Montegrossi Rentals

Close

Enter dates for more accurate prices

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more

5,112 Houses

(1) Excellent 

22

Le Diacce

Gaiole in Chianti / Montegrossi

Montegrossi farmhouse

5 10 5 nights min

  • 5 bedrooms
  • sleeps 10
  • 5 nights min
  • Nearest beach 100 mi
  • Swimming pool
  • Child Friendly

Price per night from

$171

Price per night from

$171

27

Fontecaresino Property (1 & 2)

Gaiole in Chianti / Montegrossi

Montegrossi house

6 14 7 nights min

  • 6 bedrooms
  • sleeps 14
  • 7 nights min
  • Child Friendly

Price per night from

$410

Price per night from

$410

Great rentals within 20 miles that match your search

Distance approx 14.88 km from Montegrossi

14

The Chicken Coop, one bedroom apartment walking distance Tavarnelle Val di Pesa

Province of Florence / Tavarnelle Val di Pesa

Tavarnelle Val di Pesa apartment

1 2 7 nights min

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

Price per night from

$99

Price per night from

$99

Distance approx 11.32 km from Montegrossi

35

Villa and private pool - Chianti area

Province of Arezzo / Pergine Valdarno

Pergine Valdarno villa

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly

Price per night from

$138

Price per night from

$138

Distance approx 18.22 km from Montegrossi

(4) Very Good 

14

ARIANNA Cozy for4 in a great location by the Duomo

Province of Florence / Florence

Florence apartment

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
“Fantastic!!!” We had a wonderful stay at arianna. It has a fabulous location, it's clean, and comfortable. Two bedrooms makes it perfect for a family or 4 friends. The owners Magda and Massimo are warm, friendly and extremely helpful.They made us feel
…see more

Price per night from

$137

Price per night from

$137

Distance approx 3.61 km from Montegrossi

(2) Very Good 

18

Tenuta San Jacopo - San Lorenzo-leccino

Province of Arezzo / Cavriglia

Cavriglia farmhouse

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Nearest beach 140 mi
  • Swimming pool
  • Child Friendly

Price per night from

$69

Price per night from

$69

Distance approx 8.38 km from Montegrossi

18

LYRA - CASALTA DI PESA

Province of Siena / Castellina In Chianti

Castellina In Chianti house

2 4 3 nights min

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

Price per night from

$137

Price per night from

$137

Distance approx 2.24 km from Montegrossi Show on Map

33

Casina Di Mello

Province of Siena / Gaiole in Chianti

Gaiole in Chianti villa

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Nearest beach 115 mi
  • Swimming pool
  • Child Friendly

Price per night from

$773

Price per night from

$773

Distance approx 10.81 km from Montegrossi

39

Podere Il Doccio - Casa Terra

Province of Arezzo / Cicogna

Cicogna house

1 3 min stay varies

  • 1 bedroom
  • sleeps 3
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Pet Friendly

Price per night from

$56

Price per night from

$56

Distance approx 8.38 km from Montegrossi

28

CASSIOPEA - CASALTA DI PESA

Province of Siena / Castellina In Chianti

Castellina In Chianti house

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Child Friendly

Price per night from

$183

Price per night from

$183

Distance approx 11.01 km from Montegrossi

43

Farmhouse La Papessa - Rhododendron

Tavarnelle Val di Pesa / San Donato in Poggio

San Donato in Poggio apartment

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 94 mi
  • Swimming pool
  • Child Friendly

Price per night from

$149

Price per night from

$149

Distance approx 3.99 km from Montegrossi

13

The Paggino (Jasmine)

Province of Siena / Radda in Chianti

Radda in Chianti apartment

2 6 3 nights min

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

Price per night from

$115

Responds fast!
avg. 47 minutes

Price per night from

$115

Distance approx 9.32 km from Montegrossi

20

rent rustic in the hills of Greve in Chianti

Province of Florence / Greve in Chianti

Greve in Chianti house

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Private garden

Price per night from

$115

Price per night from

$115

Distance approx 17.11 km from Montegrossi

24

BEAUTIFUL COUNTRYSIDE HOME WITH POOL AND AMAZING VIEWS, NEAR FLORENCE!

Province of Florence / Impruneta

Impruneta guest house

1 4 1 night min

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

Price per night from

$49

Price per night from

$49

Distance approx 14.36 km from Montegrossi

24

APARTMENT IN RESTORED FARMHOUSE "LITTLE SUNFLOWER HOME"

Poggibonsi / Staggia

Staggia villa

1 5 2 nights min

  • 1 bedroom
  • sleeps 5
  • 2 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$69

Price per night from

$69

Distance approx 12.56 km from Montegrossi

18

Apartment ideal for visiting the historic center

Province of Siena / Siena

Siena apartment

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Child Friendly
  • Car not necessary

Price per night from

$92

Price per night from

$92

Distance approx 13.51 km from Montegrossi

(1) Excellent 

34

Wanderlust Apartment

Greve in Chianti / Strada in Chianti

Strada in Chianti apartment

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Child Friendly
  • Private garden

Price per night from

$86

Responds fast!
avg. 31 minutes

Price per night from

$86

Distance approx 14.91 km from Montegrossi

16

Casa Belinda

Province of Florence / San Casciano in Val di Pesa

San Casciano in Val di Pesa villa

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Private garden

Price per night from

$285

Responds fast!
avg. 2 hours 35 minutes

Price per night from

$285

Distance approx 19.86 km from Montegrossi

24

Countryside apt near Siena. Holiday in Tuscany!

