Pentolina Vacation Rentals

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Our top choices for Pentolina vacation rentals

B&B Le Scalette di Piazza

B&B Le Scalette di Piazza
Montalcino
9.4 out of 10, Exceptional, (90)
"Great location and excellent staff. "
Canada
Jacek
B&B Le Scalette di Piazza

Affittacamere Mariuccia

Affittacamere Mariuccia
Montalcino
9.0 out of 10, Wonderful, (11)
"The apartment was big enough, the owner very polite and helpful. But, there were bugs at our mattress... "
United Kingdom
Angeliki
Affittacamere Mariuccia

Idolina Guest House

Idolina Guest House
Montalcino
9.4 out of 10, Exceptional, (105)
"The room met our expectations. Fulvia welcomed us and provided all info we needed. She was lovely and the room spacious and cosy. The location was perfect for our needs and we were very pleased."
United Kingdom
Kathrin
Idolina Guest House

Antico Brunello

Antico Brunello
Montalcino
$7,774 nightly
The price is $8,563
Dec 28 - Dec 29
Total with taxes and fees
Antico Brunello

Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.4 out of 10, Exceptional, (19)
"Fantastic experience with friendly hosts and an excellent breakfast! A little rustic here and there but all part of the charm!"
United Kingdom
Alasdair
Casa di Campagna in Toscana

Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (25)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
$84 nightly
The price is $96
Jan 6 - Jan 7, 2026
Total with taxes and fees
Tuscasì Aparthotel

Il Pozzo di Sant'Andrea

Il Pozzo di Sant'Andrea
Siena
9.8 out of 10, Exceptional, (16)
"Great host, lovely place near Siena"
United Kingdom
Prem
Il Pozzo di Sant'Andrea

Piazza Paradiso Accomodation

Piazza Paradiso Accomodation
Siena City Centre
9.2 out of 10, Wonderful, (155)
"What my girlfriend loved the most was the bathtub! We have been busy traveling the last week and a half and she was overjoyed with a chance to soak in a bath tub. Room was spacious and clean, the staff was helpful and friendly. The hotel was centrally located and within easy walking distance to Piazza del Campo. Looking forward to staying with Piazza Paradiso accommodation again. We will definitely recommend Piazza Paradiso to all our friends visiting Siena!"
United States
Niels G.
Piazza Paradiso Accomodation

La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House
Siena City Centre
9.8 out of 10, Exceptional, (239)
"Huge room! Great location "
Canada
karen
La Terrazza Sul Campo Rooming House

PALAZZO DEL PAPA

PALAZZO DEL PAPA
Siena City Centre
9.6 out of 10, Exceptional, (96)
"Hamza was so wonderful and accommodating, would definitely stay here again!"
United States
Elise
$183 nightly
The price is $207
Dec 27 - Dec 28
Total with taxes and fees
PALAZZO DEL PAPA

Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (422)
"A great location!"
Canada
Cheryl
$88 nightly
The price is $101
Jan 10 - Jan 11, 2026
Total with taxes and fees
Siena Vip

Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca
Siena City Centre
9.6 out of 10, Exceptional, (193)
"Great location and friendly staff. "
United States
Parissa
$153 nightly
The price is $174
Dec 29 - Dec 30
Total with taxes and fees
Il Battistero Siena - Residenza d'Epoca

B&B Palazzo del Magnifico

B&B Palazzo del Magnifico
Siena City Centre
9.8 out of 10, Exceptional, (63)
"Great location. Room spacious and clean. Personnel friendly and great service walkable to best historic places. Could find something better "
United States
Rodolfo
$100 nightly
The price is $115
Jan 12 - Jan 13, 2026
Total with taxes and fees
B&B Palazzo del Magnifico

La Coroncina Lodging

La Coroncina Lodging
Siena
10.0 out of 10, Exceptional, (42)
"Fantastic place, and I highly recommend it."
United States
Hassan
$105 nightly
The price is $121
Jan 8 - Jan 9, 2026
Total with taxes and fees
La Coroncina Lodging

ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, Very Good, (335)
"Would recommend staying here and will hopefully be back!"
Canada
Lisa
$61 nightly
The price is $71
Jan 6 - Jan 7, 2026
Total with taxes and fees
ApartHotel Anghel

Residenza d'Epoca Palazzo Borghesi

Residenza d'Epoca Palazzo Borghesi
Siena City Centre
9.6 out of 10, Exceptional, (116)
"We enjoyed our stay here. Convenient, clean, central to city center, shops, and restaurants. We would stay here again."
United States
Linda
$176 nightly
The price is $199
Jan 14 - Jan 15, 2026
Total with taxes and fees
Residenza d'Epoca Palazzo Borghesi

Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (81)
"Convenient for parking, clean and relatively easy access to the town. The rooms were functional, getting into the place after hours was easy ( check in). No breakfast but a supermarket was 300 meters away"
Canada
Marcus
Domus il Palio B&B

Al Mercato B&B

Al Mercato B&B
Siena City Centre
9.0 out of 10, Wonderful, (96)
"Hotel is a one block from main square of the city also have a good restaurant around the corner "
United States
Guillermo
$87 nightly
The price is $100
Jan 18 - Jan 19, 2026
Total with taxes and fees
Al Mercato B&B

Palazzo Masi

Palazzo Masi
Siena City Centre
8.8 out of 10, Excellent, (84)
"Very friendly and attentive, a very clean place and its location is excellent. "
United States
Gloria
$96 nightly
The price is $111
Jan 2 - Jan 3, 2026
Total with taxes and fees
Palazzo Masi

Regis Condo

Regis Condo
Siena City Centre
9.4 out of 10, Exceptional, (65)
"This was one of our favorite stays in Italy. It was spacious, clean, and in a great part of the city."
United States
Ben
$107 nightly
The price is $122
Jan 7 - Jan 8, 2026
Total with taxes and fees
Regis Condo
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Pentolina Hotel Reviews

Find out more about Pentolina

Everything you need to know about Pentolina vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Pentolina vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pentolina vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Pentolina vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pentolina. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Pentolina in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $71 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Pentolina rentals

At Expedia, we put the best Pentolina vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Pentolina rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pentolina vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pentolina. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find vacation rentals in Pentolina?

Yes, there are vacation rentals close to well known sights in Pentolina, or you can select a secluded option if you're looking for relaxation.

What's the top vacation rental in Pentolina?

Borgo Argiano: Visitors like this Pentolina vacation home rental. It is located on a river and has a balcony, a terrace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and an electric kettle. You can relax into your vacation with a garden and a library.

What can I see and do in Pentolina?

Explore the area and family-friendly sights such as Terme Petriolo, or get out into nature at a spot like I Canaloni del Torrente Farma. In the larger area, you’ll find Abbazia di San Galgano and Castello di Montepescini.

What are vacation rentals like in Pentolina?

Vacation rentals are privately owned properties you can stay in for a couple days or more in Pentolina. Vacation rentals offer amenities such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of privacy away from shared hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for a family trip or a small group gathering.