50 Best Vacation Rentals in Province of Florence - Holiday Lettings - Cabins

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Apartments Florence
2,847 properties
Montaione
527 properties
Greve in Chianti
437 properties
Montespertoli
312 properties
San Casciano in Val di Pesa
227 properties
Tavarnelle Val di Pesa
220 properties
Certaldo
216 properties
Gambassi Terme
183 properties
Impruneta
136 properties
Reggello
130 properties
Barberino Val d'Elsa
127 properties
Vinci
126 properties
Vicchio
104 properties
Rignano sull'Arno
102 properties
Figline e Incisa Valdarno
97 properties
Pontassieve
92 properties
Bagno a Ripoli
82 properties
Montelupo Fiorentino
80 properties
Castelfiorentino
79 properties
Pelago
73 properties

Province of Florence

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7,225 Vacation rentals

(2) Very Good 

24

Villa rental in Montaione with shared pool

Province of Florence / Montaione

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Giardino is a self catering indipendent villa in the farmhouse Casa Vacanze Amarrante. It's located in the middle of Tuscany between the borders of the province of Firenze, Siena and Pisa: the perfect location to reach the great art cities with daily trip or just get re …see more

from $107 / night

$621 - $1005 / week

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from $107 / night

(2) Excellent 

28

Vacation apartment with shared pool in Montaione

Province of Florence / Montaione

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Limonaia is a self catering apartment in the farmhouse Casa Vacanze Amarrante. It's located in the middle of Tuscany between the borders of the province of Firenze, Siena and Pisa: the perfect location to reach the great art cities with daily trip or just get relaxed in …see more

from $94 / night

$505 - $845 / week

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from $94 / night

(4) Excellent 

45

Vacation villa rental

Province of Florence / San Casciano in Val di Pesa

8 16 1 night min

  • 8 bedrooms
  • Sleeps 16
  • 1 night min
  • Nearest beach 90 mi
  • 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 considered …see more

from $1596 / night

$12410 - $15470 / week

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from $1596 / night

(4) Excellent 

40

Vacation villa with swimming pool in Greve in Chianti

Province of Florence / Greve in Chianti

9 18 1 night min

  • 9 bedrooms
  • Sleeps 18
  • 1 night min
  • Nearest beach 130 mi
  • Swimming pool
  • Child friendly
Villa Benedetta is a beautiful historic residence that has been for many years the beating heart of the Folonari family, a renowned name in the Italian wine panorama. Dating back to the early 1800, the villa is located at the center of the family’s agricultural holding …see more

from $828 / night

$7328 - $13237 / week

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from $828 / night

(5) Excellent 

26

Florence Vacation apartment rental

Province of Florence / Florence

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
  • Nearest beach 90 mi
  • Child friendly
  • Car not necessary
Leonardo's Rose is the ideal apartment for those who want to immerse themselves in the Sant'Ambrogio district everyday. It is located in one of Florence's most characteristic pedestrian streets. Furnished with care and functionality in a perfect mix of modern design and …see more

from $81 / night

$470 - $810 / week

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Responds fast!
avg. 1 hour 33 minutes

from $81 / night

(1) Excellent 

23

Villa rental in Greve in Chianti with swimming pool

Province of Florence / Greve in Chianti

5 10 1 night min

  • 5 bedrooms
  • Sleeps 10
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
This wonderful recently restored 5BDR villa is located in the heart of the Chianti region, just steps away from the town of Greve. The villa traces its origin back to the 1300 and has recently been tastefully renovated and exquisitely furnished. The careful atte …see more

from $603 / night

$4222 - $5805 / week

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from $603 / night

(4) Excellent 

25

Vacation apartment rental

Province of Florence / Montaione

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Bouganville is a self catering apartment in the farmhouse Casa Vacanze Amarrante. It's located in the middle of Tuscany between the borders of the province of Firenze, Siena and Pisa: the perfect location to reach the great art cities with daily trip or just get relaxed …see more

from $95 / night

$509 - $851 / week

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from $95 / night

(2) Very Good 

11

Vacation farmhouse rental

Province of Florence / Montespertoli

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
La Rocca di Montalbino stands on one of the hilltops surrounding Montespertoli. This location offers a splendid view of the Chianti landscape and all the peace and quiet of the Tuscan countryside. Surrounded by thirty hectares of vineyards, olive groves, and wood …see more

from $133 / night

$927 - $1760 / week

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from $133 / night

(9) Excellent 

16

Vacation villa with shared pool in Piazzale Michelangelo

Florence / Piazzale Michelangelo

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 80 mi
  • 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 …see more

