50 Best Vacation Rentals in Pienza - Holiday Lettings - Cabins

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140 Vacation rentals

(20) Excellent 

43

Vacation apartment in Monticchiello

Pienza / Monticchiello

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Villa PoliFlora is a modern residence in Monticchiello in Val d'Orcia, a Unesco world heritage site. The owners and creators invite you for a relaxing stay, in the triangle among Montalcino, Pienza and Montepulciano. A few kilometers away from Siena and Chianti Classico …see more

from $82 / night

$402 - $979 / week

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from $82 / night

(4) Excellent 

11

Province of Siena / Pienza

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Suitable for children age 5+
  • Ask about pets

Pricing unknown

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Pricing unknown

(2) Excellent 

22

Pienza / Monticchiello

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden

from $55 / night

$369 - $476 / week

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from $55 / night

24

Vacation farmhouse with swimming pool in Pienza

Province of Siena / Pienza

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Large Tuscan farmhouse dating back to the 15trh century built on the ruins of an ancient convent of the year 1200. This property with a charming inner courtyard, is situated in quiet and panoramic location on a large 100-hectare estate producing olive oil and wine. Thi …see more

from $533 / night

$3107 - $4254 / week

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from $533 / night

6

Apartment rental in Monticchiello

Pienza / Monticchiello

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 100 mi
  • Child friendly
The residence "Il Torrino" is a panoramic apartment obtained from the restauration of an ancient tower belonging to the boundaries of the medieval suburb Monticchiello. The structure, in proximity of the principal access to the village, has been completely restructu …see more

from $138 / night

$890 / week

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from $138 / night

(6) Excellent 

23

Vacation apartment in Pienza

Province of Siena / Pienza

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
New lower price - one of the nicest flat in Tuscany 5 star standard !! The apartment has its own entrance and occupies the whole 1st and top floors of this classical building next to the ancient city wall. Private parking, large roof terrace (55m2) with g …see more

from $152 / night

$1064 / week

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from $152 / night

(9) Excellent 

57

Vacation lodge in Pienza

Province of Siena / Pienza

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
Poggio ai Gelsi is located in the south of Tuscany between the hills of Val d'Orcia, Siena and halfway between Montepulciano and Pienza. The property enjoys a magnificent view over Montichiello and Pienza. The colours of the nature in this corner of Tuscany are beautifu …see more

from $277 / night

$1937 - $3531 / week

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from $277 / night

25

Pienza Vacation lodge rental

Province of Siena / Pienza

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Nearest beach 100 mi
  • Swimming pool
  • Air conditioning
Poggio ai Gelsi is located in the south of Tuscany between the hills of Val d'Orcia, Siena and halfway between Montepulciano and Pienza. The property enjoys a magnificent view over Montichiello and Pienza. The colours of the nature in this corner of Tuscany are beautifu …see more

from $93 / night

$646 - $1026 / week

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from $93 / night

22

Vacation villa rental

Province of Siena / Pienza

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
Casale Reggello is located in the gently rolling Tuscan hills, between the wonderful towns of Pienza and Montepulciano, just a short distance from the thermal baths of Bagno Vignoni. Reggello is a single House with 8/10 beds and as its own swimming pool and surrounding …see more

from $372 / night

$2604 - $4231 / week

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from $372 / night

5

Province of Siena / Pienza

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

Pricing unknown

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Pricing unknown

20

Vacation manor house with swimming pool in Pienza

Province of Siena / Pienza

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This large manor house was a well-known post-house for changing coaches and horses along the Via Francigena as far back as the tenth century and the architecture of the house shows its origin. A pleasant garden surrounds the elegant farmhouse, a lovely swimming pool loo …see more

from $813 / night

$5685 - $7106 / week

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from $813 / night

40

Province of Siena / Pienza

9 17 7 nights min

  • 9 bedrooms
  • Sleeps 17
  • 7 nights min
  • Child friendly
  • Pet friendly

from $80 / night

$555 / week

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from $80 / night

24

Pienza / Monticchiello

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Air conditioning

from $80 / night

$424 / week

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from $80 / night

(3) Excellent 

21

Pienza / Monticchiello

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Ask about children
  • Private garden

from $163 / night

$868 / week

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from $163 / night

34

Vacation villa in Pienza

Province of Siena / Pienza

7 13 7 nights min

  • 7 bedrooms
  • Sleeps 13
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Ancient stone farmhouse, nowadays beautiful holiday villa, set in a very panoramic position inside the Parco Artistico Naturale of Val d'Orcia. Only 2 km far we find the well-known Renaissance village of Pienza. In a short drive there are renowned villages such as Monti …see more

from $255 / night

$1779 - $2908 / week

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from $255 / night

19

Vacation villa in Pienza

Province of Siena / Pienza

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
This lovely holiday home in the Middle Ages was probably a resting place for pilgrims travelling on the Via Francigena, that passes nearby. Furthermore, opposite the property is the 13th century Castello di Spedaletto, one of the most important monastic granges of the S …see more

from $199 / night

$1389 - $2604 / week

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from $199 / night

24

Farmhouse rental in Pienza with swimming pool

Province of Siena / Pienza

8 14 7 nights min

  • 8 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Imposing farmhouse dating back to the 18th century comprising 2 independent units (rentable only together as a private property). This beautiful 5–hectare estate is situated in quiet and panoramic location, in the heart of the Val d’Orcia region, a short distance away …see more

