Montecastelli Vacation Rentals from $64: 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.

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Our top choices for Montecastelli vacation rentals

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

Residence Il Paradiso

Guardistallo

Jason

$92 nightly

Jul 8 - Jul 9

Total with taxes and fees

Premium bedding, down comforters, pillowtop beds, individually furnished

Tuscasì Aparthotel

Sovicille

Sergey

$84 nightly

Jul 19 - Jul 20

Total with taxes and fees

Villa Mucellena

Casole d'Elsa

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

$146 nightly

Jul 8 - Jul 9

Total with taxes and fees

Villa, Air conditioning, Courtyard View | Exterior

Villa Montecastello

Monteriggioni

Alvaro

$186 nightly

Jul 15 - Jul 16

Total with taxes and fees

Il Pozzo di Sant'Andrea

Siena

Prem

$114 nightly

Jul 19 - Jul 20

Total with taxes and fees

Casa Vacanze Le Case

San Gimignano

Jackie

$123 nightly

Aug 1 - Aug 2

Total with taxes and fees

Antico Borgo il Cardino

San Gimignano

Craig

$122 nightly

Jul 6 - Jul 7

Total with taxes and fees

Seasonal outdoor pool, open 9:30 AM to 7:30 PM, pool umbrellas

Fattoria Podere i Luoghi

Casale Marittimo

$78 nightly

Jul 6 - Jul 7

Total with taxes and fees

Studio, Patio, Ground Floor | Terrace/patio

Fullino Nero

Siena

Christian

$97 nightly

Jul 18 - Jul 19

Total with taxes and fees

Detached house with garden a few minutes from the abbey of San Galgano

Toscana

$135 nightly

Jul 6 - Jul 7

Total with taxes and fees

Palazzo al Torrione 2

San Gimignano City Centre

Sophie

$108 nightly

Jul 12 - Jul 13

Total with taxes and fees

Riserva di Fizzano Residence

Castellina in Chianti

Janet

$247 nightly

Jul 10 - Jul 11

Total with taxes and fees

Palazzo Pacini

Colle di Val d'Elsa

John

$149 nightly

Jul 8 - Jul 9

Total with taxes and fees

Casa di Campagna in Toscana

Sovicille

Sally

$135 nightly

Jul 7 - Jul 8

Total with taxes and fees

Podere Cagnesi: Relaxation in nature

Podere Cagnesi

$216 nightly

Jul 6 - Jul 7

Total with taxes and fees

Materia Rooms San Gimignano

San Gimignano City Centre

$119 nightly

Jul 15 - Jul 16

Total with taxes and fees

Sportland

Colle di Val d'Elsa

Giorgio

$50 nightly

Jul 19 - Jul 20

Total with taxes and fees

2 outdoor pools, pool umbrellas, sun loungers

La Lunaria di Lajatico

Lajatico

Julia

$374 nightly

Jul 12 - Jul 13

Total with taxes and fees

Beatabb

Guardistallo

Sheena

$104 nightly

Jul 7 - Jul 8

Total with taxes and fees

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Top Montecastelli Hotel Reviews

Poderi Arcangelo

10/10 Excellent

"The place and view are breathtaking. The pool is a great plus!"

Hotel Leon Bianco

10/10 Excellent

"The very clean room that I stayed in was very large and perfectly appointed extra pillows and blankets were in the closet closet. It was a very comfortable room windows had room darkening curtains. Excellent for night sleeping. The bathroom was superb with a towel dryer, a hair dryer, a bidet toilet, and the shower was supreme. In addition to the toiletries that were left you would not be disappointed if you book a room at this hotel, the breakfast and staff were great room cleanings occurred every day staff at breakfast. We readily available to prepare anything that you wanted in addition to the buffet style that had consisted of eggs, toast, croissants, plenty of fruit, variety, meat, cereals, coffee, tea, among many other things you could not complain about the breakfast. The only thing that was disappointing to a degree was parking you had to park outside of the city limit and you are assigned a certain spot to park at fairly near to where your hotel would be. You were allowed to drive up to the hotel for luggage loading and unloading, I would certainly recommend this hotel."

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

Everything you need to know about Montecastelli vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Montecastelli vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Montecastelli vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Montecastelli vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Montecastelli. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Montecastelli in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $64 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Montecastelli rentals

At Expedia, we put the best Montecastelli vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Montecastelli rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Montecastelli vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Montecastelli. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.

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Our top choices for Montecastelli vacation rentals

Residence Il Paradiso

Tuscasì Aparthotel

Villa Mucellena

Residence Arianna

Villa Montecastello

Il Pozzo di Sant'Andrea

Casa Vacanze Le Case

Antico Borgo il Cardino

Fattoria Podere i Luoghi

Fullino Nero

Detached house with garden a few minutes from the abbey of San Galgano

Palazzo al Torrione 2

Riserva di Fizzano Residence

Palazzo Pacini

Casa di Campagna in Toscana

Podere Cagnesi: Relaxation in nature

Materia Rooms San Gimignano

Sportland

La Lunaria di Lajatico

Beatabb

Find vacation rentals that suit your style

Top Montecastelli Hotel Reviews

Poderi Arcangelo

Villa Ermellina Siena, a Tribute Portfolio Hotel

Hotel Leon Bianco

Mormoraia

Villa Sabolini

Hotel Toscana Ambassador

Hotel Italia

Hotel Palazzo San Lorenzo & SPA

Borgo Santo Pietro

Find out more about Montecastelli

Frequently asked questions

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