from $300 / night

$1742 / week

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from $300 / night

(10) Excellent 

21

Figline e Incisa Valdarno Vacation apartment rental

Province of Florence / Figline e Incisa Valdarno

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Large apartment of 80 square meters overlooking the tip of an ancient former convent with swimming pool (open from June to end of September). As the bow of a ship, the apartment offers 7 amazing views over the Chianti hills. Comprises entrance hall, large living room, s …see more

from $100 / night

$692 - $821 / week

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Responds fast!
avg. 3 hours 42 minutes

from $100 / night

14

Vacation apartment with shared pool in Grassina

Province of Florence / Grassina

23 46 2 nights min

  • 23 bedrooms
  • Sleeps 46
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Country apartments Agriturismo with pool Chianti hills 15 apartments in a small ancient village, 6 km from Florence Village built in 1500 and beautifully restored in 2009 while maintaining the original character of the structure. All apartments have independent heating, …see more

from $178 / night

$1170 / week

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from $178 / night

(4) Excellent 

67

Vacation farmhouse in Montaione

Province of Florence / Montaione

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Nearest beach 50 mi
  • Swimming pool
  • Child friendly
Podere Settefrati an Impressive 17th Century Stone farmhouse originally a convent, spacious with many of its original features preserved. Its white washed walls, exposed beams, fireplaces and terracotta floors take you back to a nostalgic and romantic past. Set in …see more

from $141 / night

$986 - $2580 / week

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from $141 / night

(6) Excellent 

27

Vacation villa with swimming pool in Central Florence

Florence / Central Florence

5 10 1 night min

  • 5 bedrooms
  • Sleeps 10
  • 1 night min
  • Nearest beach 98 mi
  • Swimming pool
  • Child friendly
Only one mile away from Porta Romana square (Piazzale di Porta Romana), a historical gate into the heart of the city of Florence, this gorgeous typical Florentine villa is located on the hill of "Poggio Imperiale", immersed in the beauty of the Tuscan countryside surrou …see more

from $585 / night

$4344 - $6855 / week

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from $585 / night

100

Vacation apartment with shared pool in Castelfiorentino

Province of Florence / Castelfiorentino

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
5+1 paxAs this apartment with shared swimming pool in Chianti is on the first floor of a restored barn, it provides beautiful views of the surroundings.This apartment in Chianti features an independent area of garden in the outside and access to the swimming pool. Insid …see more

from $165 / night

$751 - $1185 / week

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from $165 / night

(1) Excellent 

30

Vacation apartment in Florence

Province of Florence / Florence

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly
House located near the historic center of Florence. It offers apartments with private bathroom and kitchenette with microwave. Free private parking and bike. free. Habitable in the building an outdoor space and a terrace equipped with tables and deck chairs. the most im …see more

from $118 / night

$821 / week

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from $118 / night

24

Vacation apartment with swimming pool in Montefiridolfi

San Casciano in Val di Pesa / Montefiridolfi

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
In the heart of Chianti, halfway between Florence and Siena The farmhouse I Greppi Di Silli located 300 mt above sea level. rises and looks out over a green valley, surrounded on all sides by cultivated hills covered in olive groves and vineyards. Alongside the bor …see more

from $269 / night

$1877 - $2077 / week

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from $269 / night

(1) Excellent 

33

Florence Vacation villa rental

Province of Florence / Florence

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 120 mi
  • Swimming pool
  • Child friendly
This wonderful recently renovated 4BR/3.5BA villa sits on top of a hill and is part of a 20 hectares biological farm, immersed in the most beautiful typical Tuscan landscape. A luxury private swimming pool as well as a private lake and the most amazing direct views on …see more

from $604 / night

$4228 / week

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from $604 / night

(16) Excellent 

24

Barberino Val d'Elsa Vacation apartment rental

Province of Florence / Barberino Val d'Elsa

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 80 mi
  • Swimming pool
  • Child friendly
The apartment is situated in the heart of Chianti Classico in the natural Sant'Agnese resort, where there are splendid hills covered by cypresses that are reproduced naturally. A pleasant, relaxing and magic environment is created by the atmosphere typical of this land …see more

from $67 / night

$821 - $1218 / week

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from $67 / night

(68) Excellent 

Certificate of Excellence

32

Vacation apartment in Central Florence

Florence / Central Florence

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Nearest beach 80 mi
  • Child friendly
  • Car not necessary
The apartment, was awarded by Tripadvisor with the "Certificate of Excellence for 2014", is located in the centre of Florence in the picturesque and characteristic area of San Frediano.It is in Via della Chiesa 111 in an excellent position, which is within few minutes f …see more

