Pieve a Maiano Vacation Rentals from CA $86: Short-Term Rentals for 2026

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Our top choices for Pieve a Maiano vacation rentals

An arched stone bridge with a white building on the right, featuring a balcony with plants.

1. Locanda Antico Borgo

Civitella in Val di Chiana

"What an absolutely beautiful stay, in a stunning place. Our host was attentive and kind, and the food was wonderful. The hotel and rooms were spotlessly clean, and particularly for my needs on a road trip with my 18 year old son, the accommodation offering two adjoining bedrooms was perfect, and we could park outside. Also very good value in my opinion. I would definitely return, it’s also ideal for couples and I would love to bring my wife here. "

Mr Andy

CA $169 total

includes taxes & fees

Oct 7 - Oct 8

A wooden table with two chairs on a balcony, overlooking a lush green landscape with trees and hills.

2. Casa Vacanze Le Fornaci

Pergine Valdarno

Lisette

CA $225 total

includes taxes & fees

Oct 4 - Oct 5

3. iConic Wellness Resort

Arezzo

Rheymarie

CA $190 total

includes taxes & fees

Sep 30 - Oct 1

A view of a historic town with prominent buildings and a church tower.

4. Cameracaffè Centro

Arezzo Centro Storico

Alexandre

CA $144 total

includes taxes & fees

Sep 14 - Sep 15

5. Palazzo Tarlati Residenza d'Epoca

Civitella in Val di Chiana

"Small family-owned inn located in center of Civitella in Val di Chiana. Room was comfortable and included all we needed. It was cold upon check-in which the co-owner tried to remedy with a space heater. It took a while. The room warmed up after the first night. The other co-owner kindly offered me our first night complimentary. (Thank you again.). The breakfast was simple and included fruit, juice, yogurt, sliced cheese and cold cut, packages sweets, tea, coffee and water. The owners were...

Marco

CA $193 total

includes taxes & fees

Sep 7 - Sep 8

A cozy living room with a stone wall, a wine rack, and two sofas.

6. Villa Cassia di Baccano

Loro Ciuffenna

Ralphvincent

CA $359 total

includes taxes & fees

Sep 8 - Sep 9

A stone building with arched windows and a gravel driveway.

7. Villa La Ginestra

Subbiano

Philippe

CA $161 total

includes taxes & fees

Sep 18 - Sep 19

A modern hotel room with large windows, a bed, a desk, and a chair.

8. B&B 52cento

Arezzo Centro Storico

Tina

CA $121 total

includes taxes & fees

Sep 14 - Sep 15

A spa area with a stone-walled arch, a hot tub, and a small window.

9. DormiVeglia B&B

Monte San Savino

Melissa Hyun Joo

CA $178 total

includes taxes & fees

Oct 5 - Oct 6

A narrow street with buildings on either side, stone walls, and a clear blue sky.

10. Tolletta 10 e Lode - One Bedroom House, Sleeps 4

Arezzo Centro Storico

Maria Gemma

CA $237 total

includes taxes & fees

Oct 1 - Oct 2

A pool area with two rectangular pools, surrounded by lounge chairs and umbrellas, set against a backdrop of vineyards and tall cypress trees.

11. Villa di Sotto

Castelnuovo Berardenga

Philippe

CA $245 total

includes taxes & fees

Sep 21 - Sep 22

A kitchen counter with a coffee maker, a paper towel holder, and a window with a view of greenery.

12. Holiday Home 'La Casina All'angolo'

Civitella in Val di Chiana

CA $254 total

includes taxes & fees

Sep 30 - Oct 1

A staircase with a wooden handrail, a potted plant, and a chair in a hallway.

13. Villa Fontis Rapolano

Rapolano Terme

Barbara

CA $143 total

includes taxes & fees

Sep 9 - Sep 10

A hotel room with a bed, two bedside lamps, a window with curtains, and a wall-mounted picture.

14. Alò - One Bedroom Apartment, Sleeps 2

Arezzo

CA $203 total

includes taxes & fees

Oct 4 - Oct 5

A courtyard with outdoor seating, a stone building with a tower, and a well-maintained garden.

15. Castello di Gargonza

Monte San Savino

Ariel

CA $361 total

includes taxes & fees

Sep 8 - Sep 9

A corridor with wooden flooring, a white cushioned bench, and shelves on both sides displaying bottles.

16. Allegra Toscana - Affittacamere Guest house

Arezzo Centro Storico

Justin

CA $149 total

includes taxes & fees

Sep 8 - Sep 9

A courtyard with a fountain, a pergola with flowers, and a building with a bell tower.

17. Relais Villa Belpoggio - Residenza d'Epoca

Loro Ciuffenna

Mona

CA $238 total

includes taxes & fees

Sep 28 - Sep 29

A hotel room with a bed, two bedside tables, a painting on the wall, and a vase with flowers on one of the tables.

18. Room-two-room Apartment

Saione

Thelma

CA $195 total

includes taxes & fees

Sep 8 - Sep 9

A balcony with a view of a sunset over a hilly landscape.

19. Stunning Loft nestled in the Tuscan countryside 15 minutes walk from the center.

Toscana

Louis / Jeanne M.

CA $166 total

includes taxes & fees

Sep 15 - Sep 16

A dining area with a wooden table, chairs, and a chandelier. There is a fireplace with a brick arch and a tiled floor.