from $682 / night

$4773 - $8678 / week

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from $682 / night

(1) Very Good 

24

Pienza / Monticchiello

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Child friendly
  • Air conditioning
  • Ask about pets

from $98 / night

$651 - $2702 / week

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from $98 / night

22

Province of Siena / Pienza

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly

from $114 / night

$684 / week

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from $114 / night

(6) Excellent 

10

Pienza / Monticchiello

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Nearest beach 80 mi
  • Private garden

from $93 / night

$608 / week

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from $93 / night

(1) Excellent 

12

Pienza / Monticchiello

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Ask about pets

from $98 / night

$543 / week

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from $98 / night

24

Province of Siena / Pienza

4 11 Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
  • Nearest beach 95 mi
  • Swimming pool
  • Child friendly

from $380 / night

$2278 - $3830 / week

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from $380 / night

(1) Excellent 

9

Province of Siena / Pienza

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 98 mi
  • Swimming pool
  • Child friendly

from $228 / night

$771 - $1248 / week

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from $228 / night

(2) Excellent 

24

Vacation apartment with shared pool in Monticchiello

Pienza / Monticchiello

3 7 5 nights min

  • 3 bedrooms
  • Sleeps 7
  • 5 nights min
  • Nearest beach 110 mi
  • Swimming pool
  • Child friendly
Casa Oriolo is an elegant apartment with 3 bedrooms and it is part of a small complex with 3 apartments total sharing a pool. Here you can enjoy a sojourn in contact with nature in a protected and uncontaminated oasis. The owners have carefully furnished the prop …see more

from $195 / night

$1356 - $2116 / week

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from $195 / night

7

Province of Siena / Pienza

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 80 mi
  • Child friendly
  • Pet friendly

Pricing unknown

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Pricing unknown

41

Pienza / Monticchiello

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

from $190 / night

$1302 - $1519 / week

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from $190 / night

(1) Excellent 

36

Province of Siena / Pienza

2 7 3 nights min

  • 2 bedrooms
  • Sleeps 7
  • 3 nights min
  • Nearest beach 100 mi
  • Ask about children
  • Pet friendly

from $71 / night

$494 / week

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from $71 / night

5

Province of Siena / Pienza

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly

from $140 / night

$753 / week

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from $140 / night

(1) Excellent 

12

Pienza / Monticchiello

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden

from $217 / night

$1085 / week

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from $217 / night

(1) Excellent 

9

Province of Siena / Pienza

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

from $76 / night

$521 - $814 / week

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from $76 / night

(1) Excellent 

6

Province of Siena / Pienza

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly

from $152 / night

$597 / week

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from $152 / night

20

Farmhouse rental in Pienza with shared pool

Province of Siena / Pienza

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Welcoming farmhouse situated in panoramic location in the beautiful area of Val D’Orcia. This property comprises 4 units (one is occupied by the owners) and offers a well-groomed garden, a private furnished area for all of the 3 apartments and a nice pool (with Jacuzzi …see more

from $100 / night

$586 - $1026 / week

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from $100 / night

(3) Excellent 

19

Pienza / Monticchiello

2 5 5 nights min

  • 2 bedrooms
  • Sleeps 5
  • 5 nights min
  • Child friendly
  • Ask about pets
  • Private garden

from $136 / night

$814 / week

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from $136 / night

16

Farmhouse rental in Pienza with shared pool

Province of Siena / Pienza

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Welcoming farmhouse situated in panoramic location in the beautiful area of Val D’Orcia. This property comprises 4 units (one is occupied by the owners) and offers a well-groomed garden, a private furnished area for all of the 3 apartments and a nice pool (with Jacuzzi …see more

from $127 / night

$748 - $1221 / week

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from $127 / night

20

Farmhouse rental in Pienza with swimming pool

Province of Siena / Pienza

6 14 7 nights min

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Beautiful stone farmhouse situated in peaceful and panoramic location near the charming medieval town of Pienza, in the heart of the Orcia Valley region. This villa which has been recently restored with all its original details preserved, comprises 3 separate units rent …see more

from $465 / night

$3255 - $8462 / week

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from $465 / night

20

Villa rental in Pienza with swimming pool

Province of Siena / Pienza

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Situated on a farm of 150 hectares producing excellent extra virgin olive oil, the farmhouse is set on a kind of natural terrace overlooking the lovely valley below. The house, built in the first half of the eighteenth century, has been renovated carefully by the couple …see more

from $614 / night

$4296 - $5695 / week

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from $614 / night

(1) Very Good 

20

Province of Siena / Pienza

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Private garden

from $109 / night

$651 - $1107 / week

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from $109 / night

17

Pienza / Monticchiello

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden

from $131 / night

$814 / week

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from $131 / night

(1) Excellent 

12

Pienza / Monticchiello

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
  • Ask about pets

from $98 / night

$543 / week

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from $98 / night

15

Vacation townhouse in Pienza

Province of Siena / Pienza

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 100 mi
  • Child friendly
  • Car not necessary
In the very center of a lovely ancient medieval village stands Casa Marelli. Recently carefully restored preserving all the traditional Tuscan characteristics of the building such as wooden beamed ceilings and brick work arches. It was meant to become the owner's reside …see more

from $136 / night

$950 - $1221 / week

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from $136 / night

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