Villas with a pool Province of Florence | Apartments to rent with swimming facilities | Holiday Lettings

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2,784 Holiday homes

Filters applied: Swimming pool (2,785)

(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

(2) Excellent 

39

Lavish 8BR Villa w pool only 10 Miles to Florence! - San Casciano in Val di Pesa villa sleeps 16

Province of Florence / San Casciano in Val di Pesa

8 16 1 night min

  • 8 bedrooms
  • Sleeps 16
  • 1 night min
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
This wonderful 8 BR – 8 BA villa is located in the beautiful village of San Casciano val di pesa, just about 8 miles away from the beginning of the historic district of the city of Florence. The villa traces back its origins to the early XVI century and is considere  …see more

from £1164 / night

£8600 - £9656 / week

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from £1164 / 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

24

Province of Florence / Greve in Chianti

5 11 7 nights min

  • 5 bedrooms
  • Sleeps 11
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden

 …see more

from £296 / night

£2069 - £3276 / week

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from £296 / night

(2) Excellent 

29

Farmhouse close to Florence, 2 bedrooms, shared outdoor pool, brilliant views - Greve in Chianti farmhouse sleeps 6

Province of Florence / Greve in Chianti

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
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 £104 / night

£689 - £1216 / week

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from £104 / night

69

Province of Florence / Greve in Chianti

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £78 / night

£544 / week

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from £78 / night

65

Province of Florence / Greve in Chianti

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Swimming pool

 …see more

from £65 / night

£453 / week

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from £65 / night

(8) Excellent 

23

Agriturismo Giulia in Tuscany, apt. Lavanda - Castelfiorentino apartment sleeps 7

Province of Florence / Castelfiorentino

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
The apartments benefits from its own pool with a spacious solarium with grass. The living still mantain its original "vaulted" ceiling in terracotta.Leading from the livingroom is a patio with table and chairs to enable you to dine in a cool, enjoying the view  …see more

from £87 / night

£426 - £1190 / week

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from £87 / night

(10) Excellent 

33

Rustic Chianti apartment rental, sleeps 5, features private garden and shared pool - San Polo in Chianti apartment sleeps 5

Greve in Chianti / San Polo in Chianti

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
The IRIS apartment is on the ground floor of a characteristic barn on the farm estate of Podere Albereto, in the heart of the Tuscan countryside on the rolling hills above Florence, overlooking the San Polo in Chianti valley. The estate of 10 hectares of fields, olive  …see more

from £65 / night

£453 / week

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from £65 / night

(3) Excellent 

16

Villa Bottai - Piazzale Michelangelo villa sleeps 8

Florence / Piazzale Michelangelo

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
Villa Bottai a splendid 13th Century Villa just 10 minutes from the historical centre of Florence. Together with Fulvio I have been renting this villa for the past 10 yrs.Recently the ground floor has been restored into 3 double bedroom, 2 bathrooms, 1 cloakroom/laundry  …see more

from £210 / night

£1350 / week

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from £210 / night

(3) Very Good 

57

Province of Florence / Florence

1 3 6 nights min

  • 1 bedroom
  • Sleeps 3
  • 6 nights min
  • Beach / lakeside relaxation
  • Nearest beach 100 km
  • Swimming pool

 …see more

from £113 / night

£785 / week

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from £113 / night

(3) Excellent 

30

Tuscan Farmhouse accomodation in the Chianti Classico area, close to Florence - Strada in Chianti farmhouse sleeps 3

Greve in Chianti / Strada 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 £74 / night

£488 - £729 / week

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from £74 / 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

