Santa Maria Holiday Rentals

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Check prices for these dates

Tonight
6 Nov - 7 Nov
Tomorrow
7 Nov - 8 Nov
This weekend
7 Nov - 9 Nov
Next weekend
14 Nov - 16 Nov

Holiday Rentals in Santa Maria

Breakfast, lunch, dinner served; local cuisine
Hotel San Gregorio
Hotel San Gregorio
3.0 star property
9.4 out of 10, Exceptional, (131)
"Excellent property! Very elegant and the service was wonderful. The breakfast was also excellent. The location could not be any better - the entry to the old town is just across from the hotel. Wish we could have stayed longer."
United States
DEBORAH
The price is NZ$396
includes taxes & fees
5 Dec - 6 Dec
Hotel San Gregorio
View from room
Abbadia Sicille Relais
Abbadia Sicille Relais
4.0 star property
8.8 out of 10, Excellent, (162)
"We stayed there for 1 night our our way to Rome. BEAUTIFUL. Bed was very comfortable as well. 10/10 will recommend to everyone "
United States
Brittnay
The price is NZ$144
includes taxes & fees
13 Nov - 14 Nov
Abbadia Sicille Relais
Front of property – evening/night
Casanova - Panoramic Rooms and Suites
Casanova - Panoramic Rooms and Suites
3.0 star property
9.0 out of 10, Wonderful, (78)
"Fantastic place"
United States
Clifford
The price is NZ$358
includes taxes & fees
9 Nov - 10 Nov
Casanova - Panoramic Rooms and Suites
Pool
Farmhouse in the hills with panoramic view and swimming pool
Farmhouse in the hills with panoramic view and swimming pool
9.6 out of 10, Exceptional, (75)
"Pros: Location Excellent pool Fantastic views Cons: Very, very outdated kitchen. Limited privacy due to people staying in outbuildings some of the time. A (not unfriendly) cat that's fed at the property and it seems to be assumed that guests will do this. There's a strong smell of cats in the kitchen and the area immediately outside it. Doors can't be left open to ventilate the property when using the pool as the cat may get inside. No consumables apart from toilet roll and cat food: not so...
United Kingdom
Calum S.
Farmhouse in the hills with panoramic view and swimming pool
Deluxe Apartment, 2 Bedrooms, Balcony
Bellarmino Boutique Apartments
Bellarmino Boutique Apartments
The price is NZ$161
includes taxes & fees
7 Nov - 8 Nov
Bellarmino Boutique Apartments
Lobby
Residenza Fabroni
Residenza Fabroni
8.8 out of 10, Excellent, (93)
"We had a great stay! Beautiful on the roof top terrace!"
United States
Jennifer
The price is NZ$172
includes taxes & fees
12 Nov - 13 Nov
Residenza Fabroni
Outdoor pool
Villa in Montalcino, exclusive for you, stunning view!!!
Villa in Montalcino, exclusive for you, stunning view!!!
10.0 out of 10, Exceptional, (86)
"We were a group of 4 couples and found there was plenty of room for all of us. The property as better in person than we had expected. We had a car so it was really easy to get around and see all the towns nearby. Very beautiful property with great vistas. So relaxing to hang out at the pool or the deck."
Canada
Elfrieda S.
Villa in Montalcino, exclusive for you, stunning view!!!
Terrace/patio
Borgo Argiano
Borgo Argiano
10.0 out of 10, Exceptional, (73)
"This place is perfect in every way. The grounds are gorgeous and the rooms smell and feel like you are at a luxury spa. Don’t look any further, this place is a must!"
United States
Marnie
Borgo Argiano
Property entrance
Il Tosco
Il Tosco
10.0 out of 10, Exceptional, (112)
"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 "
United States
Michael
The price is NZ$463
includes taxes & fees
18 Nov - 19 Nov
Il Tosco
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
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
Outdoor dining
Hilltop house in the heart of Tuscany with private pool
Hilltop house in the heart of Tuscany with private pool
9.8 out of 10, Exceptional, (94)
"Wonderful, quiet, beautiful. Everything you could want in country stay near a small village."
United States
Timothy C.
Hilltop house in the heart of Tuscany with private pool
Exterior
Il Poggio dell'Eremita
