Cycling holiday villas and apartments Tuscany | Holiday Lettings

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  • Maremma (6)
  • Province of Arezzo (818)
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  • Province of Massa Carrara (167)
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5,334 Holiday homes

Filters applied: Cycling holidays (5,334)

(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

(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

85

Apt Valle Verde with private rooftop terrace - Buti apartment sleeps 6

Province of Pisa / Buti

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Nearest beach 30 km
  • Child friendly
Lovely romantic apartment in the center of Buti! Near to it all : Pisa, Florence, Lucca, Siena, Viareggio… the perfect place to stay if you wish to visit Tuscany! The apartment is on the second floor of a secular building bought and restructured in 2000. At the entra  …see more

from £44 / night

£259 - £552 / week

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from £44 / 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

17

Province of Pistoia / Serravalle Pistoiese

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children age 5+

 …see more

from £44 / night

£259 / week

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from £44 / 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

(33) Excellent 

25

Tuscan apartment in rural setting with easy access to nearby cities, property has private garden and shared pool - Castel San Gimignano apartment sleeps 6

San Gimignano / Castel San Gimignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 55 km
  • Swimming pool
  • Child friendly
The apartment is located in the hamlet of Castel San Gimignano, very near to the best famous cities as Siena, Firenze, San Gimignano, Volterra and the sea is reachable in less than an hour by car. You can also start from here for a relaxing walk or ride through the oliv  …see more

from £87 / night

£475 - £733 / week

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from £87 / night

(13) Excellent 

24

Le Volpaie: 2 bedroom apartment with balcony overlooking stunning Tuscan countryside, shared pool and garden - Volterra apartment sleeps 6

Province of Pisa / Volterra

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 35 km
  • Swimming pool
Le Volpaie is a perfect location in so many ways , for couples wanting a romantic getaway , for relaxing or exploring the outstanding countryside and history or for families wanting a quiet safe holiday spent around the pool and exploring the many beautiful Tuscany fea  …see more

from £75 / night

£520 - £980 / week

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from £75 / 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

(25) Excellent 

20

Country villa surrounded by stunning Tuscan landsc - Saturnia farmhouse sleeps 12

Manciano / Saturnia

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 30 km
  • Swimming pool
Country house, 4 bedrooms en suite upstairs ( 1 extra bedroom just aut the corner is available on demand with no air condition price not included ), hall with fireplace, dining room and spacious kitchen downstairs.The house is surrounded by a paved floor with on  …see more

from £302 / night

£1466 - £2673 / week

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from £302 / 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

(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

9

Rio Nell'Elba / Nisportino

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Swimming pool

 …see more

from £52 / night

£363 - £992 / week

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from £52 / night

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

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

(13) 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

(5) Excellent 

25

Charming, rural Tuscan cottage with terrace and stunning sea view, sleeps 4 - Casale Marittimo cottage sleeps 5

Province of Pisa / Casale Marittimo

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 10 km
  • Child friendly
Lovely , elegant cottage in Casale Marittimo (Pisa),at only 10 Km from the beaches (Marina di Bibbona or Cecina Mare) and close to sites of historical, artistic and archeological interest (e.g. 25 minute drive to Volterra; 1 hour to Florence, Siena and Lucca, 40 minute  …see more

from £130 / night

£776 / week

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from £130 / 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

12

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

 …see more

from £68 / night

£432 - £669 / week

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from £68 / 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 £308 / night

£2156 - £4311 / week

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from £308 / night

(9) Excellent 

31

Villa Alla Marginetta: 5 bedroom luxury villa with garden, gazebos and private pool - Pescaglia villa sleeps 11

Province of Lucca / Pescaglia

5 11 7 nights min

  • 5 bedrooms
  • Sleeps 11
  • 7 nights min
  • Nearest beach 45 km
  • Swimming pool
  • Child friendly
We just received a cancellation, so we reduced 2 weeks in August from 3500 to 1999! A one off as we have never had a cancellation so late int he season before. Villa Alla Marginetta is a luxury Villa set on 6 acres of land and forest and has recently been refurbished to  …see more

from £234 / night

£1638 - £3018 / week

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from £234 / night

19

Elba Island / San Giovanni

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Ask about pets

 …see more

from £31 / night

£242 - £345 / week

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from £31 / 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 £173 / night

£1207 - £1638 / week

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from £173 / night

(1) Excellent 

8

Province of Grosseto / Santa Fiora

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly

 …see more

from £44 / night

£302 / week

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from £44 / 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

(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

(14) Excellent 

24

Monte Argentario, Cala Piccola, Porto S.Stefano - Cala Piccola apartment sleeps 6

Monte Argentario / Cala Piccola

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.4 km
  • Child friendly
Dear Guests We are pleased to present this very beautiful villa located on the most extreme point of the Argentario coast, perched on top of a rocky cliff that drops straight down into the sea and offers a breathtaking view. The position of this beach villa makes it un  …see more

from £233 / night

£1259 - £1595 / week

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from £233 / night

(1) Excellent 

15

Manciano / Saturnia

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Nearest beach 35 km
  • Ask owner if suitable for children
  • Pet friendly