24

I5.137 - Holiday home with... - Lucolena villa sleeps 6

Greve in Chianti / Lucolena

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly
This is a complex of 4 townhouses (Rosa Arancio, Rosa Bianca, Rosa Rossa and Rosa Gialla), each with its private garden, located in Dudda, a small quiet village in the Chianti Classico region, only 8 km from Greve in Chianti and 30 km from Florence. In Dudda there is a  …see more

from £104 / night

£725 - £1988 / week

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from £104 / night

23

Podere Vignola - Loggia - Sieci farmhouse sleeps 6

Pontassieve / Sieci

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Podere Vignola farmhouse is located in the heart of Tuscany, just 10 Km from Florence, in a small and hidden valley on the sweet hills of Chianti. Podere Vignola is surrounded by a wide park with swimming pool and has 5 wonderful self-catering apartments finely furnishe  …see more

from £86 / night

£561 - £1276 / week

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from £86 / night

17

Typical Tuscan holiday Farmhouse - Olivo - Lastra a Signa apartment sleeps 4

Province of Florence / Lastra a Signa

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Air conditioning
A very typical tuscan farmhouse in Florence from the 16th century the farmhouse boasts the architecture of the time of wooden beams, terracotta floors, original wooden doors and stonework. andnbsp;Outdoor dining, walks, the farmhouse is surrounded by olive groves, viney  …see more

from £173 / night

£819 / week

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from £173 / night

20

Piandaccoli - Raffaello - Malmantile apartment sleeps 8

Province of Florence / Malmantile

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning
Large apartment for 8 people located in the farmhouse. The apartment comes with: 2 charming kitchens, 2 living rooms with LCD TV - one living room with a a sofa bed with a double bed- two large bathrooms, two double bedrooms, two single bedrooms with a queen bed. Out  …see more

from £158 / night

£1105 - £1835 / week

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from £158 / night

(1) Excellent 

19

Chianti Castle lodging 6F - San Polo in Chianti apartment sleeps 6

Greve in Chianti / San Polo in Chianti

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
This beautiful 13th century castle is located on the Chianti hills completely surrounded by hectares of olive groves, in an absolute quiet position. This exquisite holiday home consists in 7 spacious self-catering apartments, tastefully furnished, all restored in respec  …see more

from £125 / night

£552 - £1147 / week

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from £125 / night

(3) Very Good 

20

Villa Calcinaia - POZZO - Montefioralle apartment sleeps 6

Greve in Chianti / Montefioralle

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
From the ancient rectory adjacent to the small church of San Piero al Pino (13th century), two apartments have been restructured. Pozzo apartment has a large kitchen (all appliances), sitting room and dining area in an open floorplan. On the ground floor is a twin bedde  …see more

from £78 / night

£535 - £3707 / week

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from £78 / night

17

Villa Bagnoli - Tavarnelle Val di Pesa villa sleeps 8

Province of Florence / Tavarnelle Val di Pesa

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 90 km
  • Swimming pool
  • Air conditioning
Tavarnelle Val di Pesa is a lovely little hilltop town, located midway between Florence and Siena. On its slopes, a mere 300 metres from its centre, is Villa Bagnoli great strength the fact that guests can easily walk into the centre of Tavarnelle's shops, bars and rest  …see more

from £111 / night

£776 - £2328 / week

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from £111 / night

25

Villa Bella Vista - Lastra a Signa villa sleeps 11

Province of Florence / Lastra a Signa

5 11 Min stay varies

  • 5 bedrooms
  • Sleeps 11
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
A Tuscan holiday farmhouse on a private estate near Florence. Located on the hills of a large estate with extensive views ,a panoramic and strategic location offers a peaceful and private vacation for people who wish to experience Tuscan living, explore the region of Tu  …see more

from £283 / night

£1983 - £2759 / week

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from £283 / night

13

Province of Florence / Certaldo

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £173 / night

£949 - £1725 / week

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from £173 / night

(14) Excellent 

25

Villa Sole in Chianti :D - San Casciano in Val di Pesa villa sleeps 6

Province of Florence / San Casciano in Val di Pesa

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 84 km
  • Swimming pool
A few minutes drive from Ponte Vecchio, among olivetrees and vineyards of the famous Chianti Wine, the villa is part of an ancient stone farmhouse, (13th century) carefully renovated.The Villa has a wonderful panoramic location, facing the incomparable Tuscany sunset.Th  …see more

from £259 / night

£949 - £1897 / week

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from £259 / night

12

Chiocciola apartment - Vinci apartment sleeps 5

Province of Florence / Vinci

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning
The Chiocciola is part of Agriturismo Podere Zollaio. Set out over 2 floors,on the ground floor is the entrance hall and the well equipped kitchen, while on the first floor are 2 double bedrooms each with en suite shower room. The beds can be separated to form single be  …see more

