Cycling holiday villas and apartments Tuscany | Holiday Lettings

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  • Maremma (6)
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5,337 Holiday homes

Filters applied: Cycling holidays (5,337)

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

(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

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

(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

Featured properties

(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

(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

(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

(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

(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

(1) Very Good 

23

Province of Lucca / Camaiore

2 4 6 nights min

  • 2 bedrooms
  • Sleeps 4
  • 6 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Ask about pets

 …see more

from £61 / night

£302 / week

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from £61 / 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

(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

(11) Very Good 

24

Province of Lucca / Viareggio

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly

 …see more

from £41 / night

£285 - £466 / week

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from £41 / 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

(2) Excellent 

16

Villa Cesare beach+playground at walking distance - Forte Dei Marmi villa sleeps 6

Province of Lucca / Forte Dei Marmi

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
Villa Cesare is an independent house with 1000sqm garden, with plenty of outdoor spaces, this villa will enrich your summer between a fully equipped relaxing garden, a sunny beach at walking distance and convenient services at just a few steps on foot.This yellow house  …see more

from £388 / night

£2069 - £2156 / week

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from £388 / 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

(8) Very Good 

16

Cecina / Marina di Cecina

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary

 …see more

from £44 / night

£259 / week

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from £44 / 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

(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

(3) Excellent 

22

Province of Massa Carrara / Marina di Carrara

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from £52 / night

£345 / week

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from £52 / 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

14

Apartment in the center of Grosseto in Tuscany - Grosseto guest house sleeps 2

Province of Grosseto / Grosseto

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Car not necessary
  • Air conditioning
The apartment is in the walled part of the center of Grosseto. The railway station is a ten minute walk and there is a car park three minutes from the apartment. Buses are many and frequent to the beach, 20 minutes away or Florence and Sienna about an hour away.The apar  …see more

from £31 / night

£190 / week

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from £31 / night

(1) Excellent 

24

Province of Florence / Sambuca

6 12 3 nights min

  • 6 bedrooms
  • Sleeps 12
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £113 / night

£738 - £1346 / week

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from £113 / 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

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

(16) Excellent 

16

Santa Luce / Orciano Pisano

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool

 …see more

from £51 / night

£354 - £509 / week

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from £51 / 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

(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

(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

(1) Very Good 

9

Province of Grosseto / Civitella Paganico

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Child friendly

 …see more

from £40 / night

£278 / week

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from £40 / night

(6) Very Good 

20

Secluded villa with private pool Chianciano Terme - Chianciano Terme villa sleeps 10

Province of Siena / Chianciano Terme

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
The villa lies at 3 kms from the town of Chianciano Terme, one of the most popular thermal Spas in Italy. The villa is located among the hills dividing Val d'Orcia and Valdichiana. The whole property is for your private use and not shared with any other person. The vill  …see more

from £216 / night

£1294 - £2285 / week

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from £216 / 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

(16) Excellent 

24

Villa Colombai: elegant with luxury pool & park - Orentano villa sleeps 12

Province of Pisa / Orentano

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Villa Colombai is a great location for a family or group of friends who want to visit the main attractions of Tuscany, thanks to its strategical position only 5 km away from the highway connecting Florence, Pisa, Lucca and other important cities. It is the perfect locat  …see more

from £369 / night

£2578 - £4302 / week

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from £369 / 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

(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

(2) Good 

26

Montecatini Terme / Pieve a Nievole

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 45 km
  • Swimming pool
  • Child friendly

 …see more

from £175 / night

£1380 / week

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from £175 / 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

(7) Excellent 

20

Relax in the countryside of Tuscany - Collodi guest house sleeps 10

Pescia / Collodi

3 10 3 nights min

  • 3 bedrooms
  • Sleeps 10
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 30 km
  • Swimming pool
Available holiday home with three bedrooms, two terraces, two bathrooms, kitchen, dining room, living room, hall, fireplace, wood-burning oven, barbecue, private pool, private parking, private garden of 2000sqm. The house is furnished and complete with all the necessary  …see more

from £86 / night

£561 - £923 / week

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from £86 / night

15

Massa / Ronchi

4 7 2 nights min

  • 4 bedrooms
  • Sleeps 7
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Child friendly

 …see more

from £156 / night

£1035 / week

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from £156 / night

Top Destination reviews

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 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
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
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
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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