850+ Vacation Rentals Near Rocca of Montestaffoli |
  1. Italy
  2. Tuscany
  3. San Gimignano
  4. Rocca of Montestaffoli

Ski Hotels - Vacation Rentals in Rocca of Montestaffoli

San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view From US $639
         

10.0 (118 Reviews)
Villa
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
  • Air Conditioner
  • Parking
  • Pool

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San Gimignano Apartment From US $138
         

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9.3 (33 Reviews)
Apartment
San Gimignano Apartment
  • Child Friendly
  • Internet

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Tenuta Guardastelle From US $297
         

10.0 (9 Reviews)
House
Tenuta Guardastelle
  • Air Conditioner
  • Parking
  • Pool

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San Gimignano - Panoramic garden and beautiful pool! From US $643
         

9.8 (42 Reviews)
Villa
San Gimignano - Panoramic garden and beautiful pool!
  • Air Conditioner
  • Parking
  • Pool

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Casolar del Pellegrino From US $63
         

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9.0 (206 Reviews)
Bed & Breakfast
Casolar del Pellegrino
  • Parking
  • Balcony/Terrace
  • Internet

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Locanda Il Pino From US $115
         

10.0 (7 Reviews)
Bed & Breakfast
Locanda Il Pino
  • Security/Safety
  • Bedding/Linens
  • Wellness Facilities

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Villa Sabrina - Luxury Villa Rental with private swimming pool in San Gimignano, Tuscany From US $388
         

10.0 (86 Reviews)
Villa
Villa Sabrina - Luxury Villa Rental with private swimming pool in San Gimignano, Tuscany
  • Air Conditioner
  • Parking
  • Pool

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TWIN TOWER - unica al mondo - unique in the world From US $317
         

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10.0 (19 Reviews)
Apartment
TWIN TOWER - unica al mondo - unique in the world
  • Balcony/Terrace
  • Security/Safety
  • Guest Services

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Lovely apartment for 4 guests with A/C, pool, WIFI and TV From US $185
         

9.6 (25 Reviews)
Apartment
Lovely apartment for 4 guests with A/C, pool, WIFI and TV
  • Air Conditioner
  • Parking
  • Pool

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Villa in a panoramic position in San Gimignano From US $520
         

10.0 (23 Reviews)
House
Villa in a panoramic position in San Gimignano
  • Air Conditioner
  • Parking
  • Pool

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san gimignano apartment in historical center, courtyard and fast free wifi From US $230
         

9.8 (41 Reviews)
Apartment
san gimignano apartment in historical center, courtyard and fast free wifi
  • Parking
  • Pool
  • Designated Smoking Area

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La Capanna - Apartment with pool From US $253
         

10.0 (15 Reviews)
Apartment
La Capanna - Apartment with pool
  • Air Conditioner
  • Parking
  • Pool

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Lovely apartment for 4 people with WIFI, pool, A/C, TV and panoramic view From US $185
         

9.6 (15 Reviews)
Apartment
Lovely apartment for 4 people with WIFI, pool, A/C, TV and panoramic view
  • Air Conditioner
  • Parking
  • Pool

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Cosy apartment for 2 guests with WIFI, A/C, pool, TV and panoramic view From US $182
         

10.0 (12 Reviews)
Apartment
Cosy apartment for 2 guests with WIFI, A/C, pool, TV and panoramic view
  • Air Conditioner
  • Parking
  • Pool

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Villa with Private Pool in the Chianti just a few kilometers from the town of San Gimignano From US $643
         

9.6 (4 Reviews)
Villa
Villa with Private Pool in the Chianti just a few kilometers from the town of San Gimignano
  • Parking
  • Pet Friendly
  • Pool

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Wonderful private villa for 5 guests with A/C, WIFI, private pool, TV and panoramic view From US $295
         

9.0 (2 Reviews)
Villa
Wonderful private villa for 5 guests with A/C, WIFI, private pool, TV and panoramic view
  • Air Conditioner
  • Parking
  • Pool

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Ovile - Apartment with pool From US $200
         

9.8 (22 Reviews)
Apartment
Ovile - Apartment with pool
  • Air Conditioner
  • Parking
  • Pool

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Vittoriana 4 - Apartment with pool From US $208
         

10.0 (14 Reviews)
Apartment
Vittoriana 4 - Apartment with pool
  • Air Conditioner
  • Parking
  • Pool

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Il Cottage - Apartment with pool From US $231
         

9.6 (8 Reviews)
Apartment
Il Cottage - Apartment with pool
  • Air Conditioner
  • Parking
  • Pool

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Villa Panizzi – Villa with private pool From US $535
         

9.4 (26 Reviews)
Villa
Villa Panizzi – Villa with private pool
  • Air Conditioner
  • Parking
  • Pool

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Nice apartment for 4 people with A/C, WIFI, pool, TV, terrace and panoramic view From US $191
         

9.6 (5 Reviews)
Apartment
Nice apartment for 4 people with A/C, WIFI, pool, TV, terrace and panoramic view
  • Air Conditioner
  • Parking
  • Pool

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MONTEGONFOLI 4, Apartment for 4 adults with amazing views on San Gimignano From US $178
         

9.4 (26 Reviews)
House
MONTEGONFOLI 4, Apartment for 4 adults with amazing views on San Gimignano
  • Parking
  • Pool
  • TV

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Nice apartment for 4 people with pool, A/C, WIFI, pets allowed and panoramic view From US $277
         

8.0 (2 Reviews)
Apartment
Nice apartment for 4 people with pool, A/C, WIFI, pets allowed and panoramic view
  • Air Conditioner
  • Parking
  • Pet Friendly

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Villa Diletta - Farmhouse with private pool From US $321
         

9.0 (2 Reviews)
Villa
Villa Diletta - Farmhouse with private pool
  • Air Conditioner
  • Parking
  • Pool

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★ Pro Tip: Skihotels makes it easy to compare the best listings on Skihotels homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Skihotels 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 Rocca of Montestaffoli.

Weather in Rocca of Montestaffoli

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

December - February
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March - May
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June - August
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September - November
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Top Attractions Around Rocca of Montestaffoli, IT

Skihotels offers a large selection of top attractions around Rocca of Montestaffoli. Research things to do on your vacation before you visit Rocca of Montestaffoli.


Fortress of Montestaffoli Piazza della Cisterna Monteriggioni Castle San GimigNoneo Communal Palace Piazza Duomo Medieval Criminal and Torture Museum Isole e Olena Winery Tenuta Torciano Winery Castello della Paneretta Porta all'Arco Cathedral of Volterra Palazzo dei Priori Sovestro in Poggio Winery Etruscan Museum Castelfalfi Golf Course Torre Grossa Val di Merse Casa del Boccaccio Vernaccia di San GimigNoneo Wine Museum Palazzo Pretorio

Other Places to Stay Near Rocca of Montestaffoli, IT


Fortress of Montestaffoli 824 Properties

Rocca of Montestaffoli Vacation Rental Frequently Asked Questions

How many vacation rentals are available in Rocca of Montestaffoli?

Currently, the total number of properties listed in 2026 is over 850 in the Rocca of Montestaffoli area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Rocca of Montestaffoli.