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8,512 Vacation rentals

(1) Excellent 

32

San Donato in Poggio Vacation apartment rental

Tavarnelle Val di Pesa / San Donato in Poggio

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This apartment is part of a property with a total of 6 apartments located in San Donato in Poggio, a town in Florentine Chianti Classico area, 21km from Florence and 25km from Siena. A spacious three-roomed apartment (90 sq.m + 240 sq.m private garden) with two large b …see more

from $206 / night

$999 - $1,373 / week

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Responds fast!
avg. 2 hours 13 minutes

from $206 / night

16

Vacation apartment with shared pool in Tavarnelle Val di Pesa

Province of Florence / Tavarnelle Val di Pesa

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
appartamentopanoramico it accessed from the private terrace of the communal garden in front of the rooftop swimming pool. Living with sofa-bed shared with a wall of 1.50 meters from the kitchen, bedroom with antique furnishings and panoramic window of San Gimignano and …see more

from $113 / night

$699 - $1,061 / week

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from $113 / night

44

Vacation apartment in Tavarnelle Val di Pesa

Province of Florence / Tavarnelle Val di Pesa

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 150 mi
  • Child friendly
  • Pet friendly
Hospitality in contact with nature and art in the quiet privacy of the Chianti hills, between Florence and Siena and other cities of art in Tuscany. The bright, welcoming apartment is on the ground floor of the barn, private entrance. Fully equipped kitchen; Satellite …see more

from $125 / night

$745 / week

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from $125 / night

(6) Excellent 

27

Vacation apartment in Tavarnelle Val di Pesa

Province of Florence / Tavarnelle Val di Pesa

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Nearest beach 90 mi
  • Child friendly
  • Ask about pets
We have chosen to live in this Villa because the beauty of the surrounding landscape, it is impossible to tell ... .. .is just to see. The apartment is very spacious and bright, is situated on the ground floor, has an independent entrance and is surrounded by a large g …see more

from $69 / night

$481 / week

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from $69 / night

24

Vacation apartment with shared pool in Tavarnelle Val di Pesa

Province of Florence / Tavarnelle Val di Pesa

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 80 mi
  • Swimming pool
  • Child friendly
This former farmhouse dating back to 1600, recently beautifully restored, is located in Noce, quait little town of Chianti. The area was recalled by Dante Alighieri in his Divine Comedy. Located in the heart of the Tuscany hills of Chianti, due to its location enjoys an …see more

from $57 / night

$393 / week

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from $57 / night

(1) Excellent 

22

Tavarnelle Val di Pesa Vacation apartment rental

Province of Florence / Tavarnelle Val di Pesa

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Nestled among the rolling hills of Chianti away from any noise, the olive grove is located in a strategic position, just a few kilometers from the beautiful medieval towns of Barberino val d'Elsa and San Gimignano and the beautiful art cities of Florence and Siena. The …see more

from $150 / night

$1,049 / week

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from $150 / night

15

Vacation apartment with shared pool in San Donato in Poggio

Tavarnelle Val di Pesa / San Donato in Poggio

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
It is here, that in summer of 1857, the Arch-Duke of Tuscany invited Pope Pius IX to enjoy the beauty of Tuscany and to savour it's fine wines and oil. It's a heavenly place to stay, perched on a hill surveying sloping vineyards and olive groves. This ancient estate cro …see more

from $250 / night

$1,747 - $2,683 / week

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from $250 / night

47

Tavarnelle Val di Pesa Vacation villa rental

Province of Florence / Tavarnelle Val di Pesa

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
Located on the gentle green hills of Chianti between Florence and Siena, Colonica Giulia enjoys stunning views of the countryside surrounding with grain fields, vineyards and olive groves. Colonica Giulia has been recently restored preserving the original characteristic …see more

from $410 / night

$2,870 - $3,993 / week

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from $410 / night

(27) Excellent 

Certificate of Excellence

44

Vacation apartment rental

Province of Florence / Tavarnelle Val di Pesa

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 100 mi
  • Child friendly
  • Private garden
Charming , authentic & sophisticated country apartment with private garden-terrace, boasting a picture-framed view of olive groves and countryside on those classic rolling hills and glorious sunsets. The lodging keeps cool in the summer and warm in the winter. Casa Mia …see more

