List your home
Apply filters
£ to

Holiday homes 3,746

Reset search

Show results on map

Filter your search

Price per night

Price per night

£ to per night

Bedrooms

Location

  • Italy Clear
  • Tuscany Clear
  • Province of Siena Clear

Location

  • All locations
  • Abbadia San Salvatore (6)
  • Asciano (134)
  • Bagni di San Filippo (2)
  • Bagno Vignoni (16)
  • Brenna (3)
  • Buonconvento (60)
  • Campiglia d'Orcia (3)
  • Casciano (2)
  • Casole d'Elsa (172)
  • Castellina In Chianti (155)
  • Castelmuzio (15)
  • Castelnuovo Berardenga (172)
  • Castiglione D'Orcia (35)
  • Cetona (68)
  • Chianciano Terme (37)
  • Chiusdino (23)
  • Chiusi (34)
  • Colle di Val d'Elsa (129)
  • Gaiole in Chianti (178)
  • Gallina (3)
  • La Piazza (1)
  • Le Piazze (11)
  • Lucarelli (4)
  • Moltacino (1)
  • Montalcino (126)
  • Montecchio (1)
  • Montepulciano (239)
  • Monteriggioni (89)
  • Monteroni d'Arbia (43)
  • Monticiano (37)
  • Montisi (22)
  • Murlo (22)
  • Orgia (2)
  • Palazzone (15)
  • Petroio (1)
  • Piancastagnaio (6)
  • Pienza (140)
  • Pievasciata (4)
  • Pievescola (17)
  • Poggibonsi (148)
  • Radda in Chianti (61)
  • Radicofani (48)
  • Radicondoli (82)
  • Rapolano Terme (65)
  • Rocca d'Orcia (2)
  • Rosia (7)
  • San Casciano dei Bagni (46)
  • San Gimignano (410)
  • San Giovanni d'Asso (36)
  • San Lorenzo a Merse (2)
  • San Quirico d'Orcia (16)
  • Sarteano (52)
  • Siena (424)
  • Sinalunga (138)
  • Sovicille (92)
  • Strove (5)
  • Tognazza (1)
  • Torre A Castello (1)
  • Torrita di Siena (33)
  • Trequanda (18)
  • Vergelle (7)
  • Ville di Corsano (14)
  • Vivo d'Orcia (2)
  • Volte Basse (2)

more +

less -

Also consider

Coastal Cottages
222 properties
Apartments Sardinia
478 properties
Apartments Tuscany
3181 properties
Apartments Lake Garda Area
103 properties
Apartments Lake Como Area
494 properties
Apartments Sicily
634 properties
Villas Siena
410 properties
Villas San Gimignano
409 properties
Villas Montepulciano
239 properties
Gaiole in Chianti
178 properties
Villas Casole d'Elsa
171 properties
Villas Castelnuovo Berardenga
169 properties
Villas Castellina In Chianti
155 properties
Villas Poggibonsi
143 properties
Villas Sinalunga
138 properties
Villas Pienza
137 properties
Apartments Colle di Val d'Elsa
128 properties
Villas Montalcino
123 properties
Asciano
122 properties
Villas Monteriggioni
86 properties
Payment Protection
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
3,746 Results   |  

Excellent 5/5 

17 Photos

Province of Siena / Abbadia San Salvatore

Farmhouse / 8 Bedrooms / sleeps 12

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £190 / night

£1324 / week

View

Key info:

  • Suitable for children over 5
  • Car essential
  • Pets welcome
  • Private garden
il casale Roccone è immerso nel verde del monte Amiata, con oltre cento ettari di parco naturale privato all'interno della riserva del Pigelleto. 12 posti letto, possibilità di avere un servizio di cuochi, visite guidate nella miniera, passeggiate nella foresta. Il Ro  …see more


20 Oct 2014

5/5

"Il Roccone fantastico podere in Toscana dove passare un fine settimana con gli amici"

Abbiamo avuto il piacere di conoscere il Podere il Roccone grazie ad una raccomandazione di una amica, siamo rimasti molto contenti sia della località che della struttura. La struttura è circondata … More

See all reviews Continue

Excellent 5/5 

24 Photos

Pienza / Monticchiello

B&B / 4 Bedrooms / sleeps 7

Excellent 5/5 

1 night min stay

Add to shortlist

from £65 / night

£449 - £463 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
B&B di charme dotato di confortevoli camere matrimoniali, tranquillità, relax e benessere per una vacanza indimenticabile. La Val d'Orcia, Monticchiello e l'accoglienza della Casa di Adelina resteranno a lungo nei vostri cuori.  …see more


12 Jan 2015

5/5

"Excellent Accommodation"

This place was wonderful, Francesco couldn't do enough for you. Its located in a gorgeous little town in Val d'Orcia area. There are three restaurants in the town and a magnificent view from the … More


27 Jan 2015

5/5

"“Soggiorno indimenticabile... in un gioiello nella Val d'Orcia”"