 …see more

from £44 / night

£302 - £561 / week

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from £44 / night

(1) Excellent 

24

Villa Montebello - Montalcinello villa sleeps 18

Chiusdino / Montalcinello

8 18 Min stay varies

  • 8 bedrooms
  • Sleeps 18
  • Min stay varies
  • Nearest beach 55 km
  • Swimming pool
  • Child friendly
Characteristic Tuscan stone farmhouse situated in a dominant position just 5 minutes’ walk from a magical medieval village 35 km west of Siena . The property has been completely renovated a few years ago and turned into a most cozy and comfortable luxury holiday vill  …see more

from £339 / night

£2156 - £3880 / week

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from £339 / night

25

ANTICO BORGO CASALAPPI Vacation villa,pool,tennis - Campiglia Marittima villa sleeps 5

Province of Livorno / Campiglia Marittima

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 7 km
  • Swimming pool
  • Child friendly
Antico Borgo Casalappi is an ancient village which lies on the top of the hills overlooking the Elba Island, a few kilometers from the beach of San Vincenzo, Baratti, Follonica and the port of Piombino (where ferries depart for the Island of Elba). The village is surrou  …see more

from £26 / night

£432 - £1380 / week

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from £26 / night

(1) Excellent 

24

Casa Bella Vista in Pereta: quaint hilltop village - Pereta townhouse sleeps 5

Province of Grosseto / Pereta

2 5 5 nights min

  • 2 bedrooms
  • Sleeps 5
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 20 km
  • Child friendly
Casa Bella Vista is a beautiful characteristic 2 bedroom house in the heart of the village which has been lovingly restored to high standards, with original wooden beams and exposed stone walls maintaining that Tuscan charm. It is beautifully furnished and is very spaci  …see more

from £56 / night

£390 - £450 / week

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from £56 / night

(41) Excellent 

19

Stunning farmhouse apartment located between Tuscan cities of San Gimignano and Volterra, shared pool, private garden, sleeps 6 - San Gimignano apartment sleeps 6

Province of Siena / San Gimignano

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning
Azzurra is an apartment in Poderra Torrichi, a gated community of three farm buildings, which is located between the medieval cities of San Gimignano and Volterra. Podera Torrichi is newly renovated and has retained the charm of the traditional Tuscan farm buildings, wi  …see more

from £185 / night

£1000 - £1462 / week

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from £185 / 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 £136 / night

£949 / week

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from £136 / night

50

Casa Brunello di Montalcino - Montalcino apartment sleeps 6

Province of Siena / Montalcino

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Suitable for children age 5+
Enjoy winelovers' paradise in Montalcino from the beautifully renovated and spacious apartment - Casa Brunello di Montalcino - in the 17th century building with some nice original pieces, combining the traditional Tuscan countryside look with modern high-quality fu  …see more

from £281 / night

£1725 - £2414 / week

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from £281 / 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

9

Castagneto Carducci / Donoratico

2 5 3 nights min

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

 …see more

from £65 / night

£354 / week

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from £65 / night

(20) Excellent 

49

3 bedroom holiday apartment near Tuscan cities, staffed property with outdoor pool - Castel San Gimignano apartment sleeps 6

San Gimignano / Castel San Gimignano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 55 km
  • Swimming pool
  • Child friendly
The apartment is placed in the hamlet of Castel San Gimignano, very near to the best famous cities as Siena, Firenze, San Gimignano, Volterra and the sea is reachable in less than an hour by car. You can also start from here for a relaxing walk or ride through the olive  …see more

from £87 / night

£475 - £604 / week

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from £87 / 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 £50 / night

£518 / week

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from £50 / night

(5) Excellent 

126

FineStay Florence Duomo Centre with Garden - Central Florence apartment sleeps 7

Florence / Central Florence

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning
Classy ground floor apartment with garden, comfortably accommodating six guests and located just a short walk from the Duomo. Accommodates 7 persons, 3 bedrooms, 2 bathrooms (both with shower), sitting room, kitchen with dining area, garden-terrace. We have also a pri  …see more

from £156 / night

£1035 - £1669 / week

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from £156 / night

Top Destination reviews

Termini - Giardino
Wonderful welcome, lovely pool for kids, great location.

The villa is perfectly located, nearby to Castelnuovo, but in the countryside overlooking the valley. It is a short drive to all the local villages and to a great high ropes park for children (and adults). Franco was brilliant - kept in touch on jour … see more
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
Agriturismo Sammonti
Perfect week in Tuscany

All previous positive reviews reflect our experience. Beautiful, quiet location. Lovely hosts. The house was cosy and a great place to come home to after sightseeing. It was also very easy to spend a whole day in the local area or enjoying the pool … 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
Casa a Corte
Peace and Tranquility......

Our holiday in Casa a Corte was delightful. The villa is in a great location up in the mountains about 45 mins from Pisa airport. The villa has three floors and was beautifully clean and well presented with lovely clean comfortable beds and a kitche … see more
Villa Toscanella
Beautiful villa, great facilities and a wonderful holiday

We stayed in the villa as our first family holiday, with our 12 week old baby, and it was great. Having a home away from home was lovely and flexible, and the villa had a travel cot we could use. The whole villa is very comfortable, spacious and well … see more

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