Top 50 San Sano Vacation Rentals

Apartments (3,323)
Villas (1,555)
Houses (830)
Golf rental (1,181)
Mountain view (221)
Beach view (39)

Explore a selection of San Sano vacation rentals

Last min. FALL Specials! Best Location. Heart of Tuscany; Great...
Guests5
Bedrooms2
Bathrooms2
Wonderful 4.9 / 5
$97 avg/night
2 beds
2 Bathrooms
Guests 5
36 reviews
Gorgeous condo with shared pool in the heart of San Sano!
Guests6
Bedrooms3
Bathrooms2
Wonderful 4 / 5
$92 avg/night
3 beds
2 Bathrooms
Guests 6
1 reviews
Apartment Borgo San Sano in Gaiole in Chianti, Tuscany Chianti...
Guests4
Bedroom1
Bathroom1
Wonderful 4 / 5
$57 avg/night
1 bed
1 Bathroom
Guests 4
1 reviews
Villa in San Sano with 3 bedrooms sleeps 8
Guests8
Bedrooms3
Bathrooms3
Wonderful 0 / 5
$265 avg/night
3 beds
3 Bathrooms
Guests 8
Villa in San Sano with 3 bedrooms sleeps 8
Guests8
Bedrooms3
Bathrooms3
Wonderful 0 / 5
$264 avg/night
3 beds
3 Bathrooms
Guests 8
Apartment Borgo San Sano in Gaiole in Chianti, Tuscany Chianti...
Guests5
Bedroom1
Bathroom1
Wonderful 0 / 5
$62 avg/night
1 bed
1 Bathroom
Guests 5
Farmhouse in the heart of the real chiantishire
Guests4
Bedrooms2
Bathrooms0
Wonderful 5 / 5
$114 avg/night
2 beds
0 Bathrooms
Guests 4
60 reviews
Architecturally stunning, historic country house in idyllic...
Guests8
Bedrooms3
Bathroom1
Wonderful 5 / 5
$221 avg/night
3 beds
1 Bathroom
Guests 8
41 reviews
Private Pool, Garden and Views family and pet friendly also for...
Guests6
Bedrooms3
Bathrooms3
Wonderful 5 / 5
$157 avg/night
3 beds
3 Bathrooms
Guests 6
15 reviews
In the heart of the Chianti, Tuscan vacation house with a shared...
Guests4
Bedrooms2
Bathrooms2
Wonderful 4.9 / 5
$153 avg/night
2 beds
2 Bathrooms
Guests 4
9 reviews
SIENA Beautiful Newly Renovated And Furnished Bright Apartment In...
Guests4
Bedrooms2
Bathrooms0
Wonderful 5 / 5
$145 avg/night
2 beds
0 Bathrooms
Guests 4
4 reviews
FABULOUS 6BD - 5BA VILLA WITH STUNNING POOL & VIEWS IN TOP CHIANTI...
Guests13
Bedrooms6
Bathrooms5
Wonderful 5 / 5
$618 avg/night
6 beds
5 Bathrooms
Guests 13
7 reviews
Charming old mill restored in the Chianti Classico
Guests7
Bedrooms3
Bathrooms2
Wonderful 4.9 / 5
$136 avg/night
3 beds
2 Bathrooms
Guests 7
26 reviews
Idyllic Rural Family-run Farmhouse
Guests10
Bedrooms5
Bathrooms3
Wonderful 4.9 / 5
$323 avg/night
5 beds
3 Bathrooms
Guests 10
13 reviews
Single-level Villa, peaceful and panoramic position, 6x16m private...
Guests11
Bedrooms4
Bathrooms2
Wonderful 5 / 5
$149 avg/night
4 beds
2 Bathrooms
Guests 11
26 reviews
wonderful Tuscan farmhouse
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.9 / 5
$64 avg/night
2 beds
2 Bathrooms
Guests 6
8 reviews
HillsideVilla overlooking the Tuscan landscape between Florence...
Guests8
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$140 avg/night
3 beds
2 Bathrooms
Guests 8
6 reviews
Apartment In Organic Farm With Pool In The Chianti
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.9 / 5
$83 avg/night
2 beds
2 Bathrooms
Guests 6
45 reviews
Quiet and Beautiful Property in Chianti, with Large Pool
Guests18
Bedrooms6
Bathrooms5
Wonderful 5 / 5
$285 avg/night
6 beds
5 Bathrooms
Guests 18
17 reviews
Charming typical properties in the heart of the countryside 5 km...
Guests4
Bedrooms3
Bathrooms3
Wonderful 5 / 5
$186 avg/night
3 beds
3 Bathrooms
Guests 4
22 reviews
Apartment / Condo in Castel San Gimignano with 1 bedrooms sleeps 3
Guests3
Bedroom1
Bathroom1
Wonderful 4.9 / 5
$66 avg/night
1 bed
1 Bathroom
Guests 3
10 reviews
Charming holiday House, Villa inside Monteriggioni Castle
Guests5
Bedrooms3
Bathroom1
Wonderful 4.9 / 5
$86 avg/night
3 beds
1 Bathroom
Guests 5
47 reviews
Converted barn with hilltop views in chianti wine region
Guests6
Bedrooms3
Bathroom1
Wonderful 4.9 / 5
$216 avg/night
3 beds
1 Bathroom
Guests 6
29 reviews
Beautiful 5BD Farmhouse with Private Pool Amongst Vineyards of...
Guests12
Bedrooms5
Bathroom1
Wonderful 4.8 / 5
$496 avg/night
5 beds
1 Bathroom
Guests 12
16 reviews
Charming typical properties in the heart of the countryside 5 km...
Guests10
Bedrooms4
Bathrooms4
