Cycling holiday villas and apartments Province of Arezzo | Holiday Lettings

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817 Holiday homes

Filters applied: Cycling holidays (817)

(3) Excellent 

31

Province of Arezzo / Badia Agnano

9 22 Min stay varies

  • 9 bedrooms
  • Sleeps 22
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £218 / night

£1522 - £3470 / week

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from £218 / night

(3) Very Good 

10

Province of Arezzo / Bibbiena

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Ask about pets

 …see more

from £51 / night

£522 / week

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from £51 / night

(1) Excellent 

14

Province of Arezzo / Cortona

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £114 / night

£396 - £579 / week

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from £114 / night

(12) Excellent 

17

Borgo il Vepri - Ambra apartment sleeps 4

Province of Arezzo / Ambra

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Vepri is the perfect base for a tranquil holiday or home in the sun.It is for the discerning-a quiet and gated private luxury development comprising a small number of apartments and townhouses surrounding a communal piazza.The swimming pool is simply wonderful, set amid  …see more

from £43 / night

£295 - £479 / week

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from £43 / night

28

Appartamento Giardino Centro - Lucignano apartment sleeps 4

Province of Arezzo / Lucignano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Ask about pets
A fully self-contained apartment located in a medieval building opening onto its own garden, right in the centre of the charming central Tuscan town of Lucicnano.Appartamento Giardino is located in a a converted frantoio, olive oil mill is the centre of the medieval tow  …see more

from £73 / night

£461 - £651 / week

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from £73 / night

26

Cortona / Farinaio

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden

 …see more

from £87 / night

£783 - £1044 / week

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from £87 / night

(1) Excellent 

4

Villa Sonia, Cortona Tuscany - Cortona villa sleeps 6

Province of Arezzo / Cortona

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 15 km
  • Swimming pool
  • Child friendly
Villa Sonia is for sure, a really special property tucked away on the sleepy hillside of Cortona and, just a short distance form the enchanting franciscan monastery of Le Celle. Villa Sonia is perfect for four to 12 guests.This ancient stone farmhouse dates back to the  …see more

from £210 / night

£1470 - £1478 / week

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from £210 / night

24

Villa Montanina - Relax in Tuscany - Castel Focognano villa sleeps 15

Province of Arezzo / Castel Focognano

7 15 Min stay varies

  • 7 bedrooms
  • Sleeps 15
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Ask about pets
Villa Montanina is situated in the beautiful valley of the Casentino. The Villa have been renovated with materiaI typical of Tuscany.The pool is open from June to 1 October.The Tuscany Holiday Villa lies on the edge of a historic hamlet, Borgo Montanina, still today is  …see more

from £261 / night

£1566 - £3174 / week

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from £261 / night

35

Villa in the Chianti hills - Malva villa sleeps 14

Loro Ciuffenna / Malva

5 14 Min stay varies

  • 5 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
For those who love nature and the Tuscany countryside, our country villa “Oliveta” is the ideal holiday destination in Tuscany. The villa is located on the Aretine Chianti hills, in a lovely countryside area at the foot of Pratomagno mountain and along to the histor  …see more

from £127 / night

£957 - £1740 / week

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from £127 / night

(22) Excellent 

33

Villa in Poppi, Tuscany set in astounding natural surroundings, features private pool, terrace and garden, sleeps 12 - Poppi villa sleeps 12

Province of Arezzo / Poppi

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 160 km
  • Swimming pool
  • Child friendly
Five bedrooms, 4 double bedrooms and one bedroom with two single beds, 3 full bathrooms each with a shower. Large living room with stereo, CD, SAT TV and a large fireplace Many outdoor eating areas - overlooking the castle, overlooking the pool and overlooking the surr  …see more

from £174 / night

£1218 - £1653 / week

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from £174 / night

(52) Excellent 

51

Casa Leana - Farmhouse - HEATED Pool & Games Room - Anghiari villa sleeps 10

Province of Arezzo / Anghiari

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 66 km
  • Swimming pool
  • Child friendly
Currently offering 15% discount for the only week left in 2016. Casa Leana is over 350 years old and brimming with gorgeous original features from chunky beamed, wood ceilings and exposed stone walls to the traditional tiled kitchen. We have also lavished a whole lot  …see more

from £248 / night

£1730 - £2630 / week

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from £248 / night

(1) Excellent 

24

Province of Arezzo / Castiglion Fibocchi

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Pet friendly

 …see more

from £40 / night

£274 / week

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from £40 / night

18

Province of Arezzo / Cortona

11 20 1 night min

  • 11 bedrooms
  • Sleeps 20
  • 1 night min
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning

