Holiday Castles - Vacation Rentals in Pentolina

Agriturismo Botralta From US $81
         

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9.0 (1 Review)
Apartment
  • Parking
  • Pet Friendly
  • Balcony/Terrace
Apartment "Casa di Franca a San Galgano" in Historical Centre From US $103
         

10.0 (1 Review)
Apartment
  • Security/Safety
  • Bedding/Linens
  • Wellness Facilities
Country House in Tuscany with Panoramic Views From US $274
         

10.0 (2 Reviews)
Apartment
  • Pet Friendly
  • TV
  • Balcony/Terrace

Luxury Places to Stay in Pentolina

Over 258+ Luxury Places to Stay in or Near Pentolina
Villa Rock Cerbaia From US $4,773
         

New
Villa
  • Pet Friendly
  • Security/Safety
  • Bedding/Linens
La Capriata From US $4,757
         

New
Apartment
  • Pet Friendly
  • Security/Safety
  • Fireplace/Heating
The Bishop Apartment From US $3,570
         

New
Apartment
  • Pet Friendly
  • Designated Smoking Area
  • Fireplace/Heating
Borgo Santo Pietro From US $2,939
         

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8.8 (30 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Honeymoon Room From US $2,384
         

New
House
  • Pet Friendly
  • Designated Smoking Area
  • Fireplace/Heating
Borgo Santo Pietro From US $1,705
         

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9.6 (57 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Podere Sant'Eugenio 14, Emma Villas From US $1,378
         

New
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Pentolina

Over 105+ Top-Rated Vacation Rentals with a Pool in or Near Pentolina
Relais Le Macine di Stigliano From US $205
         

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10.0 (15 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Elegant villa with private pool near San Galgano From US $561
         

10.0 (1 Review)
Villa
  • Parking
  • Pool
  • Designated Smoking Area
Villa Edera From US $226
         

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10.0 (1 Review)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Romantic cottage with private pool and garden. From US $222
         

10.0 (1 Review)
House
  • Parking
  • Pool
  • Designated Smoking Area
Montestigliano From US $190
         

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9.9 (11 Reviews)
House
  • Parking
  • Pet Friendly
  • Pool

Pet-Friendly Vacation Rentals in Pentolina

Over 133+ Pet-Friendly Vacation Rentals in or Near Pentolina
Country House in Chiusdino with Panoramic Views From US $150
         

10.0 (1 Review)
Apartment
  • Pet Friendly
  • TV
  • Balcony/Terrace
Casa Mancini Monticiano - Holiday Villa From US $226
         

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10.0 (1 Review)
House
  • Parking
  • Pet Friendly
  • Designated Smoking Area
Borgo Il Poggiaccio From US $241
         

8.8 (65 Reviews)
House
  • Parking
  • Pet Friendly
  • Pool
Comfort, relaxation and nature From US $130
         

10.0 (1 Review)
House
  • Parking
  • Pet Friendly
  • TV
La Capanna di Franca 6+2, Emma Villas From US $577
         

9.8 (6 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
agriturismo la roggiola From US $47
         

9.6 (112 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Detached villa with panoramic garden From US $189
         

9.6 (63 Reviews)
House
  • Parking
  • Pet Friendly
  • Pool

Large Vacation Homes & Villas in Pentolina

Over 67+ Large Vacation Homes & Villas in or Near Pentolina
La Fornace di San Galgano From US $204
         

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9.7 (223 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Villa Montalcinello in Siena, private pool From US $465
         

8.0 (1 Review)
Villa
  • Parking
  • Pool
  • Designated Smoking Area
panoramica casa con piscina privata From US $140
         

7.0 (10 Reviews)
Villa
  • Parking
  • Pet Friendly
  • Pool
villa con vista panoramica From US $157
         

6.8 (3 Reviews)
Villa
  • Parking
  • Pet Friendly
  • Pool
La Torre by Interhome From US $401
         