Certificate of Excellence

from $91 / night

$638 / week

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Responds fast!
avg. 1 hour 3 minutes

from $91 / night

(1) Excellent 

17

Tavarnelle Val di Pesa Vacation villa rental

Province of Florence / Tavarnelle Val di Pesa

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 90 mi
  • 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 $187 / night

$1,304 - $3,351 / week

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Responds fast!
avg. 2 hours 51 minutes

from $187 / night

12

Vacation apartment with shared pool in San Donato in Poggio

Tavarnelle Val di Pesa / San Donato in Poggio

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
It is here, that in summer of 1857, the Arch-Duke of Tuscany invited Pope Pius IX to enjoy the beauty of Tuscany and to savour it's fine wines and oil. It's a heavenly place to stay, perched on a hill surveying sloping vineyards and olive groves. This ancient estate cro …see more

from $250 / night

$1,747 - $2,683 / week

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from $250 / night

22

Apartment rental in Tavarnelle Val di Pesa with shared pool

Province of Florence / Tavarnelle Val di Pesa

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
apartment on the ground floor of a medieval tower with a private garden and access to communal garden and rooftop swimming pool. Living with large windows facing San Gimignano and the Elsa valley, room with antique furniture and panoramic glass door, bathroom with showe …see more

from $119 / night

$787 - $1,061 / week

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from $119 / night

17

Vacation apartment with shared pool in San Donato in Poggio

Tavarnelle Val di Pesa / San Donato in Poggio

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
It is here, that in summer of 1857, the Arch-Duke of Tuscany invited Pope Pius IX to enjoy the beauty of Tuscany and to savour it's fine wines and oil. It's a heavenly place to stay, perched on a hill surveying sloping vineyards and olive groves. This ancient estate cro …see more

from $268 / night

$1,872 - $2,746 / week

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from $268 / night

(8) Excellent 

24

Vacation apartment in Tavarnelle Val di Pesa

Province of Florence / Tavarnelle Val di Pesa

3 4 3 nights min

  • 3 bedrooms
  • Sleeps 4
  • 3 nights min
  • Suitable for children age 5+
  • Air conditioning
  • Private garden
Authentic, rooftop apartment set inside a 300 year old Tuscan villa which boasts wonderful views from every window overlooking the Chianti hills and valleys and the historic monastic hamlet of Badia Passignano. Twenty steps lead up into the apartment from the columned …see more

from $94 / night

$752 / week

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Responds fast!
avg. 2 hours 32 minutes

from $94 / night

(8) Excellent 

24

San Donato in Poggio Vacation penthouse rental

Tavarnelle Val di Pesa / San Donato in Poggio

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This apartment is one of a property consisting of a total of 6 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 $106 / night

$549 - $849 / week

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Responds fast!
avg. 2 hours 13 minutes

from $106 / night

(2) Excellent 

29

Tavarnelle Val di Pesa Vacation apartment rental

Province of Florence / Tavarnelle Val di Pesa

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 90 mi
  • Child friendly
  • Ask about pets
Beautiful stone country house, situated in the Park of an old villa in the heart of Chianti a few kilometers from Florence, Siena and San Gimignano. It also boasts a beautiful outdoor area where you can eat or relax in the open air. The apartment accommodation surround …see more

from $125 / night

$749 / week

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from $125 / night

21

Vacation farmhouse with shared pool in Tavarnelle Val di Pesa

Province of Florence / Tavarnelle Val di Pesa

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The Country House is close to a romanesque church dating back to the 5th Century, and is made of 6 charming holiday apartments with private pool belonging to the Fusi family, that ensure relaxing holidays in Chianti to all its guests. When choosing this accomodation, g …see more

