Holiday Homes in Siena

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Featured Holiday Homes in Siena and around

Beautiful stone house with garden and private pool.

9.6 out of 10, Exceptional, (62)
"Cottage is larger than described and outfitted nicely for a couple. We used the kitchen everyday for meals and while the bed was firm, it wasn’t bad. Directions to there were confusing. Basically, head to To"
Beautiful stone house with garden and private pool.

Il Palazzetto

9.6 out of 10, Exceptional, (7)
Il Palazzetto

Villa Le Tortore Tuscany private luxury pool relax

10.0 out of 10, Exceptional, (89)
"Very convenient to town and to surrounding wine regions - very good communication with host and was comfortable to stay for 3 people. Would stay again if in the area"
Villa Le Tortore Tuscany private luxury pool relax

GIULIA -1 Bedroom Country House in Monteriggioni - Siena

10.0 out of 10, Exceptional, (2)
"Ha sido una estancia maravillosa. El lugar estupendo. =)"
GIULIA -1 Bedroom Country House in Monteriggioni - Siena

Farmhouse with beautiful pool and jacuzzi, panoramic location in chianti

9.8 out of 10, Exceptional, (60)
"We spent 3 weeks in Europe from Barcelona to Cadaques to Provence to Cannes to Nice to Monaco to Rome and Castellina in Chianti. Our stay in Stella at this location was our absolute favorite. Federico was very kind kind, greeted us upon arrival, helped us with questions, and gave us suggestions around the area. We highly recommend this place and are already making our plans to return."
Farmhouse with beautiful pool and jacuzzi, panoramic location in chianti

Villa in Siena with Tuscan Hill Views

8.0 out of 10, Very good, (2)
"Fantastisch huis, alles wat je nodig hebt, mooi uitzicht, dichtbij de stad"
Villa in Siena with Tuscan Hill Views

detached villa with private pool and garden

8.8 out of 10, Excellent, (23)
"We had a wonderful time in the nice little house on the quiet edge of a lively village, with spectacular Tuscany scenery, a super clean pool and friendly and helpful owners. Both Florence and Siena are fully worth a trip, or you just stay at the house for perfect relaxing."
detached villa with private pool and garden

L'Oliviera by Interhome

9.8 out of 10, Exceptional, (6)
"Das Haus war etwas schwer zu finden (ist nicht über Navi zu finden), jedoch gaben uns die Vermieter eine genaue Anfahrtsbeschreibung per Mail. Zum Empfang standen eine Flasche Wein, sowie eine Schale mit Süßigkeiten auf dem Tisch. Kurze Zeit später brachte der Vermieter noch eine Schale mit frischen Erdbeeren vorbei. Das Ehepaar ist sehr freundlich, und Laura spricht fließend Englisch, sodass eine Unterhaltung stets möglich war. Im Garten gibt es einen Grill, Sonnenliegen und einen überdachte...
L'Oliviera by Interhome

Legnaia countryside luxury property, shared pool, ideal base to discover Tuscany

10.0 out of 10, Exceptional, (14)
"Had a great time visiting the area. The home is beautiful. "
Legnaia countryside luxury property, shared pool, ideal base to discover Tuscany

Family Tuscany Home Close Via Francigena, Monteriggioni, Italy

Family Tuscany Home Close Via Francigena, Monteriggioni, Italy

Chianti Classico Home Panoramic View, Castellina in Chianti, Italy

10.0 out of 10, Exceptional, (1)
"Lovely, large home above the Farmacia in Castellina in Chianti. Charming village, wonderful food & atmosphere. Easy drive to many sites. Very good response from Roberto when I had some questions @ the house. We stayed a month & loved it. Highly recommend. "
Chianti Classico Home Panoramic View, Castellina in Chianti, Italy

Domus Nannini SPA - Palazzo Nannini - Loggia Salimbeni

10.0 out of 10, Exceptional, (17)
"The apartment is very large, beautifully decorated, and is in a fantastic location in Siena. Couldn't be better..... Gianluca was the perfect host. We were very happy!!! Will rent again for sure!!!"
Domus Nannini SPA - Palazzo Nannini - Loggia Salimbeni

Beautiful farmhouse nestled in very sweet hills just a few minutes from Siena

10.0 out of 10, Exceptional, (13)
"The setting is truly incredible! Stunning views, a well kept and comfortable house to stay in. We spent lots of family time in the pool and loved being just 15 minutes outside of Siena yet feeling so removed from everything. I highly recommend staying here!"
Beautiful farmhouse nestled in very sweet hills just a few minutes from Siena

HOUSE WOW panoramic terrace *.*

10.0 out of 10, Exceptional, (20)
"So happy we chose this property. A wonderful home away from home, so close to everything, enchanting terrace/views, and superb communicative hosts. "
HOUSE WOW panoramic terrace *.*

Farmhouse with beautiful pool and jacuzzi, panoramic location in chianti

9.8 out of 10, Exceptional, (33)
"Perfekt ferie🤗"
Farmhouse with beautiful pool and jacuzzi, panoramic location in chianti

Family Tuscany Home Close Via Francigena

Family Tuscany Home Close Via Francigena

Belvilla by OYO Oliveta

Belvilla by OYO Oliveta

Exclusive luxury property with private pool in Siena countryside Borgo la Chiusa

10.0 out of 10, Exceptional, (1)
"Our stay at Borgo la Chiusa was fantastic. Our family of 12 all agreed that the home was more than the pictures and the descriptions could show online. We will come back and stay here again and would also refer this home to all of our family and friends. The location was perfect. We did day trips to many of the cities and towns. We had Francesca prepare us a meal in the home which was delicious. The experience that our children and grand children had watching the meal being prepared was an...
Exclusive luxury property with private pool in Siena countryside Borgo la Chiusa

Charming apartment in the Historic Center of Siena

10.0 out of 10, Exceptional, (18)
Charming apartment in the Historic Center of Siena

Beautiful private villa with A/C, WIFI, TV, terrace, pets allowed, panoramic view and parking

10.0 out of 10, Exceptional, (1)
"Petit appartement confortable avec tous les services. Une vue extraordinaire sur le vallée du Chianti. Près de tout. Très propre. Le village de Castellina a été notre coup de coeur avec d'excellents restaurants. Les petits déjeuners sur la terrasse de l'appartement devant la vallée ont été forts appréciés. Merci à notre hôte."
Beautiful private villa with A/C, WIFI, TV, terrace, pets allowed, panoramic view and parking
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.
Save an average of 15% on thousands of hotels when you're signed in