Cycling holiday villas and apartments Province of Siena | Holiday Lettings

Close

View larger map

Also consider

Europe Holidays
449718 properties
Italy Holidays
103453 properties
Tuscany Holidays
23709 properties
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 San Gimignano
435 properties
Villas Siena
414 properties
Villas Montepulciano
315 properties
Casole d'Elsa
206 properties
Gaiole in Chianti
171 properties
Villas Castellina In Chianti
165 properties
Castelnuovo Berardenga
165 properties
Poggibonsi
164 properties
Villas Pienza
152 properties
Colle di Val d'Elsa
147 properties
Sinalunga
132 properties
Villas Montalcino
124 properties
Rapolano Terme
119 properties
Asciano
95 properties

Province of Siena

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

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

959 Holiday homes

Filters applied: Cycling holidays

(15) Excellent 

22

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
“Very comfortable home away from home” Casacorvo Minore is a very comfortable apartment well located in the heart of Chianti. It has great views from its veranda which fostered perfect starts for each day as we had breakfast sitting in the morning sun.
…see more

from £100 / night

£560 - £760 / week

Enquire View

from £100 / night

(12) Excellent 

69

Holiday villa with swimming pool, tennis court in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly
“A hidden gem.” We stayed at Villa LisiDor at the end of May with family. We made the trip to Tuscany by train to Florence from the UK and hired a car from there. We arrived during an unseasonably chilly spell and in torrential rain after a very l
…see more

from £420 / night

£2934 - £4514 / week

Book View

from £420 / night

(12) Excellent 

21

Gracciano holiday cottage rental

Montepulciano / Gracciano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
“Really worth staying!” My partner and I spent a glorious week this spring at agriturismo Il Salarco surrounded by vineyards and idyllic rolling countryside. The owner, an English lady called Laura, made us both feel really welcome, was fabulously know
…see more

from £71 / night

£390 - £1824 / week

Enquire View

from £71 / night

(67) Excellent 

52

Holiday villa letting

Province of Siena / Sinalunga

12 26 Min stay varies

  • 12 bedrooms
  • Sleeps 26
  • Min stay varies
  • Nearest beach 170 km
  • Swimming pool
  • Child friendly

from £531 / night

£3717 - £7965 / week

Book View

from £531 / night

(4) Excellent 

18

Apartment rental in Siena with shared pool

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 95 km
  • Swimming pool
  • Child friendly
“Heaven on Earth” This Villa Apartment was absolutely awesome! The own was the most kind and gentle man you could ever meet! The apartment was huge and way more than we expected. The furnishings were beautiful and all the rooms were very large. Absolut
…see more

from £80 / night

£531 - £974 / week

Book View

from £80 / night

(30) Excellent 

20

Holiday apartment in Colle di Val d'Elsa

Province of Siena / Colle di Val d'Elsa

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 50 km
  • Child friendly
  • Pet friendly

from £71 / night

£425 - £593 / week

Enquire View

from £71 / night

(11) Very Good 

32

Holiday farmhouse with shared pool in San Gimignano

Province of Siena / San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“Excellent value Tuscan villa in a lovely setting” We stayed in the Agrifolo apartment at Le Fontanelle in May 2015. I was visited with my partner and my parents as we treated them to a Tuscan trip to start the summer. The villa was lovely - simple
…see more

from £62 / night

£470 - £837 / week

Book View

Responds fast!
avg. 2 hours 4 minutes

from £62 / night

(5) Excellent 

41

Holiday townhouse rental

Sinalunga / Rigomagno

5 10 2 nights min

  • 5 bedrooms
  • Sleeps 10
  • 2 nights min
  • Child friendly

from £71 / night

£496 / week

Book View

from £71 / night

(4) Excellent 

28

Holiday apartment with shared pool in San Gimignano

Province of Siena / San Gimignano

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

from £36 / night

£248 - £850 / week

Book View

Responds fast!
avg. 1 hour 27 minutes

from £36 / night

(6) Very Good 

48

Montepulciano holiday home rental

Province of Siena / Montepulciano

3 5 2 nights min

  • 3 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Ask about pets
“Great view, great town!” The villa was wonderful and so is the family renting it out. They met us at the gate and showed us around the villa and how to work everything. The mother gave us a home baked treat too! There are beautiful views of the vin
…see more

from £71 / night

£487 - £531 / week

Book View

from £71 / night

20

Holiday farmhouse in Siena

Province of Siena / Siena

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Suitable for children age 5+
  • Ask about pets