Io, mia moglie e la nostra piccola bimba abbiamo avuto il piacere di soggiornare a Maggio 2014 in questa deliziosa struttura, situata nel centro storico di Monticchiello (vicino Pienza e Montepulciano… More

See all reviews Continue

Excellent 5/5 

24 Photos

Montalcino / Val d'Orcia

Villa / 4 Bedrooms / sleeps 9

Excellent 5/5 

1 night min stay

Add to shortlist

from £200 / night

£1398 - £1839 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
A really charming and full of style apartment in a XVI th century stone villa near Montalcino, Pienza, Siena, Montichiello. An enchanted garden and an amazing swimming pool with view on Montalcino for an unforgettable holiday: good food and wine, art, sport and relax..  …see more


20 Jul 2015

5/5

"Everything we hoped for!!"

We just got back from a week at Simona and Michael's fabulous villa and I'm already planning another trip! The house itself is absolutely beautiful, exactly what you imagine when you think of a Tuscan… More

Thank you for your kind words. It was a real pleasure to meet you all and spend some time together. Special people and special guests! We hope to see you again. All our best. Simona & Michele


5 Jul 2015

5/5

"Amazing villa in a great location for exploring Tuscany"

We spent a lovely week in the ground floor apartment in late June and would definitely recommend this villa to other holidaymakers. The pool and gardens are fantastic. The pool is warm and brillia… More

We are very happy when we see guests happy and appreciating this place we love so much. Thank you for beeing with us with your kindness and enthusiasm.Hope to see you again


15 Jul 2014

5/5

"Fabulous"

Really enjoyed our stay, the hosts Michele and Simona were lovely. We had the whole place to ourselves, so really quiet. Very comfy, cozy done like a family home. All amenities (did not have a micr… More

Thank you and hope to have you again. Simona & Michele

See all reviews Continue

Featured properties

Excellent 5/5 

21 Photos

Montalcino / Val d'Orcia

Apartment / 4 Bedrooms / sleeps 9

Excellent 5/5 

1 night min stay

Add to shortlist

from £190 / night

£1324 - £1508 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
An amazing holiday in the moast beautiful area of Tuscany, in the natural park of the Val d'Orcia, near Montalcino, Pienza, Siena, Montichiello, Bagno Vignoni. A quiete, relaxing garden with swimming pool, a charming, cosy and comfortable apartment in an ancient villa.  …see more


4 Sep 2013

5/5

"The perfect Tuscan retreat"

We have just returned from a truly memorable stay in Siena. The villa is perfect! Beautifully decorated, light and airy and a huge living space - perfect for families or large groups of friends. … More

Thank you! It was a pleasure to meet you and your family.Perfect guests! Hope to see you again. Simona and Michele


3 Sep 2013

5/5

"Perfect house"

we had a great stay, the house is just beautiful!!!!!! with a lot of atention for details and confort. the garden and pool are just amazing. the owners were very nice and they gave us the best recomme… More


5 Aug 2013

5/5

"Fantastic experience in a gorgeous setting that exceeded all expectations."

My wife and I spent a week here with our three teenage boys and all of us loved the place. The reality of the home is even better than the photos and we hated to leave. Hosts are warm, friendly and gr… More

See all reviews Continue

Excellent 5/5 

12 Photos

Province of Siena / Monteriggioni

Apartment / 2 Bedrooms / sleeps 4

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £32 / night

£219 - £292 / week

View

Key info:

  • Swimming pool
  • Suitable for children over 5
  • Some pets are welcome - please contact the owner
  • Private garden
Appartamento con giardino privato. Piscina condominiale. Ottimo punto di partenza per visitare Siena, San Gimignano, Volterra, Firenze e tutto il Chianti. Noleggio biciclette (10 euro al giorno)  …see more


24 Aug 2014

5/5

"Excellent"

Logement rénovée avec goût. Piscine très spacieuse. Situation idéale au calme mais proche de Sienne et de San Gimignano, et à 50 km de Florence. Hôtes très discrets mais non moins sympathiques… More


9 Jul 2014

5/5

"Magnifique"

Propriété magnifique dans un environnement enchanteur. Accueil chaleureux et logement coquet. Les enfants et les parents ont entre autres beaucoup apprécié la piscine :-)… More


7 Jul 2014

5/5

"Senza parole"

Per il nostro secondo soggiorno nella struttura, ci siamo rivolti ai proprietari di questo appartamento (li avevamo conosciuti l'anno precedente). L'appartamento 14 è bellissimo, ben arredato, fun… More

See all reviews Continue

Very Good 4/5 

21 Photos

Province of Siena / San Gimignano

Townhouse / 2 Bedrooms / sleeps 5

Very Good 4/5 

4 Nights min stay

Add to shortlist

from £77 / night

£533 - £811 / week

View

Key info:

  • Nearest beach 77 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
It is a typical example of old Tuscan country houses, with floors made with terracotta tiles, and wooden beams on the ceiling, it also has a wide farmyard, still with floor done in terracotta tiles with an enchanting view on the heart of the Tuscan Countryside.  …see more


