Montecastelli Vacation Rentals from ￥10,903: Search Short-Term Rentals

Q: What are some of the best vacation rentals that Montecastelli has to offer?

Beautiful stone house with garden and private pool. : This vacation home rental outside of Montecastelli is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the garden in this rental home to help you unwind.

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Montecastelli vacation rentals

Residence Arianna

Sovicille

"We had a 4 night’s stay here and used it as our base for tours around Toscany. It is located in a quiet area outside Siena. The apartment was nice and clean. We used the kitchen for minor cooking and that worked well. There is a supermarket close by and small restaurants in the town. The AC was working great. The host was very keen to share information on good places to see and was eager to make our stay as pleasant as possible. The breakfast was very nice and they also have a restaurant where...

Gitte Harrits

￥26,206 total

includes taxes & fees

Jul 14 - Jul 15

Riserva di Fizzano Residence

Castellina in Chianti

Janet

￥45,641 total

includes taxes & fees

Jul 29 - Jul 30

Premium bedding, down comforters, pillowtop beds, individually furnished

Tuscasì Aparthotel

Sovicille

Sergey

￥15,731 total

includes taxes & fees

Jul 19 - Jul 20

Apartment, 1 Bedroom, Ground Floor (Garden) | Exterior

Residence Il Paradiso

Guardistallo

Jason

￥16,330 total

includes taxes & fees

Jul 15 - Jul 16

Casa di Campagna in Toscana

Sovicille

Sally

￥25,220 total

includes taxes & fees

Aug 6 - Aug 7

2 outdoor pools, pool umbrellas, sun loungers

La Lunaria di Lajatico

Lajatico

Julia

￥69,695 total

includes taxes & fees

Jul 20 - Jul 21

Antico Borgo il Cardino

San Gimignano

Craig

￥23,336 total

includes taxes & fees

Jul 13 - Jul 14

Villa, Air conditioning, Courtyard View | Exterior

Villa Montecastello

Monteriggioni

Alvaro

￥34,174 total

includes taxes & fees

Jul 14 - Jul 15

Borgo Il Poggiaccio

Sovicille

Dean

￥40,762 total

includes taxes & fees

Jul 30 - Jul 31

Residence Borgo San Lorenzo a Linari

Sovicille

Monica

￥21,889 total

includes taxes & fees

Jul 28 - Jul 29

Il Pozzo di Sant'Andrea

Siena

Prem

￥20,128 total

includes taxes & fees

Jul 26 - Jul 27

Sportland

Colle di Val d'Elsa

Giorgio

￥9,339 total

includes taxes & fees

Jul 19 - Jul 20

Camping Boschetto Di Piemma

San Gimignano

Anonymous traveler

￥10,903 total

includes taxes & fees

Aug 1 - Aug 2

Tuscan Private Estate with Pool - 5 Charming Villas at Tenuta Cantona,

Toscana

￥69,581 total

includes taxes & fees

Jul 13 - Jul 14

Palazzo Pacini

Colle di Val d'Elsa

John

￥27,439 total

includes taxes & fees

Jul 19 - Jul 20

Beatabb

Guardistallo

Sheena

￥18,418 total

includes taxes & fees

Jul 13 - Jul 14

Room 'Castagno' – Agriturismo la Taverna di Celsa with Shared Pool

Sovicille

￥46,696 total

includes taxes & fees

Jul 19 - Jul 20

Studio, Patio, Ground Floor | Terrace/patio

Fullino Nero

Siena

Christian

￥20,026 total

includes taxes & fees

Jul 13 - Jul 14

Chic Tuscan apartment pool spectacular view modern comfort wifi air conditioning

San Rocco A Pilli

Vincent S.

￥107,233 total

includes taxes & fees

Jul 13 - Jul 14

Casa Vacanze Etrusco – Leccio Apartment

San Gimignano

￥36,419 total

includes taxes & fees

Jul 13 - Jul 14

View all properties

Find vacation rentals that suit your style

Aparthotels

Apartments

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Montecastelli Hotel Reviews

Hotel Palazzo San Lorenzo & SPA

10/10 Excellent

"Great stay and this lovely property. Beautiful room, great pool, we enjoyed everything immensely. My only minor issue was that when we arrived at breakfast both days, they were out of scrambled eggs at the buffet and didn't replace them. It was a very minor issue. Otherwise we had a fantastic stay."

