50 Best Vacation Rentals in Castelfiorentino - Holiday Lettings - Cabins

Close

View larger map

Also consider

Petrazzi
16 properties

Castelfiorentino

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this vacation rental you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

8,305 Vacation rentals

(7) Excellent 

12

Castelfiorentino Vacation farmhouse rental

Province of Florence / Castelfiorentino

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 55 mi
  • Swimming pool
  • Child friendly
The Fattoria Il Petriccio is located on the hills of Valdelsa, 2 miles from Castelfiorentino (Florence) the ideal starting point to visit the Tuscan art cities: half an hour drive from Firenze, Siena, Lucca, Pisa, Volterra and San Gimignano it is really located in the h …see more

from $246 / night

$737 - $1,216 / week

Book View

from $246 / night

10

Vacation condo in Castelfiorentino

Province of Florence / Castelfiorentino

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Nearest beach 70 mi
  • Suitable for children age 5+
  • Air conditioning
At the beginning of the historical centre of Castelfiorentino in a building of 800 is two-roomed apartment (entrance-kitchen-large double-Camerina-bath). Recently renovated. Wide free parking-300 meters to train station and bus Castelfiorentino is centrally located in T …see more

from $74 / night

$492 / week

Book View

from $74 / night

15

Vacation barn with shared pool in Castelfiorentino

Province of Florence / Castelfiorentino

3 5 2 nights min

  • 3 bedrooms
  • Sleeps 5
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The Oleander is a holiday home in the heart of Tuscany between Florence and Certaldo, near Florence and Siena. Holiday House Gli Oleandri is an oasis of tranquility in Castelfiorentino, a town in the Tuscan countryside: the two Tuscan rustic style apartments and pool in …see more

from $209 / night

$1,252 / week

Book View

from $209 / night

(4) Excellent 

20

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 $142 / night

$688 - $1,585 / week

Book View

from $142 / night

36

Vacation villa with swimming pool in Castelfiorentino

Province of Florence / Castelfiorentino

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 105 mi
  • Swimming pool
  • Child friendly
Single family independent villa from the 1850’s situated in a charming village. Villa Maria is in the small and charming village of Renai, 3 km from Castelfiorentino. The villa is encircled by vineyards and olive groves. The owner Vincenzo realised the restoration work …see more

from $305 / night

$2,131 - $3,390 / week

Inquire View

from $305 / night

(8) Excellent 

23

Castelfiorentino 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. The living still mantain its original "vaulted" ceiling in terracotta. Leading from the livingroom is a patio with table and chairs to enable you to dine in a cool, enjoying the view o …see more

from $138 / night

$664 - $1,763 / week

Book View

from $138 / night

(3) Very Good 

24

Barn rental in Castelfiorentino with swimming pool

Province of Florence / Castelfiorentino

5 9 2 nights min

  • 5 bedrooms
  • Sleeps 9
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The Oleander is a holiday home in the heart of Tuscany between Florence and Certaldo, near Florence and Siena. Holiday House Gli Oleandri is an oasis of tranquility in Castelfiorentino, a town in the Tuscan countryside: the two Tuscan rustic style apartments and pool in …see more

from $357 / night

$2,259 / week

Book View

from $357 / night

28

Vacation villa with swimming pool in Castelfiorentino

Province of Florence / Castelfiorentino

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 70 mi
  • Swimming pool
  • Child friendly
Every building in the Tuscan landscape is pervaded of the many cultures that inhabited it throughout the centuries. About 30 Km from Florence, Castello del Chianti castle, built on the ancient Via Francigena connecting France to Rome, is a shining example, evoking a mul …see more

from $1,459 / night

$10,212 - $13,970 / week

Inquire View

from $1,459 / night

14

Castelfiorentino Vacation home rental

Province of Florence / Castelfiorentino

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The Oleander is a holiday home in the heart of Tuscany between Florence and Certaldo, near Florence and Siena. Holiday House Gli Oleandri is an oasis of tranquility in Castelfiorentino, a town in the Tuscan countryside: the two Tuscan rustic style apartments and pool in …see more

from $172 / night

$1,068 / week

Book View

from $172 / night

23

Vacation villa in Castelfiorentino

Province of Florence / Castelfiorentino

4 10 1 night min

  • 4 bedrooms
  • Sleeps 10
  • 1 night min
  • Nearest beach 80 mi
  • Swimming pool
  • Child friendly
Pieve vecchia estate has been included inside the historical gazzette named "Valdelsa Viva" among the forty cultural itineraries in the Valdelsa area, and it is located in the same site where once was the old Pieve(the name comes from the latin word plebs that means pe …see more