Certificate of Excellence

from $83 / night

$352 - $763 / week

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Responds fast!
avg. 2 hours 14 minutes

from $83 / night

(3) Excellent 

28

Hotel apartment rental in Montespertoli with shared pool

Province of Florence / Montespertoli

2 10 2 nights min

  • 2 bedrooms
  • Sleeps 10
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
La Rocca di Montalbino stands on one of the hilltops surrounding Montespertoli. This location offers a splendid view of the Chianti landscape and all the peace and quiet of the Tuscan countryside. Surrounded by thirty hectares of vineyards, olive groves, and wood …see more

from $225 / night

$1525 - $2807 / week

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from $225 / night

(6) Excellent 

20

Vacation b&b in Fucecchio

Province of Florence / Fucecchio

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
The Agata House is the perfect place to relax for a moment to live with nature. Our B & B is close to the major tourist attractions of Tuscany: Florence, Pisa, Lucca, Pistoia, Vinci, Certaldo San Gimignano, San Miniato ... In the heart of our green region can spend a pl …see more

from $59 / night

$329 / week

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from $59 / night

(1) Very Good 

10

B&b rental in Greve in Chianti with shared pool

Province of Florence / Greve in Chianti

16 2 2 nights min

  • 16 bedrooms
  • Sleeps 2
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
The farm is located in the heart of the Chianti region, just 20 km away. from Florence and 40 km. from Siena. The swimming pool, surrounded by olive trees and sun-kissed, is the ideal place to relax completely. The day ends in the romantic atmosphere of old-style room …see more

from $115 / night

$805 / week

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from $115 / night

(5) Very Good 

24

Vacation villa with swimming pool in Gambassi Terme

Province of Florence / Gambassi Terme

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 85 mi
  • Swimming pool
  • Child friendly
Typical villa for rent in Tuscany set in a most beautiful position in the Chianti hills half way between Florence and Siena, in an oasis of peace and tranquillity where you will be guaranteed a relaxing and reinvigorating holiday. Whilst driving along in every directio …see more

from $109 / night

$763 - $3988 / week

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from $109 / night

(3) Excellent 

18

Vacation apartment rental

Province of Florence / Castelfiorentino

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 70 mi
  • Swimming pool
  • Child friendly
The apartments benefits from its own pool with a spacious solarium with grass. Leading from the livingroom is a patio with table and chairs to enable you to dine in a cool, furnished with a BBQ. The apartment has been renovated keeping the original features t …see more

from $119 / night

$603 - $1461 / week

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from $119 / night

21

Apartment rental in Marcialla with swimming pool

Certaldo / Marcialla

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Small medieval village nestled in the Chianti countryside a short distance from Certaldo, a few kilometers from Florence, Siena and San Gimignano. Wine and oil production, panoramica.Luogo pool ideal for living and relaxing in contact with nature and animals sharing the …see more

from $71 / night

$497 / week

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from $71 / night

(8) Excellent 

67

Villa rental in Fiesole with swimming pool

Province of Florence / Fiesole

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
From Villa Acacia Florence city centre is at just 10 minutes by public bus! You will not need a car to enjoy the city and the Villa. If you have ever been to Florence you know this is a town where “suburbs” takes on a very special meaning. Just outside the very hectic …see more

from $470 / night

$3284 - $5747 / week

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Responds fast!
avg. 3 hours 21 minutes

from $470 / night

(3) Excellent 

20

San Donato in Poggio Vacation home rental

Tavarnelle Val di Pesa / San Donato in Poggio

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 94 mi
  • Child friendly
Surrounded by vineyards and the rolling hills beyond, this two bedroom villa has some wonderful panoramas of this famed region, with the fabulous hilltop town of Panzano in the distance. Prepare a BBQ and dine al fresco on the terrace overlooking the gardens and beyond …see more

from $88 / night

$587 - $704 / week

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from $88 / night

(15) Excellent 

25

Vacation villa with swimming pool in San Casciano in Val di Pesa

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 mi
  • 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 $338 / night

