Air conditioned apartments and villas to rent in Province of Siena

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452 Holiday homes

Filters applied: Air conditioning (452)

(13) Excellent 

1 / 24

Charming 2 bedroom Tuscan villa with private pool - San Gimignano villa sleeps 5

Province of Siena / San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Nearest beach 85 km; Swimming pool; Child friendly ;
Charming stone-built house located in a peaceful and panoramic position on the green, rolling hills near San Gimignano.The villa is the result of a recent renovation which has transformed this ancient barn into a beautiful and comfortable detached villa, ideal for spend  …see more

from £171 / night

£471 - £1539 / week

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from £171 / night

1 / 13

Traditional stone-built villa in Tuscan province of Siena with swimming pool, terrace and barbecue - Montisi villa sleeps 6

Province of Siena / Montisi

3 6 7 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Nearest beach 70 km; Swimming pool; Child friendly ;
Three bed stone built home with all the traditional and style of an old tuscan home yet all the modern comforts.Air Conditioning is a must in Tuscany.This property has air conditioning in all rooms and is remotly controlled in each room.Two large bathrooms one with a ba  …see more

from £122 / night

£851 - £1240 / week

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from £122 / night

(6) Excellent 

1 / 20

2 bedroom apartment in traditional Tuscan complex in village of Gaiole, sleeps 6, shared pool - Gaiole in Chianti apartment sleeps 6

Province of Siena / Gaiole in Chianti

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car advised;
A fabulous place to relax, this apartment is at the edge of the Borgo furthest from the road. Designed in a traditional style incorporating a range of modern comforts and facilities, the apartment is the best of both worlds. Stone tiled floors with chestnut beams overhe  …see more

from £70 / night

£500 - £700 / week

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from £70 / night

Featured properties

(32) Excellent 

1 / 24

LUXURY APARTMENT WITH PRIVATE GARDEN & VIEWS - Gaiole in Chianti apartment sleeps 2

Province of Siena / Gaiole in Chianti

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Not suitable for children; Car advised;
Ideal for couples looking for a relaxing romantic holiday, we provide everything you need in our fully equipped and tastefully decorated apartment, see our reviews. FREE WI-FI Walking distance to local restaurants. The large private garden for your exclusive use overlo  …see more

from £60 / night

£420 - £630 / week

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from £60 / night

1 / 7

Lovely countryside Podere San Luigi Apt Tramonto - Pancole farmhouse sleeps 2

San Gimignano / Pancole

1 2 3 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Air conditioning;
You can enjoy a relaxing holiday in the center of Tuscany surrounded by nature and the countryside. Very close to San Gimignano, on the "VIA FRANCIGENA", the casale is the starting point for visiting the important Tuscan cities of Art, villages, and the famous  …see more

from £53 / night

£342 / week

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from £53 / night

1 / 21

Suite d'Artista: Botto & Bruno - Montalcino apartment sleeps 4

Province of Siena / Montalcino

2 4 2 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
Suite d'Artista is a perfect place to enjoy a relaxing holiday combining the atmosphere of typical Tuscan countryside with Montalcino's amenities. Nestled just below Montalcino's historical centre, a peaceful spot with a large panoramic garden, swimming p  …see more

from £171 / night

£1197 / week

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from £171 / night

1 / 6

Province of Siena / Chianciano Terme

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Child friendly ; Air conditioning; Ask about pets;
 …see more

from £31 / night

£214 / week

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from £31 / night

1 / 18

galassia 18 - Gaiole in Chianti apartment sleeps 3

Province of Siena / Gaiole in Chianti

1 3 2 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 2 nights min stay
Key info: Nearest beach 120 km; Swimming pool; Not suitable for children;
appartamento, 2 - 3 persone, 2 vano/vani, 1 camera/e da letto, 1 bagno/bagni, ca. 44 m², 1 piano/piani, alloggio al piano terra. Accesso all'alloggio indipendente.TerrenoPorzione privata del terreno, giardino, lastre.Parcheggio: 1 x posto macchina in garage sotter  …see more

