Top 50 Pienza Vacation Rentals

Apartments (1,503)
Villas (1,250)
Houses (480)
Golf rental (785)
Mountain view (191)
Lake view (34)

Explore a selection of Pienza vacation rentals

Charming Ancient Watch Tower with Swimming Pool
Guests11
Bedrooms4
Bathrooms4
Wonderful 5 / 5
$370 avg/night
4 beds
4 Bathrooms
Guests 11
11 reviews
Authentic Tuscan Farmhouse with private pool and stunning view of...
Guests5
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$192 avg/night
2 beds
2 Bathrooms
Guests 5
8 reviews
The House Annavittoria / garden in the village of Monticchiello
Guests5
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$163 avg/night
3 beds
2 Bathrooms
Guests 5
3 reviews
Apartment in Monticchiello with 2 bedrooms sleeps 4
Guests4
Bedrooms2
Bathrooms2
Wonderful 4.6 / 5
$86 avg/night
2 beds
2 Bathrooms
Guests 4
7 reviews
Luxury Villa in Monticchiello, your heaven in Tuscany
Guests4
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$174 avg/night
2 beds
2 Bathrooms
Guests 4
17 reviews
Luxury B&b In Monticchiello In Tuscany With Fantastic Views of the...
Guests12
Bedrooms5
Bathrooms5
Wonderful 5 / 5
$92 avg/night
5 beds
5 Bathrooms
Guests 12
4 reviews
Very romantic Apartment in Monticchiello - Pienza
Guests4
Bedroom1
Bathrooms0
Wonderful 5 / 5
$51 avg/night
1 bed
0 Bathrooms
Guests 4
12 reviews
Villa in Pienza with 7 bedrooms sleeps 15
Guests15
Bedrooms7
Bathrooms5
Wonderful 4.9 / 5
$256 avg/night
7 beds
5 Bathrooms
Guests 15
8 reviews
holiday vacation large villa rental italy, tuscany, near siena...
Guests12
Bedrooms6
Bathrooms6
Wonderful 0 / 5
$974 avg/night
6 beds
6 Bathrooms
Guests 12
Iperbole countryhouse, villa with pool between Pienza and...
Guests11
Bedrooms6
Bathrooms2
Wonderful 5 / 5
$1,012 avg/night
6 beds
2 Bathrooms
Guests 11
3 reviews
Full Casale in Pienza
Guests12
Bedrooms4
Bathrooms6
Wonderful 0 / 5
$343 avg/night
4 beds
6 Bathrooms
Guests 12
Apartment in Monticchiello with 3 bedrooms sleeps 6
Guests6
Bedrooms3
Bathrooms3
Wonderful 4.5 / 5
$127 avg/night
3 beds
3 Bathrooms
Guests 6
2 reviews
The original symbol of Tuscany: Villa-pool in the heart of...
Guests10
Bedrooms5
Bathrooms6
Wonderful 5 / 5
$521 avg/night
5 beds
6 Bathrooms
Guests 10
16 reviews
The Villa has a panoramic view of Pienza and Val d’Orcia...
Guests4
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$179 avg/night
2 beds
2 Bathrooms
Guests 4
2 reviews
Affitto casa in Val d'Orcia
Guests7
Bedrooms3
Bathrooms3
Wonderful 5 / 5
$139 avg/night
3 beds
3 Bathrooms
Guests 7
2 reviews
Elegant and comfortable
Guests6
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$198 avg/night
3 beds
2 Bathrooms
Guests 6
1 reviews
Joy House, in the center of Pienza!
Guests5
Bedrooms2
Bathroom1
Wonderful 5 / 5
$109 avg/night
2 beds
1 Bathroom
Guests 5
2 reviews
Luxury Privacy in the Heart of Tuscany - Villa for 16 people in...
Guests16
Bedrooms8
Bathrooms11
Wonderful 0 / 5
$1,259 avg/night
8 beds
11 Bathrooms
Guests 16
Villa with stunning views in Pienza
Guests8
Bedrooms4
Bathrooms4
Wonderful 0 / 5
$226 avg/night
4 beds
4 Bathrooms
Guests 8
comfortable studio
Guests2
Bedroom1
Bathroom1
Wonderful 0 / 5
$98 avg/night
1 bed
1 Bathroom
Guests 2
Apartment in Monticchiello with 2 bedrooms sleeps 5
Guests5
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$104 avg/night
2 beds
2 Bathrooms
Guests 5
3 reviews
Unesco's heritage storical apartment
Guests5
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$131 avg/night
2 beds
2 Bathrooms
Guests 5
1 reviews
Apartment in the center of Monticchiello with Parking, Washing...
Guests6
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$63 avg/night
2 beds
2 Bathrooms
Guests 6
1 reviews
Inside real and secret Tuscany
Guests3
Bedroom1
Bathroom1
Wonderful 5 / 5
$92 avg/night
1 bed
1 Bathroom
