Province of Siena Holiday Rentals

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Top Cities in Province of Siena

Top Holiday Rentals Destinations in Province of Siena

Palazzo Pacini
Via Gracco del Secco,14, Colle di Val d'Elsa, Siena, 53034
Fully refundableReserve now, pay when you stay
The price is NZ$196 per night from 30 Aug. to 31 Aug.
Stay at this golf residence in Colle di Val d'Elsa. Enjoy free WiFi, free parking and an on-site winery. Our guests praise the breakfast and the helpful staff ...
4.8/5 Exceptional! (50 reviews)
"We loved our stay here! The owners were very welcoming from the beginning to the end. The room was cute, quiet, and clean. There was an excellent view from our room and the terrace. She recommended a restaurant near by which was amazing. Their breakfast was beautiful and the owners were there and ..."

Reviewed on 9 Jun. 2022

Palazzo Pacini
Il Tosco
Via del Poliziano 13, Montepulciano, SI, 53045
The price is NZ$412 per night from 9 Aug. to 10 Aug.
Stay at this luxury residence in Montepulciano. Enjoy free WiFi, free parking and room service. Our guests praise the helpful staff and the spacious rooms in ...
5/5 Exceptional! (67 reviews)
"I don’t do reviews, ever. But….. Genuinely one of the best places I’ve ever stayed.( and I have stayed in some amazing places around the world) Nothing was a problem, super friendly, beautiful home cooked food on display with instructions of “if it’s there, eat it”. ( as I did coming in late at night😬) ..."

Reviewed on 29 Jul. 2022

Il Tosco
Hotel San Gregorio
3 out of 5
Via Della Madonnina 4, Pienza, Siena, 53026
Fully refundableReserve now, pay when you stay
The price is NZ$255 per night from 25 Aug. to 26 Aug.
Stay at this 3-star business-friendly residence in Pienza. Enjoy free WiFi, room service and on-site parking. Our guests praise the helpful staff and the spacious ...
4.5/5 Wonderful! (63 reviews)
"Room was very spacious, clean and comfortable. Friendly and accommodating staff. A block away from the historic city center - very conveniently located."

Reviewed on 19 May 2022

Hotel San Gregorio
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Casanova - Panoramic Rooms and Suites
3 out of 5
Strada Provinciale 146 di Chianciano, Località Casanova 6/c, San Quirico d'Orcia, 53027
The price is NZ$279 per night from 28 Aug. to 29 Aug.
Stay at this 3-star spa residence in San Quirico d'Orcia. Enjoy free breakfast, free WiFi and an outdoor pool. Popular attractions Palazzo Chigi and Horti Leonini ...
4.3/5 Excellent! (8 reviews)
Good location for exploring Tuscany
"The hotel is in a good location for exploring Tuscany. A short walk into San Quirico d'Orca town for restaurants etc Had to wear face masks whilst walking around hotel - Government restrictions not hotels. View from our balcony was outstanding. Didn't use the spa facilities but they looked good."

Reviewed on 18 Apr. 2022

Casanova - Panoramic Rooms and Suites
Residenza d'Epoca Palazzo Borghesi
Via S.Pietro, 3, Siena, Toscana, 53100
The price is NZ$324 per night from 19 Aug. to 20 Aug.
Stay at this business-friendly residence in Siena. Enjoy free WiFi, an on-site winery and a rooftop terrace. Our guests praise the helpful staff and the spacious ...
4.8/5 Exceptional! (62 reviews)
"Loved our stay here. Silvia at front deck was so wonderful and helpful. Would definitely recommend this place to anyone. Lots of character and history."

Reviewed on 31 Jul. 2022

Residenza d'Epoca Palazzo Borghesi
Osteria del Borgo
Via Ricci 7, Montepulciano, SI, 53045
Stay at this business-friendly residence in Montepulciano. Enjoy free breakfast, free WiFi and free parking. Our guests praise the breakfast and the restaurant ...
4.5/5 Wonderful! (124 reviews)
A perfect B&B in Montepulciano
"Beautiful property with amazing views. The owners were incredibly kind and considerate. The location was easy to get to get to. The restaurant is also very delicious! Would definitely stay again and again!"

Reviewed on 19 Feb. 2022

Osteria del Borgo
Residenza Fabroni
Via di Gracciano nel Corso, 12, Montepulciano, SI, 53045
Fully refundableReserve now, pay when you stay
The price is NZ$194 per night from 22 Aug. to 23 Aug.
Stay at this historic residence in Montepulciano. Enjoy free breakfast, free WiFi and an on-site winery. Our guests praise the breakfast and the family amenities ...
4.8/5 Exceptional! (27 reviews)
"Great room with amazing views! Rooftop terrace that was awesome to watch the sunset. The room was plenty big. The staff was awesome! Highly recommend!"

Reviewed on 3 Jul. 2022

Residenza Fabroni
Porta Pispini Residence
2 out of 5
Via Baldassarre Peruzzi 33, Siena, Provincia di Siena, 53100
The price is NZ$230 per night from 20 Aug. to 21 Aug.
Stay at this business-friendly residence in Siena. Enjoy free WiFi, free parking and a terrace. Our guests praise the helpful staff and the convenient parking ...
4.8/5 Exceptional! (4 reviews)
"The bed was very hard, super uncomfortable and apartments around us were very noisy at night. we couldn’t finish our stay because we weren’t able to sleep. We ended up checking out a day early and getting a room somewhere else. Everything else about the apartment was great, the people were very nice. ..."

Reviewed on 6 Apr. 2022

Porta Pispini Residence
Castello di Modanella
LOC. MODANELLA, Rapolano Terme, Province of Siena, 53040
Stay at this apartment in Rapolano Terme. Enjoy free WiFi, free parking and an outdoor pool. Popular attractions Museo dell'Antica Grancia e dell'Olio and Terme ...
4.7/5 Exceptional! (6 reviews)
Dejligt !
"Dejligt, og roligt. Indkøb tæt på - god restaurant på stedet - super lokal vin. Spørg efter wifi og parasol hvis du har brug for det. Fed pool med vippe og god dybde og størrelse"

Reviewed on 18 Jul. 2022

Castello di Modanella
Camping Boschetto Di Piemma
3 out of 5
Localita' Santa Lucia 38C, San Gimignano, 53037
The price is NZ$81 per night from 8 Sep. to 9 Sep.
Stay at this 3-star campsite in San Gimignano. Enjoy free WiFi, free parking and 2 bars/lounges. Our guests praise the quiet rooms and the overall value in their ...
4.5/5 Wonderful! (37 reviews)
"Great experience, close to a beautiful city and castle on a hill."

Reviewed on 2 Aug. 2022

Camping Boschetto Di Piemma
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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.

Everything you need to know about Province of Siena holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Province of Siena holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 Province of Siena holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Province of Siena holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Province of Siena. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Province of Siena holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Province of Siena holiday rentals we have selected for you start as low as NZ$81 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Province of Siena rentals

At Expedia, we put the best Province of Siena holiday 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 Province of Siena 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 Province of Siena holiday.

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

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