from £68 / night

£342 / week

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from £68 / night

1 / 10

Province of Siena / Sinalunga

5 10 1 night min stay

  • 5 bedrooms
  • Sleeps 10
  • 1 night min stay
Key info: Swimming pool; Child friendly ; Car advised;
 …see more

from £257 / night

£1795 / week

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from £257 / night

1 / 100

Emma - Laghetto - Bagno Vignoni apartment sleeps 4

Province of Siena / Bagno Vignoni

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 80 km; Swimming pool; Child friendly ;
On the first floor of the barns can be found Laghetto apartment. This apartment includes one double bedroom and a double sofa bed and therefore can accommodate up to four guests. It has a very fresh feel with light rooms and neutral colours. A four-poster bed with drapi  …see more

from £69 / night

£419 - £599 / week

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from £69 / night

1 / 20

Cypress Manor (V037) - Sarteano manor house sleeps 18

Province of Siena / Sarteano

9 18 Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car essential;
Beautifully renovated and furnished, luxury manor house with air conditioning in each room, underfloor heating, large paved stone patio that surrounds the whole house with pergola to eat outside and a laundry room. The house is divided as follows:.On the ground floor fo  …see more

from £1020 / night

£7137 - £14060 / week

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from £1020 / night

1 / 15

Holiday cottage near Siena - Sinalunga cottage sleeps 4

Province of Siena / Sinalunga

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Child friendly ; Car advised; Air conditioning;
This one-bedroom cottage is the perfect location for those who want to have a place to rest after a busy day spent exploring Tuscany.It consists of a living room, a double bedroom, a fully equipped kitchen with fireplace and a bathroom.The kitchen leads to a small court  …see more

from £70 / night

£400 / week

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from £70 / night

1 / 8

Province of Siena / Siena

1 4 3 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 3 nights min stay
Key info: Child friendly ; Air conditioning; No pets allowed;
 …see more

from £114 / night

£796 / week

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from £114 / night

1 / 4

Ortensia - Radda in Chianti apartment sleeps 4

Province of Siena / Radda in Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Suitable for children age 5+; Air conditioning; Ask about pets;
Resort Olmo is situated in the historical heart of Tuscany and Chianti, halfway between Siena and Firenze.It is situated in a picturesque village called “Borgo di Campomaggio", which dates back to 1700. After some years of careful restoring works, that kept una  …see more

from £129 / night

£898 - £1077 / week

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from £129 / night

(2) Excellent 

1 / 14

Province of Siena / Monteriggioni

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Ask owner if suitable for children; Air conditioning; Pet friendly;
 …see more

from £103 / night

£659 / week

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from £103 / night

1 / 24

Montalcino / Val d'Orcia

1 4 1 night min stay

  • 1 bedroom
  • Sleeps 4
  • 1 night min stay
Key info: Child friendly ; Air conditioning; No pets allowed;
 …see more

from £171 / night

£1197 / week

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from £171 / night

1 / 100

Emma - Tramonto - Bagno Vignoni apartment sleeps 4

Province of Siena / Bagno Vignoni

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 80 km; Swimming pool; Child friendly ;
Tramonto is a ground floor apartment in the barns. It has one bedroom with a double bed and a double sofa-bed in the living room. This room is an open-plan style living-dining room, which, along with the sofa bed has a satellite television, dining table and chairs for u  …see more

from £69 / night

£419 - £599 / week

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from £69 / night

(2) Very Good 

1 / 17

Province of Siena / Siena

1 4 2 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 2 nights min stay
Key info: Child friendly ; Air conditioning; No pets allowed;
 …see more

from £86 / night

£556 / week

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from £86 / night

(14) Excellent 

1 / 22

Casacorvo Minore *Late Booking Discounts* - Gaiole in Chianti apartment sleeps 4

Province of Siena / Gaiole in Chianti

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 80 km; Swimming pool; Child friendly ;
Set in the Chianti Hills just 30 mins from Siena is Borgo di Gaiole, situated on the edge of Gaiole in Chianti, one of the historic 'Chianti League' townships.The Borgo comprises the best of old and new. Built in traditional Tuscan architectural style with sol  …see more