Il Poggio dell'Eremita
10.0 out of 10, Exceptional, (57)
"Located in a peaceful location, the house is charming and homey. The hosts are very kind and accommodating, and we had a wonderful stay. The view from the bedroom balcony is spectacular."
United States
Vivian K.
The price is NZ$280
includes taxes & fees
8 Nov - 9 Nov
Il Poggio dell'Eremita
Aerial view
Bosco della Spina
Bosco della Spina
9.6 out of 10, Exceptional, (169)
"We enjoyed the scenery and service! Clean and comfortable. "
United States
Sanaz
Bosco della Spina
Outdoor dining
Luxury Cortona view hilltop Villa
Luxury Cortona view hilltop Villa
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
Property grounds
Beautiful renovated stone villa - private pool,park,air conditioning,smart tv
Beautiful renovated stone villa - private pool,park,air conditioning,smart tv
9.8 out of 10, Exceptional, (35)
"Great location if you are trying to see Tuscany. The owners are the nicest people and very helpful. The house was fine for 4 of us with room to spare. Beautiful grounds, terrific, clean pool. Everything worked and everyone did their best to make us at home. It is just outside a small village so very quiet. You need a car to get around. Felt very safe --gated and secure. Would love to go back! "
United States
Tracy R.
Beautiful renovated stone villa - private pool,park,air conditioning,smart tv
Standard Room | Exterior
Osteria del Borgo
Osteria del Borgo
9.0 out of 10, Wonderful, (155)
"Very nice place to stay to experience Montepulciano. Great location, beautiful restaurant, very nice hospitality "
United States
Emily
Osteria del Borgo
Outdoor pool
BEAUTIFUL VILLA with private Pool in the heart of Chianti
BEAUTIFUL VILLA with private Pool in the heart of Chianti
10.0 out of 10, Exceptional, (27)
"We celebrated our baby turning 1 with family and friends and this property was an absolute dream! It comfortably fit our large group! We had a private chef host a dinner for us that Alessandro requested which was incredible! We are grateful for the family memories and would 100% return! Thank you for being such a great host! "
United States
Emily A.
BEAUTIFUL VILLA with private Pool in the heart of Chianti
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!
10.0 out of 10, Exceptional, (58)
"This was a stunning property and we thoroughly enjoyed our time enjoying the pool and the beautiful yard. Luigi was very helpful and quick to respond with any questions we had. The little village of Montisi is cute and we enjoyed walking there in the mornings. The location is a short drive to other towns and some of the best wines in Tuscany. It was very hot the week we were there - a few nights we found it difficult to sleep. Overall it is a beautiful location and Luigi was a fabulous host....
Canada
Neysa D.
Montalcino: Private villa in the heart of Tuscany, private pool,panoramic view!
Exterior
Casina in authentic Tuscany
Casina in authentic Tuscany
9.8 out of 10, Exceptional, (68)
"We had a lovely stay at the Casina, thank you to the family for such a welcome."
United Kingdom
David B.
Casina in authentic Tuscany
Fridge, microwave, oven, stovetop
Charming House in the heart of Montepulciano
Charming House in the heart of Montepulciano
9.8 out of 10, Exceptional, (64)
"The home was charming, spacious, and perfectly located. The host was responsive and helpful, making our stay comfortable and easy. A perfect spot to experience Tuscany—highly recommend!"
United States
Hank T.
Charming House in the heart of 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

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

10/10 Excellent
"Wow best experience, fantastic service, awesome staff, beautiful room and cortona is very impressive "
Niels 2-night trip
Posted 8 days ago
Monastero di Cortona Hotel & Spa

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, 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 NZ$144 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 kitchenware. 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.