Vacation Rentals & Villas in Montepulicano

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3,081 Houses

20

Tuscany 5 bedroom villa with private pool

Pienza / Montepulicano

Montepulicano villa

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$358

Price per night from

$358

Great rentals within 20 miles that match your search

Distance approx 8.06 km from Montepulicano

15

Design villa with pool and 360° spectacular Tuscan views near Siena

Province of Siena / Asciano

Asciano villa

11 21 min stay varies

  • 11 bedrooms
  • sleeps 21
  • min stay varies
  • Child Friendly
  • Pet Friendly

Price per night from

$911

Price per night from

$911

Distance approx 7.31 km from Montepulicano Show on Map

(17) Excellent 

38

Tigli #1, two bedrooms apartment close to Montepulciano with Wi-Fi and pool

Province of Siena / Montepulciano

Montepulciano apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 185 mi
  • Swimming pool
  • Child Friendly
“Outstanding accommodations!” Tucked away and hard to find. There was a small wooden sign which we missed, but well worth the extra miles we had to drive. The property is well kept and can't beat the views. The apartment we had was a 2br and 2bath and
…see more

Price per night from

$133

Price per night from

$133

Distance approx 16.93 km from Montepulicano

(1) Excellent 

21

Authentic Tuscan luxury farmhouse

Province of Siena / San Casciano dei Bagni

San Casciano dei Bagni villa

5 10 5 nights min

  • 5 bedrooms
  • sleeps 10
  • 5 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$644

Price per night from

$644

Distance approx 18.57 km from Montepulicano

18

Quercia house in Tuscany Chianti Hills

Province of Siena / Castelnuovo Berardenga

Castelnuovo Berardenga apartment

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Nearest beach 120 mi
  • Child Friendly
  • Air conditioning

Price per night from

$131

Responds fast!
avg. 32 minutes

Price per night from

$131

Distance approx 11.27 km from Montepulicano

8

contryhouse near siena: Apartment 2 Person

Province of Siena / Sinalunga

Sinalunga apartment

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Child Friendly
  • Pet Friendly

Price per night from

$482

Price per night from

$482

Distance approx 10.2 km from Montepulicano

28

Casabianca Girasole

Province of Siena / Asciano

Asciano apartment

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$230

Price per night from

$230

Distance approx 13.15 km from Montepulicano Show on Map

5

Apartment Il Ciliegio

Montepulciano / Valiano

Valiano apartment

2 3 2 nights min

  • 2 bedrooms
  • sleeps 3
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Pet Friendly

Price per night from

$170

Responds fast!
avg. 3 hours 11 minutes

Price per night from

$170

Distance approx 11.06 km from Montepulicano Show on Map

30

Le Manzinaie - Glicine - Romantic apartment in Tuscany

Province of Siena / Montepulciano

Montepulciano apartment

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Swimming pool

Price per night from

$125

Price per night from

$125

Distance approx 10.2 km from Montepulicano

31

Casabianca Mimosa

Province of Siena / Asciano

Asciano house

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$373

Price per night from

$373

Distance approx 5.71 km from Montepulicano

43

Six person villa in Montalcino with private pool and airco

Province of Siena / Torrenieri

Torrenieri apartment

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$638

Price per night from

$638

Distance approx 11.05 km from Montepulicano Show on Map

30

Le Manzinaie - Rose - Magic apartment for couples

Province of Siena / Montepulciano

Montepulciano apartment

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Swimming pool
  • Child Friendly

Price per night from

$124

Price per night from

$124

Distance approx 8 km from Montepulicano Show on Map

(34) Very Good 

35

Poggio Etrusco: Tuscan B&B, apts, & Cooking School

Province of Siena / Montepulciano

Montepulciano villa

6 10 2 nights min

  • 6 bedrooms
  • sleeps 10
  • 2 nights min
  • Swimming pool
  • Child Friendly
“Beyond adjectives” There is no way to describe our stay here! Pamela and Johnny were more than welcoming. We arrived with our 7 & 4 year olds in tow...and from The gate greeting, we felt as if we were at "memee's house". Each kid had a job...gate ke
…see more

Price per night from

$989

Price per night from

$989

Distance approx 19.51 km from Montepulicano

21

Castelbello 11 Bdr 11 Bth Private Pool

Province of Arezzo / Monte San Savino

Monte San Savino castle

11 20 4 nights min

  • 11 bedrooms
  • sleeps 20
  • 4 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$1,293

Responds fast!
avg. 44 minutes

Price per night from

$1,293

Distance approx 18.78 km from Montepulicano

(3) Excellent 

25

Villa, pool, patio, Garden, air-conditioning

Province of Grosseto / Cinigiano

Cinigiano apartment

1 6 2 nights min

  • 1 bedroom
  • sleeps 6
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$75

Responds fast!
avg. 3 hours 31 minutes

Price per night from

$75

Distance approx 18.08 km from Montepulicano

(1) Excellent 

19

Le Casine - Olivo Apartment

Cortona / Fratta Santa Caterina

Fratta Santa Caterina apartment

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 15 mi
  • Swimming pool

Price per night from

$78

Price per night from

$78

Distance approx 18.17 km from Montepulicano

23

Zinie

Province of Perugia / Castiglione del Lago

Castiglione del Lago townhouse

2 5 1 night min

  • 2 bedrooms
  • sleeps 5
  • 1 night min
  • Swimming pool
  • Child Friendly

Price per night from

$118

Price per night from

$118

Distance approx 18.03 km from Montepulicano

6

HEART OF TUSCANY

Province of Grosseto / Civitella Paganico

Civitella Paganico house

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Child Friendly

Price per night from

$61

Price per night from

$61

Distance approx 18.79 km from Montepulicano

40

Agriturismo La Giuiaia-Balzacorta House

Province of Perugia / Citta della Pieve

Citta della Pieve hotel apartment

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 15 mi
  • Child Friendly

Price per night from

$104

Price per night from

$104

Distance approx 9.03 km from Montepulicano Show on Map

(5) Very Good 

27

Great place for a Tuscan family holiday, 2 bedroom countryside apartments with shared pool