Pricing unknown

Book View

Responds fast!
avg. 3 hours 24 minutes

Pricing unknown

49

Holiday apartment in Colle di Val d'Elsa

Colle di Val d'Elsa / Montegabbro

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 60 km
  • Child friendly
  • Ask about pets

from £54 / night

£310 - £434 / week

Book View

Responds fast!
avg. 3 hours 16 minutes

from £54 / night

(2) Excellent 

13

Chianciano Terme holiday condo rental

Province of Siena / Chianciano Terme

2 3 2 nights min

  • 2 bedrooms
  • Sleeps 3
  • 2 nights min
  • Child friendly
  • Pet friendly

from £40 / night

£264 / week

Book View

from £40 / night

(4) Excellent 

28

Holiday apartment with shared pool in San Gimignano

Province of Siena / San Gimignano

2 7 7 nights min

  • 2 bedrooms
  • Sleeps 7
  • 7 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

from £37 / night

£257 - £877 / week

Book View

Responds fast!
avg. 1 hour 27 minutes

from £37 / night

(1) Excellent 

14

Holiday apartment in Monticiano

Province of Siena / Monticiano

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Nearest beach 60 km
  • Child friendly
  • Ask about pets

from £54 / night

£354 / week

Book View

from £54 / night

5

Home rental in Monteroni d'Arbia with swimming pool

Province of Siena / Monteroni d'Arbia

12 22 7 nights min

  • 12 bedrooms
  • Sleeps 22
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden

from £456 / night

£3186 - £4779 / week

Book View

from £456 / night

(1) Very Good 

18

B&b letting in Montepulciano with shared pool

Province of Siena / Montepulciano

2 8 1 night min

  • 2 bedrooms
  • Sleeps 8
  • 1 night min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
“nice place, nice people” Living for a bit in an old fashioned atmosphere. It is a confortable and friendly place to stay with your family , friends or alone both relaxing in a wonderful Tuscany landscape and travelling around to explore Reinassance
…see more

from £36 / night

£246 / week

Book View

Responds fast!
avg. 2 hours 15 minutes

from £36 / night

(12) Excellent 

Certificate of Excellence

26

Holiday home in Montepulciano

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly

Certificate of Excellence

from £71 / night

£553 - £755 / week

Book View

from £71 / night

(13) Very Good 

28

Holiday villa with swimming pool, tennis court in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly
“Villa PetrAlexa - excellent leisure facility” This years stay was even better than our stay last year. Despite the fact we arrived late at night due to repeated traffic jams on the motorway because of terrible weather conditions, everything was perfec
…see more

from £183 / night

£1275 - £2124 / week

Book View

from £183 / night

(10) Excellent 

Certificate of Excellence

10

Holiday townhouse with swimming pool in Sovicille

Province of Siena / Sovicille

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 72 km
  • Swimming pool
  • Child friendly

Certificate of Excellence

from £40 / night

£558 - £2324 / week

Book View

from £40 / night

(13) Excellent 

23

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

3 8 4 nights min

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Perfect and plaisant location to explore Tuscany” We were 4 people staying in this very nice apartment : comfortable, clean, modern, well equipped. We loved the location. I never heard of Gaiole before, but it was a nice discovery. Quiet village, but
…see more

from £175 / night

£1100 - £1600 / week

Enquire View

from £175 / night

(1) Excellent 

12

Apartment rental in Siena

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning

from £44 / night

£308 / week

Book View

Responds fast!
avg. 3 hours 59 minutes

from £44 / night

(8) Excellent 

Certificate of Excellence

33

Apartment rental in Montepulciano with shared pool

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
“Excellent with children or groups” We had very enjoyable stay in a peaceful location with stunning views around. Olimpia was very helpful and everything worked as foreseen. We were trying to find a place with a scent of a history and what would suit b
…see more

