Villas in Tuscany and Apartments - Holiday Lettings - Holiday Rentals Tuscany

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Tuscany

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140 Holiday homes

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

100

Holiday villa with swimming pool, tennis court in Tuscany

Province of Siena / Monteroni d'Arbia

9 18 Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
  • Swimming pool
  • Child friendly
This estate offers a main villa with space to accommodate up to 14 people, and an annex with space to sleep other 4 people  …see more

from £1232 / night

£8618 / week

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from £1232 / night

30

Tuscany holiday villa rental

Province of Siena / Ville di Corsano

9 18 7 nights min

  • 9 bedrooms
  • Sleeps 18
  • 7 nights min
  • Nearest beach 85 km
  • Swimming pool
  • Child friendly
Set on a large estate with extensive views over the Crete Senesi and Siena countryside, this villa is just perfect for family reunions or large group of friends. Built in stone and brick, this Tuscany villa consists of a main villa (sleeps 14 people) and a dependence (s  …see more

from £1577 / night

£11035 - £16595 / week

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from £1577 / night

100

Villa rental in Tuscany with swimming pool, tennis court

Province of Arezzo / Cavriglia

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
gorgeous villa sleeps 12 people, so it is ideal for a large group of friends and is located in Tuscany Italy. This property is perfect if you seek a relaxing holiday. The villa features: a swimming Pool, an internet Connection, a pet friendly space .  …see more

from £293 / night

£1707 - £2840 / week

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from £293 / night

Featured properties

(3) Very Good 

39

Province of Grosseto / Isola Del Giglio

3 6 Min stay varies

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

 …see more

from £75 / night

£518 - £1561 / week

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from £75 / night

(12) Excellent 

69

Holiday villa with swimming pool, tennis court in Tuscany

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
“Perfect holiday location” Our family group of 8 adults spent 5 nights at Villa LisiDor - a perfect location for both relaxing & a great base for exploring the local region. The roads in Chianti can be narrow & windy but worth the drive to villages lik  …see more

from £409 / night

£2858 - £4397 / week

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from £409 / night

(8) Excellent 

41

Anghiari holiday villa rental

Province of Arezzo / Anghiari

7 12 7 nights min

  • 7 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
“Perfect balance between relaxation and activity” Villa Seccarille is the perfect hide away for rest and relaxation while offering enough to keep you busy and active providing the perfect balance for indulging guilt free in the local food and wine duri  …see more

from £358 / night

£2500 - £4500 / week

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from £358 / night

100

Holiday villa with swimming pool, tennis court in Tuscany

Province of Siena / Monteroni d'Arbia

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Set in Tuscany Italy, this stunning accommodation is the perfect place for your holidays. The accommodation offers: a swimming Pool, air Conditioning, a pet friendly space .  …see more

from £1583 / night

£11085 - £16011 / week

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from £1583 / night

(3) Very Good 

35

Tuscany holiday villa rental

Province of Lucca / San Martino in Freddana

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 18 km
  • Swimming pool
The house, the garden and the swimming pool is just for your private use A beautifully restored villa with private pool near Lucca that has been tastefully renovated and is situated in the hills between Lucca. Private pool and balcony for or outdoor dining. Ideal for f  …see more

from £167 / night

£1164 - £1983 / week

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from £167 / night

(1) Excellent 

58

Holiday villa in Capraia e Limite

Province of Florence / Capraia e Limite

6 11 7 nights min

  • 6 bedrooms
  • Sleeps 11
  • 7 nights min
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly
Built in 1855, this large, imposing, two-storey villa, surrounded by magnificent gardens and extensive lawns, offers its guests a taste of luxury on a grand, antique scale. Its secluded setting on a sunny hilltop ensures utmost privacy and tranquillity, while its interi  …see more

from £341 / night

£2384 - £3733 / week

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from £341 / night

(12) Very Good 

28

Holiday villa with swimming pool, tennis court in Tuscany

Province of Siena / Gaiole in Chianti

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly
“Toscany at its best at Radda in Chianti property Villa PetrAlexa” The property itself is wonderfully placed between woods and a vinery in the picturesque Chianti area near Radda. The hospitality we have experienced was outstanding in the mean that you  …see more