from $125 / night

$874 / week

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from $125 / night

31

Vacation home with shared pool in Tavarnelle Val di Pesa

Province of Florence / Tavarnelle Val di Pesa

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Swimming pool
  • Child friendly
The charm of this places is based not only on their proximity to the most important cities in Tuscany (Florence, Siena, San Gimignano, Certaldo, Volterra), worldwide known for their unique artistic patrimony, but also and above all on the harmony of the landscape which …see more

from $118 / night

$826 / week

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from $118 / night

(12) Excellent 

30

Vacation barn in Tavarnelle Val di Pesa

Province of Florence / Tavarnelle Val di Pesa

2 6 4 nights min

  • 2 bedrooms
  • Sleeps 6
  • 4 nights min
  • Nearest beach 100 mi
  • Child friendly
  • Pet friendly
Casa al Poggio is the result of a renovation done with passion for local country architecture of this old Stone Villa with a wonderful stunning view of the Chianti Classico area, with stone walls , the terracotta floors and exposed beams.The house is a portion of the b …see more

from $138 / night

$811 - $1,246 / week

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from $138 / night

12

Vacation apartment with shared pool in San Donato in Poggio

Tavarnelle Val di Pesa / San Donato in Poggio

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
It is here, that in summer of 1857, the Arch-Duke of Tuscany invited Pope Pius IX to enjoy the beauty of Tuscany and to savour it's fine wines and oil. It's a heavenly place to stay, perched on a hill surveying sloping vineyards and olive groves. This ancient estate cro …see more

from $250 / night

$1,747 - $2,683 / week

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from $250 / night

18

Vacation studio with shared pool in San Donato in Poggio

Tavarnelle Val di Pesa / San Donato in Poggio

Studio 2 7 nights min

  • Studio
  • Sleeps 2
  • 7 nights min
  • Swimming pool
  • Ask about children
Small nice studio apartment for 2 people, on the ground floor with private terrace. Internet wi fi, Sat Tv. This holiday home in Tuscany is at 1 km from the medieval village of San Donato in Poggio, in the heart of Chianti Classico, famous for its wonderfully pre …see more

from $63 / night

$437 - $649 / week

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Responds fast!
avg. 1 hour 53 minutes

from $63 / night

(3) Very Good 

17

Home rental in Tavarnelle Val di Pesa with shared pool

Province of Florence / Tavarnelle Val di Pesa

1 6 2 nights min

  • 1 bedroom
  • Sleeps 6
  • 2 nights min
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
Comfortable apartment decorated in a Tuscan style, with views of the beautiful hills of Chianti surrounded by olive groves and vineyards. Ideally located for visiting the beautiful cities of Florence, Siena and San Gimignano. Quiet garden with panoramic swimming pool fo …see more

from $187 / night

$1,117 / week

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from $187 / night

(3) Excellent 

73

Vacation apartment with shared pool in Tavarnelle Val di Pesa

Province of Florence / Tavarnelle Val di Pesa

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
apartment on the ground floor of a villa with private garden and access to the town and the panoramic swimming pool. Large living room with kitchenette and patio doors facing San Gimignano and the Elsa valley, rooms with antique furniture and panoramic window, bathroom …see more

from $113 / night

$749 - $1,236 / week

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from $113 / night

27

Vacation farmhouse rental

Province of Florence / Tavarnelle Val di Pesa

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The Country House is close to a romanesque church dating back to the 5th Century, and is made of 6 charming holiday apartments with private pool belonging to the Fusi family, that ensure relaxing holidays in Chianti to all its guests. When choosing this accomodation, g …see more

