Walking holiday villas and apartments Tuscany | Holiday Lettings

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5,891 Holiday homes

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Travellers going to Tuscany are booking October dates now. Secure your holiday home today and have the perfect trip.

(3) Excellent 

25

Beautiful, historic 9 bedroom Tuscan villa on stunning grounds - Greve in Chianti villa sleeps 18

Province of Florence / Greve in Chianti

9 18 1 night min

  • 9 bedrooms
  • Sleeps 18
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Benedetta is a beautiful historic residence that has been for many years the pulsating heart of the Folonari family, a renowned name in the Italian wine business. Dating back to the early 1800, the villa is located at the center of the family's agricultural  …see more

from £677 / night

£4742 - £8621 / week

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from £677 / night

(9) Excellent 

24

Villa Gourmet: pool, park, food & wine - Orentano villa sleeps 14

Province of Pisa / Orentano

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 45 km
  • Swimming pool
Villa Gourmet is a 1700 renovated Tuscan Villa with salt water swimming pool, park and unique outdoor lounge and eating area by the pool. The villa for 14 guests is modern and fully-equipped with all comforts. Gourmet meals are offered on request. During your stay we wi  …see more

from £369 / night

£2578 - £4738 / week

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from £369 / night

(4) Very Good 

16

Elba Island / Rio Nell'Elba

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly

 …see more

from £95 / night

£647 / week

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from £95 / night

Featured properties

9

Grosseto / Rispescia

2 6 1 night min

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

 …see more

from £52 / night

£363 / week

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from £52 / night

20

Agriturismo Podere Torricella- Rosa e ginepro- - Montagnana Val di Pesa apartment sleeps 6

Montespertoli / Montagnana Val di Pesa

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
Romantic and cosy apartment with wooden beams and terracotta floors within a farm with pool and green area, can accommodate up to 6 people using the sofa bed in the living-room/kitchen. The apartment has a large kitchen equipped with outdoor patio where you can eat, dou  …see more

from £121 / night

£690 / week

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from £121 / night

(1) Very Good 

17

Province of Grosseto / Principina a Mare

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly

 …see more

from £65 / night

£371 - £1121 / week

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from £65 / night

18

Il Geraneo - Comano house sleeps 6

Province of Massa Carrara / Comano

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 45 km
  • Swimming pool
The property is a spacious house perfect for a family (sleeps 6 or 7). Holidaying in this beautiful old village has the convenience of being close to all local amenities, and having views out across the hills. Enjoy the short walk from the piazza (100m) where you par  …see more

from £180 / night

£1050 / week

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from £180 / night

(43) Excellent 

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
  • 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 - £900 / week

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from £90 / night

(1) Very Good 

15

Province of Lucca / Massaciuccoli

2 7 7 nights min

  • 2 bedrooms
  • Sleeps 7
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool

 …see more

from £117 / night

£776 - £949 / week

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from £117 / night

(9) Excellent 

18

3 bedroom farmhouse in the picturesque Tuscan hills boasting private pool, terrace and garden, sleeps 6 - San Gimignano farmhouse sleeps 6

Province of Siena / San Gimignano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 45 km
  • Swimming pool
  • Child friendly
Podere Le Monache set on a hillside dominates one of the most picturesque and spectacular landscapes in Tuscany. With distant views over hills, out to sea towards Livorno and Pisa. Originally a convent wrapped in history Le Monache has a magical and spiritual atmosphere  …see more

from £85 / night

£569 - £1078 / week

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from £85 / night

(22) Excellent 

18

Elegant 2 bedroom apt. in historic Siena residence - Siena apartment sleeps 5

Province of Siena / Siena

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Car not necessary
Historic Residence Palazzo Bichi Ruspoli is situated on the main street, in the heart of Siena. The entrance is from the ancient tower, one of the three buildings wich the palace is composed. The house is on the third floor with elevator and has a stunning view on the c  …see more

from £134 / night

£871 - £1962 / week

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from £134 / night

(22) Excellent 

19

Casa Boccina - 19th century Tuscan Farmhouse - Piana di Lucca farmhouse sleeps 10