from £178 / night

£1242 - £2069 / week

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from £178 / night

30

Holiday villa with swimming pool, golf nearby in Tuscany

Province of Lucca / San Martino in Freddana

3 9 7 nights min

  • 3 bedrooms
  • Sleeps 9
  • 7 nights min
  • Nearest beach 18 km
  • Swimming pool
  • Child friendly
(The house, the garden and the swimming pool is just for your private use). you will not have to share with other guests !! Villa of 1830 completely renovated with tastefully, it situated in the hills between Lucca. View of the countryside and the surrounding hills. Pe  …see more

from £174 / night

£1216 - £1828 / week

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from £174 / night

29

Cortona holiday villa rental

Province of Arezzo / Cortona

10 20 7 nights min

  • 10 bedrooms
  • Sleeps 20
  • 7 nights min
  • Nearest beach 15 km
  • Swimming pool
  • Child friendly
Villa Le Contesse is a beautiful independent villa lying on a hillside, a few minutes from the Etruscan town of Cortona. A large park with holm-oaks and secular trees surrounds the villa, which commands a stunning view over the Valdichiana. Le Contesse has been furnishe  …see more

from £555 / night

£3880 / week

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from £555 / night

100

Holiday villa with swimming pool, tennis court in Tuscany

Province of Grosseto / Gavorrano

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 34 km
  • Swimming pool
  • Child friendly
This beautiful holiday villa in vast grounds with plenty of relaxing and fun activities available for all ages is ideal for a large family or group.  …see more

from £1035 / night

£6897 - £12069 / week

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from £1035 / night

(13) Excellent 

32

Villa rental in Tuscany with swimming pool, golf nearby

Province of Lucca / San Martino in Freddana

8 18 7 nights min

  • 8 bedrooms
  • Sleeps 18
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Traditional Villa, sleeps 18, private pool, private tennis court, BBQ, pizza oven, table tennis, WIFI, maid service, Lucca area, Pisa airport 45 mins.  …see more

from £643 / night

£4500 - £5400 / week

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from £643 / night

100

Holiday villa in Tuscany

Province of Pisa / Pisa

15 27 Min stay varies

  • 15 bedrooms
  • Sleeps 27
  • Min stay varies
  • Nearest beach 20 km
  • Swimming pool
  • Child friendly
This villa sleeps up to 27 people. It boasts a large garden with swimming pool and BBQ area, parking lot and comfortable common areas inside and outside the building. Perfect for large groups celebrating a special moment together.  …see more

from £677 / night

£4738 - £9052 / week

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from £677 / night

(2) Excellent 

24

Holiday villa with tennis court in Tuscany

Montaione / Collegalli

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 50 km
  • Child friendly
  • Air conditioning
“A wonderful holiday” Last year we spent two weeks in Villa San Paolo in Montaione and we really enjoyed it. The Villa is big, with good and comfortable beds, a fully equipped kitchen and has a very nice place outside where you can have breakfast and  …see more

from £307 / night

£2147 - £2578 / week

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from £307 / night

17

Holiday villa with swimming pool, tennis court in Montaione

Province of Florence / Montaione

7 13 Min stay varies

  • 7 bedrooms
  • Sleeps 13
  • Min stay varies
  • Swimming pool
  • Child friendly
Villa Piaggia with private pool is an excellent choice for your next vacation in Tuscany. On the Francigena road only 15 minutes from San Gimignano and 45 minutes from Siena, Florence and Pisa Villa Piaggia has spacious rooms and can sleep up to 13 people.  …see more

from £715 / night

£5000 / week

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from £715 / night

(3) Excellent 

22

Holiday villa rental

Province of Siena / Siena

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Centrum of city only 15 minutes by foot ! The villa was perfectly clean when we arrived. The kitchen is well equipped and fun to cook in.We highly recommend this property for those who are looking for a peaceful setting near all that Siena has to offer.  …see more

from £255 / night

£1078 - £2285 / week

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from £255 / night

14

Province of Grosseto / Castiglione Della Pescaia

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £3695 / night

£25863 / week

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from £3695 / night

(64) 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
Villa Scopetello is the perfect holiday home for large groups and families who wish to spend their holidays together. (Between September and May it is also possible to rent just a portion of the Villa or even one bedroom) The 1000 square meter large Villa with 12 bedro  …see more

