Updating

Dates
...

Tell us your dates, and we will find the most accurate rates and availability for you

Updating

> Europe
> Italy
> Tuscany
> Province of Florence
> Montespertoli
> Trecento

Vacation homes - vacation rentals

Price per day

$1 $750 -

Bedrooms

Reviews
  • & up
  • & up
Property type
  • Apartment (9)
  • Villa (22)
  • House (1)
  • Barn (2)
  • Farmhouse (3)
  • Tower (1)
  • B&B (2)

All filters (1)

Filters (1)

Clear filters

40 Vacation rentals

Why am I receiving these results?
Applied filters (1)
Jacuzzi or hot tub

Great rentals within 20 miles that match your search

Vacation villa rental

Montespertoli villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

from $519 / night

$3,629 / week

1 / 36

Great rentals within 20 miles that match your search

Tavarnelle Val di Pesa Vacation villa rental

Tavarnelle Val di Pesa villa

  • 10 bedrooms
  • 9 bathrooms
  • sleeps 20

from $1,894 / night

$13,255 - $19,286 / week

1 / 50

Great rentals within 20 miles that match your search

Vacation tower rental

San Casciano in Val di Pesa tower

  • 1 bedroom
  • 2 bathrooms
  • sleeps 3

from $110 / night

$673 / week

1 / 16

Great rentals within 20 miles that match your search

Apartment rental in San Casciano in Val di Pesa with shared pool

San Casciano in Val di Pesa apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $306 / night

$1,370 - $1,841 / week

1 / 29

Great rentals within 20 miles that match your search

San Casciano in Val di Pesa Vacation apartment rental

San Casciano in Val di Pesa apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $367 / night

$1,669 - $2,311 / week

1 / 33

Great rentals within 20 miles that match your search

Certaldo Vacation villa rental

Certaldo villa

  • 9 bedrooms
  • 9 bathrooms
  • sleeps 18

from $885 / night

$6,194 - $10,412 / week

1 / 36

Great rentals within 20 miles that match your search

Vacation apartment with shared pool in San Casciano in Val di Pesa

San Casciano in Val di Pesa apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $306 / night

$1,370 - $1,841 / week

1 / 26

Great rentals within 20 miles that match your search

San Casciano in Val di Pesa Vacation apartment rental

San Casciano in Val di Pesa apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $159 / night

$950 - $1,241 / week

1 / 26

Great rentals within 20 miles that match your search

Vacation farmhouse rental

Montespertoli farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Pricing unknown

1 / 17

Great rentals within 20 miles that match your search

Vacation villa rental

Tavarnelle Val di Pesa villa

  • 11 bedrooms
  • 11 bathrooms
  • sleeps 20

from $1,679 / night

$11,751 / week

1 / 102

Great rentals within 20 miles that match your search

Chiesanuova Vacation b&b rental

Chiesanuova b&b

  • 1 bedroom
  • 2 bathrooms
  • sleeps 3

Pricing unknown

1 / 7

Great rentals within 20 miles that match your search

San Casciano in Val di Pesa Vacation villa rental

San Casciano in Val di Pesa villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 11

from $1,548 / night

$10,836 / week

1 / 55

Great rentals within 20 miles that match your search

Vacation villa in Sant'Appiano

Sant'Appiano villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 7

from $670 / night

$4,688 / week

1 / 46

Great rentals within 20 miles that match your search

Vacation villa with swimming pool in Montelupo Fiorentino

Montelupo Fiorentino villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $230 / night

$1,607 / week

1 / 38

Great rentals within 20 miles that match your search

Villa rental in Tavarnelle Val di Pesa with swimming pool

Tavarnelle Val di Pesa villa

  • 11 bedrooms
  • 11 bathrooms
  • sleeps 20
1 review

from $1,679 / night

$11,751 / week

1 / 101

Great rentals within 20 miles that match your search

Villa rental in Tavarnelle Val di Pesa

Tavarnelle Val di Pesa villa

  • 6 bedrooms
  • 8 bathrooms
  • sleeps 11

Pricing unknown

1 / 22

Great rentals within 20 miles that match your search

Apartment rental in Chiesanuova

Chiesanuova apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4
2 reviews

Pricing unknown

1 / 10

Great rentals within 20 miles that match your search

Farmhouse rental in Montespertoli with swimming pool

Montespertoli farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Pricing unknown

