List your home
Apply filters
£ to

52 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
2,535 properties
Florence
987 properties
Trapani
503 properties
Venice, Veneto
499 properties
Amalfi Coast
465 properties
Lucca
436 properties
Palermo
424 properties
Cortona
409 properties
Sorrento, Campania
351 properties
Cefalu
311 properties
San Gimignano
299 properties
Taormina
277 properties
Syracuse
260 properties
Greve in Chianti
258 properties

Filters applied: Shared garden (52)

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
52 Results  |  
24 Photos

Apartment | 1 Bedroom | sleeps 4

Very Good 4/5 

1 night min stay

Add to shortlist

from £55 /night

£382 - £641 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages 5
  • Pets welcome
  • Private garden
Comfortable 2 rooms apt with pool and private garden between Siena and Florence,. The apartment has a panoromic view on the vineyards and equipped of table, chairs and parasol. 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

23 Photos

Apartment | 2 Bedrooms | sleeps 6

1 night min stay

Add to shortlist

from £77 /night

£535 - £802 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Pets welcome
  • Private garden
Confortable apartment in an Holiday House with pool and private garden on a top of a hill in the Chianti, between Siena, Florence, San Gimignano , Volterra and Pisa, . A place where to relax and strategical departing point for visiting, the Tuscan citie. Massage on demande Wine tasting Horse riding at at 5 minute walking. Cooking class  …see more

23 Photos

Apartment | 1 Bedroom | sleeps 4

2 Nights min stay

Add to shortlist

from £57 /night

£399 - £577 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages 5
  • 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

Featured properties

22 Photos

Apartment | 1 Bedroom | sleeps 4

2 Nights min stay

Add to shortlist

from £51 /night

£357 - £518 / week

View

Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Pets welcome
  • Private garden
Apartments overlooking the Chianti country side and a pool surrounded of olives grove. With a double bedroom (canopy bed), a large living room with double sofà bed, a kichen corner, a bathroom ,private garden with a stunning view equipped with table and chair Massage on demande Baby sitting service Horse riding Walking in the nature  …see more

13 Photos

Apartment | 1 Bedroom | sleeps 3

2 Nights min stay

Add to shortlist

from £85 /night

£594 - £721 / week

View

Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Pets welcome
The apartment is situated in a beautiful position, just in front of the medieval castle of the structure and its gardens. The apartment is provided with parking area, FREE WIFI, fans. Close to our swimming-pool area, situated in a balcony overlooking the Chianti hills.  …see more

13 Photos

Apartment | 2 Bedrooms | sleeps 4

Excellent 5/5 

6 Nights min stay

Add to shortlist

from £68 /night

£470 - £820 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • No pets allowed
A spacious and well-equipped apartment with pool, set amongst rolling Chianti hills. You will enjoy breathtaking views and yet are within easy reach of Florence, Siena, San Gimignano and Chianti's main wine towns. Sleeps 4. Ideal for families. Only 7 Km from Certaldo with a convenient railway station with links to Florence, Siena and Pisa.  …see more

7 Photos

Villa | 3 Bedrooms | sleeps 6

Short stays welcome

Add to shortlist

from £200 /night

£1400 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
  • Private garden
Tuscan Villa with amazing tuscan views  …see more

9 Photos

Apartment | 1 Bedroom | sleeps 2

7 Nights min stay

Add to shortlist

from £91 /night

£632 - £712 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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

12 Photos

Villa | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £148 /night

£1032 - £1112 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
The elegant farmstead Villa Olivo is located in the most coveted region of central Tuscany.  …see more

17 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £98 /night

£680 - £912 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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

12 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £143 /night

£1000 - £1096 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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

8 Photos

Apartment | 1 Bedroom | sleeps 2

7 Nights min stay

Add to shortlist

from £91 /night

£632 - £712 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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

23 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £98 /night

£680 - £912 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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

21 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £98 /night

£680 - £912 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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

11 Photos

Apartment | 1 Bedroom | sleeps 2

7 Nights min stay

Add to shortlist

from £91 /night

£632 - £712 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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

13 Photos

Apartment | 1 Bedroom | sleeps 3

7 Nights min stay

Add to shortlist

from £136 /night

£952 - £1032 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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

Apartment | 1 Bedroom | sleeps 2

7 Nights min stay

Add to shortlist

from £124 /night

£864 - £1000 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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