Lucca / Piana di Lucca

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 28 km
  • Swimming pool
Casa Boccina is an early 19th century Tuscan farmhouse set in fourteen acres of gardens and forest by Monte San Quirico, a village just outside of Lucca. It is only a five minutedrive/ 35 minute walk from the beautiful walled city of Lucca. It is 14 acres of mostly fla  …see more

from £270 / night

£1850 - £3400 / week

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from £270 / night

(5) Excellent 

28

Portoferraio / Magazzini

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly

 …see more

from £61 / night

£423 / week

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from £61 / night

(5) Very Good 

32

Tuscan country house close to Florence with pool, sleeps 3 - Greve in Chianti farmhouse sleeps 3

Province of Florence / Greve in Chianti

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
We are farmhouse in the Chianti Classico area, in fact we produce red and white wine and also olive oil, extravergine and we offer some different flats.We offer apartments for rent with SWIMMING POOL, WIFI FREE IN EVERY HOUSE, FREE INTERNET POINT, INCLUDING AIR CONDI  …see more

from £61 / night

£401 - £651 / week

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from £61 / night

(16) Very Good 

19

Sunny, upper floor Chianti apartment with large terrace and astounding views, sleeps 5 - Poggio alla Croce apartment sleeps 5

Greve in Chianti / Poggio alla Croce

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 100 km
  • Child friendly
  • Ask about pets
Apartments Il Castagno is a family-run holiday houses rentals s in the central part of Toscana near to Firenze on one of the most beautiful hills of Chianti in the quiet and beautiful village of Poggio alla Croce (a few km from Greve). Danilo Becattini, the owner, symp  …see more

from £78 / night

£397 - £432 / week

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from £78 / night

(6) Excellent 

64

Villa Acacia - Fiesole villa sleeps 12

Province of Florence / Fiesole

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
This 17th century villa occupies a hillside on the old road to Bologna, just fifteen minutes north of the city centre. It has its own 4500 square foot garden, with a swimming pool that occupies one of the natural terraces where lemon trees used to be cultivated in a gr  …see more

from £345 / night

£2199 - £4311 / week

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from £345 / night

(1) Excellent 

13

Province of Grosseto / Porto Ercole

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Child friendly

 …see more

from £74 / night

£518 - £2328 / week

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from £74 / night

(11) Excellent 

21

charming cottage in peaceful country setting - Gracciano cottage sleeps 6

Montepulciano / Gracciano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
The cottage is opposite the owner's house and consists of two double bedrooms, two bathrooms and a large living room with cooking area. The living area opens onto a patio and pergola and the downstairs bedroom also opens onto a small patio. There is access for the disa  …see more

from £69 / night

£380 - £1776 / week

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from £69 / night

(9) Very Good 

18

Elba Island / Fetovaia

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly

 …see more

from £52 / night

£216 / week

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from £52 / night

(2) Excellent 

15

Province of Grosseto / Montiano

3 9 1 night min

  • 3 bedrooms
  • Sleeps 9
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Child friendly

 …see more

from £87 / night

£604 / week

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from £87 / night

(8) Excellent 

24

Peaceful 6 bedroom Tuscan villa with private outdoor pool and amazing views - Monte San Savino villa sleeps 11

Province of Arezzo / Monte San Savino

6 11 7 nights min

  • 6 bedrooms
  • Sleeps 11
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Villa al Monte is uniquely situated on the edge of the medieval hamlet Monte San Savino, in a peaceful panoramic position with views of 180° of the surrounding countryside. This ancient home has been finely and elegantly restored with every modern comfort and lies in a  …see more