Mormoraia

10/10 Excellent

"Unforgettable experience! Gorgeous scenery, we spent so much time just relaxing by the stunning pool and taking advantage of the poolside bar. The best hotel breakfast we had in Italy, included daily. The staff were so helpful and kind. They truly go the extra mile. My only minor critique is that the air conditioning was weaker than expected but we were also there during a heat wave! Staff helped remedy the situation with a fan- thank you! We will be back!"

Villa Sabolini

10/10 Excellent

"We came to this hotel unexpectedly and were so happy we found it. The staff are truly exceptional, friendly, attentive, accommodating, effective, welcoming. We arrived due to my wife having emergency surgery in Siena, we were supposed to be in Venice, and this hotel staff went to work making sure we were taken care of. The grounds are stunning as well, an amazing place to recover after surgery. The pool is beautiful and the restaurant is fantastic. I truly have enjoyed each meal I have had. The lunch I ordered of sliced beef with rocket, pecorino and tomato was perfectly cooked and so tasty. The bartender Bruno makes a fantastic Negroni and I have had the chance to taste it with 3 different small gins all from this region. The front office staff from Silvia, Valentina and each person we interacted with have been amazing. We were looking forward to the basset hounds as well, we have seen them lounging about but hope to get to meet them before our stay ends. A wonderful place to stay in the Tuscan countryside, and only a 20 minute drive to Siena."

Hotel Italia

10/10 Excellent

"Hotel Italia was an absolute gem. The staff were incredibly friendly and helpful — they understood we were tired from traveling with teens and even nailed a salon recommendation that turned out to be the best hair wash of my life, just minutes from the hotel. Our room was spotless, quiet, and the A/C worked perfectly; we didn’t hear a sound from neighbors or stair traffic. The location is a sweet spot — only 5 to 10 minutes from the tourist sights, yet tucked in a local neighborhood with bakeries and grocery stores, giving us that refreshing, peaceful feeling of being disconnected from the tourist rush. Breakfast was amazing, and the little teen-approved Duomo and gelato challenges made exploring even more fun. Bottom line: we’d come back and stay here again in a heartbeat. For anyone visiting Siena, Hotel Italia at Porta Camollia gives you that perfect “live like a local” buffer before diving into the Duomo and Piazza del Campo — and if you need a salon, just ask reception; their pick is solid."

Find out more about Montecastelli

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

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

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

Frequently asked questions

Are there vacation rentals in Montecastelli?

Yes, we offer vacation rentals close to top points of interest in Montecastelli, or you can select a more remote option if you're looking for a relaxing stay.

What are some of the best vacation rentals that Montecastelli has to offer?

Beautiful stone house with garden and private pool.: This vacation home rental outside of Montecastelli is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the garden in this rental home to help you unwind.

How many vacation rentals will I find in Montecastelli?

Expedia has 16 vacation rentals for your stay in Montecastelli.

What can I see and do in Montecastelli?

Explore the area and family-friendly sights such as Terre di Vini, or get out into nature at a spot like Alta Val d'Elsa River Park. In the larger area, you’ll find Medici Fortress and Porta all'Arco.

What are vacation rentals like in Montecastelli?

Vacation rentals are privately owned accommodations you can reserve for several days or longer in Montecastelli. Vacation rentals feature amenities like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about cleanliness, vacation rentals can offer a sense of safety away from shared hotel elevators and busy concierge desks while still allowing you to travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for family gatherings.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Montecastelli vacation rentals

Residence Arianna

Riserva di Fizzano Residence

Tuscasì Aparthotel

Residence Il Paradiso

Casa di Campagna in Toscana

La Lunaria di Lajatico

Antico Borgo il Cardino

Villa Montecastello

Borgo Il Poggiaccio

Residence Borgo San Lorenzo a Linari

Il Pozzo di Sant'Andrea

Sportland

Camping Boschetto Di Piemma

Tuscan Private Estate with Pool - 5 Charming Villas at Tenuta Cantona,

Palazzo Pacini

Beatabb

Room 'Castagno' – Agriturismo la Taverna di Celsa with Shared Pool

Fullino Nero

Chic Tuscan apartment pool spectacular view modern comfort wifi air conditioning

Casa Vacanze Etrusco – Leccio Apartment

Find vacation rentals that suit your style

Top Montecastelli Hotel Reviews

Hotel Palazzo San Lorenzo & SPA

Mormoraia

Villa Ermellina Siena, a Tribute Portfolio Hotel

Riparbella Country Suite

Hotel Sovestro

Poderi Arcangelo

Villa Sabolini

Hotel Toscana Ambassador

Hotel Italia

Find out more about Montecastelli

Frequently asked questions

Go further with the Expedia app