Guests 3
7 reviews
Spacious and beautiful apartment and swimming pool. Unique view...
Guests2
Bedroom1
Bathrooms0
Wonderful 4.3 / 5
$38 avg/night
1 bed
0 Bathrooms
Guests 2
3 reviews
Small lovely house in Pienza
Guests2
Bedroom1
Bathroom1
Wonderful 5 / 5
$68 avg/night
1 bed
1 Bathroom
Guests 2
1 reviews
Nice one Bedroom in the center of Pienza, prov. of Siena
Guests3
Bedroom1
Bathroom1
Wonderful 0 / 5
$134 avg/night
1 bed
1 Bathroom
Guests 3
Luxurious and scenic 2bdr in the heart of Val d'Orcia
Guests4
Bedrooms2
Bathrooms2
Wonderful 0 / 5
$144 avg/night
2 beds
2 Bathrooms
Guests 4
Enchanting Villa Pienza
Guests12
Bedrooms8
Bathrooms8
Wonderful 0 / 5
$837 avg/night
8 beds
8 Bathrooms
Guests 12
Authentic farmhouse in the Val D'Orcia with pool and stunning views
Guests6
Bedrooms2
Bathrooms0
Wonderful 4 / 5
$68 avg/night
2 beds
0 Bathrooms
Guests 6
5 reviews
Spacious apartment in Farmhouse, unique views, lots of cost...
Guests4
Bedrooms2
Bathrooms0
Wonderful 4 / 5
$62 avg/night
2 beds
0 Bathrooms
Guests 4
3 reviews
Beautiful Villa in Monticchiello - Tuscany
Guests5
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$131 avg/night
2 beds
2 Bathrooms
Guests 5
5 reviews
Agritourismo on a hill in Tuscany.
Guests5
Bedrooms2
Bathrooms0
Wonderful 4.9 / 5
$70 avg/night
2 beds
0 Bathrooms
Guests 5
9 reviews
beautiful holidayhome close to Pienza with private pool
Guests8
Bedrooms3
Bathrooms4
Wonderful 0 / 5
$292 avg/night
3 beds
4 Bathrooms
Guests 8
CHARMING APARTMENT near Monticchiello with Pool & Wifi. **Up to...
Guests6
Bedrooms3
Bathrooms2
Wonderful 0 / 5
$246 avg/night
3 beds
2 Bathrooms
Guests 6
CHARMING APARTMENT near Monticchiello with Pool & Wifi. **Up to...
Guests6
Bedrooms3
Bathrooms2
Wonderful 4.5 / 5
$245 avg/night
3 beds
2 Bathrooms
Guests 6
2 reviews
Podere Osteria In Pienza, Tuscany
Guests8
Bedrooms4
Bathrooms4
Wonderful 0 / 5
$236 avg/night
4 beds
4 Bathrooms
Guests 8
Beautiful Medieval Apartment in Monticchiello, Tuscany
Guests5
Bedrooms2
Bathrooms2
Wonderful 4.4 / 5
$87 avg/night
2 beds
2 Bathrooms
Guests 5
16 reviews
Classic 1bdr 80m2 in the historic center of Pienza, near Siena
Guests4
Bedroom1
Bathroom1
Wonderful 0 / 5
$113 avg/night
1 bed
1 Bathroom
Guests 4
Exquisite 2bdr in the province of Siena
Guests2
Bedrooms2
Bathrooms0
Wonderful 0 / 5
$147 avg/night
2 beds
0 Bathrooms
Guests 2
House / Villa - Pienza
Guests10
Bedrooms4
Bathrooms0
Wonderful 5 / 5
$205 avg/night
4 beds
0 Bathrooms
Guests 10
6 reviews
Sophisticated 1bdr in the center of Pienza, near Siena
Guests4
Bedroom1
Bathroom1
Wonderful 0 / 5
$106 avg/night
1 bed
1 Bathroom
Guests 4
A lovingly restored Tuscan farmhouse set amongst 17 hectares of...
Guests10
Bedrooms4
Bathrooms4
Wonderful 0 / 5
$1,675 avg/night
4 beds
4 Bathrooms
Guests 10
Villa in Bagno Vignoni with 4 bedrooms sleeps 8
Guests8
Bedrooms4
Bathrooms4
Wonderful 0 / 5
$217 avg/night
4 beds
4 Bathrooms
Guests 8
Villa in Pienza with 8 bedrooms sleeps 14
Guests14
Bedrooms8
Bathrooms8
Wonderful 0 / 5
$825 avg/night
8 beds
8 Bathrooms
Guests 14
Apartment in Monticchiello with 3 bedrooms sleeps 6
Guests6
Bedrooms3
Bathrooms3
Wonderful 0 / 5
$133 avg/night
3 beds
3 Bathrooms
Guests 6
Villa in Pienza with 6 bedrooms sleeps 14
Guests14
Bedrooms6
Bathrooms6
Wonderful 0 / 5
$716 avg/night
6 beds
6 Bathrooms
Guests 14
Luxury Farmhouse In Tuscany,val D'orcia With Two Large Independent...
Guests12
Bedrooms6
Bathrooms7
Wonderful 0 / 5
$614 avg/night
6 beds
7 Bathrooms
Guests 12
Bona Dea Farmhouse - Organic Farm & Spa in a World Heritage Park...
Guests8
Bedrooms4
Bathrooms5
Wonderful 0 / 5
$602 avg/night
4 beds
5 Bathrooms
Guests 8
Apartment in Monticchiello with 2 bedrooms sleeps 5
Guests5
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$106 avg/night
2 beds
2 Bathrooms
Guests 5
1 reviews