from £85 / night

£525 - £725 / week

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from £85 / night

(40) Excellent 

1 / 25

Lovingly restored stone-built Tuscan barn - San Gimignano house sleeps 4

Province of Siena / San Gimignano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 55 km; Swimming pool; Child friendly ;
Podere Torricchi is a small collection of beautifully renovated 16th Century farm buildings converted into houses and apartments. Set on a hill the entire site has stunning views of the rolling Tuscan countryside. I'l Granario' is a house set on two floors, tastefully r  …see more

from £90 / night

£625 - £925 / week

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from £90 / night

(1) Excellent 

1 / 23

Province of Siena / Siena

3 10 1 night min stay

  • 3 bedrooms
  • Sleeps 10
  • 1 night min stay
Key info: Child friendly ; Air conditioning; Pet friendly;
 …see more

from £112 / night

£778 / week

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from £112 / night

1 / 12

Pienza / Monticchiello

2 2 1 night min stay

  • 2 bedrooms
  • Sleeps 2
  • 1 night min stay
Key info: Not suitable for children; Air conditioning; No pets allowed;
 …see more

from £84 / night

£368 / week

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from £84 / night

1 / 17

A historic estate in the Crete Senesi, Tuscany - Trequanda house sleeps 4

Province of Siena / Trequanda

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car essential;
The property is located on the top of a hill. The apartment is equipped with heating, air conditioning and cooking, it has a separate entrance and overlooks the courtyard of the villa and the hills on the back. It is near the pool. It is located on the ground floor and  …see more

from £95 / night

£633 - £915 / week

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from £95 / night

1 / 11

Province of Siena / San Gimignano

1 2 1 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Not suitable for children; Air conditioning; No pets allowed;
 …see more

from £69 / night

£479 / week

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from £69 / night

1 / 4

Apartment Il Vino - San Fabiano apartment sleeps 5

Monteroni d'Arbia / San Fabiano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car advised;
Large apartment at the ground floor of the villa.Vaulted ceilings, large rooms, all comforts. Large master bedroom om with king size bed, living room with two beds, large dining and cooking room, bathroom with shower.The area is famous for the Dante Alighieri Divina Com  …see more

from £129 / night

£684 - £1026 / week

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from £129 / night

(1) Excellent 

1 / 12

Rapolano Terme / Serre di Rapolano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 110 km; Child friendly ; Car advised;
 …see more

from £52 / night

£300 - £582 / week

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from £52 / night

(1) Excellent 

1 / 6

Province of Siena / Pienza

2 4 1 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay
Key info: Child friendly ; Air conditioning; Pet friendly;
 …see more

from £120 / night

£471 / week

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from £120 / night

1 / 12

Province of Siena / Torrita di Siena

9 19 1 night min stay

  • 9 bedrooms
  • Sleeps 19
  • 1 night min stay
Key info: Not suitable for children; Air conditioning; No pets allowed;
 …see more

from £86 / night

£599 / week

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from £86 / night

(1) Excellent 

1 / 32

The yellow house - Le Piazze house sleeps 6

Province of Siena / Le Piazze

3 6 2 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min stay
Key info: Child friendly ; Car advised; Air conditioning;
The house has three floors and it is simple furnished. The ground floor has a living room with a kitchen and a double bedroom with bathroom. In the second floor there's a double bedroom with a beautiful panorama view and a big bathroom with a nice bathtub in the centre.  …see more

from £42 / night

£257 - £377 / week

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from £42 / night

(6) Excellent 

1 / 26

Just 5 minutes from the centre of the Gaiolie, wonderful apartment with pool and breathtaking terrace, sleeps 6 - Gaiole in Chianti apartment sleeps 6

