Ugento Italy - 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
Villa Il Masseto, Gaiole in Chianti, Siena and Chianti From US $465
         

Montechioccioli by Interhome From US $111
         

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

Luxury Places to Stay in Montegrossi

Over 368+ Luxury Places to Stay in or Near Montegrossi
Villa Radda - Florence Area From US $5,002
         

Tenuta Altaluce From US $1,274
         

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New
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Montegrossi

Over 285+ 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 (71 Reviews)
House
  • Parking
  • Pool
  • Designated Smoking Area
Il Colombaio by VacaVilla From US $399
         

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10.0 (3 Reviews)
Villa
  • Parking
  • Pool
  • View
Sestuccina From US $202
         

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10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Casa Boccaccio From US $713
         

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10.0 (1 Review)
Villa
  • Air Conditioner
  • Parking
  • Pool
Casanova di Bricciano From US $600
         

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10.0 (1 Review)
Villa
  • Air Conditioner
  • Parking
  • Pool
Villa Bellavista - Teloni From US $562
         

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10.0 (1 Review)
Villa
  • Parking
  • Pet Friendly
  • Pool
Villa Gittori From US $436
         

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10.0 (1 Review)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Ciacchieri From US $233
         

10.0 (1 Review)
Villa
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Montegrossi

Over 188+ Pet-Friendly Vacation Rentals in or Near Montegrossi
La stalla From US $149
         

8.0 (1 Review)
House
  • Parking
  • Pet Friendly
  • Pool
Villa Bellavista - Homelike Villas From US $690
         

New
Villa
  • Air Conditioner
  • Pet Friendly
  • Pool
Podere Belvedere 6, Emma Villas From US $657
         

New
Villa
  • Air Conditioner
  • Pet Friendly
  • Pool
Cozy apartment with terrace and pool From US $182
         

New
Apartment
  • Pet Friendly
  • Security/Safety
  • Bedding/Linens

Large Vacation Homes & Villas in Montegrossi

Over 164+ Large Vacation Homes & Villas in or Near Montegrossi
Agriturismo La Poggiarina From US $118
         

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9.8 (17 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Wheelchair Accessible Vacation Homes in Montegrossi

Over 10+ Wheelchair Accessible Vacation Homes in or Near Montegrossi
Casa Vacanze Chianti Summer From US $279
         

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9.5 (14 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
Le Lappe From US $391
         

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9.3 (206 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Podere Erbolino From US $1,041
         

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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
         

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8.7 (674 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Montegrossi Vacation Rentals and Airbnb Places to Stay Under $200

Over 138+ Montegrossi Vacation Rentals and Airbnb Places to Stay Under $200
Locazione Turistica Belvedere From US $113
         

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

10.0 (13 Reviews)
House
  • Air Conditioner
  • TV
  • Balcony/Terrace
Villa Gaiole, Borgo di Gaiole From US $136
         

9.4 (24 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Tribolina by Interhome From US $129
         

9.8 (8 Reviews)
House
  • Parking
  • Pet Friendly
  • TV

Instantly Bookable Vacation Homes in Montegrossi

Over 149+ Instantly Bookable Vacation Homes in or Near Montegrossi
Podere Vecciale' estate From US $622
         

New
Other
  • Pool
  • Private Pool
  • Balcony/Terrace
Villa in Gaiole In Chianti with 4 bedrooms sleeps 8 From US $1,166
         

10.0 (1 Review)
Villa
  • Air Conditioner
  • Pool
  • Designated Smoking Area
Awesome home in Gaiole in Chianti SI From US $696
         

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

About Montegrossi Vacation Rentals

With more than 377 Montegrossi vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Ugentoitaly 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 Ugentoitaly 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 1360.93 ft² on average, with prices averaging US $645 a night.

Ugentoitaly 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 146
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: Ugentoitaly makes it easy to compare the best listings on Ugentoitaly homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Ugentoitaly 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 377 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.