Wonderful 5 / 5
$409 avg/night
4 beds
4 Bathrooms
Guests 10
31 reviews
A view of San Gimignano from the top of a hill covered with...
Guests6
Bedrooms3
Bathrooms2
Wonderful 4.7 / 5
$172 avg/night
3 beds
2 Bathrooms
Guests 6
15 reviews
Beautiful 9BR Villa with Amazing Pool & Views, right in the Heart...
Guests18
Bedrooms9
Bathrooms7
Wonderful 5 / 5
$808 avg/night
9 beds
7 Bathrooms
Guests 18
17 reviews
Apartment House with garden Tuscany Chianti , Florence 15km...
Guests5
Bedrooms2
Bathrooms2
Wonderful 4.8 / 5
$68 avg/night
2 beds
2 Bathrooms
Guests 5
40 reviews
Apartment in historic center of Siena
Guests4
Bedroom1
Bathroom1
Wonderful 4.8 / 5
$82 avg/night
1 bed
1 Bathroom
Guests 4
15 reviews
Elegant Villa 5 minutes motoring from Siena
Guests14
Bedrooms6
Bathrooms7
Wonderful 4.9 / 5
$585 avg/night
6 beds
7 Bathrooms
Guests 14
18 reviews
Ultra Stunning 2 Br Apt In Tuscany, With Pool, Stoned Arch And...
Guests4
Bedrooms2
Bathroom1
Wonderful 4.8 / 5
$141 avg/night
2 beds
1 Bathroom
Guests 4
14 reviews
Surrounded by wineyards and olive trees - Mimosa
Guests3
Bedroom1
Bathroom1
Wonderful 4.8 / 5
$54 avg/night
1 bed
1 Bathroom
Guests 3
27 reviews
Farmhouse apartment with swimming pool and sensational views
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.8 / 5
$87 avg/night
2 beds
2 Bathrooms
Guests 6
40 reviews
VILLA IRIS SAN GIMIGNANO 6 SUITES, SWIMMING POOL, SPA, SAUNA...
Guests12
Bedrooms6
Bathrooms7
Wonderful 5 / 5
$577 avg/night
6 beds
7 Bathrooms
Guests 12
41 reviews
80 sqm in restored farmhouse with pool Fw, 600sqm private garden.
Guests4
Bedrooms2
Bathrooms0
Wonderful 4.9 / 5
$145 avg/night
2 beds
0 Bathrooms
Guests 4
20 reviews
Wonderful villa with breathtaking views and private pool, 5 km...
Guests12
Bedrooms6
Bathrooms7
Wonderful 4.9 / 5
$576 avg/night
6 beds
7 Bathrooms
Guests 12
36 reviews
In the heart of Chianti: view over the valley, Recreation & Ar...
Guests5
Bedrooms2
Bathroom1
Wonderful 4.9 / 5
$104 avg/night
2 beds
1 Bathroom
Guests 5
31 reviews
Apartment House with garden Tuscany Chianti , Florence 15km...
Guests6
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$86 avg/night
2 beds
2 Bathrooms
Guests 6
43 reviews
Country Villas in Chianti Classico - Yellow house
Guests9
Bedrooms3
Bathrooms3
Wonderful 5 / 5
$68 avg/night
3 beds
3 Bathrooms
Guests 9
42 reviews
Bright apartment with views, near Piazza del Campo
Guests5
Bedroom1
Bathroom1
Wonderful 4 / 5
$86 avg/night
1 bed
1 Bathroom
Guests 5
1 reviews
STUNNING 6BR VILLA WITH WONDERFUL POOL AND GROUNDS, JUST MINUTES...
Guests11
Bedrooms6
Bathrooms5
Wonderful 4.9 / 5
$654 avg/night
6 beds
5 Bathrooms
Guests 11
21 reviews
Luxury Villa on private Chianti estate - 20% discount between Sep...
Guests10
Bedrooms5
Bathrooms5
Wonderful 4.9 / 5
$342 avg/night
5 beds
5 Bathrooms
Guests 10
35 reviews
Typical apartment in the historical center
Guests3
Bedroom1
Bathroom1
Wonderful 4.8 / 5
$75 avg/night
1 bed
1 Bathroom
Guests 3
34 reviews
House with a large garden in the hills of Chianti
Guests7
Bedrooms3
Bathrooms2
Wonderful 4.6 / 5
$60 avg/night
3 beds
2 Bathrooms
Guests 7
16 reviews
Apartment with two bedrooms and two bathrooms ideal for families...
Guests4
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$87 avg/night
2 beds
2 Bathrooms
Guests 4
2 reviews
Beautiful Tuscan farmhouse with stunning views of Chianti...
Guests6
Bedrooms3
Bathrooms2
Wonderful 4.7 / 5
$250 avg/night
3 beds
2 Bathrooms
Guests 6
27 reviews
Old charming and characteristic farm house with Pool - 10 km from...
Guests11
Bedrooms6
Bathrooms2
Wonderful 4.8 / 5
$135 avg/night
6 beds
2 Bathrooms
Guests 11
22 reviews
Agricola Neci: Tuscan Rural Luxury
Guests9
Bedrooms4
Bathrooms4
Wonderful 5 / 5
$513 avg/night
4 beds
4 Bathrooms
Guests 9
20 reviews
An enchanting small villa, perfect for two, with an unparalleled...
Guests2
Bedroom1
Bathroom1
Wonderful 5 / 5
$236 avg/night
1 bed
1 Bathroom
Guests 2
6 reviews
Villa on the Tuscan hills near Florence
Guests6
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$142 avg/night
3 beds
2 Bathrooms
Guests 6
6 reviews

