Italy may have travel restrictions in place, including self-quarantine, due to COVID-19.

Find out moreOpens in new tab or window

Vacation Rentals in Siena

Search over 1 million properties and 550 airlines worldwide

Members save 10% more on select hotels, cars, activities and vacation rentals. Sign up.

Free cancellation on most hotels. Because flexibility matters.

Top Vacation Rentals in Siena

Borgo al Cerro

Borgo al Cerro

Loc. Casanova snc, Casole d'Elsa, SI

This family-friendly Casole d'Elsa residence is located in a rural location, 0.8 mi (1.3 km) from Archeological and Collegiate Church Museum, and within 9 mi ...

4.5/5Wonderful! (13 reviews)
In the heart of Tuscany

"Beautiful property and great rooms. This hotel is in the heart of Tuscany and 30-60 minutes from most of the hill towns of Tuscany and many other sites."…"

Reviewed on Oct 2, 2017

Borgo al Cerro
Antico Convento I Cappuccini - Villa & Wedding Venue

Antico Convento I Cappuccini - Villa & Wedding Venue

Montalcino, Tuscany

Situated in Montalcino, this villa is within 3 mi (5 km) of Fortress of Montalcino, Civic and Diocesan Museum of Sacred Art of Montalcino, and Poggio Antico. ...

5/5Exceptional! (1 review)
Very nice Villa, spacious, well kept, in a quiete place in the middle of the forest.

"Very nice Villa, spacious, well kept, in a quiete place in the middle of the forest but close the most beautiful towns in Tuscany. The manager is the kindest person. Huge swimming pool. Ideal for families."…"

Reviewed on Aug 12, 2019

Antico Convento I Cappuccini - Villa & Wedding Venue
Villetta Capanna

Villetta Capanna

Loc. Marmoraia Casole d'Elsa, Casole d'Elsa, Tuscany

Situated in Casole d'Elsa, this vacation home is 0.9 mi (1.4 km) from Val di Merse and within 12 mi (20 km) of San Leonardo al Lago and Museo del Cristallo di ...

Villetta Capanna
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.
"Il Fienile del Sole": Quality private house

"Il Fienile del Sole": Quality private house

Colle di Val d'Elsa, Tuscany

This family-friendly Colle di Val d'Elsa vacation home is located in a rural location, within a 5-minute walk of Piazza Arnolfo di Cambio and Museo del Cristallo ...

5/5Exceptional! (6 reviews)
A wonderful week in this fabulous Tuscan property!

"We are a family of four, (parents with two children of 8 and 3). We were looking for a property that ticked all the boxes for our summer holiday. The house is in a very good location, close to everything the area has to offer. The property is within a private gated condominium, and is split into ..."…"

Reviewed on Sep 8, 2019

"Il Fienile del Sole": Quality private house
Castel Brunello

Castel Brunello

Via del Ferralino, Sant'Angelo in Colle, Montalcino, Siena

Situated in a rural location, this apartment building is within 6 mi (10 km) of Poggio Antico, Abbazia di Sant'Antimo, and Fortress of Montalcino. Civic and ...

5/5Exceptional! (19 reviews)
ecc

"GreAt place to stay. Very friendly staff"…"

Reviewed on Sep 1, 2020

Castel Brunello
Hotel Residence San Gregorio

Hotel Residence San Gregorio

3 out of 5
Via Della Madonnina 4, Pienza, Siena
The price is ¥8,123 per night from Feb 16 to Feb 17

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 ...

4.5/5Wonderful! (51 reviews)

"overall all was great. It deserves to be a four star"…"

Reviewed on Feb 10, 2020

Hotel Residence San Gregorio
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 ...

4.5/5Wonderful! (117 reviews)

"We stayed 2 days and one night at this beautiful hotel and would definitely return in the future. Giacomo’s service made us feel welcome and was very helpful providing us with directions to get to the hotel and finding the parking. This place looks like an apartment with kitchen, living room and ..."…"

Reviewed on Oct 12, 2020

Osteria del Borgo
Casanovina, Castellina in Chianti, Siena and Chianti

Casanovina, Castellina in Chianti, Siena and Chianti

Castellina in Chianti, Tuscany

Situated in a rural location, this villa is within 1 mi (2 km) of Casa Vinicola Luigi Cecchi and City Hall Castellina In Chianti. Chianti Observatory and Isole ...

Casanovina, Castellina in Chianti, Siena and Chianti
Panoramic and cosy house in Tuscany countryside near Montalcino and Siena

Panoramic and cosy house in Tuscany countryside near Montalcino and Siena

Montalcino, Tuscany

Situated in Montalcino, this historic apartment building is 1.9 mi (3 km) from Torrenieri Montalcino Station and within 6 mi (10 km) of Museo del Tartufo and ...

