Pentolina Vacation Rentals from $63: Search Short-Term Rentals

Q: 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.

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Our top choices for Pentolina vacation rentals

Palazzo Saloni

Montalcino

BRIAN

$325 nightly

Jul 9 - Jul 10

Total with taxes and fees

Residence Arianna

Sovicille

"We had a 4 night’s stay here and used it as our base for tours around Toscany. It is located in a quiet area outside Siena. The apartment was nice and clean. We used the kitchen for minor cooking and that worked well. There is a supermarket close by and small restaurants in the town. The AC was working great. The host was very keen to share information on good places to see and was eager to make our stay as pleasant as possible. The breakfast was very nice and they also have a restaurant where...

Gitte Harrits

$145 nightly

Jul 19 - Jul 20

Total with taxes and fees

Premium bedding, down comforters, pillowtop beds, individually furnished

Tuscasì Aparthotel

Sovicille

Sergey

$84 nightly

Jul 11 - Jul 12

Total with taxes and fees

Standard Double Room (La Piazza) | Desk, soundproofing, free WiFi, bed sheets

B&B Le Scalette di Piazza

Montalcino

Chris

$140 nightly

Jul 8 - Jul 9

Total with taxes and fees

Bosco della Spina

Murlo

Lizl

$140 nightly

Jul 8 - Jul 9

Total with taxes and fees

Riserva di Fizzano Residence

Castellina in Chianti

Janet

$248 nightly

Jul 10 - Jul 11

Total with taxes and fees

Ca' Bianca Tuscany Relais

Siena

Talha

$296 nightly

Jul 22 - Jul 23

Total with taxes and fees

Villa Curina Resort

Castelnuovo Berardenga

Dr Anne

$151 nightly

Jul 12 - Jul 13

Total with taxes and fees

Casa di Campagna in Toscana

Sovicille

Sally

$132 nightly

Jul 12 - Jul 13

Total with taxes and fees

Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti

Monteaperti

Ian F.

$188 nightly

Jul 8 - Jul 9

Total with taxes and fees

Antico Borgo il Cardino

San Gimignano

Craig

$122 nightly

Jul 9 - Jul 10

Total with taxes and fees

Borgo Il Poggiaccio

Sovicille

Dean

$171 nightly

Jul 13 - Jul 14

Total with taxes and fees

Country House il Ciliegio

Roccastrada

Maaike

$114 nightly

Jul 8 - Jul 9

Total with taxes and fees

Palazzo Pacini

Colle di Val d'Elsa

John

$141 nightly

Jul 15 - Jul 16

Total with taxes and fees

Residence Borgo San Lorenzo a Linari

Sovicille

Monica

$120 nightly

Jul 28 - Jul 29

Total with taxes and fees

Il Pozzo di Sant'Andrea

Siena

Prem

$110 nightly

Jul 27 - Jul 28

Total with taxes and fees

Borgo Argenina

Gaiole in Chianti

Sasha

$312 nightly

Jul 9 - Jul 10

Total with taxes and fees

Panorama-Ferien-Toscana Your vacation home in Tuscany

Massa Marittima

stefano f.

$168 nightly

Jul 14 - Jul 15

Total with taxes and fees

B&B Il Corso

Siena City Centre

Mario Humberto

$94 nightly

Jul 8 - Jul 9

Total with taxes and fees

Villa, Air conditioning, Courtyard View | Exterior

Villa Montecastello

Monteriggioni

Alvaro

$187 nightly

Jul 15 - Jul 16

Total with taxes and fees

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Top Pentolina Hotel Reviews

Hotel Chiusarelli

8/10 Good

"Very cute hotel. We booked last min and it’s a great place to have a base to explore the city. Staff is very friendly. They directed me to free parking spaces 10 min walk away which was perfect."

Dievole Wine Resort

10/10 Excellent

"Our stay at this Tuscan wine resort was nothing short of magical. Surrounded by stunning vineyards and ancient olive groves, the property is impeccably maintained and exudes refined, quiet elegance. The rooms and dining areas are spotless and sophisticated, providing the perfect backdrop for the truly elevated, delicious meals we enjoyed. The service was exceptional throughout, with a special thank you to Veronica and Gianluca, whose warmth and impeccable care made our experience unforgettable. This is the ultimate Tuscan escape— we cannot wait to return!"

Hotel Le Fontanelle

10/10 Excellent

"Our stay at Hotel Le Fontanelle was truly exceptional. From the moment we arrived, we were captivated by the beauty of the property, the breathtaking Tuscan scenery, and the peaceful elegance of the entire resort. The grounds are absolutely picturesque, the rooms are immaculate and beautifully maintained, and every detail reflects the charm and quality you hope to experience in Tuscany. What made our stay even more special was the incredible staff — everyone was warm, attentive, professional, and genuinely committed to making our visit memorable. We enjoyed every moment of our stay and honestly did not want to leave. Hotel Le Fontanelle is one of those rare places that creates lasting memories, and we would highly recommend it to anyone looking for an authentic luxury Tuscan experience. Our only small recommendation would be to improve the WiFi coverage around the pool area, as the connection was very limited. Aside from that minor detail, our experience was absolutely outstanding. Thank you to the entire Hotel Le Fontanelle team for a wonderful stay — we look forward to returning."

Palazzo Ravizza

10/10 Excellent

"This is a traditional and historic building with high ceilings and a beautiful garden overlooking the surrounding countryside.It is not a modern contemporary hotel, but the rooms are lovely, the garden was beautiful and a good breakfast too. There is a small bar in the evening, but no restaurant for an evening meal, but frankly you will likely want to explore and eat out at one of the many restaurants in the old town. A great find."

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 $63 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.

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Check prices for these dates

Our top choices for Pentolina vacation rentals

Palazzo Saloni

Residence Arianna

Tuscasì Aparthotel

B&B Le Scalette di Piazza

Bosco della Spina

Riserva di Fizzano Residence

Ca' Bianca Tuscany Relais

Villa Curina Resort

Casa di Campagna in Toscana

Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti

Antico Borgo il Cardino

Borgo Il Poggiaccio

Country House il Ciliegio

Palazzo Pacini

Residence Borgo San Lorenzo a Linari

Il Pozzo di Sant'Andrea

Borgo Argenina

Panorama-Ferien-Toscana Your vacation home in Tuscany

B&B Il Corso

Villa Montecastello

Find vacation rentals that suit your style

Top Pentolina Hotel Reviews

Hotel Chiusarelli

Villa Ermellina Siena, a Tribute Portfolio Hotel

Dievole Wine Resort

Hotel Executive

Hotel Athena

Hotel Minerva

Hotel Le Fontanelle

Villa Scacciapensieri Boutique Hotel

Palazzo Ravizza

Find out more about Pentolina

Frequently asked questions

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