20 May 2015

4/5

"Great Cottage,lovely patio with wonderful views"

We stayed here for a week in early May with my mother. The owners were waiting with a warm and friendly greeting for us, even though we arrived late due to delays en route. Though they only spoke Ital… More

See all reviews Continue

23 Photos

Montepulciano / Valiano

Villa / 7 Bedrooms / sleeps 23

Min stay varies

Add to shortlist

from £473 / night

£3309 - £5148 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Casale, montepulciano, villa, piscina, vigneti, matrimonio in toscana, matrimonio in Italia, Italy, Tuscany Antico casale, completamente restaurato e suddiviso in 7 accoglienti appartamenti  …see more

17 Photos

Province of Siena / Montepulciano

B&B / 3 Bedrooms / sleeps 6

2 Nights min stay

Add to shortlist

from £53 / night

£368 / week

View

Key info:

  • Great for children of all ages
  • Car essential
  • Pets welcome
Every morning the lady of the house makes amazing and always new breakfasts, created with the genuine products of the area and with a deep experience of cooking. Gluten intolerant breakfast. Please notify us in advance.  …see more

24 Photos

Gaiole in Chianti / Lecchi

Castle / 6 Bedrooms / sleeps 16

5 Nights min stay

Add to shortlist

from £358 / night

£2500 - £3802 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Castle, tuscany, italy, swimmingpool, bed and breakfast, gaiole in chianti, events, wedding, private castle, private villa, Yoga, wine  …see more

27 Photos

Province of Siena / Sarteano

Farmhouse / 7 Bedrooms / sleeps 14

7 Nights min stay

Add to shortlist

from £809 / night

£5662 - £7500 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
La proprietà comprende 800 alberi di ulivo, un piccolo vigneto, frutteto e bosco; meravigliosi giardini paesaggistici, laghetto con fiori di loto e ninfee, vasca idromassaggio con acqua calda e una bellissima piscina con piscina per i piccoli e vasca idromassaggio. Ag  …see more

10 Photos

Pienza / Monticchiello

Townhouse / 2 Bedrooms / sleeps 4

Min stay varies

Add to shortlist

from £85 / night

£589 - £846 / week

View

Key info:

  • Beach / lakeside relaxation
  • Not suitable for children
  • No pets allowed
The hospitality and refinement of the Bed and Breakfast “La Casa di Adelina” continues in the quiet apartment situated in the center of Monticchiello. The nock will leave you speechless! This capability provides our guests to stay in a context of value, architectu  …see more

9 Photos

Province of Siena / Gaiole in Chianti

Apartment / 2 Bedrooms / sleeps 6

1 night min stay

Add to shortlist

from £37 / night

£258 - £2574 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Gaiole Suites 1 is a beautiful apartment in Gaiole in Chianti. The apartment located in a completely renovated Borgo can comfortably host up to 6 people.  …see more

12 Photos

Province of Siena / Castiglione D'Orcia

Villa / 8 Bedrooms / sleeps 25

7 Nights min stay

Add to shortlist

from £263 / night

£1839 - £3677 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Tuscany, Toscana, Casale, Piscina, Vigneto, Corsi cucina, Caccia al tartufo, Villa, Casa Vacanze, Italia, Equitazione, Matrimonio, matrimoni, eventi, lusso, Catering ;Tastings and Wine Tour's; Truffle Hunting ;Cooking Classes; Excursions; Horse Riding  …see more

9 Photos

Province of Siena / Gaiole in Chianti

Apartment / 2 Bedrooms / sleeps 6

1 night min stay

Add to shortlist

from £39 / night

£273 - £2574 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Gaiole Suites 9 is a beautiful and comfrortable apartment in the heart of Chianti. The apartment, furnished with all the necessary, can host up to 6 people.  …see more

5 Photos

Province of Siena / Montepulciano

Apartment / 2 Bedrooms / sleeps 3

Min stay varies

Add to shortlist

Pricing unknown

View

Key info:

  • Great for children of all ages
  • No pets allowed
  • Private garden
Agriturismo Raggio di Sole is about few meters from the city of Montepulciano, famous all over the world for the Vino Nobile and rich in artistical and cultural events: Cantiere Internazionale d'Arte, Bruscello, Bravìo etc..  …see more

22 Photos

Province of Siena / Colle di Val d'Elsa

House / 2 Bedrooms / sleeps 4

3 Nights min stay

Add to shortlist

from £42 / night

£292 - £365 / week

View

Key info:

  • Suitable for children over 5
  • Car not necessary
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Casa con giardino nel centro storico di Colle di Val d'Elsa. Finemente ristrutturata ed arredata.  …see more

25 Photos

Province of Siena / Castelnuovo Berardenga

Apartment / 2 Bedrooms / sleeps 5

1 night min stay

Add to shortlist

from £49 / night

£343 - £830 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Appartamento Papavero is an amazing apartment in Borgo Rocche di Valiano in the heart of Chianti region.The recently renovated apartment, made in typical Tuscan style, can comfortably hosts up to 5 people. City tax, cleaning fee and consumption services are not included  …see more

