Holiday Benefits - Vacation Rentals in Montegrossi

Casa Pieralli From US $100
         

9.0 (5 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • Child Friendly
Cavarchino B&B From US $187
         

10.0 (45 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
Tribolina by Interhome From US $129
         

9.8 (8 Reviews)
House
  • Parking
  • Pet Friendly
  • TV
Awesome home in Gaiole in Chianti SI From US $696
         

6.0 (2 Reviews)
House
  • Parking
  • Pet Friendly
  • Pool

Luxury Places to Stay in Montegrossi

Over 369+ Luxury Places to Stay in or Near Montegrossi
New
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Chianti villa rental From US $5,704
         

New
Villa
  • Air Conditioner
  • Parking
  • Pool
Villa Radda - Florence Area From US $5,307
         

Villa Radda - Florence Area From US $4,661
         

Top-Rated Vacation Rentals with a Pool in Montegrossi

Over 287+ Top-Rated Vacation Rentals with a Pool in or Near Montegrossi
"La Casina delle Fate" a pretty little house in Tuscany From US $90
         

10.0 (69 Reviews)
House
  • Parking
  • Pool
  • Designated Smoking Area
Villa Radda by MMega From US $974
         

10.0 (7 Reviews)
Villa
  • Air Conditioner
  • Pool
  • Private Pool
Il Boschetto, Radda in Chianti, Siena and Chianti From US $388
         

10.0 (4 Reviews)
Villa
  • Air Conditioner
  • Pet Friendly
  • Pool
Apartment Cortona From US $141
         

10.0 (4 Reviews)
House
  • Parking
  • Pool
  • Designated Smoking Area
Villa Oliveta, Gaiole in Chianti, Siena and Chianti From US $454
         

Pet-Friendly Vacation Rentals in Montegrossi

Over 191+ Pet-Friendly Vacation Rentals in or Near Montegrossi
La stalla From US $149
         

8.0 (1 Review)
House
  • Parking
  • Pet Friendly
  • Pool
Apartment Siena From US $229
         

10.0 (2 Reviews)
House
  • Parking
  • Pet Friendly
  • Pool
Gittori, Gaiole in Chianti, Siena and Chianti From US $505
         

10.0 (1 Review)
Villa
  • Air Conditioner
  • Pet Friendly
  • Pool
Montechioccioli by Interhome From US $146
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Montegrossi

Over 167+ Large Vacation Homes & Villas in or Near Montegrossi
Casa Boccaccio From US $713
         

|
10.0 (1 Review)
Villa
  • Air Conditioner
  • Parking
  • Pool
Lo Scoiattolo n° 10 by Interhome From US $354
         

9.0 (7 Reviews)
House
  • Parking
  • Pet Friendly
  • Pool

Wheelchair Accessible Vacation Homes in Montegrossi

Over 9+ Wheelchair Accessible Vacation Homes in or Near Montegrossi
Le Lappe From US $391
         

|
9.3 (206 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Rocca di Castagnoli From US $180
         

9.2 (28 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Holiday Apartment Chianti Summer From US $228
         

4.8 (6 Reviews)
Villa
  • Pet Friendly
  • Pool
  • Wheelchair Accessible
Podere Erbolino From US $1,041
         

|
9.2 (22 Reviews)
Villa
  • Parking
  • Pet Friendly
  • View
Agri Resort La Forra From US $128
         

9.0 (104 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Castello Di Meleto From US $227
         

|
8.7 (674 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Ultimo Mulino Country Hotel From US $210
         

|
8.6 (864 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Montegrossi Vacation Rentals and Airbnb Places to Stay Under $200

Over 137+ Montegrossi Vacation Rentals and Airbnb Places to Stay Under $200
La Farfalla n°5 by Interhome From US $176
         

9.0 (4 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • Pool
Locazione Turistica Belvedere From US $113
         

|
6.0 (2 Reviews)
House
  • Parking
  • Pet Friendly
  • Pool
L' Eroico From US $171
         

10.0 (13 Reviews)
House
  • Air Conditioner
  • TV
  • Balcony/Terrace
La Colomba n°4 by Interhome From US $169
         

9.0 (2 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • Pool
Il Ghiro n°8 by Interhome From US $159
         

9.0 (2 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • Pool
Pulcino n°3 by Interhome From US $90
         

9.0 (2 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • Pool
Cerbiatto n°5A by Interhome From US $82
         

8.8 (3 Reviews)
House
  • Parking
  • Pet Friendly
  • Pool

Instantly Bookable Vacation Homes in Montegrossi

Over 145+ Instantly Bookable Vacation Homes in or Near Montegrossi
Podere Vecciale' estate From US $622
         

New
Other
  • Pool
  • Private Pool
  • Balcony/Terrace
Coccinella n°6 by Interhome From US $154
         

6.0 (2 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • Pool
Tuscan farmhouse at the gates of Chianti From US $439
         

About Montegrossi Vacation Rentals

With more than 378 Montegrossi vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Holidaybenefits and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Montegrossi.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Holidaybenefits Montegrossi, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Montegrossi. Places to stay near Montegrossi are 1383.39 ft² on average, with prices averaging US $651 a night.

Holidaybenefits makes it easy and safe to find and compare vacation rentals in Montegrossi with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Montegrossi

Type Count
Villas 147
Vacation Homes 99
Holiday Apartments 96
Hotels 11
Others 11
Cottages 8
B&B 4
Resorts 1

Use these Quick Filters to Find a Vacation Rental in Montegrossi

Pro Tip: Holidaybenefits makes it easy to compare the best listings on Holidaybenefits homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Holidaybenefits homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Montegrossi.

Weather in Montegrossi

View the weather forecast for Montegrossi before booking your Montegrossi Vacation Rentals to confirm your best time to go.

December - February
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Complexes around Montegrossi, IT


Montegrossi Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Montegrossi?
How many vacation rentals are available in Montegrossi?

Currently, the total number of properties listed in 2026 is over 378 in the Montegrossi area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Montegrossi.