Pienza, Siena, Italy Vacation Rentals

Discover popular destinations in and around Pienza

Charming Ancient Watch Tower with Swimming Pool

Authentic Tuscan Farmhouse with private pool and stunning view of...

The House Annavittoria / garden in the village of Monticchiello

Apartment in Monticchiello with 2 bedrooms sleeps 4

Luxury Villa in Monticchiello, your heaven in Tuscany

Luxury B&b In Monticchiello In Tuscany With Fantastic Views of the...

Very romantic Apartment in Monticchiello - Pienza

Villa in Pienza with 7 bedrooms sleeps 15

holiday vacation large villa rental italy, tuscany, near siena...

Iperbole countryhouse, villa with pool between Pienza and...

Full Casale in Pienza

Apartment in Monticchiello with 3 bedrooms sleeps 6

The original symbol of Tuscany: Villa-pool in the heart of...

The Villa has a panoramic view of Pienza and Val d’Orcia...

Affitto casa in Val d'Orcia

Elegant and comfortable

Joy House, in the center of Pienza!

Luxury Privacy in the Heart of Tuscany - Villa for 16 people in...

Villa with stunning views in Pienza

comfortable studio

Apartment in Monticchiello with 2 bedrooms sleeps 5

Unesco's heritage storical apartment

Apartment in the center of Monticchiello with Parking, Washing...

Inside real and secret Tuscany

Spacious and beautiful apartment and swimming pool. Unique view...

Small lovely house in Pienza

Nice one Bedroom in the center of Pienza, prov. of Siena

Luxurious and scenic 2bdr in the heart of Val d'Orcia

Enchanting Villa Pienza

Authentic farmhouse in the Val D'Orcia with pool and stunning views

Spacious apartment in Farmhouse, unique views, lots of cost...

Beautiful Villa in Monticchiello - Tuscany

Agritourismo on a hill in Tuscany.

beautiful holidayhome close to Pienza with private pool

CHARMING APARTMENT near Monticchiello with Pool & Wifi. **Up to...

CHARMING APARTMENT near Monticchiello with Pool & Wifi. **Up to...

Podere Osteria In Pienza, Tuscany

Beautiful Medieval Apartment in Monticchiello, Tuscany

Classic 1bdr 80m2 in the historic center of Pienza, near Siena

Exquisite 2bdr in the province of Siena

House / Villa - Pienza

Sophisticated 1bdr in the center of Pienza, near Siena

A lovingly restored Tuscan farmhouse set amongst 17 hectares of...

Villa in Bagno Vignoni with 4 bedrooms sleeps 8

Villa in Pienza with 8 bedrooms sleeps 14

Apartment in Monticchiello with 3 bedrooms sleeps 6

Villa in Pienza with 6 bedrooms sleeps 14

Luxury Farmhouse In Tuscany,val D'orcia With Two Large Independent...

Bona Dea Farmhouse - Organic Farm & Spa in a World Heritage Park...

Apartment in Monticchiello with 2 bedrooms sleeps 5