from £518 / night

£3621 - £7759 / week

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from £518 / night

100

Holiday villa with swimming pool, tennis court in Tuscany

Province of Arezzo / Bucine

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 150 km
  • Swimming pool
  • Child friendly
This authentic Tuscan villa can be found in a rural location amidst extensive vineyards and olive groves- the classic landscape of the region. I has its own garden and pool to enjoy and guests can enjoy a tour of the wine cellars and a tasting.  …see more

from £828 / night

£5794 - £8276 / week

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from £828 / night

100

Impruneta holiday villa rental

Province of Florence / Impruneta

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
stunning villa, located in Tuscany Italy, has a max. capacity of 8 people. This stunning villa is perfect for families and friends  …see more

from £185 / night

£1294 - £3431 / week

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from £185 / night

(8) Excellent 

24

Holiday villa with swimming pool, tennis court in Vorno

Capannori / Vorno

18 34 1 night min

  • 18 bedrooms
  • Sleeps 34
  • 1 night min
  • Nearest beach 30 km
  • Swimming pool
  • Child friendly
“I thought I was dreaming!!” From the moment I arrived in this magical place I knew my last minute weekend plans had been a success. The warm welcome I received from everyone at Villa Michaela made me feel part of the family straight away. Delicious  …see more

from £3104 / night

£21725 / week

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from £3104 / night

100

Holiday villa in Bucine

Province of Arezzo / Bucine

10 19 Min stay varies

  • 10 bedrooms
  • Sleeps 19
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
This Villa is truly a splendid property, ideal for all ages, seasons and occasions, from weddings and professional meetings to very special large group holidays. Situated in the beautiful Chianti on a marvellous wine and olive-oil producing estate.  …see more

from £1164 / night

£7069 - £10259 / week

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from £1164 / night

(14) Excellent 

51

Holiday villa rental

Province of Florence / Tavarnelle Val di Pesa

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
“Tuscany at Its Best” What more could one want to celebrate a 50th Wedding Anniversary than a Tuscan villa to comfortably house 11 members of one's family; Annagloria and Enzo nearby to assist; easy access to Siena, Volterra, San Gimignano, Pisa, Carra  …see more

from £776 / night

£4569 - £7845 / week

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from £776 / night

(4) Excellent 

24

Holiday villa with swimming pool, tennis court in Tuscany

Province of Pisa / Casciana Terme Lari

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 20 km
  • Swimming pool
  • Child friendly
“Perfect family holiday” We stayed at the Tuscan villa in September 2015 for two weeks and thoroughly enjoyed our time there. The house is very private and offers every comfort you may need. The downstairs offers a lovely kitchen, dining area and livin  …see more

from £148 / night

£1035 - £1914 / week

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from £148 / night

100

Holiday villa with swimming pool, tennis court in Castiglione Della Pescaia

Province of Grosseto / Castiglione Della Pescaia

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 6 km
  • Swimming pool
  • Child friendly
Villa Armonia is the ultimate in comfort with top facilities for those who appreciate the best. It boasts a fabulous position on the coast of Tuscany also ideal for excursions to the famous cities, Siena, Florence and Pisa.  …see more

from £1638 / night

£11466 - £13276 / week

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from £1638 / night

(2)  

27

Orbetello / Ansedonia

5 4 1 night min

  • 5 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from £52 / night

£345 / week

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from £52 / night

16

Holiday villa with tennis court in Tuscany

Province of Lucca / Lucca

7 15 7 nights min

  • 7 bedrooms
  • Sleeps 15
  • 7 nights min
  • Child friendly
  • Air conditioning
among the historic villas dotted around the countryside near lucca, villa oliva, which lies just 6 kms from the town of lucca, occupies an important post due to its special historic and artistic value. It was built around the year 1500 for the buonvisi family. The groun  …see more

