Province of Siena Holiday Rentals

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Top Cities in Province of Siena

Top Holiday Rentals Destinations in Province of Siena

Exterior
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
10.0 out of 10, Exceptional, (50)
"Great villa - perfect for large family stay"
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Interior
Delcorto Suites
10.0 out of 10, Exceptional, (12)
"This was a beautiful property well maintained and perfectly located in a historic building. The breakfast was delicious, Ricardo the host was wonderful and our room was space and comfortable! The only comment was without A/C the windows needed to stay open and the street was loud."
The price is NZ$317
includes taxes & fees
6 Jun - 7 Jun
Delcorto Suites
Terrace/patio
Borgo Argiano
10.0 out of 10, Exceptional, (51)
"Beautiful small hotel. We received a nice upgrade without asking for it. The apartments are very comfortable and has complete kitchens. They received us with a bottle of wine and some groceries. The hotel doesn't have a restaurant but there are some options nearby. I would only recommend staying here if you have a car. Good option to stay here and make day trips to different Tuscan towns."
Borgo Argiano
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Property entrance
Il Tosco
10.0 out of 10, Exceptional, (87)
"Il Tosco is a quiet, clean and charming place to stay while traveling in Tuscany. The common rooms are cozy and the elegant breakfasts are the best we encountered in Italy. This is a wonderful place to stay with a local quality. Well worth the higher cost. "
The price is NZ$550
includes taxes & fees
4 Jun - 5 Jun
Il Tosco
Outdoor pool
Villa with pool, 4 rooms en suite, Wi-Fi, walking distance from San Gimignano
10.0 out of 10, Exceptional, (83)
"AMAZING! GORGEOUS! SPACIOUS! SPOTLESS! CHARMING! VIEWS SECOND-TO-NONE! CONVENIENT! Everything we could have hoped for and more booking a villa sight unseen! Alessandro - the owner - could not possibly have been more accommodating! From beginning to end, he was responsive, kind, bending over backwards to accommodate our needs. The spacious bedrooms with en suite bathrooms were perfect for 5 sisters to have their own space after a day of sightseeing! We flew into Florence, rented a vehicle and...
Villa with pool, 4 rooms en suite, Wi-Fi, walking distance from San Gimignano
Exterior
Magnificent stone farmhouse in the heart of Tuscany
10.0 out of 10, Exceptional, (24)
"The property has beautiful views and a peaceful, remote location. It is well equipped for cooking meals and they conveniently provide a starter supply of necessities (kitchen spices, hand soap, laundry soap, toilet paper, etc.). The property owner, as well as the local property manager, were both very responsive to our questions and the check in and out processes are simple. We thoroughly enjoyed our stay."
Magnificent stone farmhouse in the heart of Tuscany
Fridge, stovetop, coffee/tea maker, cookware/dishes/utensils
The Gelda house, relax with a view
10.0 out of 10, Exceptional, (6)
"This apartment is in a charming medieval village just outside Montalcino that brings you back in time. The views are phenomenal. The apartment is very comfortable and with all the amenities! The host Francesco is amazing and helped us with planning some outings while in town. Highly recommend!"
The price is NZ$245
includes taxes & fees
28 May - 29 May
The Gelda house, relax with a view
Outdoor pool
VILLA IRIS LUXURY SAN GIMIGNANO, 6 EN SUITE ROOMS, SWIMMING POOL, SPA, SAUNA.
10.0 out of 10, Exceptional, (107)
"Great villa and property that was fantastic for our group of 12, including 6 children between ages 5 and 11. So much for them to do with the open spaces, various games, pool, etc. I’ve stayed in Italy with my family three times now and I think this was the best villa and location for driving to many of the great Tuscan cities."
VILLA IRIS LUXURY SAN GIMIGNANO, 6 EN SUITE ROOMS, SWIMMING POOL, SPA, SAUNA.
Fridge, microwave, oven, stovetop
La Luna, Montefiorile, Gaiole in Chianti, Siena and Chianti
10.0 out of 10, Exceptional, (1)
"Enjoyed it"
La Luna, Montefiorile, Gaiole in Chianti, Siena and Chianti
Exterior
Family apartment with magical view on the old city, balcony, wifi & parking
9.8 out of 10, Exceptional, (35)
"The apartment is very spacious with lots of antiques and has a home from home feel. It is about a 20 min walk into town, uphill in places but straight forward. Parking is tight so bring a small car 😊. The views across to the old town are great and the balcony space a plus."
Family apartment with magical view on the old city, balcony, wifi & parking
Bar (on property)