 …see more

from £522 / night

£3479 / week

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from £522 / night

(11) Excellent 

35

Villa Nobile is a stunning 19th Century Villa - Cortona villa sleeps 24

Province of Arezzo / Cortona

7 24 3 nights min

  • 7 bedrooms
  • Sleeps 24
  • 3 nights min
  • Nearest beach 250 km
  • Swimming pool
  • Child friendly
Villa Nobile is a stunning 19th Century classical style villa recently restored authentically and with artistic charm, with a private pool 13 m x 6 m. Sitting in 4 acres of natural Tuscan rural land. A private avenue of young cypresses bringing you to our doorstep. Tran  …see more

from £66 / night

£479 / week

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from £66 / night

16

Province of Arezzo / Badia Tedalda

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Nearest beach 85 km
  • Child friendly

 …see more

from £38 / night

£261 / week

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from £38 / night

(1) Excellent 

27

Province of Arezzo / Cortona

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £87 / night

£566 - £827 / week

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from £87 / night

(32) Excellent 

24

Tuscan Villa. Borgo Valecchie. Cortona - Montanare villa sleeps 10

Cortona / Montanare

4 10 5 nights min

  • 4 bedrooms
  • Sleeps 10
  • 5 nights min
  • Nearest beach 180 km
  • Swimming pool
  • Child friendly
Our villa offers an ideal combination of elegant simplicity and historical charm which create a unique experience and can comfortably accommodate up to 10 guests. Located just five minutes away from The Hill town Cortona. Along with a private swimming pool, this holida  …see more

from £205 / night

£1435 - £2566 / week

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from £205 / night

(3) Excellent 

32

11th Century Castle Apartment near Siena&Florence - Ambra b&b sleeps 5

Province of Arezzo / Ambra

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 127 km
  • Suitable for children age 5+
  • Ask about pets
Elevated position,quiet with great views from all windows, also from a big south facing terrace, this is a spacious,airy and comfortable apartment. It has been totally renovated to a high standard..everything works!. Good quaiity beds and bed linen. Strong WiFi through-  …see more

from £100 / night

£700 / week

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from £100 / night

24

Villa Margherita Tre - Cortona villa sleeps 4

Province of Arezzo / Cortona

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Located in a true oasis of peace and tranquillity, Villa Margherita Tre is a sweet indipendent villa with private pool offering breathtaking views over the hills surrounding the sought after town of Cortona as well as unbeatable value for money. With 2 bedrooms, 2 bathr  …see more

from £35 / night

£244 - £1054 / week

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from £35 / night

(53) Excellent 

32

Villa Carda, luxury villa in Tuscany with private heated pool, jacuzzi, sauna and garden, sleeps up to 12 - Arezzo villa sleeps 12

Province of Arezzo / Arezzo

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Located on the hills that divide the Casentino valley from Chianti, the Villa is ideally positioned for those wishing to visit cities such as Florence, Arezzo or Siena.It is also the perfect base to experience and explore the Tuscan countryside.Now restored to perfectio  …see more

from £311 / night

£2174 - £4348 / week

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from £311 / night

22

AGRITURISMO CASAVECCHIA-NIBBIO Castiglion Fibocchi - Castiglion Fibocchi apartment sleeps 6

Province of Arezzo / Castiglion Fibocchi

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
A breathtaking view, an age-old sense of peace and unspoiled nature together with the high level of comfort of the three apartments make this house the ideal destination for those who wish to spend a relaxing holiday in Tuscany. The beauty of natural surroundings, the h  …see more

from £74 / night

£514 - £887 / week

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from £74 / night

(4) Excellent 

16

Province of Arezzo / Cavriglia

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Nearest beach 150 km
  • Child friendly
  • Air conditioning

 …see more

from £53 / night

£366 / week

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from £53 / night

(6) Excellent 

40

Casa Terrazza: Grand Tuscan house in medieval village with large terrace for alfresco dining, sleeps 7 - Lucignano house sleeps 7

Province of Arezzo / Lucignano

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning
Casa Terrazza is located in Lucignano, one of the most outstanding examples of a fortified Tuscan mediaeval village. Casa Terrazza, is just a few steps away from restaurants and cafes.. Featuring a large terrace opening off main living area with views of the Val di Chi  …see more

from £130 / night

£853 - £1259 / week

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from £130 / night

28

Province of Arezzo / Castiglion Fibocchi

2 2 1 night min

  • 2 bedrooms
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from £27 / night