9 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £124 /night

£864 - £1000 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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

22 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £102 /night

£712 - £952 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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

11 Photos

Apartment | 1 Bedroom | sleeps 2

7 Nights min stay

Add to shortlist

from £91 /night

£632 - £712 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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

9 Photos

Studio | sleeps 3

1 night min stay

Add to shortlist

from £25 /night

£170 / week

View

Key info:

  • Great for children of all ages 5
  • Pets welcome
A lovely holiday in one of the most beautiful medieval town, in the heart of Tuscany, Certaldo is a town and located in the middle of Valdelsa. It was the home of the family of Giovanni Boccaccio, poet of "Vita di Dante," It is about 35 km southwest of Florence Duomo. The flat is compact but well heated in winter and really fresh and cool in summer.  …see more

9 Photos

Apartment | 2 Bedrooms | sleeps 4

4 Nights min stay

Add to shortlist

from £153 /night

£1068 - £1188 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
andlt;bandgt;Apartment Giuseppaandlt;/bandgt; is part of a beautiful villa in the central Chianti region, splendidly located between Florence and Siena. The villa offers breathtaking views which span the entire area, starting with the magnificent hills right up to the  …see more

23 Photos

House | 1 Bedroom | sleeps 2

7 Nights min stay

Add to shortlist

from £48 /night

£335 - £745 / 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

9 Photos

Apartment | 1 Bedroom | sleeps 3

4 Nights min stay

Add to shortlist

from £138 /night

£960 - £1080 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
andlt;bandgt;Apartment Giustinaandlt;/bandgt; is part of a beautiful villa in the central Chianti region, splendidly located between Florence and Siena. The villa offers breathtaking views which span the entire area, starting with the magnificent hills right up to the  …see more

11 Photos

Apartment | 2 Bedrooms | sleeps 4

3 Nights min stay

Add to shortlist

from £52 /night

£364 - £520 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Apartment Antonellaandnbsp;is on theandnbsp;first floorandnbsp;of a historic building in a narrow street in the old, picturesque village, an oasis of peace and quiet, and has its own private entrance.andnbsp;andnbsp; Particular attention has been reserved for the  …see more

12 Photos

Apartment | 2 Bedrooms | sleeps 4

4 Nights min stay

Add to shortlist

from £138 /night

£962 - £1070 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Apartment Nicolina is part of a beautiful country estate located in the heart of Chianti conveniently situated between Florence and Siena and a stones throw from the charming 'city of towers' San Gimignano. The property is located on a hill, amidst a lush working farm  …see more

13 Photos

Apartment | 2 Bedrooms | sleeps 4

5 Nights min stay

Add to shortlist

from £138 /night

£962 - £1070 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Set in the heart of Tuscany,andnbsp;Apartment Lucianaandnbsp;is a wonderful venue for a relaxing vacation in the middle of stunning landscapes that seem to have been taken out from renaissance masterpiece paintings.andnbsp; Accommodatingandnbsp;2 double bedrooms with  …see more

9 Photos

Apartment | 1 Bedroom | sleeps 3

7 Nights min stay

Add to shortlist

from £121 /night

£843 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
andlt;bandgt;Apartment Agataandlt;/bandgt; is found in a lovely villa, centrally placed in Chianti. The villa spreads across a low-lying cliff, surrounded on all sides by a dense, inviting farm which houses olive orchards and teeming vineyards. Should you choose to  …see more

24 Photos

House | 1 Bedroom | sleeps 3

7 Nights min stay

Add to shortlist

from £77 /night

£536 - £1004 / 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 4

7 Nights min stay

Add to shortlist

from £93 /night

£650 - £1750 / 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 2

7 Nights min stay

Add to shortlist

from £69 /night

£478 - £1147 / 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

17 Photos

Cottage | 3 Bedrooms | sleeps 6

4 Nights min stay

Add to shortlist

from £355 /night

£2484 - £2700 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Cottage Lisanaandnbsp;is one of the Tuscan apartments in the town of Certaldo. This beautiful apartment can comfortably accommodate up to 6 people with its 3 double bedrooms and 4 bathrooms.andnbsp; It has a large living room that exudes Tuscan class and beauty,  …see more