San Sano SI, Italy Vacation Rentals

Last min. FALL Specials! Best Location. Heart of Tuscany; Great...

Gorgeous condo with shared pool in the heart of San Sano!

Apartment Borgo San Sano in Gaiole in Chianti, Tuscany Chianti...

Villa in San Sano with 3 bedrooms sleeps 8

Villa in San Sano with 3 bedrooms sleeps 8

Apartment Borgo San Sano in Gaiole in Chianti, Tuscany Chianti...

Farmhouse in the heart of the real chiantishire

Architecturally stunning, historic country house in idyllic...

Private Pool, Garden and Views family and pet friendly also for...

In the heart of the Chianti, Tuscan vacation house with a shared...

SIENA Beautiful Newly Renovated And Furnished Bright Apartment In...

FABULOUS 6BD - 5BA VILLA WITH STUNNING POOL & VIEWS IN TOP CHIANTI...

Charming old mill restored in the Chianti Classico

Idyllic Rural Family-run Farmhouse

Single-level Villa, peaceful and panoramic position, 6x16m private...

wonderful Tuscan farmhouse

HillsideVilla overlooking the Tuscan landscape between Florence...

Apartment In Organic Farm With Pool In The Chianti

Quiet and Beautiful Property in Chianti, with Large Pool

Charming typical properties in the heart of the countryside 5 km...

Apartment / Condo in Castel San Gimignano with 1 bedrooms sleeps 3

Charming holiday House, Villa inside Monteriggioni Castle

Converted barn with hilltop views in chianti wine region

Beautiful 5BD Farmhouse with Private Pool Amongst Vineyards of...

Charming typical properties in the heart of the countryside 5 km...

A view of San Gimignano from the top of a hill covered with...

Beautiful 9BR Villa with Amazing Pool & Views, right in the Heart...

Apartment House with garden Tuscany Chianti , Florence 15km...

Apartment in historic center of Siena

Elegant Villa 5 minutes motoring from Siena

Ultra Stunning 2 Br Apt In Tuscany, With Pool, Stoned Arch And...

Surrounded by wineyards and olive trees - Mimosa

Farmhouse apartment with swimming pool and sensational views

VILLA IRIS SAN GIMIGNANO 6 SUITES, SWIMMING POOL, SPA, SAUNA...

80 sqm in restored farmhouse with pool Fw, 600sqm private garden.

Wonderful villa with breathtaking views and private pool, 5 km...

In the heart of Chianti: view over the valley, Recreation & Ar...

Apartment House with garden Tuscany Chianti , Florence 15km...

Country Villas in Chianti Classico - Yellow house

Bright apartment with views, near Piazza del Campo

STUNNING 6BR VILLA WITH WONDERFUL POOL AND GROUNDS, JUST MINUTES...

Luxury Villa on private Chianti estate - 20% discount between Sep...

Typical apartment in the historical center

House with a large garden in the hills of Chianti

Apartment with two bedrooms and two bathrooms ideal for families...

Beautiful Tuscan farmhouse with stunning views of Chianti...

Old charming and characteristic farm house with Pool - 10 km from...

Agricola Neci: Tuscan Rural Luxury

An enchanting small villa, perfect for two, with an unparalleled...

Villa on the Tuscan hills near Florence