Santa Maria Vacation Rentals from $106: Search Short-Term Rentals

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

Borgo Argiano : Visitors like this Santa Maria vacation home rental. It 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 kitchenware. You can relax into your vacation with a garden and a library.

Check prices for these dates

In two weeks

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Our top choices for Santa Maria vacation rentals

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

1. DormiVeglia B&B

Monte San Savino

Melissa Hyun Joo

$103 nightly

Oct 6 - Oct 7

Total with taxes and fees

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

2. Villa Fontis Rapolano

Rapolano Terme

Barbara

$83 nightly

Sep 9 - Sep 10

Total with taxes and fees

A stone building with a balcony, surrounded by lush greenery and flowering plants.

3. Il Poggio dell'Eremita

Sinalunga

Paul Q.

$180 nightly

Sep 7 - Sep 8

Total with taxes and fees

An arched stone gateway leading to a pathway lined with potted plants and lights.

4. Castello di Modanella

Rapolano Terme

Dennis

$140 nightly

Oct 1 - Oct 2

Total with taxes and fees

A historic building with a tower, a courtyard, and a well-lit entrance.

5. Abbadia Sicille Relais

Trequanda

Robert

$125 nightly

Oct 6 - Oct 7

Total with taxes and fees

A paved pathway lined with potted plants and neatly trimmed hedges, leading to a building with a red roof.

6. Artisti del Cavallo Tourism

Foiano della Chiana

Heiner

$84 nightly

Sep 7 - Sep 8

Total with taxes and fees

An outdoor seating area with a pergola, a fire pit, and a flower arrangement.

7. Fontelunga Hotel & Villas

Foiano della Chiana

Shelby

$328 nightly

Sep 19 - Sep 20

Total with taxes and fees

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

8. Castello di Gargonza

Monte San Savino

Ariel

$228 nightly

Oct 7 - Oct 8

Total with taxes and fees

A building with a sign for 'Residence Leccio' and a café named 'La Rumba Café'.

9. RESIDENCE LECCIO

Asciano

Corey

A patio area with outdoor seating, potted plants, and a view of the landscape.

10. Affitacamere Maria Gabriella

Pienza

Young Rok

$135 nightly

Oct 4 - Oct 5

Total with taxes and fees

A stone building with a sloped roof, a small porch, and a gravel driveway.

11. Podere La Chiusella

Rapolano Terme

"We enjoyed our stay. Everything was clean and comfortable, and the complex itself was impressive and a stunning place to stay. The location was also a convenient base for seeing Tuscany, and we had a great meal nearby in Rapolano Terme. Overall, it has the potential to be one of the coolest places you'll ever stay, though we did encounter a few technical issues regarding the shower and WiFi (which the hosts were quickly responsive about). I'd still recommend it, but it's helpful if you go in...

Kevin

$98 nightly

Sep 7 - Sep 8

Total with taxes and fees

A stone building with a tiled roof, surrounded by a well-maintained garden with various plants and a cactus in the foreground.

12. La Murata

Rapolano Terme

Elizabeth

$127 nightly

Oct 6 - Oct 7

Total with taxes and fees

An aerial view of a historic building complex with multiple structures, surrounded by lush greenery and vineyards.

13. Laurel House

Toscana

$387 nightly

Sep 7 - Sep 8

Total with taxes and fees

A pool surrounded by lush greenery and a distant view of a town.

14. Vacation Home 'Il Granaio' with Pool, Private Terrace & Wi-Fi

Monte San Savino

$404 nightly

Sep 7 - Sep 8

Total with taxes and fees

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

15. 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

$107 nightly

Oct 7 - Oct 8

Total with taxes and fees

A crowded restaurant with brick walls and multiple tables and chairs.

16. La Locanda di San Francesco

Montepulciano

Isabelle

$216 nightly

Sep 27 - Sep 28

Total with taxes and fees

A stone building with a gravel driveway and lush greenery.

17. Luxury resort in the Tuscan countryside

Trequanda

$232 nightly

Oct 6 - Oct 7

Total with taxes and fees

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

18. Villa di Sotto

Castelnuovo Berardenga

Philippe

$161 nightly

Sep 21 - Sep 22

Total with taxes and fees

An interior courtyard with stone columns, arches, and a mosaic.

19. Meublé Il Riccio

Montepulciano

Marlenne

$162 nightly

Sep 15 - Sep 16

Total with taxes and fees

A villa with a swimming pool, outdoor seating, and a tennis court.

20. Villa Curina Resort

Castelnuovo Berardenga

Mary

$150 nightly

Oct 4 - Oct 5

Total with taxes and fees

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Top Santa Maria 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"

Precise Tale Poggio Alla Sala

10/10 Excellent

"Incredible stay in a beautiful location. The staff were amazing and the hospitality was top tier. We will most definitely be back. The recommendations given were brilliant and the room was stunning along with the rest of the hotel. We didn’t dine in the restaurant but our breakfast each morning was also wonderful."

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! 🇮🇹🍷✨"

Palazzuolo

10/10 Excellent

"Slight problem on check in. I'd booked a triple room with balcony as we thought we'd have a bit more space also my husband and I like separate beds. We were given our key and found a double bed in a double room. Went back to reception and the explanation was a bit odd. Lots of ' but there are are only 2 of you' went on and no amount of me explaing would pacify them. I just kept getting told there was only 2 of us. Eventually after a very long journey we were tired so I gave in with promise of twin beds would be available the next morning. Still not sure that I got what id paid for. The room had a superb view and a very small balcony but it had sun all day. The view was amazing. Perfect view of the city of Montecattini. True Tuscan scenary and absolutely stunning sunsets. Bathroom a bit small but it was clean and had a walk in shower. Beds very comfortable with nice pillows."

Find out more about Santa Maria

Everything you need to know about Santa Maria 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 Santa Maria 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 Santa Maria vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Santa Maria vacation 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 low season months. For more hustle and bustle, you may prefer to visit Santa Maria 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 $106 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 Santa Maria rentals

At Expedia, we put the best Santa Maria 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 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 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 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 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: Visitors like this Santa Maria vacation home rental. It 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 kitchenware. 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 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 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.

Room 1

Check prices for these dates

Our top choices for Santa Maria vacation rentals

1. DormiVeglia B&B

2. Villa Fontis Rapolano

3. Il Poggio dell'Eremita

4. Castello di Modanella

5. Abbadia Sicille Relais

6. Artisti del Cavallo Tourism

7. Fontelunga Hotel & Villas

8. Castello di Gargonza

9. RESIDENCE LECCIO

10. Affitacamere Maria Gabriella

11. Podere La Chiusella

12. La Murata

13. Laurel House

14. Vacation Home 'Il Granaio' with Pool, Private Terrace & Wi-Fi

15. Locanda Antico Borgo

16. La Locanda di San Francesco

17. Luxury resort in the Tuscan countryside

18. Villa di Sotto

19. Meublé Il Riccio

20. Villa Curina Resort

Find vacation rentals that suit your style

Top Santa Maria Hotel Reviews

Monastero di Cortona Hotel & Spa

Il Falconiere - Relais e Chateaux

Villa Tiberini Wine Relais

Precise Tale Poggio Alla Sala

Borgo San Felice Resort

L'Orto delle Terme

Palazzuolo

Villa di Piazzano - Small Luxury Hotel of the World

Hotel Corsignano

Find out more about Santa Maria

Frequently asked questions