New
House
  • Parking
  • Pet Friendly
  • TV

Wheelchair Accessible Vacation Homes in Pentolina

Over 8+ Wheelchair Accessible Vacation Homes in or Near Pentolina
House / Villa - Radicondoli From US $441
         

9.6 (13 Reviews)
House
  • Parking
  • Pet Friendly
  • Pool
Castellare From US $777
         

9.7 (4 Reviews)
Villa
  • Parking
  • Pet Friendly
  • Pool
Residence Arianna From US $193
         

9.6 (4 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Borgo Il Poggiaccio Residenza Turistico Alberghiera From US $197
         

Agriturismo Le Vigne From US $124
         

9.2 (13 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Relais Le Macine Di Stigliano From US $397
         

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9.5 (229 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Casale San Galgano From US $91
         

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9.4 (179 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Hapimag Resort Pentolina From US $197
         

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8.4 (8 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • Pool

Pentolina Vacation Rentals and Airbnb Places to Stay Under $200

Over 156+ Pentolina Vacation Rentals and Airbnb Places to Stay Under $200
Apartment "Casa di Franca a San Galgano" in Historical Centre From US $89
         

10.0 (1 Review)
Apartment
  • Security/Safety
  • Bedding/Linens
  • Wellness Facilities
Casa Betta - A 700 Year Old Tuscan Gem From US $147
         

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10.0 (1 Review)
House
  • Parking
  • Pet Friendly
  • Designated Smoking Area
Casa di Campagna in Toscana From US $90
         

9.4 (20 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Villa Amedeo Raffaello Apartment - Sovicille From US $185
         

8.4 (7 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • TV
Casa Francesca by Interhome From US $119
         

8.0 (4 Reviews)
House
  • Parking
  • Pet Friendly
  • TV
Torre 2 by Interhome From US $90
         

8.0 (1 Review)
Apartment
  • Parking
  • Pet Friendly
  • TV
Montana Escape, Tuscan Stay From US $132
         

6.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Instantly Bookable Vacation Homes in Pentolina

Over 98+ Instantly Bookable Vacation Homes in or Near Pentolina
Sunflower Room From US $1,197
         

New
House
  • Pet Friendly
  • Designated Smoking Area
  • Fireplace/Heating
Camera Romeo & Juliet From US $1,195
         

New
House
  • Pet Friendly
  • Designated Smoking Area
  • Fireplace/Heating
Four-room flat for 6/8 people No. 5 From US $347
         

New
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Four-room flat 6/8 sleeps Nr 4 From US $344
         

New
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Tiziano-Leonardo - Villa Amedeo Tuscan countryside From US $317
         

New
Apartment
  • Security/Safety
  • Bedding/Linens
  • Wellness Facilities
Three-room flat 4/5 beds Nr 2 From US $234
         

New
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Casa Betta: Step Back in Time – A 700-Year-Old Tuscan Gem From US $187
         

About Pentolina Vacation Rentals

With more than 267 Pentolina vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Holidaycastles 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 Pentolina.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Holidaycastles Pentolina, 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 Pentolina. Places to stay near Pentolina are 1057.58 ft² on average, with prices averaging $317 a night.

Holidaycastles makes it easy and safe to find and compare vacation rentals in Pentolina 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 Pentolina

Type Count
Holiday Apartments 98
Vacation Homes 85
Villas 35
Others 33
Cottages 6
Hotels with Suites 5
B&B 4

Use these Quick Filters to Find a Vacation Rental in Pentolina

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

Weather in Pentolina

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

December - February
High 60°F       Low 38°F
March - May
High 66°F       Low 44°F
June - August
High 87°F       Low 64°F
September - November
High 75°F       Low 53°F

Pentolina Vacation Rental Frequently Asked Questions

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

Currently, the total number of properties listed in 2026 is over 267 in the Pentolina area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Pentolina.