12 Photos

Apartment | 1 Bedroom | sleeps 2

4 Nights min stay

Add to shortlist

from £103 /night

£720 - £828 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
andlt;bandgt;Apartment Felicitaandlt;/bandgt; is part of a beautiful villa in the central Chianti region, splendidly located between Florence and Siena. The villa offers breathtaking views which span the entire area, starting with the magnificent hills right up to the  …see more

10 Photos

Apartment | 1 Bedroom | sleeps 2

4 Nights min stay

Add to shortlist

from £138 /night

£960 - £1080 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
andlt;bandgt;Apartment Goriandlt;/bandgt; is part of a beautiful villa in the central Chianti region, splendidly located between Florence and Siena. The villa offers breathtaking views which span the entire area, starting with the magnificent hills right up to the  …see more

23 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £54 /night

£372 - £966 / 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

21 Photos

Apartment | 1 Bedroom | sleeps 2

7 Nights min stay

Add to shortlist

from £49 /night

£342 - £615 / 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

15 Photos

Apartment | 1 Bedroom | sleeps 4

3 Nights min stay

Add to shortlist

from £43 /night

£297 - £424 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Some pets are welcome - please contact the owner
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

10 Photos

Apartment | 3 Bedrooms | sleeps 8

1 night min stay

Add to shortlist

from £170 /night

£1188 - £2338 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
  • Private garden
Ground-floor: living room with a fireplace, bathroom and dining room with kitchen. - First floor: double bedroom with private bathroom and studio with sofa bed. - Second floor: 2 double bedrooms with bathroom. Maximum capacity 8 people  …see more

13 Photos

Apartment | 2 Bedrooms | sleeps 6

1 night min stay

Add to shortlist

from £145 /night

£1010 - £1870 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
  • Private garden
Now it is composed of a living room with a fireplace, kitchen, one double bedroom with a loft with a single bed and private bathroom with shower, one double bedroom with en suite bathrooms with shower.  …see more

11 Photos

Apartment | 3 Bedrooms | sleeps 9

1 night min stay

Add to shortlist

from £153 /night

£1069 - £2150 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
  • Private garden
Frantoio house features a spacious living room with dining room and a loft to be used as studio with a single bedroom, 3 bedrooms (one with en-suite bathroom with shower and two bedrooms with the same bathroom with shower), 2 bathrooms, a big kitchen,  …see more

12 Photos

Apartment | 2 Bedrooms | sleeps 4

1 night min stay

Add to shortlist

from £110 /night

£764 - £1496 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
  • Private garden
Forno house features a "double" kitchen (with cooking and washing area, fridge and pantry), a living room with a fireplace and 2 bedrooms (one large and one small perfect for children) both with en-suite bathrooms and a private garden  …see more

14 Photos

B&B | 4 Bedrooms | sleeps 8

1 night min stay

Add to shortlist

from £81 /night

£561 - £891 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
Paluffo features four independent apartments, each of them with a private garden – Torre, Stillo, Forno and Frantoio -, and the owner's Main House, with four rooms available for B&B.  …see more

20 Photos

Apartment | 2 Bedrooms | sleeps 6

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £82 /night

£570 - £944 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • 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

20 Photos

Apartment | 2 Bedrooms | sleeps 5

3 Nights min stay

Add to shortlist

from £49 /night

£340 - £467 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Not suitable for children
  • Car essential
  • No pets allowed
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

20 Photos

Apartment | 6 Bedrooms | sleeps 14

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £158 /night

£1103 - £1696 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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

15 Photos

Apartment | 1 Bedroom | sleeps 3

3 Nights min stay

Add to shortlist

from £37 /night

£255 - £382 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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

13 Photos

Apartment | 5 Bedrooms | sleeps 12

3 Nights min stay

Add to shortlist

from £122 /night

£848 - £1357 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Pets welcome
  • Private garden
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

12 Photos

Apartment | 1 Bedroom | sleeps 4

3 Nights min stay

Add to shortlist

from £43 /night

£297 - £424 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Car essential
  • No pets allowed
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

17 Photos

House | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £156 /night

£1086 / 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

21 Photos

Farmhouse | 2 Bedrooms | sleeps 6

3 Nights min stay

Add to shortlist

from £107 /night

£747 - £933 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
campagna toscana, giardino privato pieno di fiori e alberi da frutta, silenzio e tranquillita', piscina panoramica,  …see more