17 Photos

Province of Siena / Sovicille

Apartment / 2 Bedrooms / sleeps 4

2 Nights min stay

Add to shortlist

from £63 / night

£438 - £548 / week

View

Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
Warm and welcoming, ten kilometres away from Sienna this is an ancient, XVth century villa, recently restored by a sensitive and art historically conscious architect and designer who has chosen to preserve the very best of the Tuscan tradition Ideal for every configurat  …see more

24 Photos

Province of Siena / Sovicille

Apartment / 2 Bedrooms / sleeps 5

2 Nights min stay

Add to shortlist

from £68 / night

£475 - £584 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
Warm and welcoming, ten kilometres away from Sienna this is an ancient, XVth century villa, recently restored by a sensitive and art historically conscious architect and designer who has chosen to preserve the very best of the Tuscan tradition  …see more

25 Photos

Province of Siena / Castelnuovo Berardenga

Apartment / 2 Bedrooms / sleeps 7

1 night min stay

Add to shortlist

from £49 / night

£343 - £830 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Geranio Apartment is a beautiful apartment located in Borgo Rocche di Valiano, in the heart of Chianti region.The recently renovated apartment, can comfortably hosts up to 7 people. City tax, cleaning fee and consumption services are not included and must be paid cash a  …see more

Excellent 5/5 

20 Photos

Province of Siena / Montepulciano

Apartment / 2 Bedrooms / sleeps 4

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £95 / night

£662 - £1103 / week

View

Key info:

  • Great for children of all ages
  • No pets allowed
At MOntorio is easy to arrive and difficult to live, will be your home in Tuscany. Montorio has a special and unique spot , and you will feel in love for it  …see more


1 Jul 2014

5/5

"Exactly what we were looking for"

Situated on a hill below the imposing hill which Montepulciano itself rests on, Montorio is a unit of several self-catering apartments of various sizes able to accommodate various size groups. We t… More


27 Jun 2014

5/5

"A magical setting that exceeded expectations in every way!"

My husband, 20-year-old daughter and I enjoyed 4 nights at Montorio in mid-June, 2014. We stayed in the two-bedroom, one bath unit which is spotless, very spacious and charming. The entire property is… More


30 Oct 2013

5/5

"Wonderful historic rental in heart of Tuscany"

We spent a week in the studio apartment in October. It was great! The buildings are a remodeled convent or something--thick walls, tile floors, beautiful. The apartment is larger than we expected--… More

See all reviews Continue

Excellent 5/5 

11 Photos

Province of Siena / Castiglione D'Orcia

Apartment / 2 Bedrooms / sleeps 4

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £46 / night

£317 - £325 / week

View

Key info:

  • Great for children of all ages
  • Car essential
  • Pets welcome
The house offers everything you need for a relaxing holiday and has free Wi-Fi, microwave oven, drip coffee maker, toaster and kettle as well as being supplied with all bedroom and bathroom linen.  …see more


5 Mar 2015

5/5

"Location suggestiva...."

Abbiamo soggiornato in questo borgo medievale per due notti ai primi di marzo, appartamento carino, pulito e abbastanza comodo per una famiglia con due bambini. Gode di una parziale vista della Val d… More


8 Sep 2014

5/5

"fuori dal mondo"

avevo prenotato con un po' di paura come sempre.arrivati...il borgo ci conquista!incantevole bello da sognar di prender casa li'.chiamiamo la sig.barbara e ci accoglie.la casa ci lascia stupiti.grande… More


18 Aug 2014

5/5

"ottimo soggiorno in un paese d'altri tempi"

abbiamo soggiornato in questo bellissimo appartamento a fine Dicembre 2013. Nel cuore di Rocca d'Orcia, borgo medievale di altri tempi, sembra di vivere in una favola. La casa è curate nei minimi par… More

See all reviews Continue

Very Good 4/5 

14 Photos

Province of Siena / Siena

Apartment / 3 Bedrooms / sleeps 8

Very Good 4/5 

1 night min stay

Add to shortlist

from £106 / night

£736 / week

View

Key info:

  • Great for children of all ages
  • Pets welcome
  • Private garden
Federico Frati I' m a art teacher 50 years old i have three fantastic sons There are two little buses each 7' minutes that bring you in 5' minutes in Piazza del Campo or in Piazza del  …see more


19 Aug 2015

4/5

"Agréable"

Calme,belle vue de la terrasse tout autour Propriétaire sympathique Agréable séjour passé en Toscane… More

See all reviews Continue

Excellent 5/5 

17 Photos

Province of Siena / Cetona

Apartment / 1 Bedroom / sleeps 4

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £36 / night

£252 - £256 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Cetona is the perfect small Tuscan village offering ambiance, tranquility, and character. Cetona has all the services you will need also; restaurants, bars and cafes, shops, and services, right in the piazza, just a short walk from the apartment. Please be advised the  …see more


27 Jun 2015

5/5

"Fabulous apartment, fantastic location"

Short walk to shops, supermarket and restaurants. Apartment spotless, well equipped, free wifi, pool area very quiet and pretty, stunning views. Approx. 1 hour drive from Perugia airport. Upon reques… More


22 Jul 2014

5/5

"Fabulous Apartment."