1 / 8

Great rentals within 20 miles that match your search

Vacation barn with swimming pool, golf nearby in Montelupo Fiorentino

Montelupo Fiorentino barn

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $306 / night

$3,302 / week

1 / 14

Great rentals within 20 miles that match your search

Vacation apartment with shared pool in Certaldo

Certaldo apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from $123 / night

$856 / week

1 / 32

Great rentals within 20 miles that match your search

Vacation b&b in San Casciano in Val di Pesa

San Casciano in Val di Pesa b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2
2 reviews

Pricing unknown

1 / 7

Great rentals within 20 miles that match your search

Castelfiorentino Vacation villa rental

Castelfiorentino villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

from $1,617 / night

$11,319 - $13,971 / week

1 / 99

Great rentals within 20 miles that match your search

Vacation villa in San Benedetto

San Benedetto villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

from $684 / night

$4,785 / week

1 / 46

Great rentals within 20 miles that match your search

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

San Casciano in Val di Pesa house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

from $245 / night

$3,672 / week

1 / 40

Great rentals within 20 miles that match your search

Apartment rental in Certaldo with shared pool

Certaldo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $123 / night

$856 / week

1 / 30

Great rentals within 20 miles that match your search

Vacation villa with swimming pool in Montelupo Fiorentino

Montelupo Fiorentino villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $230 / night

$1,607 / week

1 / 18

Great rentals within 20 miles that match your search

Certaldo Vacation apartment rental

Certaldo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $123 / night

$856 / week

1 / 29

Great rentals within 20 miles that match your search

Vacation villa in Certaldo

Certaldo villa

  • 9 bedrooms
  • 10 bathrooms
  • sleeps 18

from $636 / night

$4,402 - $11,983 / week

1 / 45

Great rentals within 20 miles that match your search

Vacation barn in Tavarnelle Val di Pesa

Tavarnelle Val di Pesa barn

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6
12 reviews

from $172 / night

$1,199 / week

1 / 28

Great rentals within 20 miles that match your search

Vacation villa with swimming pool in Tavarnelle Val di Pesa

Tavarnelle Val di Pesa villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

from $1,068 / night

$7,475 / week

1 / 56

Great rentals within 20 miles that match your search

Villa rental in Tavarnelle Val di Pesa with swimming pool

Tavarnelle Val di Pesa villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

from $1,068 / night

$7,475 / week

1 / 55

Great rentals within 20 miles that match your search

Vacation apartment with shared pool in Certaldo

Certaldo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $123 / night

$856 / week

1 / 31

Great rentals within 20 miles that match your search

Tavarnelle Val di Pesa Vacation villa rental

Tavarnelle Val di Pesa villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

from $1,373 / night

$9,606 / week

1 / 76

Great rentals within 20 miles that match your search

Vacation villa accommodation

Tavarnelle Val di Pesa villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

from $1,573 / night

$11,007 / week

1 / 56

Great rentals within 20 miles that match your search

Villa rental in Mercatale di Val di Pesa

Mercatale di Val di Pesa villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

from $2,441 / night

$17,083 / week

1 / 4

Great rentals within 20 miles that match your search

Villa rental in Montelupo Fiorentino with swimming pool

Montelupo Fiorentino villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 11
1 review

from $533 / night

$3,730 / week

1 / 27

Great rentals within 20 miles that match your search

San Casciano in Val di Pesa Vacation farmhouse rental

San Casciano in Val di Pesa farmhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6
2 reviews

from $361 / night

$2,525 / week

1 / 23

Great rentals within 20 miles that match your search

Vacation villa with swimming pool in Tavarnelle Val di Pesa

Tavarnelle Val di Pesa villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12
1 review

from $1,373 / night

$9,606 / week

1 / 76

Great rentals within 20 miles that match your search

Vacation villa in Barberino Val d'Elsa

Barberino Val d'Elsa villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8
2 reviews

from $465 / night

$3,253 / week

1 / 71

Great rentals within 20 miles that match your search

Vacation villa in San Casciano in Val di Pesa

San Casciano in Val di Pesa villa

  • 8 bedrooms
  • 7 bathrooms
  • sleeps 17

from $540 / night

$3,776 / week

1 / 22