Il Battistero Siena - Residenza d'Epoca
9.6 out of 10, Exceptional, (117)
"The staff is friendly and helpful, an asset to this hotel. "
The price is NZ$394
includes taxes & fees
27 May - 28 May
Il Battistero Siena - Residenza d'Epoca
Minibar
Residenza d'Epoca Palazzo Borghesi
9.6 out of 10, Exceptional, (97)
"Excellent location blocks from the Duomo. Beautiful large rooms. Access to a small roof area with panoramic view. Breakfast—you order what you want the day before with plenty of options. "
The price is NZ$422
includes taxes & fees
18 Jun - 19 Jun
Residenza d'Epoca Palazzo Borghesi
Suite | Balcony view
La Terrazza Sul Campo Rooming House
9.6 out of 10, Exceptional, (209)
"La Terrassa is great! The location and view over Il Campo in Siena is simply spectacular. The welcome from host Viola is brilliant (so many hotels could learn from her skills and warmth). The Suite is huge, feels like your own apartment. Breakfast snacks and lots of drinks provided. Highly recommended! "
The price is NZ$311
includes taxes & fees
11 Jun - 12 Jun
La Terrazza Sul Campo Rooming House
Superior Double Room Single Use, 1 Queen Bed, Balcony, Hill View | View from room
Palazzo Pacini
9.6 out of 10, Exceptional, (70)
"The bedroom was small but had a lovely view from the bathroom window and balcony. Breakfast was delicious and staff were friendly. It was disappointing that the room was hot and stuffy even with air-conditioning on (temp 24.5 degrees). We opened the balcony doors which helped however let insects in. It was also disappointing for the price that parking was a few minutes walk from property. "
The price is NZ$271
includes taxes & fees
27 May - 28 May
Palazzo Pacini
Exterior
The House of Alice, charm and relaxation
9.6 out of 10, Exceptional, (43)
"Loved our stay at House of Alice. It’s very centrally located in Tuscany. Francesco was wonderful and took care of reservations and recommendations for us. The village itself is very small. The house was clean and well appointed. Small recommendations are; it could have used more efficient seating in the living room, a few more kitchen items, larger coffee maker etc. Also the bathrooms could use hooks and a shelf. Overall a wonderful and charming place! I would highly recommend!"
The price is NZ$313
includes taxes & fees
28 May - 29 May
The House of Alice, charm and relaxation
Outdoor pool
Tuscany Luxury Spacious Villa Private Pool Wi-Fi free near Siena Family Frendly
9.6 out of 10, Exceptional, (47)
"This villa is a dream. You really feel like you’re in a Disney castle in the home and in the little village! Our hosts were so easy to communicate with and so patient with us as we arrived much later than planned. They even went to great lengths to try and help us find food upon arrival because our kids were starving. It’s a fantastic location if you plan to take day trips all over Tuscany. It was nice to be centrally located so we could head out to Florence, San Gimignano, Lucca, and Pisa and...
Tuscany Luxury Spacious Villa Private Pool Wi-Fi free near Siena Family Frendly
Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas
Casanova - Panoramic Rooms and Suites
3.0 star property
9.4 out of 10, Exceptional, (18)
"The location is great, you have beautiful Tuscan view in front of yard. The room and bathroom are large, clean and modern with full kitchen. Good choice of breakfast, restaurant onsite is good for dinner. Free parking is good for travel by car."
The price is NZ$323
includes taxes & fees
14 Jun - 15 Jun
Casanova - Panoramic Rooms and Suites
Pool
A private luxury retreat in Montalcino
9.4 out of 10, Exceptional, (48)
"I did not want to leave. Cheerful, stylish color pallet & decor. Good internet. Postcard views. Peaceful. Relaxing. Lovely outside terrace & pool. The quibbles-no television, no coffee machine, no microwave. Sofa & coffee table are more shabby than chic. Stains. Need replacing."
A private luxury retreat in Montalcino
Grand Apartment with Garden | Private kitchen
Regis Condo
9.4 out of 10, Exceptional, (38)
"It was a beautiful updated condo with an historic architecture and great central location."
The price is NZ$320
includes taxes & fees
3 Jun - 4 Jun
Regis Condo
Exterior
Apartment in a historic residence in the center of Siena
9.4 out of 10, Exceptional, (93)
"We loved this historic apartment in Siena. Our host was super helpful and always there for us. Its authenticity is just what we love."
Apartment in a historic residence in the center of Siena
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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$78 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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