£183 / week

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from £27 / night

(2) Excellent 

21

Cottage with pool in the heart of Tuscany - Stia apartment sleeps 5

Province of Arezzo / Stia

2 5 6 nights min

  • 2 bedrooms
  • Sleeps 5
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Appartamento GIRASOLELa Fagiana Holiday Rental is in an optimal position. You will be able to fully enjoy the peace and the quietness of the region as well as being in a good position for numerous outdoor activities, such as horse riding, golf, tennis, mountain biking,  …see more

from £66 / night

£461 - £644 / week

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from £66 / night

(3) Very Good 

24

Gargoyle di Sotto - Casa Nonna - Chiusi della Verna apartment sleeps 2

Province of Arezzo / Chiusi della Verna

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
The idyllic hamlet of “Doccione di Sotto” which consists of three former farm houses, is located in a quite remote area of the Tuscan mountains. We carefully restored our old stone cottages. To the houses belong two large lawns with a pool (9x6m) for swimming, pla  …see more

from £50 / night

£322 - £479 / week

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from £50 / night

(2) Excellent 

21

Villa Cicaleta within walking distance to Cortona - Cortona farmhouse sleeps 7

Province of Arezzo / Cortona

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 8 km
  • Swimming pool
Surrounded by olive groves and a 3000sqm private garden, the fenced-in holiday villa offers absolute peace and quiet at only 1,5 kilometres from the Etruscan Cortona, which can be easily reached on foot. The Trasimeno lake with its nice beaches and islands is at 8km and  …see more

from £150 / night

£1044 - £1305 / week

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from £150 / night

(1) Excellent 

32

Villa Sant Angelo FARM, luxurious villa in Tuscany - Arezzo villa sleeps 13

Province of Arezzo / Arezzo

6 13 7 nights min

  • 6 bedrooms
  • Sleeps 13
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 107 km
  • Swimming pool
Ideal for Family reunions or Groups of friendsThe entire structure consists of the main villa, dependants buildings and communal annex building: ideal place to prepare meals and eat together outside. It is situated in the middle of the garden and has a large dining room  …see more

from £237 / night

£1653 - £3044 / week

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from £237 / night

18

Rustic two bedroom Tuscan apartment close to Cortona's main square, wifi and parking available - Cortona apartment sleeps 2

Province of Arezzo / Cortona

2 2 1 night min

  • 2 bedrooms
  • Sleeps 2
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 20 km
  • Ask owner if suitable for children
Quintani Sole - central apartmentApartment for 2 person and 1/2, compose by one bedroom + lounge with kitchen + 2 bathroom. WIFI, TV led, microwave, washing machine, toaster, kettle. Central position, near public parking and restaurants. Only 3 minute from main square a  …see more

from £70 / night

£435 / week

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from £70 / night

(2) Very Good 

32

Nice villa in Tuscany hills with large garden and private pool, sleeps 9 - Capolona villa sleeps 9

Arezzo / Capolona

3 9 7 nights min

  • 3 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Caterina is a nice villa with large garden and private swimming pool. Located in Casavecchia (Capolona) a few Km far from Arezzo on Tuscany hills, Villa Caterina enjoys a spectacular view over the city of Arezzo.Villa Caterina is equipped with 3 spacious bedrooms  …see more

from £112 / night

£783 / week

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from £112 / night

(4) Excellent 

13

Impressive stone built Tuscan holiday villa with private grounds and swimminig pool, sleeps 10 - Castiglion Fiorentino villa sleeps 10

Province of Arezzo / Castiglion Fiorentino

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 27 km
  • Swimming pool
  • Child friendly
Just a short distance from the medieval town of Castiglion Fiorentino is "Casa Usignoli". This very old manor house dates back to 1759. It has been fully renovated to provide a stylish family home with 5 large bedrooms and two bathrooms. The villa sits in one  …see more

from £192 / night

£1341 / week

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from £192 / night

(1) Excellent 

24

Beautiful villa with pool and amazing Tuscan view - Cortona villa sleeps 10

Province of Arezzo / Cortona

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 161 km
  • Swimming pool
  • Child friendly
Villa Cortona is a beautifully restored luxury tuscan villa with 5 double bedrooms and 6 bathrooms.Each bedroom has its own different style and character and en-suite bathroom with wonderful views.The interior of Villa Cortona is large, bright and spacious, with two lar  …see more