I stayed In Cetona for a month in June July this year. The apartment was beautifully situated a little way out side of Cetona. An easy walk to the piazza. Lovely swimming pool. Great views of the Tusc… More

See all reviews Continue

9 Photos

Province of Siena / San Gimignano

House / 2 Bedrooms / sleeps 4

Min stay varies

Add to shortlist

Pricing unknown

View

Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
  • Private garden
Casale, tipica struttura toscana Casanova di Larniano è un'antica casa colonica situata in Toscana, vicino a San Gimignano (Siena). La sua ottima posizione geografica consente facili spostamenti per Firenze (50 Km), Siena (40 Km), Pisa (50 Km), Volterra (30 Km).  …see more

23 Photos

Province of Siena / Siena

Villa / 5 Bedrooms / sleeps 10

1 night min stay

Add to shortlist

from £736 / night

£5148 - £9192 / week

View

Key info:

  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Amazing villa,with pool and large garden close to Siena  …see more

27 Photos

Province of Siena / Gaiole in Chianti

Villa / 2 Bedrooms / sleeps 5

5 Nights min stay

Add to shortlist

from £58 / night

£405 - £809 / week

View

Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
The Chianti As You Always Dreamed It. A charming Medieval borgo in the heart of Chianti Classico, 15 km far from Siena. Relax and discovery hour incredible landes. The charme of an ancient Medieval borgo in the heart of Chianti Classico  …see more

23 Photos

Province of Siena / Gaiole in Chianti

House / 1 Bedroom / sleeps 3

5 Nights min stay

Add to shortlist

from £43 / night

£295 - £589 / week

View

Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
The house, composed of 5 delightful apartments, has as it's main objective the idea of offering guests the opportunity to enjoy the calm, the beauty and all the pleasures our region has to offer. Our apartments have been renovated with respect for tradition.  …see more

13 Photos

Province of Siena / Radda in Chianti

House / 4 Bedrooms / sleeps 10

7 Nights min stay

Add to shortlist

from £127 / night

£883 / week

View

Key info:

  • Great for children of all ages
  • No pets allowed
  • Private garden
Very confortable countryhouse, in the heart of Chianti hills, ideal for family or groups who wants to visit the best of Tuscany and relax in the country. Four large bedrooms, two bathrooms, large livingroom with fireplace, kitchen, big garden, internet wifi.  …see more

8 Photos

San Gimignano / Castel San Gimignano

Apartment / 1 Bedroom / sleeps 5

1 night min stay

Add to shortlist

from £27 / night

£184 - £441 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Situated in the heart of tuscany (hills, between volterra, famous etruscan and medieval city and san gimignano, famous all over the world for its characteristic towers. You can easily visit florence, siena and pisa, chianti region, thyrrenian sea, monteriggioni. Charac  …see more

24 Photos

Province of Siena / Castellina In Chianti

Apartment / 2 Bedrooms / sleeps 8

3 Nights min stay

Add to shortlist

from £81 / night

£567 - £608 / week

View

Key info:

  • Nearest beach 90 km
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Large, elegant, comfortable apartment in incomparable surroundings. Peaceful and relaxing with spectacular scenery. 3 km from Castellina in Chianti with its medieval town centre, shops, bars, restaurants. 22 km from Siena., 37km from Florence. No neighbours or noise. P  …see more

12 Photos

Montalcino / Val d'Orcia

Villa / 3 Bedrooms / sleeps 7

7 Nights min stay

Add to shortlist

from £211 / night

£1471 - £1765 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
As the house is part of a company that produces Brunello di Montalcino is possible to follow the stages of production or do a tasting tour to discover one of the best wines in the world in our cave.  …see more

7 Photos

San Gimignano / Santa Maria, San Gimignano

House / 2 Bedrooms / sleeps 5

1 night min stay

Add to shortlist

from £42 / night

£292 - £438 / week

View

Key info:

  • Nearest beach 60 km
  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Un' abitazione in pieno relax..  …see more

4 Photos

Province of Siena / Pienza

B&B / 1 Bedroom / sleeps 2

1 night min stay

Add to shortlist

from £37 / night

£256 - £285 / week

View

Key info:

  • Great for children of all ages
  • Pets welcome
  • Private garden
All'interno di un'antica dimora del 1700 troverete una camera con atmosfere di altri tempi per una vacanza rilassante.  …see more

5 Photos

Province of Siena / Pienza

Apartment / 2 Bedrooms / sleeps 5

1 night min stay

Add to shortlist

from £68 / night

£475 - £548 / week

View

Key info:

  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
Nel centro storico di Pienza, in via Condotti 13, scoprirete "Il Giardino Segreto": un' antica dimora del 1700 con uno splendido giardino interno a disposizione degli ospiti dove potersi rilassare e godere del silenzio e della tranquillità.  …see more

