List your home
Apply filters
£ to

51 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
2,512 properties
Florence
983 properties
Venice, Veneto
498 properties
Trapani
483 properties
Lucca
468 properties
Amalfi Coast
452 properties
Cortona
424 properties
Palermo
412 properties
Sorrento, Campania
351 properties
Cefalu
316 properties
San Gimignano
289 properties
Taormina
276 properties
Greve in Chianti
262 properties
Massa Lubrense
245 properties

Filters applied: Wi-Fi available (51)

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
51 Results  |  
24 Photos

Apartment | 1 Bedroom | sleeps 4

Very Good 4/5 

1 night min stay

Add to shortlist

from £55 /night

£385 - £539 / week

View

Key info:

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

14 Photos

Apartment | 1 Bedroom | sleeps 4

3 Nights min stay

Add to shortlist

from £47 /night

£325 - £513 / week

View

Key info:

  • Nearest beach 80 km
  • Great for children of all ages
  • Car not necessary
  • Some pets are welcome - please contact the owner
Charming House in the medieval town near Florence - Siena - Pisa - Lucca - Volterra.  …see more

23 Photos

Apartment | 2 Bedrooms | sleeps 6

1 night min stay

Add to shortlist

from £77 /night

£539 - £719 / week

View

Key info:

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

Featured properties

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

22 Photos

Apartment | 1 Bedroom | sleeps 4

2 Nights min stay

Add to shortlist

from £52 /night

£360 - £475 / week

View

Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • 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

15 Photos

Apartment | 1 Bedroom | sleeps 4

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £49 /night

£342 - £530 / week

View

Key info:

  • Nearest beach 80 km
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
Ideal for a romantic vacation in a relaxing surrounding, rich of history and culture in the hearth of Tuscany.  …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

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
  • 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

21 Photos

Apartment | 1 Bedroom | sleeps 3

7 Nights min stay

Add to shortlist

from £80 /night

£557 - £621 / 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

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

24 Photos

Apartment | 1 Bedroom | sleeps 2

7 Nights min stay

Add to shortlist

from £74 /night

£517 - £581 / 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

5 Photos

Apartment | 1 Bedroom | sleeps 2

7 Nights min stay

Add to shortlist

from £109 /night

£759 - £831 / 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

17 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

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
  • 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

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

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

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

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

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

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

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

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

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

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

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

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

9 Photos

Studio | sleeps 3

1 night min stay

Add to shortlist

from £25 /night

£171 / week

View

Key info:

  • Great for children of all ages
  • 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

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

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

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

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

20 Photos

Villa | 2 Bedrooms | sleeps 6

4 Nights min stay

Add to shortlist

from £34 /night

£238 - £847 / week

View

Key info:

  • Nearest beach 85 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Beautiful traditional house recently restored and converted to the highest standard. Central location ideal to explore the whole region of Tuscany, private pool, modern facilities, excellent value for money. Flexible arrival/departure day also during high season.  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 8

3 Nights min stay

Add to shortlist

from £194 /night

£1355 - £2371 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
lovely accommodation sleeps 8 people, so it is ideal for a large group of friends and is located in Tuscany Italy. This property is ideal if you seek peace and quiet. The villa offers: a swimming Pool, an internet Connection .  …see more

20 Photos

Apartment | 2 Bedrooms | sleeps 5

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £55 /night

£385 / week

View

Key info:

  • Great for children of all ages
  • Pets welcome
L'appartamento, in tipico stile toscano, con travi a vista e pavimenti in cotto, gode del silenzio e della tranquillità caratteristica del piccolo borgo e di un'ottima veduta panoramica sul meraviglioso paesaggio toscano. Certaldo è facilmente raggiungibile sia in auto, in aereo o in treno.  …see more

14 Photos

B&B | 4 Bedrooms | sleeps 8

1 night min stay

Add to shortlist

from £81 /night

£566 - £898 / 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

11 Photos

Apartment | 3 Bedrooms | sleeps 9

1 night min stay

Add to shortlist

from £154 /night

£1078 - £2168 / 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

£770 - £1508 / 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

10 Photos

Apartment | 3 Bedrooms | sleeps 8

1 night min stay

Add to shortlist

from £171 /night

£1197 - £2356 / 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 £146 /night

£1018 - £1885 / 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

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

24 Photos

Apartment | 2 Bedrooms | sleeps 4

2 Nights min stay

Add to shortlist

from £43 /night

£300 - £385 / week

View

Key info:

  • Great for children of all ages
  • Car not necessary
  • Some pets are welcome - please contact the owner
Casa Francesca, nel borgo medioevale di Certaldo Alto, è un grazioso appartamento situato al primo piano e con ingresso indipendente, composto da cucina/soggiorno, una camera matrimoniale, un camera doppia con letto a castello ed un bagno.  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 6

2 Nights min stay

Add to shortlist

from £47 /night

£325 - £428 / week

View

Key info:

  • Great for children of all ages
  • Car not necessary
  • Some pets are welcome - please contact the owner
Casa Al Pozzo, nel borgo medioevale di Certaldo Alto, nel cuore della Toscana, è caratterizzata dal tipico stile toscano, con pavimenti in cotto e soffitti con travi a vista, ed ha il suo ingresso nella via principale, Via Boccaccio.  …see more

23 Photos

Apartment | 2 Bedrooms | sleeps 3

2 Nights min stay

Add to shortlist

from £42 /night

£291 - £385 / week

View

Key info:

  • Great for children of all ages
  • Car not necessary
  • Some pets are welcome - please contact the owner
Casa l'Edera è un accogliente appartamento in stile toscano, situato lungo la via principale di Certaldo Alto, Via Boccaccio. L'appartamento è composto da soggiorno/pranzo con cucina in muratura, una camera matrimoniale, una singola ed un bagno.  …see more

16 Photos

Apartment | 1 Bedroom | sleeps 4

2 Nights min stay

Add to shortlist

from £43 /night

£300 - £411 / week

View

Key info:

  • Great for children of all ages
  • Car not necessary
  • No pets allowed
Casa Giulia, un piccolo gioiello nello scenografico borgo medioevale di Certaldo Alto, patria dello scrittore Giovanni Boccaccio. Casa Giulia, un'alternativa Suite Nuziale per la vostra indimenticabile "Luna di Miele" in Toscana.  …see more

21 Photos

Farmhouse | 2 Bedrooms | sleeps 6

3 Nights min stay

Add to shortlist

from £108 /night

£753 - £941 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • 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

6 Photos

Castle | 19 Bedrooms | sleeps 40

Excellent 5/5 

1 night min stay

Add to shortlist

from £3053 /night

£21371 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
  • Private garden
Castello medioevale adatto per un soggiorno indimenticabile, al centro della Toscana vicino alle città d'arte come Firenze, Siena, San Gimignano, Volterra, Lucca e Pisa oltre a altre città medioevali come Monteriggioni, San Donato in Poggio, Castellina in Chianti.  …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