Holiday Homes in Province of 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
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Top Cities in Province of Siena

Holiday HomesHoliday Homes

Siena

Siena

Featured Holiday Homes in Province of Siena

Beautiful stone house with garden and private pool.
Escape to a serene garden setting with a charming stone building, surrounded by lush flowering plants and a meandering stone pathway.

Beautiful stone house with garden and private pool.

9.6 out of 10, Exceptional, (63)
"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
Relax in this open-plan living area with a patio offering a serene view of lush green surroundings.

Il Palazzetto

9.6 out of 10, Exceptional, (7)
Il Palazzetto
Borgo Argiano
Relax and socialize in this serene outdoor space, surrounded by breathtaking views and comfortable seating.

Borgo Argiano

10.0 out of 10, Exceptional, (67)
"Very comfortable stay. "
Borgo Argiano
The House of Alice, charm and relaxation
Experience the warm welcome of this traditional building, featuring a charming arched entrance and lush greenery.

The House of Alice, charm and relaxation

9.6 out of 10, Exceptional, (61)
"Beautiful accommodations, very remote and tranquil, loved the area and had a great time at the local restaurants.💕 Will be back!"
The price is AU$421
includes taxes & fees
17 Aug - 18 Aug
The House of Alice, charm and relaxation
Villa Le Tortore Tuscany private luxury pool relax
Relax by the pool surrounded by a lush olive tree and comfortable seating.

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
Experience the perfect blend of architecture and outdoor living with a brick facade, large windows, and comfortable seating areas.

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 in the heart of the real chiantishire
Traditional stone building with a charming entrance, surrounded by potted plants and a wooden door.

Farmhouse in the heart of the real chiantishire

10.0 out of 10, Exceptional, (140)
"The house was beautiful and the location was wonderfully quiet and set back from the main road. It’s quaint and cozy. There’s a short gravel road up to the cottage but it’s an easy drive. I would definitely book again."
Farmhouse in the heart of the real chiantishire
Porcilaia tiny countryside property, shared pool, ideal base to discover Tuscany
Relax by the tranquil pool surrounded by lounge chairs and a permanent structure.

Porcilaia tiny countryside property, shared pool, ideal base to discover Tuscany

10.0 out of 10, Exceptional, (25)
"Lovely place, lovely people, lovely environment "
Porcilaia tiny countryside property, shared pool, ideal base to discover Tuscany
Villa with large garden in the Chianti hills
Relax in a serene outdoor space with a gazebo, dining table, and comfortable seating.

Villa with large garden in the Chianti hills

9.4 out of 10, Exceptional, (70)
"Our group enjoyed staying in this location. It was comfortable and a perfect central location for exploring Tuscany."
Villa with large garden in the Chianti hills
The Casetta di Brunello, quiet and breathtaking views
Traditional building with a rustic door, brass knocker, and wooden shutters.

The Casetta di Brunello, quiet and breathtaking views

9.8 out of 10, Exceptional, (13)
"Looking for a village away from the tourist crowds, this is it!"
The price is AU$429
includes taxes & fees
6 Aug - 7 Aug
The Casetta di Brunello, quiet and breathtaking views
Spacious Luxury Apartment: pool, stunning views, 15-min walk from Siena center!
Relax by the serene pool surrounded by lush greenery and comfortable deck chairs.

Spacious Luxury Apartment: pool, stunning views, 15-min walk from Siena center!

9.6 out of 10, Exceptional, (32)
"Renting this villa was a relaxing, enjoyable way to experience Siena and the surrounding countryside. Lovely pool and grounds."
Spacious Luxury Apartment: pool, stunning views, 15-min walk from Siena center!
Casa Vacanze Le Case
Relax by the serene pool surrounded by a pebble-lined deck and lounge chairs.