Certificate of Excellence

from £62 / night

£430 / week

Book View

Responds fast!
avg. 2 hours 15 minutes

from £62 / night

(6) Excellent 

23

Holiday apartment in Pienza

Province of Siena / Pienza

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Child friendly
  • Air conditioning
“Fantastic place - great selection of restaurants” Truly a maginificent apartment exceeding our expectations - really nice to cool down in the jacuzzi overlooking Montalcino when the weather was at its hottest ! Also very convenient with regards to
…see more

from £133 / night

£930 / week

Book View

Responds fast!
avg. 3 hours 5 minutes

from £133 / night

12

Holiday apartment in San Quirico d'Orcia

Province of Siena / San Quirico d'Orcia

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £70 / night

£474 - £686 / week

Book View

from £70 / night

(21) Excellent 

Certificate of Excellence

43

Holiday apartment in Monticchiello

Pienza / Monticchiello

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden

Certificate of Excellence

from £66 / night

£325 - £792 / week

Book View

from £66 / night

21

San Gimignano holiday farmhouse rental

Province of Siena / San Gimignano

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £85 / night

£576 - £691 / week

Book View

from £85 / night

5

Holiday barn in Monteriggioni

Province of Siena / Monteriggioni

1 5 2 nights min

  • 1 bedroom
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Pet friendly

from £66 / night

£461 / week

Book View

from £66 / night

(1) Excellent 

99

Holiday villa with shared pool in San Gimignano

Province of Siena / San Gimignano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £111 / night

£682 - £1018 / week

Book View

from £111 / night

(6) Excellent 

32

Holiday home with swimming pool in Radicondoli

Province of Siena / Radicondoli

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly
“Fabulous house in glorious location” Lovely welcome from Elsa - an fantastic traditional meal mid week. The house was beautiful and spacious with everything you could need. Children - 8, 10, 12, 13 loved house and garden - especially the tortoise!
…see more

from £102 / night

£708 - £1107 / week

Book View

from £102 / night

(22) Excellent 

24

Holiday apartment in Montepulciano

Province of Siena / Montepulciano

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Nearest beach 170 km
  • Child friendly
  • Car not necessary
“Well maintained apartment and very helpful owner” Elias iwas most helpful meeting us on arrival and going through everything with us and all places to visit in the area even giving us a map with this all marked on The apartment is beautifully kept and
…see more

from £106 / night

£619 - £1097 / week

Book View

Responds fast!
avg. 2 hours 27 minutes

from £106 / night

(2) Excellent 

12

Sovicille holiday apartment rental

Province of Siena / Sovicille

1 5 1 night min

  • 1 bedroom
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden

from £40 / night

£266 - £377 / week

Book View

from £40 / night

(9) Very Good 

41

Holiday farmhouse with shared pool in Montepulciano

Province of Siena / Montepulciano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly
“Stunning Views” We had a most enjoyable time at this house and would recommend it for its location and closeness to Montepulciano. The house was delightful and the views across the valley and surrounding countryside were excellent. We can recommend
…see more

from £100 / night

£625 - £895 / week

Book View

from £100 / night

(1) Excellent 

26

Holiday home in Rigomagno

Sinalunga / Rigomagno

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from £83 / night

£576 - £1319 / week

Book View

from £83 / night

(8) Excellent 

24

Sarteano holiday farmhouse rental

Province of Siena / Sarteano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Fantastic Villa and location shame about the weather” The villa was fantastic with extremely hospitable hosts. Grandma provided us with her fantastic home made cake and olive oil. Grandad provided us with home grown beans and lettuce. The Villa is sit
…see more

from £98 / night

£620 - £974 / week

Book View

from £98 / night

10

Macciano holiday farmhouse rental

Chiusi / Macciano

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets

from £89 / night

£443 - £629 / week

Book View

from £89 / night

(50) Excellent 

Certificate of Excellence

21

Holiday cottage in Montepulciano

Province of Siena / Montepulciano

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • Nearest beach 158 km
  • Child friendly
  • Air conditioning
“Clean, comfortable and cozy house with privacy and convenience to Montepuciano” We had a very enjoyable stay at Davide's house. It is a truly charming place offering the privacy you need as a family and at the same time the convenience of being close
…see more

Certificate of Excellence

from £62 / night

£354 - £620 / week

Book View

from £62 / night

(3) Excellent 

16

Townhouse rental in Casole d'Elsa

Province of Siena / Casole d'Elsa

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 80 km
  • Child friendly

from £40 / night

£279 / week

Book View

from £40 / night

(7) Very Good 

25

Holiday apartment in Monteriggioni

Province of Siena / Monteriggioni

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden

from £53 / night

£316 - £514 / week

Book View

Responds fast!
avg. 2 hours 44 minutes

from £53 / night

14

Holiday villa with swimming pool in Monteroni d'Arbia

Province of Siena / Monteroni d'Arbia

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden

from £279 / night

£1947 - £2832 / week

Book View

from £279 / night

1