from $528 / night

$3,697 / week

Book View

from $528 / night

(4) Good 

16

Vacation farmhouse with shared pool in Castelfiorentino

Province of Florence / Castelfiorentino

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 55 mi
  • Swimming pool
  • Child friendly
The Fattoria Il Petriccio is located on the hills of Valdelsa, 2 miles from Castelfiorentino (Florence) the ideal starting point to visit the Tuscan art cities: half an hour drive from Firenze, Siena, Lucca, Pisa, Volterra and San Gimignano it is really located in the h …see more

from $406 / night

$614 - $1,044 / week

Book View

from $406 / night

(2) Excellent 

12

Vacation farmhouse in Castelfiorentino

Province of Florence / Castelfiorentino

6 20 3 nights min

  • 6 bedrooms
  • Sleeps 20
  • 3 nights min
  • Child friendly
  • Pet friendly
A home away from home in the heart of Tuscany, Belvedere Farmhouse has timeless appeal. Belvedere Farmhouse (sleeps 10-20) is a beautifully restored 19th Century farmhouse, ideally positioned on a Tuscan hilltop, boasting magnificent panoramic views over the vineyards …see more

from $1,597 / night

$5,029 - $8,468 / week

Book View

from $1,597 / night

8

Vacation apartment with shared pool in Castelfiorentino

Province of Florence / Castelfiorentino

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Fico is a charming apartment situated in near Florence. This wonderful country home is the idyllic solution for exciting escapes in Tuscany. The airport is within 35 Km from the house allowing you the freedom to explore the region with a rental car. The property consist …see more

from $148 / night

$762 - $1,216 / week

Book View

from $148 / night

(8) Very Good 

29

Vacation villa with swimming pool in Castelfiorentino

Province of Florence / Castelfiorentino

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
A glass of Prosecco awaits your arrival at this idyllic villa set on top of a hill with vineyards, olive groves and panoramic views of sublime Tuscany. Here you can enjoy a tranquil holiday with all the privacy that a large garden patio and newly installed swimmingpool …see more

from $192 / night

$1,216 - $1,597 / week

Book View

from $192 / night

(3) Excellent 

12

Farmhouse rental in Castelfiorentino with shared pool

Province of Florence / Castelfiorentino

5 11 Min stay varies

  • 5 bedrooms
  • Sleeps 11
  • Min stay varies
  • Nearest beach 55 mi
  • Swimming pool
  • Child friendly
In a large farmhouse are available 2 apartments, restored according to the traditional tuscan style, with terracotta floors and wooden beam ceilings, some with open fireplace, that can accommodate from 5 and 6 people for a total of 11 beds. (additional beds on requests …see more

from $737 / night

$1,474 - $2,334 / week

Book View

from $737 / night

102

Vacation apartment with shared pool in Castelfiorentino

Province of Florence / Castelfiorentino

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
4 pax This enchanting apartment in Chianti affords access to the swimming pool and its own garden area. One of the accesses to this apartment leads guests into its parqueted living room with an inviting fireplace. In the same room there is a kitchen and a dining area. T …see more

Pricing unknown

Inquire View

Pricing unknown

100

Villa rental in Castelfiorentino with swimming pool

Province of Florence / Castelfiorentino

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
ExteriorThis restored 13th century castle, a real fairy-tale image, can be found in the Chianti region of Tuscany between the historical towns of San Miniato and San Gimignano. Standing atop a hill it has sweeping views of the estate's 120 hectares of vineyards, olive g …see more

Pricing unknown

Inquire View

Pricing unknown

100

Vacation apartment with shared pool in Castelfiorentino

Province of Florence / Castelfiorentino

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
4 pax (Superior)This apartment in Chianti with swimming pool is an ideal way to spend holidays in this captivating land.Located on the ground floor, there is a living room with fireplace, kitchen, two double bedrooms, two bathrooms with shower (one designed for disabled …see more

Pricing unknown

Inquire View

Pricing unknown

100

Vacation apartment with shared pool in Castelfiorentino

Province of Florence / Castelfiorentino

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 70 mi
  • Swimming pool
  • Child friendly
The wooden ceiling, brick walls and country style furnishings create a country style atmosphere. The apartment is 45m2 and features a masonry kitchenette equipped with refrigerator with freezer, microwave oven and dishwashing machine and dining area. There is a double s …see more