Province of Siena / Montepulciano

Montepulciano apartment

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Nearest beach 120 mi
  • Swimming pool
  • Child Friendly

Price per night from

$92

Responds fast!
avg. 2 hours 54 minutes

Price per night from

$92

Distance approx 11.95 km from Montepulicano

20

Cypress

Asciano / Crete Senesi

Crete Senesi apartment

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$243

Price per night from

$243

Distance approx 7.46 km from Montepulicano Show on Map

(16) Excellent 

18

Antica Quercia Villa & Spa Opale Double Room

Province of Siena / Chianciano Terme

Chianciano Terme b and b

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$129

Price per night from

$129

Distance approx 6.49 km from Montepulicano

39

Molino of Tuoma apartment 1

Province of Siena / San Quirico d'Orcia

San Quirico d'Orcia apartment

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$196

Responds fast!
avg. 57 minutes

Price per night from

$196

Distance approx 9.88 km from Montepulicano Show on Map

(7) Very Good 

22

First Palace-app. ' Cypress '

Province of Siena / Montepulciano

Montepulciano apartment

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Child Friendly

Price per night from

$117

Price per night from

$117

Distance approx 6.08 km from Montepulicano

(3) Excellent 

32

The Lair of the White Rabbit

Province of Siena / Castiglione D'Orcia

Castiglione D'Orcia villa

6 15 1 night min

  • 6 bedrooms
  • sleeps 15
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Pet Friendly

Price per night from

$785

Price per night from

$785

Distance approx 5.6 km from Montepulicano

(2) Very Good 

21

The Mandola of Rocca d'Orcia

Province of Siena / Rocca d'Orcia

Rocca d'Orcia townhouse

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$105

Price per night from

$105

Distance approx 6.31 km from Montepulicano Show on Map

40

AGRITURISMO LUCCIOLA BELLA

Province of Siena / Pienza

Pienza farmhouse

9 17 7 nights min

  • 9 bedrooms
  • sleeps 17
  • 7 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$95

Price per night from

$95

Distance approx 7.63 km from Montepulicano

8

Oak Apartment

Province of Siena / Trequanda

Trequanda apartment

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$149

Price per night from

$149

Distance approx 11.63 km from Montepulicano

23

country resort in the Crete Senesi area T6-Bs

Province of Siena / Asciano

Asciano apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly

Price per night from

$106

Price per night from

$106

Distance approx 10.26 km from Montepulicano

100

Barbara - 5

Province of Siena / Trequanda

Trequanda apartment

3 5 min stay varies

  • 3 bedrooms
  • sleeps 5
  • min stay varies
  • Nearest beach 90 mi
  • Swimming pool
  • Child Friendly
Inquire for Rates
Inquire for Rates

Distance approx 16.55 km from Montepulicano

24

10 bedroom Tuscany villa with private pool

Province of Siena / Monteroni d'Arbia

Monteroni d'Arbia villa

10 20 min stay varies

  • 10 bedrooms
  • sleeps 20
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Private garden

Price per night from

$915

Price per night from

$915

Distance approx 11.9 km from Montepulicano

(1) Excellent 

24

3 bedrooms house with private garden and terrace

Province of Siena / Asciano

Asciano house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$156

Responds fast!
avg. 3 hours 23 minutes

Price per night from

$156

Distance approx 3.38 km from Montepulicano Show on Map

32

Hawthorn Zampugna Estate

Torrita di Siena / Montefollonico

Montefollonico house

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Pet Friendly

Price per night from

$98

Responds fast!
avg. 1 hour 50 minutes

Price per night from

$98

Distance approx 17.2 km from Montepulicano

4

Locanda Bandini casa di Piero

Province of Perugia / Citta della Pieve

Citta della Pieve house

1 2 7 nights min

  • 1 bedroom
  • sleeps 2
  • 7 nights min
  • Swimming pool
  • Private garden

Price per night from

$123

Price per night from

$123

Distance approx 15.03 km from Montepulicano

(3)  

7

Farm house Podere dei Frati

Province of Grosseto / Arcidosso

Arcidosso farmhouse

8 15 1 night min

  • 8 bedrooms
  • sleeps 15
  • 1 night min
  • Swimming pool
  • Ski

Price per night from

$39

Price per night from

$39

Distance approx 12.8 km from Montepulicano

25

Attic Of Olives

Sinalunga / Rigomagno

Rigomagno apartment

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$65

Price per night from

$65

Distance approx 18.67 km from Montepulicano

20

B & B THE OLD Lieutenancy Suite Double

Province of Perugia / Citta della Pieve

Citta della Pieve b and b

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Child Friendly
  • Pet Friendly

Price per night from

$104

Price per night from

$104

Distance approx 2.97 km from Montepulicano Show on Map

31

Podere Isabella, the pearl of Val d'Orcia

Pienza / Monticchiello

Monticchiello villa

9 20 min stay varies

  • 9 bedrooms
  • sleeps 20
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Pet Friendly

Price per night from

$937

Price per night from

$937