Santa Maria Vacation Rentals

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Our top choices for Santa Maria vacation rentals

A Cottage Wrapped in Cypress Dreams

A Cottage Wrapped in Cypress Dreams
Lucignano
9.4 out of 10, Exceptional, (19 reviews)
"Really nice agriturismo. Good beds, kitchen and living room are suffficient. Pool is really great."
United States
Anonymous traveller
The price is CA $153
CA $398 total
includes taxes & fees
May 22 - May 23
A Cottage Wrapped in Cypress Dreams

Cottage in Tuscany with Pool & Olive Groves

Cottage in Tuscany with Pool & Olive Groves
Lucignano
9.4 out of 10, Exceptional, (18 reviews)
"Het was een prima verblijf, het enige minpuntje was dat een badkamer in de kelder was, dus een stel moest 2 trappen naar beneden. Verder alles goed geregeld, schoon en mooi zwembad. De barbecue werd na gebruik door de eigenaar ‘s morgens vroeg helemaal schoongemaakt. Super lux 😃"
Germany
sylvia w.
The price is CA $73
CA $318 total
includes taxes & fees
Jun 7 - Jun 8
Cottage in Tuscany with Pool & Olive Groves

Rustic Retreat With Pool

Rustic Retreat With Pool
Lucignano
The price is CA $290
CA $324 total
includes taxes & fees
Jun 3 - Jun 4
Rustic Retreat With Pool

Tuscan Retreat with Pool

Tuscan Retreat with Pool
Lucignano
9.6 out of 10, Exceptional, (56 reviews)
"Had a pleasant stay at this Tuscan gem, The owners were incredibly hospitable, and we enjoyed the peaceful atmosphere, While we did not use the pool since it opens in June, the garden was a perfect spot for relaxation, A great home base for our Tuscany adventures"
United States
Anonymous traveller
The price is CA $220
CA $305 total
includes taxes & fees
Jun 10 - Jun 11
Tuscan Retreat with Pool

Tuscan Retreat With Pool

Tuscan Retreat With Pool
Lucignano
The price is CA $280
CA $313 total
includes taxes & fees
Jun 8 - Jun 9
Tuscan Retreat With Pool

Cottage in Tuscany With Pool & Olive Groves

Cottage in Tuscany With Pool & Olive Groves
Lucignano
The price is CA $281
CA $313 total
includes taxes & fees
Jun 7 - Jun 8
Cottage in Tuscany With Pool & Olive Groves

DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (28 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
The price is CA $130
CA $149 total
includes taxes & fees
May 24 - May 25
DormiVeglia B&B

TuscanyLettings Studio&Room

TuscanyLettings Studio&Room
Pienza
10.0 out of 10, Exceptional, (2 reviews)
"Lugar maravilhoso, localização perfeita, super limpo e aconchegante."
Brazil
Lucas
The price is CA $142
CA $162 total
includes taxes & fees
Jun 14 - Jun 15
TuscanyLettings Studio&Room

Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (32 reviews)
"Beautiful villa, very spacious, gorgeous property and great restaurant on the property to have a delicious meal. Staff very welcoming. Close to other main cities, like Siena, for day trips. We loved sitting by the pool, although it wasn’t heated, so too cold to use in April. We did love using the indoor heated pool and hot tub each day. We had a fabulous time and hope to go back someday! "
Canada
Jeremy
The price is CA $206
CA $226 total
includes taxes & fees
May 29 - May 30
Villa di Sotto

Dolce Casa 2 Summary:

Dolce Casa 2 Summary:
Arezzo
The price is CA $122
CA $170 total
includes taxes & fees
May 27 - May 28
Dolce Casa 2 Summary:

Holiday home with panoramic terrace ideal for families and couples

Holiday home with panoramic terrace ideal for families and couples
Cortona
The price is CA $101
CA $129 total
includes taxes & fees
May 28 - May 29
Holiday home with panoramic terrace ideal for families and couples

Eagle House

Eagle House
CHIANCIANO
10.0 out of 10, Exceptional, (3 reviews)
"Paolo and Monica were such gracious and enthusiastic hosts. The property is beautiful, and the hospitality was great. Paolo and Monica helped plan our itinerary each day which made for a stress-free week. The highlight was the interaction with owls, eagles, and other animals, as well as the wine cave and the history behind it. Thanks again, Paolo and Monica! "
United States
Rob C.
The price is CA $287
CA $420 total
includes taxes & fees
May 25 - May 26
Eagle House

Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (85 reviews)
"We loved our stay and wish we could have stayed longer. Our room was clean & comfortable. The view was AMAZING. We had breakfast included daily which was very good and had a bunch of gluten free options. Our bodies were tired after the hustle & bustle of Florence & Rome so we booked into the “light spa” and had the hot pools to ourselves. It was a short walk to town. We wish we could have stayed longer and plan to be back. "
Canada
Ron
The price is CA $262
CA $294 total
includes taxes & fees
Jun 5 - Jun 6
Casanova - Panoramic Rooms and Suites

Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (102 reviews)
"Beautiful apartment, well located, best host and yummy breakfast in a beautiful cafeteria close by. "
United States
Johanna
The price is CA $126
CA $145 total
includes taxes & fees
Jun 9 - Jun 10
Residenza Fabroni

Albergo Diffuso Borgo Santo

Albergo Diffuso Borgo Santo
Asciano
The price is CA $305
CA $344 total
includes taxes & fees
Jun 9 - Jun 10
Albergo Diffuso Borgo Santo

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (175 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is CA $289
CA $323 total
includes taxes & fees
May 26 - May 27
Abbadia Sicille Relais

Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti

Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti
Monteaperti
10.0 out of 10, Exceptional, (2 reviews)
"We loved this place. Modern cabin set in a rustic Tuscan setting. Beautiful property, very comfortable stay, and very attentive staff. Family owned and operated. Amazing restaurant just steps away. A perfect place for respite"
United States
Ian F.
The price is CA $255
CA $298 total
includes taxes & fees
Jun 15 - Jun 16
Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti

Castello di Modanella

Castello di Modanella
Rapolano Terme
7.8 out of 10, Good, (16 reviews)
"To far out"
United States
Dennis
The price is CA $131
CA $198 total
includes taxes & fees
May 26 - May 27
Castello di Modanella

Oasi del Borgo Montefollonico

Oasi del Borgo Montefollonico
Montefollonico
The price is CA $388
CA $442 total
includes taxes & fees
May 24 - May 25
Oasi del Borgo Montefollonico

Tolletta 10 e Lode - One Bedroom House, Sleeps 4

Tolletta 10 e Lode - One Bedroom House, Sleeps 4
Arezzo Centro Storico
10.0 out of 10, Exceptional, (1 review)
" La casa pulitissima è molto bella, l’host molto disponibile e gentile, risponde sempre e anche subito. La posizione ottimale per fare il giro dei mercatini e di tutta la città. Consigliatissima "
Italy
Maria Gemma
The price is CA $132
CA $243 total
includes taxes & fees
May 28 - May 29
Tolletta 10 e Lode - One Bedroom House, Sleeps 4
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

Find out more about Santa Maria

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 Santa Maria. 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 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 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 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.