Pricing unknown

Inquire View

Pricing unknown

(17) Excellent 

29

Vacation villa with swimming pool in Castelfiorentino

Province of Florence / Castelfiorentino

5 12 7 nights min

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 70 mi
  • Swimming pool
  • Child friendly
Villa Antica sosta, is situated in the small and charming village called Renai, to 3 Km from Castelfiorentino, encircled from vineyards and olive groves. In the small country of Castelfiorentino you will be able to find: Railway station, supermarket, banks, post …see more

from $316 / night

$2,211 / week

Book View

from $316 / night

100

Vacation apartment with shared pool in Castelfiorentino

Province of Florence / Castelfiorentino

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
Ciliegio is an apartment with shared access to the swimming pool, perfect to enjoy the Chianti sun.It affords a private garden. This Tuscan style apartment offers a living room with an enormous open fireplace in which there is a kitchen area, a spacious double bedroom a …see more

Pricing unknown

Inquire View

Pricing unknown

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

Pricing unknown

Inquire View

Pricing unknown

16

Vacation farmhouse with swimming pool in Castelfiorentino

Province of Florence / Castelfiorentino

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Charming small independent villa with private pool situated on the hills surrounding the small town of Cambiano, approx. 45 km from Florence. This villa, built in 2009, offers nice outdoor areas with a beautiful panoramic terrace, gazebo, furnished garden and private po …see more

from $96 / night

$664 - $1,106 / week

Inquire View

from $96 / night

(3) Very Good 

51

Castelfiorentino Vacation castle rental

Province of Florence / Castelfiorentino

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Cabbiavoli, a beautifully restored 13th century castle, is available for letting throughout the year for families and groups of friends for up to 12 guests. Just 30 minutes from Florence, ideally positioned on a Tuscan hilltop, Castello di Cabbiavoli is immersed in bre …see more

from $1,465 / night

$10,255 - $13,976 / week

Book View

from $1,465 / night

22

Castelfiorentino Vacation home rental

Province of Florence / Castelfiorentino

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
This renovated farmhouse is surrounded by the countryside and have large view of vineyards and olive groves. Furnished with taste and stylish tuscan furniture. Ideal to visit the most famous places in Tuscany. Swimming-towels available for the clients (extra). Beautiful …see more

from $126 / night

$834 - $2,032 / week

Book View

from $126 / night

19

Home rental in Castelfiorentino

Province of Florence / Castelfiorentino

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
Historical villa "Ortimino", from the 18th century, renovated. 4 km from the centre of Castelfiorentino, in a sunny position on top of a hill, in the countryside. Private: beautiful garden to relax. Linen change weekly (suppl. charge extra). Parking on the premises. Sho …see more

from $113 / night

$786 - $1,062 / week

Book View

from $113 / night

11

Vacation apartment in Petrazzi

Castelfiorentino / Petrazzi

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Old farm estate "La Pineta", renovated. In the hamlet Varna 6 km from the centre of Gambassi, in a sunny position on top of a hill, located by a road. For shared use: property (fenced), beautiful garden with flowers, swimming pool (6 x 16 m, depth 100 - 250 cm, 05.05.-2 …see more

from $121 / night

$841 - $1,450 / week

Book View

Responds fast!
avg. 3 hours 38 minutes

from $121 / night

7

Castelfiorentino Vacation apartment rental

Province of Florence / Castelfiorentino

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly
New apartment located on the ground floor, separate entrance with kitchen / dining room, bedroom with access to the outdoors started directly with double bed and possibility of a cot for children under 2 years of age and bathroom with shower. Outside courtyard with priv …see more

from $50 / night

$344 / week

Book View

from $50 / night

13

Vacation apartment in Petrazzi

Castelfiorentino / Petrazzi

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Old farm estate "La Pineta", renovated. In the hamlet Varna 6 km from the centre of Gambassi, in a sunny position on top of a hill, located by a road. For shared use: property (fenced), beautiful garden with flowers, swimming pool (6 x 16 m, depth 100 - 250 cm, 05.05.-2 …see more

from $91 / night

$628 - $1,210 / week

Book View

from $91 / night

23

Castelfiorentino Vacation apartment rental

Province of Florence / Castelfiorentino

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Villa "Ortimino", built in 1800, renovated in 2015. 4 apartments in the property. 3700 km from the centre of Castelfiorentino, 40 km from the centre of Firenze, 65 km from the centre of Pisa, in the countryside. Motor access to the house (800 m via unmade road). Parking …see more

from $89 / night

$619 - $850 / week

Book View

from $89 / night

25

Castelfiorentino Vacation home rental

Province of Florence / Castelfiorentino

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Beautiful cottage "Fiammetta", 3 storeys, detached, renovated, surrounded by fields and vineyards. Above Castelfiorentino-Cambiano, in a hamlet, in a sunny, elevated position, in the countryside. For shared use: swimming pool (6 x 13 m, depth 140 - 180 cm, 17.03.-03.11. …see more

