Antigua Cottages - Vacation Rentals in Pentolina

Agriturismo Botralta From US $81
         

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9.0 (1 Review)
Apartment
  • Parking
  • Pet Friendly
  • Balcony/Terrace
Casa di Campagna in Toscana From US $90
         

9.4 (21 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Villa La Capanna dello scrittore From US $140
         

10.0 (2 Reviews)
Villa
  • Air Conditioner
  • Parking
  • TV

Luxury Places to Stay in Pentolina

Over 269+ Luxury Places to Stay in or Near Pentolina
Villa Rock Cerbaia From US $4,781
         

New
Villa
  • Pet Friendly
  • Security/Safety
  • Bedding/Linens
La Capriata From US $4,686
         

New
Apartment
  • Pet Friendly
  • Security/Safety
  • Fireplace/Heating
The Bishop Apartment From US $3,517
         

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

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8.9 (30 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Honeymoon Room From US $2,367
         

New
House
  • Pet Friendly
  • Designated Smoking Area
  • Fireplace/Heating
Beautiful Luxury Villa with Superb View From US $1,619
         

New
Villa
  • Parking
  • Pool
  • Designated Smoking Area
Villa Le Querce - San Galgano From US $1,599
         

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10.0 (1 Review)
Villa
  • Parking
  • Pool
  • TV

Top-Rated Vacation Rentals with a Pool in Pentolina

Over 111+ Top-Rated Vacation Rentals with a Pool in or Near Pentolina
Relais Le Macine di Stigliano From US $388
         

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10.0 (15 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Elegant villa with private pool near San Galgano From US $701
         

10.0 (1 Review)
Villa
  • Parking
  • Pool
  • Designated Smoking Area
Casa Sofi, Monticiano, Italy From US $288
         

10.0 (1 Review)
House
  • Parking
  • Pet Friendly
  • Pool
Villa Edera From US $226
         

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10.0 (1 Review)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Podere La Castellina From US $152
         

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9.8 (51 Reviews)
Apartment
  • Parking
  • Pool
  • View
Casa Viale dei Cipressi From US $163
         

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9.8 (29 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Pentolina

Over 143+ Pet-Friendly Vacation Rentals in or Near Pentolina
Casa Betta - A 700 Year Old Tuscan Gem From US $147
         

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10.0 (2 Reviews)
House
  • Parking
  • Pet Friendly
  • Designated Smoking Area
Borgo Il Poggiaccio From US $184
         

8.8 (65 Reviews)
House
  • Parking
  • Pet Friendly
  • Pool
Comfort, relaxation and nature From US $96
         

10.0 (1 Review)
House
  • Parking
  • Pet Friendly
  • TV
La Capanna di Franca 6+2, Emma Villas From US $675
         

9.8 (6 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
agriturismo la roggiola From US $71
         

9.6 (112 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Detached villa with panoramic garden From US $229
         

9.6 (63 Reviews)
House
  • Parking
  • Pet Friendly
  • Pool
Tuscan Charm: Frassini Cottage From US $183
         

9.4 (3 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Pentolina

Over 68+ Large Vacation Homes & Villas in or Near Pentolina
Castellare From US $777
         

9.8 (4 Reviews)
Villa
  • Parking
  • Pet Friendly
  • Pool
Villa Montalcinello in Siena, private pool From US $541
         

8.0 (1 Review)
Villa
  • Parking
  • Pool
  • Designated Smoking Area
panoramica casa con piscina privata From US $156
         

7.0 (10 Reviews)
Villa
  • Parking
  • Pet Friendly
  • Pool
villa con vista panoramica From US $161
         

6.8 (3 Reviews)
Villa
  • Parking
  • Pet Friendly
  • Pool
La Torre by Interhome From US $551
         

New
House
  • Parking
  • Pet Friendly
  • TV

Wheelchair Accessible Vacation Homes in Pentolina

Over 7+ Wheelchair Accessible Vacation Homes in or Near Pentolina
House / Villa - Radicondoli From US $441
         

9.6 (13 Reviews)
House
  • Parking
  • Pet Friendly
  • Pool
Borgo Il Poggiaccio Residenza Turistico Alberghiera From US $217
         

Residence Arianna From US $173
         

9.6 (4 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
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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9.6 (221 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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9.2 (9 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • Pool

Pentolina Vacation Rentals and Airbnb Places to Stay Under $200

Over 153+ Pentolina Vacation Rentals and Airbnb Places to Stay Under $200
Apartment "Casa di Franca a San Galgano" in Historical Centre From US $119
         

10.0 (1 Review)
Apartment
  • Security/Safety
  • Bedding/Linens
  • Wellness Facilities
Trilocale vicino Siena a Due Passi Da Terme Petriolo From US $110
         

10.0 (2 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • Balcony/Terrace
L'Antico Borgo di Torri From US $108
         

8.0 (1 Review)
House
  • TV
  • Security/Safety
  • Bedding/Linens
Casa Francesca by Interhome From US $129
         

8.0 (4 Reviews)
House
  • Parking
  • Pet Friendly
  • TV
Torre 2 by Interhome From US $125
         

8.0 (1 Review)
Apartment
  • Parking
  • Pet Friendly
  • TV
Montana Escape, Tuscan Stay From US $195
         

7.8 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Instantly Bookable Vacation Homes in Pentolina

Over 105+ Instantly Bookable Vacation Homes in or Near Pentolina
Sunflower Room From US $1,189
         

New
House
  • Pet Friendly
  • Designated Smoking Area
  • Fireplace/Heating
Apartment "Casa di Franca a San Galgano" in Historical Centre From US $103
         

10.0 (1 Review)
Apartment
  • Security/Safety
  • Bedding/Linens
  • Wellness Facilities
The Tower Room From US $1,189
         

New
House
  • Pet Friendly
  • Designated Smoking Area
  • Fireplace/Heating
Camera Romeo & Juliet From US $1,187
         

New
House
  • Pet Friendly
  • Designated Smoking Area
  • Fireplace/Heating
Four-room flat for 6/8 people No. 5 From US $467
         

New
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Four-room flat 6/8 sleeps Nr 4 From US $449
         

New
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Three-room flat 4/5 beds Nr 2 From US $337
         

New
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV

About Pentolina Vacation Rentals

With more than 278 Pentolina vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Antiguacottages 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 Antiguacottages 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 1060.01 ft² on average, with prices averaging US $329 a night.

Antiguacottages 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 100
Vacation Homes 91
Villas 37
Others 33
Cottages 6
Hotels 6
B&B 4

Use these Quick Filters to Find a Vacation Rental in Pentolina

Pro Tip: Antiguacottages makes it easy to compare the best listings on Antiguacottages homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Antiguacottages 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 278 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.