from £73 / night

£509 - £604 / week

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from £73 / night

24

Orcio - Barberino Val d'Elsa villa sleeps 4

Province of Florence / Barberino Val d'Elsa

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Country cottage in Tuscany sleeping 4 - Orcio is located mid-way between Florence and Siena deep in Chianti countryside. This carefully restored, stone-built apartment is part of a larger building housing two other apartments, each with independent entrance and grounds.  …see more

from £163 / night

£1140 - £1750 / week

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from £163 / night

(1) Excellent 

6

Reggello / Leccio

2 4 Min stay varies

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

 …see more

Pricing unknown

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(16) Very Good 

18

Idyllic villa in Tuscan villa with 7 bedrooms, private swimming pool, garden, terrace and amazing views - Impruneta villa sleeps 13

Province of Florence / Impruneta

7 13 7 nights min

  • 7 bedrooms
  • Sleeps 13
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
For those seeking a memorable holiday discovering the pleasures of Tuscany Ville le Dame has it all.Villa Le Dame is situated in a privileged position, immersed in total tranquillity of the countryside and at the same time is just a short distance (1.7km) from the town  …see more

from £201 / night

£1401 - £4483 / week

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from £201 / night

20

Piandaccoli - Brunelleschi - Montespertoli apartment sleeps 6

Province of Florence / Montespertoli

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Large apartment for 6 people located in Residenze Piandaccoli farmhouse. The apartment has: 2 kitchens, 2 living rooms with LCD TV and one of each with a sofa bed with a double bed in fron of a lovely fireplace, 2 large bathrooms with shower, 2 double bedrooms with a do  …see more

from £126 / night

£882 - £1467 / week

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from £126 / night

(7) Excellent 

23

Villa Mary at 20mn from Florence pool & BBQ - Tavarnuzze villa sleeps 9

Impruneta / Tavarnuzze

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
Villa Sabrina is located on a hill in the surroundings of Florence, is a medieval farmhouse: the building was in poor conditions in the late Fifties, when it was bought by an italian-dutch young couple, who decided to settle down here. The house was the totally renovate  …see more

from £285 / night

£1294 - £2156 / week

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from £285 / night

(5) Excellent 

24

Villa Bobolino Holiday Home - Montelupo Fiorentino villa sleeps 13

Province of Florence / Montelupo Fiorentino

6 13 Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
  • Nearest beach 55 km
  • Swimming pool
  • Child friendly
Bobolino is the most beautiful neighborhood of Montelupo Fiorentino near Florence, Siena, Pisa and Lucca.Villa Bobolino is located on the hills and has 6 bedrooms. Each room has a TV, a beautiful private bathroom with all of the comforts (towel-warmer, hairdrier and lar  …see more

from £156 / night

£1552 - £2535 / week

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from £156 / night

24

I5.230 - Villa with pool n... - Lucolena villa sleeps 10

Greve in Chianti / Lucolena

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly
Large villa with a beautiful panoramic view, located near the ancient town of Figline Valdarno which is in the centre of a triangle formed by the cities of Florence, Siena and Arezzo. The town’s historic area has a medieval piazza surrounded by buildings of importance  …see more

from £184 / night

£1286 - £2939 / week

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from £184 / night

(6) Excellent 

24

Chianti Penthouse with View - San Donato in Poggio penthouse sleeps 2

Tavarnelle Val di Pesa / San Donato in Poggio

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
This apartment is one of a property consisting of a total of 5 apartments located in San Donato in Poggio, a town in Florentine Chianti Classico area, 21km from Florence and 25km from Siena. The brand-new large open-plan penthouse (37 sq.m + 1 terrace 18 sq.m + 1 balcon  …see more

