 Bedroom | sleeps 4

7 Nights min stay

Add to shortlist

from £97 /night

£674 - £1815 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
The apartments are located in the heart of the Chianti area, near San Gimignano, a small Tuscan village within the municipality of Capezzano which stands at the top of a hill - a breathtaking landscape. The ancient houses of the village, with a splendid view of San G...  …see more

16 Photos

Villa | 8 Bedrooms | sleeps 18

2 Nights min stay

Add to shortlist

from £535 /night

£3741 - £4476 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
Staying at Farmhouse Villa Sticci, if even only for a few days, will allow you to spend valuable time indulging yourself and sharing special moments with your loved ones.  …see more

9 Photos

Apartment | 3 Bedrooms | sleeps 7

7 Nights min stay

Add to shortlist

from £77 /night

£533 - £881 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
Apartment for 7 persons, with swimming pool , in Chianti  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

Add to shortlist

from £140 /night

£979 - £1710 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Attractive holiday house for 6 persons, with swimming pool , in Chianti  …see more

19 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

Add to shortlist

from £47 /night

£327 - £453 / week

View

Key info:

  • Great for children of all ages
  • Car not necessary
  • Pets welcome
Apartment for 4 persons in San Gimignano  …see more

21 Photos

Apartment | 1 Bedroom | sleeps 2

7 Nights min stay

Add to shortlist

from £51 /night

£355 - £638 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
The apartments are located in the heart of the Chianti area, near San Gimignano, a small Tuscan village within the municipality of Capezzano which stands at the top of a hill - a breathtaking landscape.The ancient houses of the village, with a splendid view of San Gi...  …see more

24 Photos

House | 1 Bedroom | sleeps 2

7 Nights min stay

Add to shortlist

from £71 /night

£496 - £971 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
The apartments are located in the heart of the Chianti area, near San Gimignano, a small Tuscan village within the municipality of Capezzano which stands at the top of a hill - a breathtaking landscape. The ancient houses of the village, with a splendid view of San G...  …see more

24 Photos

House | 1 Bedroom | sleeps 3

7 Nights min stay

Add to shortlist

from £80 /night

£556 - £873 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
The apartments are located in the heart of the Chianti area, near San Gimignano, a small Tuscan village within the municipality of Capezzano which stands at the top of a hill - a breathtaking landscape. The ancient houses of the village, with a splendid view of San G...  …see more

20 Photos

Villa | 9 Bedrooms | sleeps 18

7 Nights min stay

Add to shortlist

from £488 /night

£3412 - £6000 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
This is one of the most important Renaissance Villas in Chianti area, located in a few km from Certaldo village, exactly between Florence and Siena.  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 4

1 night min stay

Add to shortlist

from £42 /night

£291 - £372 / week

View

Key info:

  • Great for children of all ages
  • Car not necessary
  • Some pets are welcome - please contact the owner
Casa Chiara, appartamento completamento ristrutturato, lungo la famosa Via del Castello, strada di accesso al pittoresco borgo medioevale di Certaldo Alto.  …see more

20 Photos

Apartment | 6 Bedrooms | sleeps 14

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £159 /night

£1112 - £2052 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
Il complesso dista circa 4 km da Certaldo, dove si trovano negozi di tutti i generi, 8 km da Poggibonsi, 10 km da Barberino Val d'Elsa, 15 km da San Gimignano, 30 km da Siena e 40 km da Firenze.  …see more

24 Photos

Farmhouse | 4 Bedrooms | sleeps 10

7 Nights min stay

Add to shortlist

from £184 /night

£1283 - £2138 / week

View

Key info:

  • Nearest beach 85 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Villa San Martino typical Tuscan farmhouse with private pool, situated in the peaceful hills between Florence and Siena, surrounded by vineyards and olives trees.  …see more

17 Photos

House | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £157 /night

£1095 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
  • Private garden
La Poggiolaia is surrounded by the stunning landscapes of Renaissance paintings. Infinite gradations of colors will amaze our guests at every footstep. You may walk or ride through endless fields of sunflowers and gravel paths surrounded by rows of cypresses. You can visit the wonderful churches and museums of Florence and Siena, just 20 and 15 miles away.  …see more

24 Photos

Apartment | 3 Bedrooms | sleeps 8

2 Nights min stay

Add to shortlist

from £49 /night

£342 - £573 / week

View

Key info:

  • Great for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Casa I Cedri, elegante e spazioso appartamento nel cuore della Toscana, nel paese di Giovanni Boccaccio, autore del Decameron. L'appartamento è dotato di tutti i comfort per ospitare anche persone anziane e portatori di handicap.  …see more

12 Photos

Apartment | 2 Bedrooms | sleeps 6

2 Nights min stay

Add to shortlist

from £49 /night

£342 - £659 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Troverete ogni confort nel nostro appartamento, così da poter trascorrere una stupenda vacanza nel cuore della Toscana  …see more

23 Photos

Villa | 13 Bedrooms | sleeps 30

Min stay varies

Add to shortlist

from £109 /night

£761 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Free Wi-Fi 11 apartments, 4 in the main building. Air conditioning in 4 apartments  …see more

7 Photos

House | 2 Bedrooms | sleeps 4

4 Nights min stay

Add to shortlist

from £80 /night

£556 / week

View

Key info:

  • Nearest beach 50 km
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Il Vecchio Forno, luogo dell'antico forno di panificazione di Certaldo Alto di recente ristrutturato in una confortevole abitazione, offre un ampio soggiorno/pranzo, due camere distinte, bagno, cucina ed un altro locale con un divano/letto, il tutto con mobili in stile.  …see more