Province of Siena / Gaiole in Chianti

2 6 7 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
The apartment is just 5 minutes walk from the center of Gaiole, where you will find all the services you need. Like restaurants, bars, wineshops, banks, food shop, hairdressers etc.Gaiole is one of several traditional Chianti villages in the region. Others worth visitin  …see more

from £85 / night

£590 - £936 / week

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from £85 / night

1 / 16

Il Borghetto, Gaiole-in-Chianti - Lecchi b&b sleeps 2

Gaiole in Chianti / Lecchi

1 2 1 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Nearest beach 95 km; Swimming pool; Not suitable for children;
Adjacent apartment with terra-cotta floors and furnished with a double Chianti iron bed (subsequently with a madonna picture above), a large armadio and an en suite bathroom. Through French doors the room leads to a 55 square meter terrace with an antique iron sofa, a f  …see more

from £95 / night

£513 / week

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from £95 / night

(1) Excellent 

1 / 20

Casa Giardino - Gaiole in Chianti apartment sleeps 3

Province of Siena / Gaiole in Chianti

1 3 7 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 7 nights min stay
Key info: Nearest beach 105 km; Swimming pool; Child friendly ;
A cosy and lovingly furnished 1 bedroom apartment located in the spectacular Borgo di Gaiole, a popular hamlet just a short walk from the centre of the renown Gaiole in Chianti, right in the heart of the Chianti region, and only 20 minutes away from the wonderful SienaT  …see more

from £44 / night

£308 - £530 / week

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from £44 / night

1 / 100

Emma - Corbezzolo - Bagno Vignoni apartment sleeps 8

Province of Siena / Bagno Vignoni

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Nearest beach 80 km; Swimming pool; Child friendly ;
This large apartment on the ground floor of the barn consists of three en suite double bedrooms, two of which have private bathrooms with both showers and hydro-massage bathtubs. It is a real fairy-tale apartment with its light and spacious rooms, draping fabrics, prett  …see more

from £197 / night

£1257 - £1676 / week

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from £197 / night

1 / 7

Casa Brogi - Bettolle apartment sleeps 4

Sinalunga / Bettolle

2 4 1 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay
Key info: Child friendly ; Air conditioning; Pet friendly;
Ideally located between Montepulciano and Cortona in the small town of Bettolle, this holiday apartment is the perfect location to venture out and explore Tuscany. The apartment is on two levels. On the first floor there is the kitchen with a big dining table for 4 and  …see more

from £60 / night

£342 / week

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from £60 / night

(5) Excellent 

1 / 6

Province of Siena / San Gimignano

1 2 1 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Not suitable for children; Air conditioning; Pet friendly;
 …see more

from £69 / night

£479 / week

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from £69 / night

1 / 7

Province of Siena / Colle di Val d'Elsa

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Not suitable for children; Air conditioning; No pets allowed;
 …see more

Pricing unknown

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Pricing unknown

1 / 19

Antico Borgo Poggiarello - Monteriggioni house sleeps 30

Province of Siena / Monteriggioni

15 30 Min stay varies

  • 15 bedrooms
  • Sleeps 30
  • Min stay varies
Key info: Nearest beach 84 km; Swimming pool; Child friendly ;
The structure consists of apartments (surrounded by 30.000 meters of olive trees and wood), charmingly furnished in the old style of Tuscany and telephone line for internet connection. From May 1st until September 15th it's possible to enjoy the swimming pool of 1  …see more

Pricing unknown

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Pricing unknown

1 / 22

Province of Siena / Pienza

3 2 1 night min stay

  • 3 bedrooms
  • Sleeps 2
  • 1 night min stay
Key info: Child friendly ; Air conditioning; Pet friendly;
 …see more

from £90 / night

£539 / week

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from £90 / night

1 / 22

Province of Siena / Siena

1 2 3 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay
Key info: Nearest beach 120 km; Swimming pool; Not suitable for children;
 …see more

from £85 / night

£593 / week

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from £85 / night

1 / 21

Castelnuovo Berardenga / Pianella

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Swimming pool; Child friendly ; Air conditioning;
 …see more

from £137 / night

£941 - £1077 / week

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from £137 / night

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