Photo by Tim & Nat ✈

Holiday Homes in Montisi

    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
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Holiday Homes in Montisi

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. "
The price is AU$1,079
includes taxes & fees
31 Aug - 1 Sept
Borgo Argiano
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, (90)
"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
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

9.6 out of 10, Exceptional, (15)
"Looking for a village away from the tourist crowds, this is it!"
The price is AU$433
includes taxes & fees
7 Aug - 8 Aug
The Casetta di Brunello, quiet and breathtaking views
Casa Bacco - private house with a remarkable garden in the centre of Cortona
Traditional stone building with a charming outdoor seating area and balcony.

Casa Bacco - private house with a remarkable garden in the centre of Cortona

10.0 out of 10, Exceptional, (8)
"This home was outstanding from the moment we arrived. There were 6 adults and we had plenty of room to gather together. The courtyard is lovely for early morning coffee or evening wine. Close to everything that Cortona offers."
Casa Bacco - private house with a remarkable garden in the centre of Cortona
Podere Casorbica with free parking, large garden, private pool.
Stunning roses bloom against a trellis in a lush, garden.

Podere Casorbica with free parking, large garden, private pool.

9.4 out of 10, Exceptional, (15)
"The property was lovely. Wifi was intermittently availble throughout our stay."
Podere Casorbica with free parking, large garden, private pool.
old barn on Via Francigena
Cozy bedroom with a neatly made bed, bedside table, and chair, set against a rustic brick ceiling and natural light.

old barn on Via Francigena

9.8 out of 10, Exceptional, (12)
" Very nice place and Sara just awesome"
old barn on Via Francigena
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!
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
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
The Old Fashion House
Relax in this stylish living area with a sofa and dining table, featuring a kitchen with a stove and window.

The Old Fashion House

10.0 out of 10, Exceptional, (7)
"My husband and I spent a week here in April. We have been to Italy seven times, always staying in VRBO-type rentals and this rental stands apart as among the nicest. Recently renovated, well-equipped kitchen, balcony, comfortable heat, etc. You can see the owner, Giovanni, took great care with the design and remodeling. The location is perfect — just off the main street. We highly recommend this home! "
The Old Fashion House
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
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$297
includes taxes & fees
26 Aug - 27 Aug
Exclusive Stone Tower.
Relaxing Margherita Home Private Garden, Bucine, Italy
Enjoy al fresco dining and games on the patio, featuring a barbecue grill and ping pong table.

Relaxing Margherita Home Private Garden, Bucine, Italy

10.0 out of 10, Exceptional, (1)
"Our stay was awesome. Thank you very much.Only complaint: there was no toilet paper when we arrived. Although our host hopped on the problem right away, he brought us 2 rolls. Total. 1 for each bathroom. There were 5 of us and we stayed Mon-Thu. Kind of odd…Other than that, it was great. Would do it again."
Relaxing Margherita Home Private Garden, Bucine, Italy
Borgo Santa Lucia, Casa Legnaia
Relax by the serene pool surrounded by lush greenery and a historic town view.

Borgo Santa Lucia, Casa Legnaia

Borgo Santa Lucia, Casa Legnaia
Charming house in historical Chianti Estate
Relax on the patio surrounded by lush flowers and comfortable seating.

Charming house in historical Chianti Estate

Charming house in historical Chianti Estate
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)
"Very authentic dwelling. Just what we wanted to experience. It looked just like what life in this area must have looked 200 years ago. "
The price is AU$425
includes taxes & fees
17 Aug - 18 Aug
The House of Alice, charm and relaxation
Farmhouse in the greenery of the Tuscany countryside with private pool and view
Relax by the serene pool surrounded by lush greenery and rolling hills.

Farmhouse in the greenery of the Tuscany countryside with private pool and view

9.6 out of 10, Exceptional, (48)
"Wonderful garden, swimming pool and house, nice welcome by Marina."
Farmhouse in the greenery of the Tuscany countryside with private pool and view
Il Roseto - Special prices for 2024-25! ! Get a quote ! ! "Plan your dream"
Stroll through this historic square, surrounded by a traditional building with a clock tower and charming outdoor seating areas.

Il Roseto - Special prices for 2024-25! ! Get a quote ! ! "Plan your dream"

9.8 out of 10, Exceptional, (55)
"The location of Il Roseto made for a comfortable stay near all of the important venues and activities in Cortona."
Il Roseto - Special prices for 2024-25! ! Get a quote ! ! "Plan your dream"
A MAGICAL HOLIDAY IN TUSCANY
Cozy retreat with a large bed and floral-patterned bedspread, wooden door, and staircase.

A MAGICAL HOLIDAY IN TUSCANY

10.0 out of 10, Exceptional, (4)
"It was great, right in the main area of town. We had 2 full families of 4 and it worked out really well for us."
A MAGICAL HOLIDAY IN TUSCANY
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