$1300 - $2364 / week

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from $338 / night

(4) Excellent 

25

Vacation apartment with swimming pool in Arno River

Florence / Arno River

5 8 Min stay varies

  • 5 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
A typical Tuscan country house at 15 minuts by car from the historical city center of Florence Master apartment in a historic villa from the 15th century, in the Florentine hills that rise above the Arno valley. The villa is surrounded by large green areas with olive t …see more

from $178 / night

$1419 - $2482 / week

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Responds fast!
avg. 3 hours 27 minutes

from $178 / night

7

Vacation apartment in Florence

Province of Florence / Florence

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Ask about children
In a beautiful palace of Via San Niccolò, in two steps from Ponte Vecchio, Palazzo Pitti and Piazza Santa Croce, a charming studio of bygone and modern details that allows to live in comfort the city. The apartment is quiet and located inside the courtyard of the palac …see more

from $77 / night

$528 / week

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from $77 / night

38

Apartment rental in Santo Stefano

Montaione / Santo Stefano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 60 mi
  • Child friendly
  • Pet friendly
Relaxation and comfort characterize this complex in the heart of Toscana, it is made up of a villa in the centre and three groups of independent apartments. They are carefully restored, respecting the environment, so friendly, functional and fully equipped. They have t …see more

from $101 / night

$634 - $1150 / week

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from $101 / night

36

Apartment rental in Santo Stefano

Montaione / Santo Stefano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 60 mi
  • Child friendly
  • Pet friendly
Relaxation and comfort characterize this complex in the heart of Toscana, it is made up of a villa in the centre and three groups of independent apartments. They are carefully restored, respecting the environment, so friendly, functional and fully equipped. They have t …see more

from $94 / night

$563 - $1032 / week

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from $94 / night

(4) Excellent 

24

Vacation apartment with swimming pool in San Silvestro

Barberino Val d'Elsa / San Silvestro

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
The apartment Leonardo is the perfect place for your farm holidays in Tuscany, the farmhouse San Silvestro is located in the heart of Chianti area, between Florence and Siena. The Chianti hills are a strategic location to visit the famous historic cities and most beauti …see more

from $118 / night

$704 - $1232 / week

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from $118 / night

(1) Excellent 

100

Vacation apartment in Certaldo Alto

Certaldo / Certaldo Alto

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Ask about pets
The apartment "The rooms of Boccaccio" is located along the main street of Certaldo Alto, medieval town in the province of Florence, which has been the birthplace of Giovanni Boccaccio, celebrated author of the Decameron. The apartment is on the first floor of a histori …see more

from $83 / night

$493 - $669 / week

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Responds fast!
avg. 3 hours 8 minutes

from $83 / night

78

Florence Vacation b&b rental

Province of Florence / Florence

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning
B & B FLO is a family run bed and breakfast, just few minutes walking from Firenze Rifredi station. Run by Felice, Stefania and her daughter Barbara, who's a tour guide. Recently renovated and tastefully refurbished, it is equipped with every comfort including air condi …see more

from $88 / night

$616 / week

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from $88 / night

(18) Very Good 

19

Vacation apartment in Poggio alla Croce

Greve in Chianti / Poggio alla Croce

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Nearest beach 100 mi
  • 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 $100 / night

$540 - $575 / week

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from $100 / night

11

Vacation finca in Montebonello

Pontassieve / Montebonello

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden
monolocale inserito nel fabbricato principale, con accesso indipendente,disponibilità di utilizzo giardino attrezzato, passeggiate lungo le strade di accesso alle aree coltivate a vigneto e oliveto con suggestiva vista panoramica, proposta di degustazione prodotti tip …see more

from $36 / night

$294 / week

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from $36 / night

(1) Excellent 

10

Vicchio Vacation apartment rental

Vicchio / Ponte a Vicchio

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This ground floor apartment can accommodate two people. Situated in front of the swimming pool it has an outdoor living too. It comprises: kitchen, double bedroom, bathroom with tub and shower. The apartment is equipped with oven, washing machine and dishwasher. < …see more

from $59 / night

$411 / week

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Responds fast!
avg. 2 hours 40 minutes

from $59 / night

17

Apartment rental in Marcialla with shared pool

Certaldo / Marcialla

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 80 mi
  • Swimming pool
  • Child friendly
La Certaldina Holiday Villa is on the top of a hill in the country side of Chianti An ideal place for a relaxing and peaceful holiday, with the swimming pool surrounded by olive trees and an nice view on the vineyards. The position is perfect as starting point, for …see more

from $71 / night

$775 - $857 / week

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from $71 / night

(1) Very Good 

15

Vacation apartment in Campi Bisenzio

Province of Florence / Campi Bisenzio

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Air conditioning
The apartment consists of entrance hallway, lounge/dining room with fully equipped kitchen and balcony, attic floor, accessed by internal staircase, there is a room with a bed, toilet, terrace to Pocket, plus a very high not with two single beds. All rooms are equipped …see more

from $88 / night

$587 - $751 / week

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from $88 / night