20. Casa Biffoli Apartment

Bucine

CA $407 total

includes taxes & fees

Sep 7 - Sep 8

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Top Pieve a Maiano Hotel Reviews

Monastero di Cortona Hotel & Spa

10/10 Excellent

"Fantastic hotel, great staff, and great location One draw back was being charged for the hotel spa (Turkish bath, Sauna, Steam Room) it was €30 per person which isn’t terrible. But really should just be included with the amenities of the hotel Other than that it’s a great stay! Recommendation: Email about parking prior to arriving or don’t rent a car. Limited parking and saying the streets are narrow is an understatement"

Borgo San Felice Resort

10/10 Excellent

"An unforgettable stay in Tuscany!** Our stay at Borgo San Felice was truly incredible from beginning to end. From the moment our private driver picked us up at the train station and brought us through the beautiful Tuscan countryside to the resort, everything felt seamless and special. The property itself is absolutely breathtaking pictures truly don’t do it justice. We enjoyed dinner on the property, a wonderful couples massage, a private wine tour and tasting, and a relaxing pool day. We especially loved the live piano music in the evenings; it added such a romantic and elegant touch to the entire experience. The service was one of the highlights of our stay. A special shout-out to **Herman at the pool**, who was always attentive and completely on point with everything we needed. We also had an amazing experience at **Poggio Rosso**, where **Matia provided top-notch service** and made our Michelin-starred dinner feel even more memorable. Every detail from the beautiful grounds and peaceful atmosphere to the food, wine, spa, and exceptional hospitality—made our time here unforgettable. Borgo San Felice gave us exactly the Tuscany experience we were hoping for and more. We absolutely loved our stay and would return in a heartbeat. Highly recommend! 🇮🇹🍷✨"

Relais Villa Baldelli

8/10 Good

"The property was relaxing and quaint. The pool was nice and the overall Tuscan country vibe and decor was nice. The location was good and the rooms were spacious. It was not walkable to anything but if you have a rental car the location is great because Cortana is a wonderful town. The staff is kind and responsive however I had an issue with the cleaning ladies where they disposed of thing of my mine thinking it was trash. I found it odd that cleaning folks would take it upon themselves to touch my things as all. I asked them to not to clean our room anymore and they did it again the next day due to poor internal communication. It was annoying to deal with that but still I would say the staff tried their best to be helpful. Lastly, I was not a fan of their breakfast. They had the basics that were heavily rooted in sweets and pork both of which I don’t eat. They made fresh plain eggs but some veggies and maybe turkey meat would have been nice. Overall, for the price point this place is good."

Chapter Chianti, a Member of Design Hotels

10/10 Excellent

"We had a great stay at Chapter Chianti Resort! The staff were incredibly friendly and provided excellent customer service throughout our stay. Our room was very clean and comfortable, and the air conditioning worked great, which was especially appreciated during the summer heat. The resort has really nice amenities and was very peaceful and quiet. It never felt crowded, which made it a relaxing place to stay and enjoy Chianti. We drove from Florence and it took us about an hour, so it was an easy trip and a great escape from the city. Overall, we really enjoyed our stay and would definitely recommend Chapter Chianti Resort if you’re looking for a clean, comfortable, and relaxing place to stay in the Chianti area!"

Castello di Tornano Wine Resort

8/10 Good

"We really like this place. Pool was very nice and staff were mostly helpful. Its a pretty good location to visit multiple areas as well. Room air conditioner did an ok job upstairs in bedroom loft but struggled to keep it cool in the sitting area on main level. The view from the tower is awesome but its a climb"

Find out more about Pieve a Maiano

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Pieve a Maiano. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Pieve a Maiano?

Yes, we have vacation rentals near the most popular local attractions in Pieve a Maiano, or you can go with a more secluded option if you want a relaxing place to stay.

What's the top vacation rental that Pieve a Maiano has to offer?

Idyllic guest house in Tuscan country house style with swimming pool: This vacation home rental outside of Pieve a Maiano is located in a rural location and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You can relax into your vacation with a patio and a garden.

How many vacation rentals are there in Pieve a Maiano?

Expedia has 4 vacation rentals for your stay in Pieve a Maiano.

What’s there to see and do in Pieve a Maiano?

Explore the area and family-friendly sights such as Berardenga Riding Centre, or get out into nature at a spot like Piazza Guido Monaco. Fattoria La Vialla and Arezzo Equestrian Centre are a couple of places you'll find in the larger area.

What’s a vacation rental in Pieve a Maiano like?

Vacation rentals are private properties you can stay in for a long or short time in Pieve a Maiano. Vacation rentals feature extras such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of safety away from public hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive option for a small group gathering.

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Check prices for these dates

Our top choices for Pieve a Maiano vacation rentals

1. Locanda Antico Borgo

2. Casa Vacanze Le Fornaci

3. iConic Wellness Resort

4. Cameracaffè Centro

5. Palazzo Tarlati Residenza d'Epoca

6. Villa Cassia di Baccano

7. Villa La Ginestra

8. B&B 52cento

9. DormiVeglia B&B

10. Tolletta 10 e Lode - One Bedroom House, Sleeps 4

11. Villa di Sotto

12. Holiday Home 'La Casina All'angolo'

13. Villa Fontis Rapolano

14. Alò - One Bedroom Apartment, Sleeps 2

15. Castello di Gargonza

16. Allegra Toscana - Affittacamere Guest house

17. Relais Villa Belpoggio - Residenza d'Epoca

18. Room-two-room Apartment

19. Stunning Loft nestled in the Tuscan countryside 15 minutes walk from the center.

20. Casa Biffoli Apartment

Find vacation rentals that suit your style

Top Pieve a Maiano Hotel Reviews

Monastero di Cortona Hotel & Spa

Il Falconiere - Relais e Chateaux

Borgo San Felice Resort

Hu Norcenni Girasole Village

Relais Villa Baldelli

Villa Casagrande Resort & SPA

Agriturismo San Sano

Chapter Chianti, a Member of Design Hotels

Castello di Tornano Wine Resort

Find out more about Pieve a Maiano

Frequently asked questions

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