Province of Siena / Pievescola

Pievescola apartment

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Air conditioning

Price per night from

$52

Price per night from

$52

Distance approx 13.21 km from Montegrossi

23

Farm Wine Farm THE COLOMBAIO

Province of Siena / Monteriggioni

Monteriggioni farmhouse

1 24 2 nights min

  • 1 bedroom
  • sleeps 24
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$149

Price per night from

$149

Distance approx 7.53 km from Montegrossi

(1) Excellent 

26

'Arco al Poggio', Arceno Rentals Club, Exclusive Private Tranquil Villa & Pool

Province of Siena / Castelnuovo Berardenga

Castelnuovo Berardenga apartment

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Private garden

Price per night from

$236

Price per night from

$236

Distance approx 17.72 km from Montegrossi

16

Casale Bella

Certaldo / Marcialla

Marcialla house

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Child Friendly
  • Pet Friendly

Price per night from

$65

Price per night from

$65

Distance approx 17.42 km from Montegrossi

9

Agriturismo San Fabiano suite Il Pozzo

Province of Siena / Monteroni d'Arbia

Monteroni d'Arbia apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Nearest beach 80 mi
  • Child Friendly
  • Pet Friendly

Price per night from

$149

Price per night from

$149

Distance approx 8.53 km from Montegrossi

26

Detached villa (1-15) with swimming pool and pizza oven.

Province of Siena / Castellina In Chianti

Castellina In Chianti villa

5 15 min stay varies

  • 5 bedrooms
  • sleeps 15
  • min stay varies
  • Nearest beach 100 mi
  • Swimming pool
  • Child Friendly

Price per night from

$324

Responds fast!
avg. 1 hour 8 minutes

Price per night from

$324

Distance approx 8.81 km from Montegrossi

40

Charme in the heart of Chianti

Province of Siena / Castellina In Chianti

Castellina In Chianti apartment

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Nearest beach 127 mi
  • Swimming pool
  • Child Friendly

Price per night from

$138

Price per night from

$138

Distance approx 17.07 km from Montegrossi

7

Bed & Breakfast located in the beautiful Tuscany, near Siena, Firenze, Arezzo

Province of Arezzo / Monte San Savino

Monte San Savino apartment

1 2 1 night min

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

Price per night from

$57

Price per night from

$57

Distance approx 9.39 km from Montegrossi

29

Agrivacanze studio Blue

Province of Arezzo / Terranuova Bracciolini

Terranuova Bracciolini apartment

1 3 2 nights min

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

Price per night from

$69

Responds fast!
avg. 3 hours 23 minutes

Price per night from

$69

Distance approx 2.94 km from Montegrossi

32

Villa Vasarri Le Piaggiole

Province of Arezzo / Cavriglia

Cavriglia villa

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Pet Friendly

Price per night from

$343

Price per night from

$343

Distance approx 9.85 km from Montegrossi

4

We rent villas / houses for short periods with all the comforts.

Province of Florence / Greve in Chianti

Greve in Chianti villa

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$245

Price per night from

$245

Distance approx 4.76 km from Montegrossi

32

The Star in Montefiorile

Province of Siena / Lecchi in Chianti

Lecchi in Chianti house

2 4 7 nights min

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

Price per night from

$115

Price per night from

$115

Distance approx 3.37 km from Montegrossi Show on Map

17

Fattoria di Starda Castle Suite Apartment, 4 Bedrooms

Gaiole in Chianti / Nusenna

Nusenna apartment

4 8 1 night min

  • 4 bedrooms
  • sleeps 8
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Pet Friendly

Price per night from

$212

Price per night from

$212

Distance approx 12.64 km from Montegrossi

12

Tenuta Wild (double room with private bath)

Reggello / Cancelli

Cancelli farmhouse

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Nearest beach 140 mi
  • Child Friendly
  • Pet Friendly

Price per night from

$47

Price per night from

$47

Distance approx 18.64 km from Montegrossi

(2) Excellent 

28

Casa La Ciucola, near Canto del Fiume, Tuscany

Province of Arezzo / Ortignano Raggiolo

Ortignano Raggiolo cottage

2 5 1 night min

  • 2 bedrooms
  • sleeps 5
  • 1 night min
  • Child Friendly
  • Pet Friendly

Price per night from

$137

Price per night from

$137

Distance approx 7.76 km from Montegrossi

(1) Excellent 

24

Holiday House

Province of Florence / Greve in Chianti

Greve in Chianti manor house

5 9 7 nights min

  • 5 bedrooms
  • sleeps 9
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Private garden

Price per night from

$423

Price per night from

$423

Distance approx 11.29 km from Montegrossi

12

VILLA I PORTICI - Casa Marta with swimming pool and tennis court

Province of Arezzo / Loro Ciuffenna

Loro Ciuffenna house

3 6 7 nights min

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

Price per night from

$126

Price per night from

$126

Distance approx 13.2 km from Montegrossi

27

Palazzo Fineschi Sergardi

Province of Siena / Siena

Siena apartment

5 8 2 nights min

  • 5 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly

Price per night from

$263

Price per night from

$263

Distance approx 16.96 km from Montegrossi

(1)  

12

EYE LASER RELAX

Province of Siena / Poggibonsi

Poggibonsi house

2 4 2 nights min

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

Price per night from

$69

Responds fast!
avg. 3 hours 25 minutes

Price per night from

$69

Distance approx 17.08 km from Montegrossi

10

Podere il Pino 3 - 2 bedroom apartment with private garden and shared pool

Province of Siena / San Gimignano

San Gimignano apartment

2 6 2 nights min

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

Price per night from

$194

Price per night from

$194