from $125 / night

$874 / week

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from $125 / night

(7) Excellent 

25

Farmhouse rental in Tavarnelle Val di Pesa with swimming pool

Province of Florence / Tavarnelle Val di Pesa

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 90 mi
  • 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 a small …see more

from $125 / night

$874 - $1,747 / week

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Responds fast!
avg. 1 hour 58 minutes

from $125 / night

14

Vacation apartment in Tavarnelle Val di Pesa

Province of Florence / Tavarnelle Val di Pesa

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Nearest beach 60 mi
  • Child friendly
  • Private garden
In a panoramic position, apartment in one of the most beautiful areas of the Chianti classico region, immersed in greenery and surrounded by vineyards, olive groves and coppices. Its location surrounded by nature in a very quiet area is located halfway between the beaut …see more

from $81 / night

$497 / week

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from $81 / night

19

San Donato in Poggio Vacation apartment rental

Tavarnelle Val di Pesa / San Donato in Poggio

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
Apartment Duchessina 3: 50 sq.m., ground level; living room, kitchen (4 hobs, oven), double bed room, twin bedded room, bathroom with shower, balcony, covered and equipped (garden furniture) outdoor area. Splendid views and easy access to the pool.- The estate consists …see more

from $97 / night

$807 - $1,117 / week

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from $97 / night

13

Vacation farmhouse in San Donato in Poggio

Tavarnelle Val di Pesa / San Donato in Poggio

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Nice property with pool situated near the beautiful medieval hamlet of San Donato in Poggio, half-way between Florence and Siena. This property comprises 3 comfortable apartments all of which recently restored and tastefully furnished. Beautiful vineyards and olive grov …see more

from $163 / night

$1,061 - $1,685 / week

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from $163 / night

(1) Excellent 

29

San Donato in Poggio Vacation villa rental

Tavarnelle Val di Pesa / San Donato in Poggio

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 130 mi
  • Swimming pool
  • Child friendly
Visiting Podere Erica provides a unique opportunity to experience the best that Tuscany has to offer. Situated on over 30 acres with grape vines, olive trees, pastures and woodland, Podere Erica ensures total privacy with sweeping views over the countryside. The beauti …see more

from $981 / night

$6,863 - $9,359 / week

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from $981 / night

47

Vacation villa rental

Province of Florence / Tavarnelle Val di Pesa

11 20 7 nights min

  • 11 bedrooms
  • Sleeps 20
  • 7 nights min
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
Immersed in the green countryside of the Chianti hills, surrounded by the typical olive groves and vineyards, Villa Tavarnelle is a centuries old farmhouse which has belonged to the Fusi family for many years now. Recently restored to the highest standards, the villa h …see more

from $1,337 / night

$9,359 - $16,846 / week

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from $1,337 / night

65

Tavarnelle Val di Pesa Vacation villa rental

Province of Florence / Tavarnelle Val di Pesa

10 20 7 nights min

  • 10 bedrooms
  • Sleeps 20
  • 7 nights min
  • Child friendly
Halfway between Florence and Siena, among the verdant hills and the vineyards of Tuscany – where the sound of nature pervades over silence and privacy stands this magnifique villa. It is ideal fort he unforgettable weddings as well. We host only small Weddings (maxim …see more

from $1,337 / night

$9,359 / week

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from $1,337 / night

(14) Excellent 

62

Vacation townhouse with shared pool in Tavarnelle Val di Pesa

Province of Florence / Tavarnelle Val di Pesa

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
L'appartmento L'Olivo si trova all'interno dell' Agriturismo La Villa Romita, un ex convento del 1500 completamente ristrutturato e composto da 5 appartamenti indipendenti. Con i suoi ambienti sobri nello stile rustico Toscano, è il luogo ideale per trascorrere una …see more

