Vacation Rentals in Province of Siena

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Top Cities in Province of Siena

Top Vacation Rentals in Province of Siena

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 ¥49,209
¥54,803 total
includes taxes & fees
May 27 - May 28
Il Tosco
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 ¥28,274
¥31,438 total
includes taxes & fees
Jun 6 - Jun 7
Delcorto Suites
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Terrace/patio
Borgo Argiano
10.0 out of 10, Exceptional, (50)
"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
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
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
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 ¥16,829
¥23,224 total
includes taxes & fees
May 19 - May 20
The Gelda house, relax with a view
A heated pool
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS
10.0 out of 10, Exceptional, (37)
"Three generations of our family spent two weeks at this beautiful villa, and it was a very special vacation. The villa, grounds and pool are maintained in perfect condition - just the right combination of old-world charm with modern conveniences. The kids loved the pool, and the adults very much enjoyed the cocktail hour in the beautiful grounds by the pool at the end of the day. We love to cook, as a family, and found everything we needed to prepare meals in the huge kitchen. We also had...
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS
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
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.
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, (116)
"Center of everything. Great service and communication. "
The price is ¥30,155
¥33,843 total
includes taxes & fees
May 19 - May 20
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 ¥35,250
¥39,448 total
includes taxes & fees
Jun 3 - Jun 4
Residenza d'Epoca Palazzo Borghesi
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 ¥23,002
¥25,639 total
includes taxes & fees
May 27 - May 28
Palazzo Pacini
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 ¥26,119
¥29,404 total
includes taxes & fees
Jun 11 - Jun 12
La Terrazza Sul Campo Rooming House
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 ¥21,878
¥29,619 total
includes taxes & fees
May 19 - May 20
The House of Alice, charm and relaxation
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 ¥27,369
¥30,610 total
includes taxes & fees
May 29 - May 30
Casanova - Panoramic Rooms and Suites
Grand Apartment with Garden | Private kitchen | Full-size fridge, microwave, oven, stovetop
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 ¥27,263
¥34,028 total
includes taxes & fees
May 30 - May 31
Regis Condo
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
Seasonal outdoor pool, sun loungers
Hotel San Gregorio
3.0 star property
9.2 out of 10, Wonderful, (98)
"Very nice staff, great service, super clean. Will stay again."
The price is ¥29,258
¥32,521 total
includes taxes & fees
May 29 - May 30
Hotel San Gregorio
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