Holiday Rentals in Santa Maria

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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Holiday Rentals in Santa Maria

Breakfast, lunch, dinner served; local cuisine
Hotel San Gregorio

Hotel San Gregorio

3.0 star property
Pienza
9.4 out of 10, Exceptional, (134)
"Such friendly staff, loved Pienza and the property was such a good location! "
United Kingdom
Bethan
The price is €199
includes taxes & fees
5 Jan - 6 Jan 2026
Hotel San Gregorio
View from room
Abbadia Sicille Relais

Abbadia Sicille Relais

4.0 star property
Trequanda
8.8 out of 10, Excellent, (165)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is €79
includes taxes & fees
10 Dec - 11 Dec
Abbadia Sicille Relais
Pool
Farmhouse in the hills with panoramic view and swimming pool

Farmhouse in the hills with panoramic view and swimming pool

Ristonchia
9.6 out of 10, Exceptional, (75)
"Was wonderful and beautiful. "
United States
Alana A.
Farmhouse in the hills with panoramic view and swimming pool
Front of property – evening/night
Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites

3.0 star property
San Quirico d'Orcia
9.0 out of 10, Wonderful, (78)
"Fantastic place"
United States
Clifford
The price is €182
includes taxes & fees
11 Dec - 12 Dec
Casanova - Panoramic Rooms and Suites
Exterior
Il Poggio dell'Eremita

Il Poggio dell'Eremita

Sinalunga
10.0 out of 10, Exceptional, (59)
"Amazing property! Could not recommend more."
United States
Annika P.
The price is €146
includes taxes & fees
9 Dec - 10 Dec
Il Poggio dell'Eremita
Deluxe Apartment, 2 Bedrooms, Balcony
Bellarmino Boutique Apartments

Bellarmino Boutique Apartments

Montepulciano
6.0 out of 10, (1)
"Heat didnt work, it was FREEZING. Contact didnt seem to be local, seemed like they were managing remotely and couldnt or wouldnt send anyone to help. Nor did they really seem to care. Beautiful area though!"
United States
JON
The price is €105
includes taxes & fees
9 Dec - 10 Dec
Bellarmino Boutique Apartments
Lobby
Residenza Fabroni

Residenza Fabroni

Montepulciano
8.8 out of 10, Excellent, (93)
"We had a great stay! Beautiful on the roof top terrace!"
United States
Jennifer
The price is €83
includes taxes & fees
9 Dec - 10 Dec
Residenza Fabroni
Outdoor pool
17th century farmhouse with private pool and Wi-Fi and air conditioning

17th century farmhouse with private pool and Wi-Fi and air conditioning

Arezzo
9.2 out of 10, Wonderful, (39)
"We stayed as a family of 10 and had a great time. The accommodation is definitely rustic and traditional. It won’t suit everyone but if you’re looking to get back to basics look no further! For us as an Australian family it could have cleaner and we ended up doing cleaning ourselves to make it more comfortable. The bed linen and towels are also ready for a refresh. The host was great and provided a good summary of the local area and sights. Arezzo is a lovely day out. "
Australia
Anonymous traveller
17th century farmhouse with private pool and Wi-Fi and air conditioning
Property entrance
Il Tosco

Il Tosco

Montepulciano
10.0 out of 10, Exceptional, (114)
"The staff was courteous, the food was amazing, and the location was great. We were very impressed"
United States
Joshua
The price is €252
includes taxes & fees
9 Dec - 10 Dec
Il Tosco
Outdoor pool
Montalcino: Private villa in the heart of Tuscany, private pool,panoramic view!

Montalcino: Private villa in the heart of Tuscany, private pool,panoramic view!

Montisi
10.0 out of 10, Exceptional, (60)
"Beautiful property comfortable beds. Amazing views room two sit outside and enjoy sunsets."
United States
Darrel W.
Montalcino: Private villa in the heart of Tuscany, private pool,panoramic view!
Outdoor pool
Villa in Montalcino, exclusive for you, stunning view!!!

Villa in Montalcino, exclusive for you, stunning view!!!

Montalcino
10.0 out of 10, Exceptional, (86)
"Lovely villa in a beautiful location. "
United Kingdom
helen S.
Villa in Montalcino, exclusive for you, stunning view!!!
Terrace/patio
Borgo Argiano

Borgo Argiano

Castelnuovo Berardenga
10.0 out of 10, Exceptional, (73)
"Borgo Argiano is a beautiful property, very well run by Dario and staff. We highly recommend staying there if you are interested in exploring the Tuscan region. The apartments are large and they stock the kitchen for convenience It is also a winery and you could get a tour was well as a tasting of the delicious wines."
United States
Aurora
Borgo Argiano
Outdoor dining
Luxury Cortona view hilltop Villa