from $110 / night

$687 - $799 / week

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from $110 / night

(3) Excellent 

16

Vacation home with shared pool in Tavarnelle Val di Pesa

Province of Florence / Tavarnelle Val di Pesa

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Private garden
The beautiful Chianti area awaits you for a fantastic holiday! Inside at Le Quercioline propose stay in comfortable fully furnished apartment, we include in the price all utilities, final cleaning, linen, a walk to the Tuscan countryside with our guide, mountain biking, …see more

from $87 / night

$559 / week

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from $87 / night

12

Vacation home in San Donato in Poggio

Tavarnelle Val di Pesa / San Donato in Poggio

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Suitable for children age 5+
  • Private garden
Casa Silana si trova nel Chianti, zona famosa per fattorie della produzione di vino e olio (Cantina Antinori, Castello di Meleto, Badia a Passignano, Greve in Chianti, Panzano, Montalcino, San Gimignano). La struttura può ricevere famiglie o gruppi di persone fino ad un …see more

from $113 / night

$624 / week

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Responds fast!
avg. 3 hours 29 minutes

from $113 / night

(7) Excellent 

58

Vacation townhouse with shared pool in Tavarnelle Val di Pesa

Province of Florence / Tavarnelle Val di Pesa

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
Situato all'interno dell'agriturismo La Villa Romita in una costruzione a sé stante nei locali che un tempo erano destinati granaio del convento, questo luminoso bilocale ha camera da letto con tre posti letto, una cucina-soggiorno e bagno. Gode inoltre di una terraz …see more

from $106 / night

$699 - $799 / week

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from $106 / night

15

Vacation apartment in Tavarnelle Val di Pesa

Province of Florence / Tavarnelle Val di Pesa

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Ask about pets
Si trova a metà strada tra Firenze e Siena, proprio nel centro del paese, è luminosissimo e molto silenzioso, al secondo piano di un piccola palazzina. A 2 minuti a piedi dalla fermata del bus e a 5 minuti di auto dalla autostrada. Parcheggio senza problemi nelle im …see more

from $57 / night

$350 - $524 / week

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from $57 / night

17

Vacation farmhouse with shared pool in Tavarnelle Val di Pesa

Province of Florence / Tavarnelle Val di Pesa

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Torre Tavarnelle is a beautiful property comprising 5 units created from the restoration of an ancient medieval tower, located about 20 km from San Gimignano. This vacation rental, situated in one of the most beautiful corners in Tuscany, offers stunning views over a va …see more

from $116 / night

$823 - $1,180 / week

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from $116 / night

22

Vacation apartment in San Donato in Poggio

Tavarnelle Val di Pesa / San Donato in Poggio

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This apartment is one of a property consisting of a total of 6 apartments located in San Donato in Poggio, a town in Florentine Chianti Classico area, 21km from Florence and 25km from Siena. The brand-new apartment (50 sq.m + 30 sq.m private garden) is built in traditi …see more

from $106 / night

$549 - $849 / week

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Responds fast!
avg. 2 hours 13 minutes

from $106 / night

48

Villa rental in Tavarnelle Val di Pesa with swimming pool

Province of Florence / Tavarnelle Val di Pesa

11 20 7 nights min

  • 11 bedrooms
  • Sleeps 20
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
South Florence large Tuscany holiday villa - Located in the Chianti region of Italy, just 19 miles south of Florence, Il Capoccio is a large, luxurious property with private wellbeing centre set in a green oasis of olive trees and Mediterranean plants, ideally located j …see more

from $1,444 / night

$10,103 - $17,209 / week

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from $1,444 / night

(14) Excellent 

41

Vacation b&b rental

Province of Florence / Tavarnelle Val di Pesa

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 90 mi
  • Child friendly
  • Air conditioning
The two bedrooms and the bathroom that I put at the disposal of the guests are on the first floor of my house which is a portion of a farmhouse in the Chianti area. It is located one kilometer from the center of the village of Tavarnelle Val di Pesa, and in the countrys …see more

from $138 / night

$749 - $1,623 / week

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Responds fast!
avg. 1 hour 32 minutes

from $138 / night