7 Photos

Province of Siena / Cetona

Townhouse / 2 Bedrooms / sleeps 4

2 Nights min stay

Add to shortlist

from £62 / night

£431 - £814 / week

View

Key info:

  • Suitable for children over 5
  • Some pets are welcome - please contact the owner
L'appartamento dispone di un ampio ripostiglio e dell utilizzo della cassaforte. Le finestre delle camere da letto offrono una panoramica completa di tutta la piazza principale. Per soggiorni inferiori alla settimana sono richiesti 50 €. per le spese di pulizia final  …see more

Very Good 4/5 

10 Photos

Province of Siena / San Gimignano

Apartment / 3 Bedrooms / sleeps 7

Very Good 4/5 

3 Nights min stay

Add to shortlist

from £127 / night

£883 - £1471 / week

View

Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
.This charming accommodation lies in the countryside enjoying the most marvellous views of the undulating landscape and the towers of the city of San Gimignano only 3km away. It is a lovely location for enjoying country walks and relaxing The pool and the garden are no  …see more


21 Sep 2014

5/5

"very beautiful location"

At the end of a narrow lane set amongst the vine groves looking to wards the beautiful hill top town of San Gimignano this Villa attached to the owners house is typical Tuscan accommodation, with its … More


17 Aug 2015

3/5

"No frills"

This villa is on the rustic side, but sadly not in a particularly charming way! Really the interior gives the impression of not being terribly suitable for paying guests - the furniture appears to be… More

See all reviews Continue

Excellent 5/5 

16 Photos

Province of Siena / Buonconvento

House / 7 Bedrooms / sleeps 12

Excellent 5/5 

1 night min stay

Add to shortlist

from £45 / night

£309 / week

View

Key info:

  • Swimming pool
  • Suitable for children over 5
  • Some pets are welcome - please contact the owner
L'agriturismo Bellavista si trova su una coolina in mezzo  …see more


13 Aug 2015

5/5

"Five star Agriturismo, very nice hosts"

Bellavista is as close to perfection as possible : fantastic location, 40 minute drive from Siena, the whole region is worthy of a travel brochure on Tuscany. The house itself sits by itself on top of… More

Grazie! Siete una bella famiglia ed è stato un piacere avervi con noi a Bellavista! Claudia

See all reviews Continue

Very Good 4.5/5 

21 Photos

Province of Siena / Monticiano

Villa / 9 Bedrooms / sleeps 18

Very Good 4.5/5 

2 Nights min stay

Add to shortlist

from £788 / night

£5515 - £5809 / week

View

Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Ideal family and wedding Tuscan villa with private salt water pool. Tucked away yet not isolated. All amenities in the nearby village, walking distance. Siena 25 minutes.All Tuscan art cities and seaside daily outings. Nature, art, peace and quiet.  …see more


10 Jul 2015

5/5

"Perfect in every way"

Coming to Villa Podernova was the absolute highlight of our holiday. We found the place by accident as we had to move from our original villa (long story!!). Hosts were so welcoming as was Spike the… More


16 May 2015

5/5

"Amazing"

We stayed at this villa for a friends wedding and we completely loved it. The property is beautiful and well managed. The rooms are simple and very country style. We loved the huge garden and the tree… More


30 Apr 2013

4/5

"un podere caratteristico curato nel dettaglio e pieno di charme"

Un podere bellissimo, immerso nel verde delle colline senesi, circondaro dalla natura ma allo stesso tempo a 10 min a piedi da Monticiano dove si puo fare la spesa o cenare. Le camere e gli appartame… More

See all reviews Continue

Very Good 4/5 

10 Photos

Province of Siena / Siena

Apartment / 1 Bedroom / sleeps 4

Very Good 4/5 

5 Nights min stay

Add to shortlist

from £81 / night

£567 - £1103 / week

View

Key info:

  • Nearest beach 105 km
  • Not suitable for children
  • Car not necessary
  • Air conditioning
  • No pets allowed
Best views of Siena.The apartment being only a few minutes from the Campo. The terrace is magnificent with 360°panoramic views of the centre of town, Duomo,the bell tower.It's very quite and you can relax on the roof deck taking a sunbath on the long chair. flat apa  …see more


10 Sep 2014

5/5

"The view from the roof terrace is breath taking"

We have completely enjoyed our stay at this wonderful apartment in Siena. The apartment is on the top floor of a beautiful building, on piazza Giacomo Matteotti which is right on the edge of the histo… More


13 Jul 2014

5/5

"Wonderful month spent here"

We loved it! You can see for yourself the fantastic views from the terrace and the small living/dining room. The location couldn't have been more convenient. A one-minute walk to the Gramsci bus plaza… More


20 Aug 2015

5/5

"The most spectacular way to see Siena!"