Luxury Cortona view hilltop Villa

cortona
10.0 out of 10, Exceptional, (50)
"Perfect location for day trips covering so many of the hilltop towns. Perfect accommodation for a group of 12 friends as each bedroom has it’s own bathroom.Perfect Villa for relaxing at home coffee every morning, lying by the pool and dinner watching the incredible sunsets.Perfect hosts. Denise takes care of everything while you are at the villa including cooking us a wonderful dinner. Mieke answered all our questions prior to our arrival very promptly. She has set the villa up perfectly and...
Australia
Belinda P.
Luxury Cortona view hilltop Villa
Standard Room | Exterior
Osteria del Borgo

Osteria del Borgo

Montepulciano
9.0 out of 10, Wonderful, (156)
"Staff and location were both excellent."
United States
Nicholas
Osteria del Borgo
Exterior
Casina in authentic Tuscany

Casina in authentic Tuscany

Cortona
9.8 out of 10, Exceptional, (69)
"This was a perfect stay. Picturesque location, close to Cortona and wineries and shops- we even walked to one of them. Best of all though was the kindness of the host who left us wine, salad, bruschette and cantucci. We would LOVE to come back one day! "
Australia
Catherine G.
Casina in authentic Tuscany
Aerial view
Bosco della Spina

Bosco della Spina

Murlo
9.6 out of 10, Exceptional, (169)
"Views are amazing. Staff are very pleasant and helpful. "
Canada
Maureen
Bosco della Spina
Panoramic Apartment, 2 Bedrooms, Balcony, Hill View | Terrace/patio
Borgo Argenina

Borgo Argenina

Gaiole in Chianti
9.8 out of 10, Exceptional, (22)
"A planned Tuscany trip in the making for over a year. Saw this property came up while doing research and had a wonderful and romantic history. The property was even more beautiful than the pictures posted. It definitely caters to all types of travellers. A perfect bed and breakfast stay. Definitely recommend and will be back again. "
Canada
Nancy
Borgo Argenina
Pool
House with garden and panoramic view over Lake Trasimeno

House with garden and panoramic view over Lake Trasimeno

Tuoro Sul Trasimeno
9.8 out of 10, Exceptional, (47)
"We had a very pleasant stay and enjoyed the house and surroundings to the fullest. The view of the lake is breathtaking.We had very good communication with the owner and bought some of his very good wines."
Denmark
Lars B.
House with garden and panoramic view over Lake Trasimeno
Interior
Delcorto Suites

Delcorto Suites

Montepulciano
10.0 out of 10, Exceptional, (32)
"Exceptional service great building felt like a Medici!"
United States
gaetano
The price is €173
includes taxes & fees
9 Dec - 10 Dec
Delcorto Suites
Outdoor pool
Villa with private pool, air conditioning near wineries at 3km from village

Villa with private pool, air conditioning near wineries at 3km from village

CHIANCIANO terme
9.4 out of 10, Exceptional, (46)
"It was amazing!! Great space for 7 adults. Pool area is great. Definitely do a meal with Leonardo. "
United States
Carol W.
Villa with private pool, air conditioning near wineries at 3km from village
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

Abbadia Sicille Relais

Abbadia Sicille Relais

10/10 Excellent
" In the middle of literally nowhere (for me) but so peaceful and serene! I love the history of this monastery. I must say as a solo traveler I was a little nervous at first because it’s very remote. I saw maybe 3 cars in the parking lot and two other guests. But it was safe! Checked in and got a restaurant recommendation for Ristorante Conte Matto, ten minutes away in a small town. The food was excellent and my server was very friendly, even walked me out when I left. Definitely worth the visit. I had the room at the end of the building with the ginormous tub. It was clean, very spacious and simply furnished with a very comfortable bed and pillows. Not gonna lie, I did push my couch up against the door since I was alone but I went to sleep that night and had the most peaceful sleep, waking up to the most beautiful sunrise. "
Safeena 1-night trip
Posted 5 days ago
Abbadia Sicille Relais

Find out more about Santa Maria

Everything you need to know about Santa Maria holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Santa Maria holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 Santa Maria holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Santa Maria holiday rentals: An excellent choice for every season

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

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Santa Maria holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Santa Maria holiday rentals we have selected for you start as low as €79 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Santa Maria rentals

At Expedia, we put the best Santa Maria holiday 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 Santa Maria 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 Santa Maria holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Santa Maria. 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

Can I find a holiday rental in Santa Maria?

Yes, there are holiday rentals close to the most popular sights in Santa Maria, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Santa Maria has to offer?

Borgo Argiano: This holiday home rental outside of Santa Maria is located on a river, and has a balcony, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a coffee maker. You can relax into your holiday with a garden and a library.

How many holiday rentals are there in Santa Maria?

With 3 Expedia holiday rentals, you're guaranteed 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 Siena Circuit, 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 wider area.

What’s a holiday rental in Santa Maria like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Santa Maria. Holiday rentals feature extras like kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, holiday rentals can provide a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for family trips.