Casa Vacanze Le Case

9.0 out of 10, Wonderful, (7)
"Situata in una posizione ideale per trascorrere un momento di relax accompagnati da una vista eccezionale. Davvero bella location."
The price is AU$193
includes taxes & fees
24 Aug - 25 Aug
Casa Vacanze Le Case
12km North of Siena with a stunning view pool & tenniscourt 3 bedrooms ensuite
Relax by the serene pool surrounded by lush greenery and comfortable lounge chairs.

12km North of Siena with a stunning view pool & tenniscourt 3 bedrooms ensuite

10.0 out of 10, Exceptional, (23)
"Lovely place"
12km North of Siena with a stunning view pool & tenniscourt 3 bedrooms ensuite
Fattoria di Fugnano by Interhome
Cozy space with a stone wall, wooden beams, and a large window offering a view of the outdoors.

Fattoria di Fugnano by Interhome

9.0 out of 10, Wonderful, (10)
Fattoria di Fugnano by Interhome
Farmhouse in old mill nestled in the beautiful Chianti hills
Archways and brick columns frame this spacious room with a high ceiling, perfect for showcasing artwork or photography.

Farmhouse in old mill nestled in the beautiful Chianti hills

8.6 out of 10, Excellent, (17)
"A beautiful place to stay and very friendly hosts; Roberto and Rafaella will do anything to make your stay unforgettable. The house has everything you need and the pool is nice and beautiful. Lots of nice places to visit in the neighbourhood. I can surely recommend this Farmhouse!!!!"
Farmhouse in old mill nestled in the beautiful Chianti hills
Historic home in Montalcino
Cozy space with a stone wall, arched window, and traditional wooden furniture.

Historic home in Montalcino

10.0 out of 10, Exceptional, (3)
"Excellent host, clean home, beautifully appointed, and located in the heart of Montalcino. Walkable to grocery store and many restaurants."
Historic home in Montalcino
Borgo Buio Town House, house in the historic center
Kitchen area with microwave, sink, and central island.

Borgo Buio Town House, house in the historic center

10.0 out of 10, Exceptional, (17)
"The hosts were very helpful and friendly and made our stay easy! The town of Montepulciano is very special and we would gladly stay again!"
Borgo Buio Town House, house in the historic center
Air Conditioned 15th Century House with Pool on Wine Estate
Cozy living room with a fireplace, sofa set, and dining area featuring a kitchen with pendant lighting.

Air Conditioned 15th Century House with Pool on Wine Estate

10.0 out of 10, Exceptional, (66)
"Beautiful peaceful place to stay. Well stocked with everything we needed and comfortable living spaces."
Air Conditioned 15th Century House with Pool on Wine Estate
Farmhouse in Tuscany With Pool and Organic Garden
Traditional architecture meets serene garden surroundings, offering a peaceful dining area with a table and chairs.

Farmhouse in Tuscany With Pool and Organic Garden

7.0 out of 10, Good, (2)
"Beautiful views out in the Tuscan countryside in a vineyard. If you are looking for peace and quiet, this place is wonderful. "
Farmhouse in Tuscany With Pool and Organic Garden
Exclusive Stone Tower.
Enjoy dining and entertaining in this spacious kitchen with a large dining table, stove, and wine bottle and glasses.

Exclusive Stone Tower.

9.6 out of 10, Exceptional, (5)
"The tower was a perfect place for our trip to Tuscany! It had a ton of space with a full kitchen and living room. The town it is located in is fantastic. There is a small grocery store, a pizza place, and a fantastic restaurant where two people can get a delicious meal and drinks for about €30 all within walking distance. You can easily drive from the tower to Siena, Florence, Montalcino, Montepulciano, and I'm sure many other places that we didn't have time to get to. Sauro was a great host and...
The price is AU$269
includes taxes & fees
27 Aug - 28 Aug
Exclusive Stone Tower.
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
Sign in
Sign up, it's free

Top Province of Siena Hotel Reviews

La Certosa di Pontignano

La Certosa di Pontignano

10/10 Excellent
"Nice and cozy hotel situated in a quiet town, and we loved every moment of our stay here."
Mehmed 5-night trip
Posted 1 day ago
La Certosa di Pontignano