from £137 / night

£953 - £2802 / week

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from £137 / night

(5) Very Good 

17

Campo nell'Elba / Sant'Ilario

2 6 1 night min

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

 …see more

from £65 / night

£367 - £432 / week

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from £65 / night

(15) Very Good 

26

Golf Hotel Punta Ala Rta appartamento - Punta Ala apartment sleeps 5

Castiglione Della Pescaia / Punta Ala

1 5 7 nights min

  • 1 bedroom
  • Sleeps 5
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Swimming pool
Bilocale a Punta Ala, con una camera matrimoniale con soggiorno con divano letto, angolo cottura bagno e antibagno. Posto auto, Aria condizionata. Biancheria per letti e bagno. Rta a Punta Ala immersa nel parco a 800 metri dallo stabilimento balneare, servizio navetta o  …see more

from £53 / night

£371 / week

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from £53 / night

20

Peacock Manor (v020) - Foiano Della Chiana manor house sleeps 26

Province of Arezzo / Foiano Della Chiana

12 26 7 nights min

  • 12 bedrooms
  • Sleeps 26
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
An independent residence (sleeps 24+2) divided into 6 apartments and on the ground floor a large communal lounge with a fireplace, kitchenette with oven and dishwasher, washing machine.Peony (sleeps 4) on the ground floor, there is a living room with a kitchenette with  …see more

from £518 / night

£3621 - £4138 / week

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from £518 / night

17

Oak Villa (v047) - Volterra villa sleeps 18

Province of Pisa / Volterra

6 18 7 nights min

  • 6 bedrooms
  • Sleeps 18
  • 7 nights min
  • Nearest beach 32 km
  • Swimming pool
  • Child friendly
Beautiful villa divided into 4 apartments:Quail on the ground floor: (sleeps 2 +2) there is a veranda, living room with sofa bed, a double bedroom, bathroom with shower suitable for those with restricted mobility. Private outdoor area. Pets allowed.Hare on the ground fl  …see more

from £180 / night

£1259 - £1828 / week

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from £180 / night

(1) Excellent 

14

Province of Grosseto / Monte Argentario

2 3 1 night min

  • 2 bedrooms
  • Sleeps 3
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly

 …see more

from £52 / night

£604 / week

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from £52 / night

(1) Excellent 

22

Greve in Chianti / Strada in Chianti

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Child friendly
  • Ask about pets

 …see more

from £82 / night

£574 / week

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from £82 / night

18

Villa Rossa - Greve in Chianti - Greve in Chianti villa sleeps 6

Province of Florence / Greve in Chianti

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Rossa is a beautiful indipendent Villa, suitable for 6 person, located in Greve in Chianti within walking distance from all facilities (restaurants, shopping, grocery, banks, church, bus stop etc.). It has an ideal position, between vineyards and olive groves, a  …see more

from £151 / night

£932 - £1888 / week

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from £151 / night

(5) Excellent 

10

Province of Pisa / Lustignano

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 35 km
  • Car not necessary

 …see more

from £44 / night

£285 / week

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from £44 / night

5

Province of Grosseto / Grosseto

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach / lakeside relaxation

 …see more

from £44 / night

£302 / week

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from £44 / night

(5) Excellent 

24

Province of Pisa / Peccioli

3 6 2 nights min

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

 …see more

from £69 / night

£388 / week

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from £69 / night

(8) Excellent 

41

Villa Seccarille - Anghiari villa sleeps 12

Province of Arezzo / Anghiari

7 12 7 nights min

  • 7 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Exceptional views. Sleeps 12. Pool, gardens, tennis court and basketballOriginally a 16th century farmhouse, Villa Seccarille is situated in 57 hectares of fields and woodlands, on the lower slopes of the Appennine Mountains. The villa offers breathtaking views of the s  …see more

from £358 / night

£2500 - £3750 / week

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from £358 / night

(29) Excellent 

20

Amazing Tuscan holiday apartment in the historical Town centre of Colle di Val d'Elsa, sleeps 4 - Colle di Val d'Elsa apartment sleeps 4

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
The Dietro Le Mura holiday home has been completely renovated and is located in the historical town centre of Colle di Val d'Elsa, a characteristically medieval town steeped in history. The apartment is on the first floor, has its own entrance and possible parking  …see more

from £69 / night

£466 - £578 / week

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from £69 / night

(2) Very Good 

17

Tuscan hillside farmhouse with private pool, terrace and garden, great for family holidays - San Gimignano farmhouse sleeps 6