from £413 / night

£2887 - £6420 / week

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from £413 / night

21

Holiday villa with swimming pool, tennis court in Tuscany

Province of Florence / Greve in Chianti

9 18 7 nights min

  • 9 bedrooms
  • Sleeps 18
  • 7 nights min
  • Swimming pool
  • Air conditioning
  • Ask about pets
Surrounded by vineyards and nestling in the heart of the Chianti Classico region, Villa Rignana is Historical Estate producing wine, olive oil, organic vegetables. Fully staffed with infinity swimming pool, tennis court, sauna and jacuzzi.<br />On the Estate there  …see more

from £1848 / night

£12932 / week

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from £1848 / night

100

Holiday villa in Tuscany

Tuscany / Province of Arezzo

10 20 7 nights min

  • 10 bedrooms
  • Sleeps 20
  • 7 nights min
  • Nearest beach 180 km
  • Swimming pool
  • Child friendly
Nature, culture, history and traditions meet in this splendid villa in Cortona, in the Tuscan region. Large and with an adjacent cottage for two, this villa is perfect for big groups.  …see more

from £555 / night

£3880 - £5542 / week

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from £555 / night

22

Holiday villa with swimming pool, tennis court in Castiglione Della Pescaia

Province of Grosseto / Castiglione Della Pescaia

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 7 km
  • Swimming pool
Luxury rental villa with private pool,and tennis at 7km from the beaches of Castiglione della Pescaia– sleeps 6From 4200€ to 5600€ a week  …see more

from £518 / night

£3621 - £4828 / week

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from £518 / night

24

Province of Pistoia / Quarrata

7 16 7 nights min

  • 7 bedrooms
  • Sleeps 16
  • 7 nights min
  • Nearest beach 85 km
  • Swimming pool
  • Child friendly

 …see more

from £285 / night

£1992 / week

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from £285 / night

16

Tuscany holiday villa rental

Province of Siena / Buonconvento

10 20 Min stay varies

  • 10 bedrooms
  • Sleeps 20
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Il Casale is an outstanding country villa located in the Chianti just minutes from Siena and nearby Montalcino.  …see more

from £4813 / night

£33688 / week

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from £4813 / night

(55) Excellent 

26

Holiday villa with swimming pool, tennis court in Tuscany

Barberino Val d'Elsa / Petrognano

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
“Best Birthday Ever in A Magical Villa in Tuscany” If you have to face turning 50, Villa il Santo is a place to do it! From the ease of booking the property to Annagloria’s marvelous suggestions and help with daytime excursions, nothing could have bee  …see more

from £1035 / night

£6380 - £10432 / week

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from £1035 / night

37

Torrita di Siena holiday villa rental

Province of Siena / Torrita di Siena

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Beautiful villa situated in an extremely panoramic position surrounded by greenery in the peace and quietness of the Siena countryside.  …see more

from £221 / night

£1544 - £2975 / week

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from £221 / night

35

Tuscany holiday villa rental

Castelfranco Piandisco / Pian di Sco

5 11 3 nights min

  • 5 bedrooms
  • Sleeps 11
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 133 km
  • Swimming pool
Family holidays, small groups, couple of friends, honeymooners, wedding destination, villa rental Arezzo, villa rental Chianti  …see more

from £190 / night

£1328 - £2371 / week

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from £190 / night

100

Holiday villa with swimming pool, tennis court in San Gimignano

Province of Siena / San Gimignano

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Villa Gaia is a stunning villa for 14 people, conveniently located in the heart of Tuscany, within easy reach of the region’s main cities, such as Florence, Lucca, Pisa, and Siena.  …see more

from £317 / night

£2216 - £3173 / week

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from £317 / night

14

Holiday villa with swimming pool, tennis court in Tuscany

Ponsacco / Camugliano

7 13 Min stay varies

  • 7 bedrooms
  • Sleeps 13
  • Min stay varies
  • Swimming pool
  • Child friendly
Villa La Grillaia is one of our villas with pool in Tuscany. This beautiful home with 7 bedrooms and private swimming pool once belonged to the Medici family. Fully refurnished, this quality property is ideal for your next family holiday near Florence.  …see more

from £1100 / night

£7700 / week

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from £1100 / night

(3) Very Good 

18

Lucca / Massa Pisana

11 26 3 nights min

  • 11 bedrooms
  • Sleeps 26
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £2156 / night

£13794 / week

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from £2156 / night