5/5Exceptional! (6 reviews)
A wonderful, idyllic find & welcoming hosts

"'Montechiari' is a wonderful converted tuscan farmhouse at the top of a hill near Torrenieri. We couldn't have asked for a more beautiful or peaceful location and the 360 views were stunning. Angela and her husband were lovely and made us feel very welcome. It was a great location to explore the ..."…"

Reviewed on Sep 1, 2019

Panoramic and cosy house in Tuscany countryside near Montalcino and Siena
Podere Scopeto

Podere Scopeto

SP 541, Traversa Maremmana, Casole d'Elsa, Siena

Situated in Casole d'Elsa, this apartment building is 0.9 mi (1.4 km) from Val di Merse and within 12 mi (20 km) of Archeological and Collegiate Church Museum ...

Podere Scopeto
Residenza Fabroni

Residenza Fabroni

Via di Gracciano nel Corso, 12, Montepulciano, SI
The price is ¥16,303 per night from Feb 9 to Feb 10

Situated in Montepulciano, this historic residence is steps from Val di Chiana, Torre di Pulcinella, and Church of St. Augustine. Palazzo di Bucelli and Palazzo ...

4.8/5Exceptional! (22 reviews)
lmost perfect

"Stunning property run by a young, friendly and helpful couple. They’ve recently taken over the property and whilst it’s not quite perfect yet, it’s definitely a treat to stay there"…"

Reviewed on Aug 30, 2020

Residenza Fabroni
Best toscany’ s view

Best toscany’ s view

Poggibonsi, Tuscany

Situated in Poggibonsi, this apartment building is within 1 mi (2 km) of Church of San Lorenzo, Fountain of Fate, and Archeodromo di Poggibonsi. Poggio Imperiale ...

Best toscany’ s view
Girasole Country House

Girasole Country House

Podere Beccanella NR 19, Asciano, Siena

Situated near the airport, this cottage is within 6 mi (10 km) of Val di Chiana, San Giovanni Terme Rapolano, and Terme Antica Querciolaia. Saltalbero Adventure ...

Girasole Country House
Casa Vostra in Toscana, Nella Terra del Brunello

Casa Vostra in Toscana, Nella Terra del Brunello

Montalcino, Tuscany

Situated in Montalcino, this vacation home is within 6 mi (10 km) of Poggio Antico, Civic and Diocesan Museum of Sacred Art of Montalcino, and Fortress of Montalcino. ...

Casa Vostra in Toscana, Nella Terra del Brunello
Antico Brunello

Antico Brunello

Argiano Sant'Angelo in Colle 53024 Monta, lcino (Si), Montalcino, Tuscany
The price is ¥358,666 per night from Jan 17 to Jan 18

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
Charming Apartment,  In Typical Tuscan Agriturismo

Charming Apartment, In Typical Tuscan Agriturismo

Montepulciano, Tuscany

Situated in Montepulciano, this historic apartment building is within 2 mi (3 km) of Val di Chiana, Church of St. Agnes, and Colonna del Marzocco. Palazzo Avignonesi ...

Charming Apartment, In Typical Tuscan Agriturismo
RICCIOLO,4 sleeps, villa with private pool at exclusive use!

RICCIOLO,4 sleeps, villa with private pool at exclusive use!

San Gimignano, Tuscany

Located in the heart of San Gimignano, this romantic villa is within 6 mi (10 km) of San Lucchese Convent, Fountain of Fate, and Archeodromo di Poggibonsi. Poggio ...

RICCIOLO,4 sleeps, villa with private pool at exclusive use!
Tuscany is Open - Villa Apt - Amazing Views!

Tuscany is Open - Villa Apt - Amazing Views!

Montalcino, Tuscany

Situated in Montalcino, this historic apartment building is within 3 mi (5 km) of Museo del Tartufo, Val di Chiana, and San Giovanni d'Asso Station. Bosco della ...

4.9/5Exceptional! (11 reviews)
Gateway to Tuscany

"As two couples renting the villa, we appreciated the space available to us. Two bedrooms (the third we did not use), two full bathrooms, AND a partial bath on the main floor. The villa is decorated wonderfully but still feels quite homey. The kitchen was well equipped and there is a grill on the ..."…"

Reviewed on Oct 28, 2019

Tuscany is Open - Villa Apt - Amazing Views!
Beautiful farmhouse apartment in Tuscany with pool access

Beautiful farmhouse apartment in Tuscany with pool access

Rapolano Terme, Tuscany

Set in Rapolano Terme, this family-friendly apartment building is within 6 mi (10 km) of Terme Antica Querciolaia, Saltalbero Adventure Park, and Berardenga ...

Beautiful farmhouse apartment in Tuscany with pool access
Sarna Residence

Sarna Residence

Strada di Ripa d'Orcia, 1, San Quirico d'Orcia, SI

Situated in San Quirico d'Orcia, this residence is within a 15-minute walk of Horti Leonini and Collegiate Church of San Quirico. Chapel of our Lady of Vitaleta ...

4.7/5Exceptional! (23 reviews)

"Property in close proximity to points of interest, and transit to Siena by car is easy. Staff is very communicative and helpful. Rooms and common areas are clean, quiet and pleasantly set back from the road."…"

Reviewed on Dec 16, 2019

Sarna Residence
Don't see what you're looking for?
See all available properties in 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.

Vacation Apartments in Siena

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

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

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