Province of Siena Vacation Rentals

Search over 1 million properties and 550 airlines worldwide.

Save 10% or more on select stays with Expedia Rewards

Free cancellation on most hotels. Because flexibility matters.

Featured Province of Siena Vacation Rentals

Hotel San Gregorio

Hotel San Gregorio

3 out of 5
Via Della Madonnina 4, Pienza, Siena
The price is P5,172 per night from 23 Dec to 23 Dec
Located in the heart of Pienza, this residence is within a 5-minute walk of Palazzo Piccolomini, Historic Centre of Pienza, and Palazzo Comunale. Pienza Cathedral ...
4.5/5 Wonderful! (57 reviews)
Clean hotel, good for short stay on city doorstep
"Right outside the old city centre which means it's only a very short stroll to all the sights and restaurants while easy to reach by car. Big room albeit a bit tired round the edges, but clean, and the bed was comfy."

Reviewed on Jun 15, 2021

Hotel San Gregorio
Il Tosco

Il Tosco

Via del Poliziano 13, Montepulciano, SI
The price is P13,965 per night from 23 Dec to 23 Dec
This family-friendly Montepulciano residence is located in the historical district, just steps from Val di Chiana and Torre del Pulcinella. Civic Museum and ...
5/5 Exceptional! (56 reviews)
Our Tuscan Home away from home
"This is our second visit to IL Tosco and I look forward to our next visit and the one after that and the one .......... The accommodations the food the staff ( all family members) are the best. Beautiful decorations a mix of antiques and modern comfort items. Worth a visit anytime of the year."

Reviewed on May 22, 2021

Il Tosco
Osteria del Borgo

Osteria del Borgo

Via Ricci 7, Montepulciano, SI
Situated in Montepulciano, this residence is steps from Val di Chiana, Palazzo Ricci, and Civic Museum. Piazza Grande and Consorzio del Vino Nobile di Montepulciano ...
4.5/5 Wonderful! (119 reviews)
"The location of this property is amazing, right in the center. However, it is very dated and could use updating. The mattress was very uncomfortable to sleep on."

Reviewed on Sep 23, 2021

Osteria del Borgo
You could be seeing lower prices

You could be seeing lower prices

With member prices, you could save 10% or more right now on thousands of properties.
Villa Cassia

Villa Cassia

Strada Provinciale, Pienza
Situated in Pienza, this villa is 3 mi (4.8 km) from Piazza delle Sorgenti and within 6 mi (10 km) of Fortress of Tentennano and Horti Leonini. Palazzo Chigi ...
Villa Cassia
Villa Sodi

Villa Sodi

Loc Bibbiano, Castellina in Chianti
Situated in a rural location, this villa is within 6 mi (10 km) of The Rock of Staggia, Monteriggioni Castle, and Church of San Lorenzo. City Hall Castellina ...
Villa Sodi
Villa Danilo

Villa Danilo

Loc Campo dell Amato, San Casciano dei Bagni, SI
Situated in San Casciano dei Bagni, this villa is 0.1 mi (0.1 km) from Val di Chiana and within 12 mi (20 km) of Archaeological Museum of Sarteano and Sarteano ...
Villa Danilo
Villa Nova

Villa Nova

Via del Gallo Nero, Villa a Sesta, Castelnuovo Berardenga, SI
Situated in Castelnuovo Berardenga, this villa is 3.1 mi (4.9 km) from Castle of Brolio and within 6 mi (10 km) of Felsina and Vittorio Alfieri Theater. Torre ...
Villa Nova
Fabio Apartments

Fabio Apartments

Vicolo delle Vergini 2, Angolo Piazza del Duomo, San Gimignano, SI
Located in San Gimignano City Centre, this apartment building is steps from Collegiate Church of Santa Maria Assunta, Loggia del Comune, and Podesta's Palace. ...
4.9/5 Exceptional! (25 reviews)
"Great location in the centre of town. Massimo is a great host who made it easy to check in and out. Apartment is very comfortable."