Simone was completely helpful from start to finish. He greeted us warmly and gave us a complete tour of the flat--wi fi, guide books and maps of Siena, coffee maker, dishwasher, washing machine, and a… More

See all reviews Continue

Excellent 5/5 

19 Photos

Province of Siena / Rapolano Terme

Farmhouse / 3 Bedrooms / sleeps 6

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £74 / night

£515 / week

View

Key info:

  • Nearest beach 50 km
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
In the Crete Senesi, a working organic farm focused on breeding/training thoroughbred horses. The two traditional farmhouses are beautifully furnished with family pieces. The Rapolano thermal spas are just a few minutes' drive, and Siena is within easy reach. A traditio  …see more


26 May 2014

5/5

"Pferdeparadies und Menschenparadies - wer Ruhe und Natur sucht ist hier genau richtig"

Einer der wunderschönsten, entspanntesten Urlaube, die ich je verbracht habe. Eine Woche Ruhe und Erholung pur. Wer das Landleben und die Natur liebt, kann sich hier wunderbar niederlassen. So viel F… More

See all reviews Continue

Very Good 4.5/5 

21 Photos

Province of Siena / Chiusi

Guest house / 15 Bedrooms / sleeps 30

Very Good 4.5/5 

Min stay varies

Add to shortlist

Pricing unknown

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
Tuscany hamlet, nature, relax, historical sigh, holiday, tours, walking, swimmingpool  …see more


4 Feb 2015

5/5

"Week End meraviglioso e rilassante"

Sono stato dal 30 Gennaio al 1° Febbraio per un week end con mia moglie. La struttura è veramente bella, gli appartamenti sono ben tenuti, puliti e molto accoglienti. Gli arredi rustici, puliti e be… More

Gent.mi...cosa aggiungere..!?! Ci fa enormemente piacere che abbiato "toccato con mano", quanta attenzione ed impegno quotidiano destiniamo alla totale soddisfazione dei nostri gentili clienti. Abbiamo la fortuna di gestire una meravigliosa proprietà, nel cuore di una zona di "eccellenze", di storia, cultura, tradizione e l'essere molto vicino a tantissime località anche molto più famose ci aiuta tantissimo.... a presto allora...!!!!!! luigi e paola


10 May 2014

5/5

"incantevole borgo nelle colline senesi"

Un vecchio borgo ottimamente ristrutturato immerso nel verde e nella quiete delle colline senesi. Ideale per rilassarsi e come base per visitare splendidi borghi mediovali quali Pienza, Montepulciano,… More


24 Mar 2014

5/5

""Come a casa""

Soggiornare a BorgoDolciano è stato come trovarsi a casa. L'accoglienza di Luigi e della Paola...unica! Sono due persone meravigliose. Consiglierei questo posto a tutti, sia per la posizione in cui s… More

See all reviews Continue

Excellent 5/5 

9 Photos

Province of Siena / Montalcino

House / 3 Bedrooms / sleeps 8

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £64 / night

£442 / week

View

Key info:

  • Nearest beach 55 km
  • Great for children of all ages
  • Pets welcome
  • Private garden
In una casa recentemente ristrutturata, nel comune di Montalcino, tra viti, olivi e macchia mediterranea, nella più assoluta tranquillità all'esterno come all'interno, l'agriturismo Villetta Caprili offre ospitalità fino a 8 persone con parcheggio privato.  …see more


3 Sep 2014

5/5

"Bellissima struttura e ottima location"

Ho soggiornato in questa struttura per 4 notti dal 28 agosto al 1 settembre. E' una casa indipendente all'interno del podere i cui proprietari (Caprili) sono produttori di ottimi vini (ovviamente Brun… More


28 Apr 2015

5/5

"Tuscany dream vacation"

The Caprili family made our stay in there vineyard amazing. Very friendly and helpful. While secluded it's not far from all the tourist destinations. Also you really can't beat the Caprili label on wi… More

See all reviews Continue

Very Good 4.5/5 

15 Photos

Province of Siena / Siena

House / 1 Bedroom / sleeps 3

Very Good 4.5/5 

1 night min stay

Add to shortlist

from £53 / night

£368 - £493 / week

View

Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
The apartment is located just 5 minutes drive from the walls surrounding the old town (10 min by bus) and its location also allows you to quickly reach the surroundings of the Sienese countryside. Supermarket and shops nearby. Being a one bedroom apartment of about 45  …see more


27 May 2014

5/5

"Excellent"

A great place to stay. The apartment is large and lovingly decorated, the kitchen has literally everything, there's WiFi. It's in a quiet area, but only a short and direct drive away from Siena's city… More


13 May 2014

5/5

"Sehr empfehlenswert - immer gern wieder"

Wir haben uns bisher immer (bereits 3 x) sehr wohl gefühlt. Die Vermieter wohnen im Objekt und sind sehr freundlich und kinderlieb. Die Wohnung ist sehr sauber und liebevoll eingerichtet. Die Außena… More


7 Jul 2014

4/5

"Uitstekende uitvalsbasis om Siena te bezoeken."