from £74 / night

£367 - £587 / week

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from £74 / night

(1) Very Good 

19

LINDA Apartment with POOL - Campoli in Chianti apartment sleeps 6

San Casciano in Val di Pesa / Campoli in Chianti

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly
LINDA is an apartment (WITH PRIVATE SWIMMING POOL USED ONLY by WHOM RENTING LINDA!!!) that sleep up to 5 or 6 people, placed in the village of Campoli, in the heart of Chianti, only 12 km far from the famous town of Greve in Chianti and 13,5 km far from Panzano in Chian  …see more

from £147 / night

£949 - £1841 / week

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from £147 / night

6

Province of Florence / Grassina

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £138 / night

£966 / week

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from £138 / night

(1) Very Good 

21

Chianti castle lodging 4p - San Polo in Chianti apartment sleeps 4

Greve in Chianti / San Polo in Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
This beautiful 13th century castle is located on the Chianti hills completely surrounded by hectares of olive groves, in an absolute quiet position. There 7 spacious self-catering apartments, tastefully furnished, all restored in respect of the traditional Tuscan style,  …see more

from £91 / night

£384 - £772 / week

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from £91 / night

96

San Casciano in Val di Pesa / Chiesanuova

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly

 …see more

from £161 / night

£1121 - £1897 / week

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from £161 / night

23

Apartments in Villa with pool in the Chianti C5 - San Polo in Chianti apartment sleeps 5

Greve in Chianti / San Polo in Chianti

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
This amazing villa is hidden in the green shades of the olive groves and vineyards of the hills, at just a few km from Greve in Chianti (15km), the heart of the wine production. The villa is a typical Tuscan 17th century manor house, totally renovated, which hosts 4 com  …see more

from £95 / night

£380 - £725 / week

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from £95 / night

(2) Excellent 

14

Warm 2 bedroom villa situated not far from Florence features shared pool and garden - Mugello Valley villa sleeps 6

Londa / Mugello Valley

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Swimming pool
Villa Le Corti is situated in Londa, about 30 Km far from Florence, 80 Km from Arezzo and 100 Km from Siena. Londa is in the hearth of the "Parco delle Foreste Casentinesi", an area of parks and green forests protected as Tuscan heritage. Here, you can choose  …see more

from £52 / night

£345 / week

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from £52 / night

(7) Excellent 

28

Farmhouse with private garden and pool in Tuscany - Tavarnelle Val di Pesa farmhouse sleeps 6

Province of Florence / Tavarnelle Val di Pesa

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
Casalfiorito is an ancient estate dated back to 1500 surrounded by two private hectares of beautiful natural forest and hills. In the heart of Casalfiorito you will find the main “Villa” (inhabited by landlord) and a lovely “Barn”. CasalFiorito Holiday Home is  …see more

from £75 / night

£518 - £1207 / week

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from £75 / 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

Top Destination reviews

Column Suite
Great, big apartment, near everything

The apartment sits on a quieter street away from the crowds. The Duomo and other sights of Florence are a quick walk away. The apartment is very spacious, clean and has everything you could want. The pictures are completely accurate. There is a bust … see more
Terrace Riverside, Amazing View, Central location
Strategic location with Arno river view..

Big apartment (three bathrooms, three bedrooms .....) furnished with everything you need and also with air conditioning. Very beautiful terrace overlooking the Arno river where we could dine out every night. It is accessed from the kitchen through a … see more
Lungarno Luxury App. close to the Florence Center
LUNGARNO APARTMENT IS FABULOUS!!!!

One could not ask for a better place to stay in Florence. This apartment took up the entire fourth floor of the building. It was spacious, clean, convenient. The apartment had two huge living rooms, large dining room, 3 balconies. It had every co … 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
Right in the heart of Florence, Santa Croce
Cozy, Stylish Center Located Apartment

We spent an unforgettable 3 wonderful days in Florence leaving in the apartment. Lucia is excellent host were keeping in touch with us all the time before arriving and met us in front of the building. The apartment is really stylish, delicious, and i … see more
La Casina Countryside Cottage with Pool
Torre Di Sopra - a little gem

We stayed in La Casina and what a little gem of a place, just south of Florence with easy access by car and bus. Sitting outside on the couch, sipping wine watching the sunset over the Tuscan landscape was breathtaking. Highly recommend this place, c … see more

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