Reviewed on Jan 17, 2020

Fabio Apartments
Antico Brunello

Antico Brunello

Argiano Sant'Angelo in Colle 53024 Monta, lcino (Si), Montalcino, Tuscany
The price is P162,718 per night from 2 Dec to 2 Dec
Situated in Montalcino, this villa is within 9 mi (15 km) of Fortress of Montalcino, Civic and Diocesan Museum of Sacred Art of Montalcino, and Poggio Antico. ...
Antico Brunello
Il Poggiarone

Il Poggiarone

Loc. Poggiarone, Montepulciano, Siena
Situated in a rural location, this villa is 0.1 mi (0.1 km) from Val di Chiana and within 6 mi (10 km) of Church of St. Agnes and Colonna del Marzocco. Palazzo ...
Il Poggiarone
Le Pratola Luxury Villa

Le Pratola Luxury Villa

Località Le Pratola Gaiole in Chianti, Gaiole in Chianti
Situated in Gaiole in Chianti, this villa is 1.6 mi (2.5 km) from Meleto Castle and 2.2 mi (3.6 km) from Cantalici Winery. Church of San Sigismondo and Gaiole ...
Le Pratola Luxury Villa
Bellavista Della Rocca

Bellavista Della Rocca

Località Cispiano, Castellina in Chianti, Tuscany
Situated in a rural location, this apartment building is 3 mi (4.8 km) from Casa Vinicola Luigi Cecchi and 3.1 mi (5 km) from City Hall Castellina In Chianti. ...
Bellavista Della Rocca
Resort Olmo

Resort Olmo

Loc. Campo Maggio 66, Radda in Chianti
Situated in Radda in Chianti, this apartment building is 2.4 mi (3.9 km) from Il Molino di Grace Winery and within 6 mi (10 km) of Castello di Radda Winery and ...
Resort Olmo
Villa Rachele

Villa Rachele

Podere Civieri 10, Casole d'Elsa
Situated in Casole d'Elsa, this villa is 1.4 mi (2.3 km) from Archeological and Collegiate Church Museum and within 9 mi (15 km) of Art in Color and Ranuccio ...
Villa Rachele
Villa Giulia

Villa Giulia

Loc Santo Pietro frazione Pancole, San Gimignano, SI
Situated in a rural location, this villa is within 6 mi (10 km) of Sant'Agostino Church, Rocca of Montestaffoli, and Fortress of Montestaffoli. Ornithological ...
Villa Giulia
Villa Montalcinello

Villa Montalcinello

Via Montalcinello, Chiusdino, Siena
Situated in Chiusdino, this villa is 9.4 mi (15.1 km) from Abbazia di San Galgano and within 25 mi (40 km) of Piazza del Campo and I Canaloni del Torrente Farma. ...
Villa Montalcinello
Castelmuzio

Castelmuzio

Via della Pieve, Trequanda
Situated in Trequanda, this villa is 0.1 mi (0.1 km) from Val di Chiana and within 6 mi (10 km) of The Saints Peter and Andrew Church and Pieve di Corsignano. ...
Castelmuzio
Wonderful Private Villa With Private Pool, TV, Pets Allowed and Parking, Close to Montepulciano

Wonderful Private Villa With Private Pool, TV, Pets Allowed and Parking, Close to Montepulciano

Via S. Bono, Ascianello, Montepulciano, SI
Situated in a rural location, this villa is 0.1 mi (0.1 km) from Val di Chiana and within 3 mi (5 km) of Church of St. Agnes and Tenuta Valdipiatta. Colonna ...
Wonderful Private Villa With Private Pool, TV, Pets Allowed and Parking, Close to Montepulciano
Wonderful private villa for 4 people with WIFI, pool, A/C, TV, terrace and parking

Wonderful private villa for 4 people with WIFI, pool, A/C, TV, terrace and parking

Podere S. Ippolito, 38, Asciano, Tuscany
This family-friendly Asciano villa is located in the suburbs, 1.2 mi (1.9 km) from Crete Senesi, and within 6 mi (10 km) of Val di Chiana and Museo dell'Antica ...
Wonderful private villa for 4 people with WIFI, pool, A/C, TV, terrace and parking
Il Mercatale di Radda

Il Mercatale di Radda

Via Giorgio Amendola, Radda in Chianti
Situated in Radda in Chianti, this villa is 1.9 mi (3 km) from Castello di Radda Winery and 2.8 mi (4.5 km) from Castello d'Albola. Church of San Sigismondo ...
Il Mercatale di Radda
Don't see what you're looking for?
See all available properties in Province of Siena
View all properties
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.

Holiday Apartments in Province of Siena

Search for holiday rentals in Province of Siena on Expedia.com.ph! You can easily find your home rentals, villas, holiday apartments in Province of Siena using one of the methods below:

  • View our selection of featured holiday rentals in Province of Siena 
  • Use the map to find apartments and other holiday homes in the Province of Siena neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Province of Siena while they last

Look no further and take a look at our great range of rental properties in Province of Siena!

Top Cities in Province of Siena