Province of Siena / San Gimignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 45 km
  • Swimming pool
  • Child friendly
Podere Le Monache set on a hillside dominates one of the most picturesque and spectacular landscapes in Tuscany. With distant views over hills, out to sea towards Livorno and Pisa. Originally a convent wrapped in history Le Monache has a magical and spiritual atmosphere  …see more

from £57 / night

£345 - £949 / week

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from £57 / night

(4) Very Good 

22

3 bedroom villa on beautiful Elba Island, privae terrace and garden, sleeps 8 - Porto Azzurro villa sleeps 8

Elba Island / Porto Azzurro

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
Situated within the beautiful setting of the island, Villa Laura is an independent dwelling of 130m2, surrounded by a not fenced front garden (2000 m2) and private pine forest (2000 m2), which can accommodate up to 8 by ensuring a stay of utmost privacy and relaxation.T  …see more

from £62 / night

£432 - £604 / week

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from £62 / night

(1) Excellent 

14

Gorgeous holiday villa rental with sea view in Tuscan seaport town of Porto Santo Stefano, sleeps 6 - Porto Santo Stefano villa sleeps 6

Province of Grosseto / Porto Santo Stefano

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Child friendly
Details (DE) Die Halbinsel Monte Argentario mit ihren beiden Badeorten Porto Ercole und Porto Santo Stefano, liegt an der südlichen Küste der Toskana, 150 km nördlich von Rom. Der Monte Argentario erhebt sich wie eine Insel aus dem Meer, und durch eine von zwei schma  …see more

from £87 / night

£604 - £733 / week

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from £87 / night

(1) Very Good 

8

Province of Pisa / Vicopisano

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from £39 / night

£276 / week

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from £39 / night

26

Podere Capanne Rigomagno - Rigomagno house sleeps 6

Sinalunga / Rigomagno

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Part of an old farmhouse set on a hill overlooking the charming medieval village of Rigomagno and a large part of the Chiana Valley. In this area the hills are mostly covered with the silver-green foliage of olive trees, interspersed now and then with a small vineyard o  …see more

from £81 / night

£561 - £1285 / week

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from £81 / night

28

Province of Grosseto / Follonica

1 5 2 nights min

  • 1 bedroom
  • Sleeps 5
  • 2 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary

 …see more

from £31 / night

£212 - £302 / week

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from £31 / night

18

Province of Pisa / Lorenzana

4 6 2 nights min

  • 4 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

 …see more

from £31 / night

£250 - £341 / week

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from £31 / night

Top Destination reviews

La Capanna 2 - Upper
Beautifully situated

Fabulous views, lovely garden, very comfortable accommodation. Great for exploring garfagnana. Would recommend … see more
Mengarino 
Outstanding view and fabulous infinity pool.

Marco and Simonetta were the most helpful hosts we have ever met. Nothing was too much trouble, and we had a fantastic holiday. … see more
Ponte Vecchio accomodation, Florence Oltrarno area
Best Location

Great location to explore the key areas of Florence. Everything you will need in an apartment. Very helpful input from the owner. As a family with teenagers we found the space tight but we were never there except to sleep so it was not an is … see more
Caprignana, private pool, WIFI, wood oven, views!
Lovely stay for 2 families with teenagers

We were 2 families - totally 11 peoples - with children from 12 to 18 years. We rented the entire house, and had all the teenagers staying at the upper floor. The house is really nice - big kitchen area, nice big rooms, and good bathrooms - and we … see more
La Lecciatina - La Rosa
Fantistica Holidays in an amazing nature

It awas the second time we enjoyed the peace and tranquillity of la Lecciatina every day. It was a perfect stay with beautiful surroundings, absolute quiet and a charming authentic Tuscan accommodation. The views of Tuscany from the apartment and th … see more
Montecarlo 
Very relaxing with wonderful views

We had a great time at the villa with our hosts looking after us really well without us noticing they were even there. There were wonderful views from the garden down the Lucca valley with plenty of different seating options outside to suit or needs … see more

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