Santa Maria Vacation Rentals

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Aug 3 - Aug 4
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Aug 15 - Aug 17

Vacation Rentals in Santa Maria

Casanova - Panoramic Rooms and Suites
Stroll through the serene courtyard, surrounded by lush greenery and beautifully lit by outdoor lights.

Casanova - Panoramic Rooms and Suites

3.0 star property
9.0 out of 10, Wonderful, (62)
"My fiancée and I enjoyed ourselves! It’s a beautiful place and I adored walking around in the nearby town. "
Casanova - Panoramic Rooms and Suites
Hotel San Gregorio
Enjoy dining under a shaded pergola surrounded by lush greenery and brick walls.

Hotel San Gregorio

3.0 star property
9.2 out of 10, Wonderful, (121)
"Fabulous location just outside the entrance to the main part of town. Property is stylish in an olde worlde way, perfect for relaxation."
The price is P13,080
P14,792 total
includes taxes & fees
Aug 10 - Aug 11
Hotel San Gregorio
Bosco della Spina
Surrounded by lush greenery and vineyards, this traditional complex offers a tranquil setting with a swimming pool and sun loungers.

Bosco della Spina

9.6 out of 10, Exceptional, (161)
"We enjoyed the scenery and service! Clean and comfortable. "
Bosco della Spina
Abbadia Sicille Relais
Relax in a serene outdoor space surrounded by lush greenery and tall trees, featuring a cozy fire pit and comfortable seating.

Abbadia Sicille Relais

4.0 star property
8.8 out of 10, Excellent, (159)
"An amazing place with a luxury feel. Comfy, welcoming and peacefully relaxing "
The price is P10,586
P11,847 total
includes taxes & fees
Aug 4 - Aug 5
Abbadia Sicille Relais
Residenza Fabroni
Stunning staircase with a grand, curved ceiling and elegant details.

Residenza Fabroni

8.8 out of 10, Excellent, (88)
"We had a wonderful stay, the staff was extremely friendly and helpful. Restaurants and shops were right at our doorstep."
The price is P4,896
P5,655 total
includes taxes & fees
Aug 4 - Aug 5
Residenza Fabroni
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 P36,448
P40,632 total
includes taxes & fees
Aug 31 - Sep 1
Borgo Argiano
Delcorto Suites
Adorned with intricate frescoes, this grand interior space features a series of arches leading to ornate metal gates.

Delcorto Suites

10.0 out of 10, Exceptional, (22)
"Rooms are magnificent "
The price is P11,870
P13,326 total
includes taxes & fees
Aug 5 - Aug 6
Delcorto Suites
Il Tosco
Wander through historic streets lined with traditional stone buildings and arched doorways.

Il Tosco

10.0 out of 10, Exceptional, (111)
"The people here are authentic and welcoming! The building, rooms and facilities are gorgeous! One of our most beautiful stays in our many trips to Italy "
The price is P16,909
P18,869 total
includes taxes & fees
Aug 4 - Aug 5
Il Tosco
Osteria del Borgo
Enjoy a panoramic view of the rolling hills and stone tower from the large arched window.

Osteria del Borgo

9.2 out of 10, Wonderful, (146)
"Jacopo and his family were super friendly, the restaurant is the best in Montepulciano and the views are breathtaking. If we come back we will stay at Osteria del Borgo again without a doubt. "
Osteria del Borgo
Podere La Chiusella
Relax by the pool surrounded by lounge chairs and umbrellas in a serene outdoor space.

Podere La Chiusella

9.4 out of 10, Exceptional, (30)
Podere La Chiusella
Castello di Modanella
Stroll through the historic entrance, lined with lush greenery and soft lighting.

Castello di Modanella

7.6 out of 10, Good, (14)
"Property is closing and looks like it. Very unfortunate, I was there 30 years ago with fond memories! Obviously I should have done more homework!! Very sad."
Castello di Modanella
Albergo Diffuso Borgo Santo
Relax by the serene pool surrounded by lush greenery and tall trees.

Albergo Diffuso Borgo Santo

The price is P22,239
P24,799 total
includes taxes & fees
Aug 5 - Aug 6
Albergo Diffuso Borgo Santo
Castello di Gargonza
Enjoy dining under the stars in our beautifully set outdoor area.

Castello di Gargonza

3.0 star property
9.2 out of 10, Wonderful, (39)
"Beautiful area and friendly staff. We stayed here several years ago and were so excited to return."
Castello di Gargonza
Borgo Argenina
Terrace/patio

Borgo Argenina

9.8 out of 10, Exceptional, (21)
"It is an amazing location nested among wineries and rolling hills. If you like a quiet and sophisticated location this is your ideal place. You will need a car to move around but, you will be rewarded by the view and the opportunities for wine tastings and small villages visits. "
Borgo Argenina
B&B in Montepulciano
Stroll through this charming passageway to a serene courtyard oasis.

B&B in Montepulciano

B&B in Montepulciano
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.
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Top Santa Maria Hotel Reviews

Hotel Relais II Chiostro di Pienza

Hotel Relais II Chiostro di Pienza

10/10 Excellent
"Loved this hotel - great location. Really quiet despite such a central location. Yes rooms are not super modern but they reflect the history of the building. Great pool and breakfast on the terrace."
Rachel 1-night trip
Posted 3 days ago
Hotel Relais II Chiostro di Pienza

Frequently asked questions

Can I find a vacation rental in Santa Maria?

Yes, we have vacation rentals near top local attractions in Santa Maria, or you can choose a secluded option if you're looking for a relaxing stay.

What are some of the best vacation home rentals in Santa Maria?

Borgo Argiano: You might want to consider this vacation home rental near Santa Maria, which is located on a river and has a balcony, a terrace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and an electric kettle. You can relax into your vacation with a garden and a library.

How many vacation rentals are there in Santa Maria?

With 3 Expedia vacation rentals, you're sure to find just the right place for your Santa Maria stay.

What’s there to see and do in Santa Maria?

Explore the area and family-friendly sights such as Arezzo Equestrian Centre, or get out into nature at a spot like Terme Antica Querciolaia. Valdichiana Outlet Village and San Giovanni Terme Rapolano are a couple of places you'll find in the larger area.

What’s a vacation rental in Santa Maria like?

Vacation rentals are privately owned properties where you can stay for a couple of days or more in Santa Maria. Vacation rentals feature extras like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from public hotel elevators and bustling concierge desks while still allowing you to travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for families.