from £423 / night

£2957 - £4696 / week

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from £423 / night

(1) Excellent 

27

Villa Monterosi - Anghiari villa sleeps 8

Province of Arezzo / Anghiari

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Set in 40 acres of olive groves, oak woods and fields full of wild flowers, Villa Monterosi is a jewel of peace with it's own private swimming pool, rolling gardens and terraces. A place to dream of, this stone built house has been renovated to the highest ecolog  …see more

from £174 / night

£870 - £1566 / week

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from £174 / night

(6) Excellent 

15

Extraordinary Tower in the Tuscan hills with pool, - Sansepolcro tower sleeps 3

Province of Arezzo / Sansepolcro

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Nearest beach 110 km
  • Swimming pool
Torre the Brancialino nestles beautifully in the Tuscan Hills some 10 kilometres from the Renaissance town of Sansepolcro.Being part of a remarkably restored medieval castle (where the owner lives) the tower offers the perfect romantic hideaway with comfortable accommod  …see more

from £50 / night

£350 - £420 / week

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from £50 / night

(2) Excellent 

10

Province of Arezzo / Cortona

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Private garden

 …see more

from £79 / night

£522 - £1066 / week

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from £79 / night

17

Province of Arezzo / Cortona

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 10 km
  • Child friendly

 …see more

from £66 / night

£444 - £505 / week

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from £66 / night

33

Province of Arezzo / Loro Ciuffenna

2 3 7 nights min

  • 2 bedrooms
  • Sleeps 3
  • 7 nights min
  • Nearest beach 150 km
  • Swimming pool
  • Child friendly

 …see more

from £37 / night

£253 - £435 / week

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from £37 / night

24

Villa Fonte - Cortona villa sleeps 12

Province of Arezzo / Cortona

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
Villa Fonte is located in an extraordinary panoramic position in the open countryside surrounded by olive trees and other typical Tuscan plants but within walking distance from the famous historical town of Cortona just 400 meters away. The perfect place for a holiday d  …see more

from £417 / night

£2914 - £4522 / week

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from £417 / night

23

Il Bagnolino - Anghiari farmhouse sleeps 10

Province of Arezzo / Anghiari

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
Anghiari, a beautiful hilltop medieval Tuscan town is less than 30 minutes drive from the house but when you are at Bagnolino you will feel as though you have escaped from the whole world. A local family has owned this beautifully kept farmhouse for decades and have onl  …see more

from £237 / night

£1653 - £1740 / week

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from £237 / night

(17) Excellent 

24

Cortona / Montecchio, San Lorenzo

2 7 1 night min

  • 2 bedrooms
  • Sleeps 7
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £40 / night

£274 / week

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from £40 / night

Top Destination reviews

Casa Dei Sogni, Tuscan Villa, Private Pool, A/C
Not to be missed

This Tuscan farmhouse has been tastefully and sympathetically restored. It is situated at the top of the valley with spectacular views of the surrounding countryside. You do need a car to stay here but most of the towns and villages to be explored … see more
Stunning Tuscan villa with five bedrooms, private
A true TUSCAN experience. Better than words can describe.

It is quite a challenge to put into words a description of this place, the family and the amazing time we had at Vila Papale. The house and the entire property has so much history and character making this place a unforgettable experience. The garden … see more
Spacious and airy Volta Apartment - 2 bedrooms
Excellent apartment with friendly owner

We had a very warm welcome through Louise and her husband. What a wondeful flat, very spacious, lots of rooms and very much light through large windows. Louzise even purchased wine and some basic fod for the first days which was VERY generous and was … see more
Luxury villa with private swimming pool
AMAZING!!!

I've had the most wonderful stay in this Tuscan gem! Jacopo is such a great host and was always there to answer my questions. The villa is just beautiful! Each room and corner has something unique about it. The gardner Giancarlo came to make sure the … see more
To Stones
Amazing Home Away From Home

The best first impression was to be greeted late at night by Ester and her partner in the dark and in poor weather just so we could find a parking spot and get situated in the property. Ester was amazing and has gone to great lengths to ensure her ho … see more
Casa dei Sogni, Stefano - An attractive air conditioned stone farmhouse with Private Pool - set within a small Tuscan borgo
Not to be missed

This Tuscan farmhouse has been tastefully and sympathetically restored. It is situated at the top of the valley with spectacular views of the surrounding countryside. You do need a car to stay here but most of the towns and villages to be explored … see more

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