Mooi verzorgd appartement, ingericht in Italiaanse stijl. Heel aardige mensen. Ondanks dat het op een industriegebied ligt waan je je in de tuin op een Toscaans landgoed. Het is hier goed vertoeven en… More

See all reviews Continue

Excellent 5/5 

20 Photos

Province of Siena / Cetona

Apartment / 2 Bedrooms / sleeps 4

Excellent 5/5 

4 Nights min stay

Add to shortlist

from £43 / night

£300 - £325 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
The apartment is designed in a typical Italian style - it feels like a house. It offers wrought iron and marble accents, tile floors, wood beams and small yard. Cetona is the ideal spot to explore southeast Tuscany and Umbria.  …see more


17 Aug 2015

5/5

"Parfait!!"

Nous avons passé un excellent séjour de 2 semaines dans cet appartement avec nos deux enfants (8 et 11 ans). L'appartement est très bien équipé, il n'y a qu'à poser ses valises et profiter. Un … More


2 Sep 2014

5/5

"Wonderful location, spotlessly clean, thought of everything!"

We stayed here with our two girls (5 and 7) for ten nights and it was wonderful. Cristina was brilliant from day one at responding to any questions via email prior to our arrival and when we got there… More


9 Sep 2013

5/5

"clean, comfortable, great location!!!"

2nd apartment we have stayed in on this complex and wasn't dissapointed. The apartment was clean had everything we needed and more, with a well equipped kitchen. It was nice to be able to sit in the g… More

Grazie! Great family - we would love to host you again. All the best, a presto.

See all reviews Continue

Very Good 4/5 

10 Photos

Province of Siena / Siena

Apartment / 1 Bedroom / sleeps 4

Very Good 4/5 

1 night min stay

Add to shortlist

from £53 / night

£365 / week

View

Key info:

  • Great for children of all ages
  • No pets allowed
Ampio bilocale nel centro storico di Siena  …see more


17 Apr 2015

4/5

"A comfortable stay"

- The apartment is a bit old, but good to stay. -Basic facilities/ but meets the requirements -Communication with Owners could be a problem (if you do not speak Italian) / but they are good ( son wi… More

See all reviews Continue

Excellent 5/5 

17 Photos

Province of Siena / Cetona

House / 2 Bedrooms / sleeps 4

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £58 / night

£402 / week

View

Key info:

  • Not suitable for children
  • Car advised
  • Some pets are welcome - please contact the owner
Opportunity awaits you to experience your Italian holiday in this unique home. The history and character of the home, neighborhood and Cetona will make you feel immersed in the lifestyle and truly feel like a local. We specialize in bike tours,rental and itineraries  …see more


19 Aug 2015

5/5

"A wonderful, relaxing environment set in beautiful surroundings"

A very enjoyable relaxing holiday. The house lived up to expectations and was very spacious and well appointed. There is lots to do in the area and the little town of Cetona is lovely, the people ver… More


25 Oct 2014

5/5

"a fantastic base for a wonderful trip"

This is a wonderful property in a lovely village and was an ideal base for our exploration of Tuscany and parts of Umbria. Linda is knowledgeable, helpful and available, The house is beautiful, Cetona… More

Thank you/Grazie! I enjoyed meeting you - your enthusiasiam and appreciation of the house, village and the area was delightful! We hope to see you again. Best wishes.


20 Jun 2014

5/5

"A real tase of Tuscany"

If you're looking for an authentic old town stay then you'll be very happy. Great location in the old town and so close to lots small towns to explore. Train to Florence as a day trip. Large rooms cum… More

Grazie! We enjoyed having you in our "little corner" of Tuscany. You were wonderful guests and we hope to see you again some day.

See all reviews Continue

22 Photos

Province of Siena / Sovicille

Villa / 5 Bedrooms / sleeps 14

3 Nights min stay

Add to shortlist

from £72 / night

£500 - £3000 / week

View

Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Italy, Tuscany, Siena , beautiful villa with swimming pool. Incredible views, perfect holiday location.  …see more

11 Photos

Province of Siena / San Gimignano

Apartment / 2 Bedrooms / sleeps 5

3 Nights min stay

Add to shortlist

from £74 / night

£515 - £809 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
This charming apartment lies in the countryside enjoying the most marvellous views of the undulating landscape and the towers of the city of San Gimignano only 3km away Next to the garden and enjoying a spectacular panorama is the splendid new swimming pool (12m x 5m)  …see more

24 Photos

Province of Siena / Sarteano

B&B / 20 Bedrooms / sleeps 48

1 night min stay

Add to shortlist

from £34 / night

£232 - £278 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Terre di Siena, enogastronomia, benessere termale e città d'arte. Casale in pietra toscana, sala congressi, piscina scoperta, parcheggio e parco privato. Camere arredate con mobili di antiquariato. Sala congressi posti a sedere 320 per convegni ed eventi.  …see more

Don’t let an old browser slow down your holiday

Your browser is out of date and might not work well with our website. Download the latest version to speed up your hunt for the perfect holiday home.

Just click on the icons to get to the download page