from $155 / night

$1,081 - $2,540 / week

Book View

from $155 / night

23

Castelfiorentino Vacation home rental

Province of Florence / Castelfiorentino

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Very beautiful, comfortable "rustico" cottage "Aurelia", 2 storeys, renovated. Above Castelfiorentino, outside the resort, 2 km from the centre, on top of a hill, excellent location: right in the centre but still quiet, in the countryside. Private: property 2 ha, large, …see more

from $162 / night

$1,127 - $3,593 / week

Book View

Responds fast!
avg. 3 hours 38 minutes

from $162 / night

37

Vacation home in Castelfiorentino

Province of Florence / Castelfiorentino

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
Very beautiful, comfortable farmhouse "Tassinaia", 3 storeys, from the 19th century, renovated, surrounded by vineyards. Above Castelfiorentino (2 km), in a secluded, quiet, sunny position on top of a hill, excellent location: right in the centre but still quiet. For sh …see more

from $225 / night

$1,387 - $3,593 / week

Book View

Responds fast!
avg. 3 hours 38 minutes

from $225 / night

11

Vacation apartment in Petrazzi

Castelfiorentino / Petrazzi

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Old farm estate "La Pineta", renovated. In the hamlet Varna 6 km from the centre of Gambassi, in a sunny position on top of a hill, located by a road. For shared use: property (fenced), beautiful garden with flowers, swimming pool (6 x 16 m, depth 100 - 250 cm, 05.05.-2 …see more

from $73 / night

$508 - $1,127 / week

Book View

from $73 / night

39

Vacation villa in Castelfiorentino

Province of Florence / Castelfiorentino

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Child friendly
  • Ask about pets
  • Private garden
Villa ' Parker ' lies in Castelfiorentino, in the heart of Tuscany, surrounded by beautiful countryside and only a few Km from important cities of art like Florence, Siena, Pisa, San Gimignano, Volterra, Certaldo Alto etc. The villa offers two apartments for guests (and …see more

from $99 / night

$602 / week

Book View

from $99 / night

11

Vacation apartment in Petrazzi

Castelfiorentino / Petrazzi

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Old farm estate "Il Giardino", renovated. In the hamlet Varna 6 km from the centre of Gambassi, 45 km from the centre of Firenze, 12 km from the centre of San Gimignano, in a secluded, sunny position on top of a hill, located by a road. For shared use: property (fenced) …see more

from $89 / night

$619 - $1,016 / week

Book View

from $89 / night

12

Vacation apartment in Petrazzi

Castelfiorentino / Petrazzi

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Old farm estate "Il Giardino", renovated. In the hamlet Varna 6 km from the centre of Gambassi, 45 km from the centre of Firenze, 12 km from the centre of San Gimignano, in a secluded, sunny position on top of a hill, located by a road. For shared use: property (fenced) …see more

from $89 / night

$619 - $1,016 / week

Book View

from $89 / night

7

Vacation apartment in Petrazzi

Castelfiorentino / Petrazzi

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Old farm estate "Il Giardino", renovated. In the hamlet Varna 6 km from the centre of Gambassi, 45 km from the centre of Firenze, 12 km from the centre of San Gimignano, in a secluded, sunny position on top of a hill, located by a road. For shared use: property (fenced) …see more

from $78 / night

$519 - $933 / week

Book View

Responds fast!
avg. 3 hours 38 minutes

from $78 / night

(1) Excellent 

23

Vacation farmhouse in Castelfiorentino

Province of Florence / Castelfiorentino

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
In a farmhouse in the heart of Chianti, in a splendid panoramic position, in the tranquility of the Tuscan countryside. At the center of a triangle formed by the beautiful cities of Florence, Pisa and Siena will be surrounded by rolling hills, decorated with cypress tre …see more

from $74 / night

$381 - $725 / week

Book View

from $74 / night

34

Vacation villa rental

Province of Florence / Castelfiorentino

9 21 Min stay varies

  • 9 bedrooms
  • Sleeps 21
  • Min stay varies
  • Child friendly
  • Ask about pets
Owner's description:Main Description : Beautiful property with swimming pool and tennis court located roughly 40km from Florence. The property is a part of a large agricultural business managed directly by the owners: inside boasts large spaces while outside offers a fa …see more

from $887 / night

$2,761 - $6,212 / week

Inquire View

from $887 / night