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Santa Maria Holiday Rentals

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Our top choices for Santa Maria holiday rentals

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.
Cottage in Tuscany with Pool & Olive Groves

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
A Cottage Wrapped in Cypress Dreams

Tuscan Retreat with Pool

Tuscan Retreat with Pool
Lucignano
9.6 out of 10, Exceptional, (56 reviews)
"Absolutely loved the peaceful atmosphere here! The shared swimming pool was perfect for a refreshing dip, We also enjoyed al fresco dining under the gazebo with the BBQ, The owners were friendly and helpful, making our stay even more enjoyable,"
United States
Anonymous traveller
Tuscan Retreat with Pool

Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (33 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 NZ$306
includes taxes & fees
5 July - 6 July
Villa di Sotto

Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (111 reviews)
"It was very well located ."
Canada
Marlenne
The price is NZ$321
includes taxes & fees
23 June - 24 June
Meublé Il Riccio

Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (68 reviews)
"This was our second stay. The property is beautiful and our room was lovely. The breakfast was one of the best on our trip in Italy."
Canada
Dr Anne
The price is NZ$345
includes taxes & fees
23 June - 24 June
Villa Curina Resort

Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (91 reviews)
"Very good accommodation in the heart of Val’d’Orcia. Reasonably priced"
Finland
Jarkko
The price is NZ$346
includes taxes & fees
25 June - 26 June
Casanova - Panoramic Rooms and Suites

Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (103 reviews)
"Staff was great, and they even scheduled transportation to and from the train station for us. Great location on the main strip of Montepluciano!"
United States
Nicholas
The price is NZ$178
includes taxes & fees
13 July - 14 July
Residenza Fabroni

RESIDENCE LECCIO

RESIDENCE LECCIO
Asciano
9.6 out of 10, Exceptional, (7 reviews)
"Very nice, affordable place in beautiful area"
United States
Corey
The price is NZ$164
includes taxes & fees
29 June - 30 June
RESIDENCE LECCIO

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (177 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is NZ$403
includes taxes & fees
22 June - 23 June
Abbadia Sicille Relais

La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (144 reviews)
"Great location."
United States
James
The price is NZ$274
includes taxes & fees
19 July - 20 July
La Locanda di San Francesco

Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (138 reviews)
"Wonderful place - clean, comfortable, quiet with excellent hosts. Perfect location near everything in town including the parking. Can’t wait to return!"
United States
Shelly
The price is NZ$243
includes taxes & fees
25 June - 26 June
Bed & Breakfast Vicolo dell'Oste

Ca' Bianca Tuscany Relais

Ca' Bianca Tuscany Relais
Siena
10.0 out of 10, Exceptional, (44 reviews)
"Clean room, amazing staff"
Canada
Talha
The price is NZ$571
includes taxes & fees
22 June - 23 June
Ca' Bianca Tuscany Relais

Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (147 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
The price is NZ$386
includes taxes & fees
30 June - 1 July
Hotel San Gregorio

Bosco della Spina

Bosco della Spina
Murlo
9.6 out of 10, Exceptional, (172 reviews)
"Lovely stay! I would highly recommend this hotel. The indoor pool was just so enjoyable after a day out sightseeing. "
United Kingdom
Lizl
The price is NZ$230
includes taxes & fees
24 June - 25 June
Bosco della Spina

L'Olmo

L'Olmo
Pienza
10.0 out of 10, Exceptional, (25 reviews)
"Absolutely first class and friendly Perfect location "
United States
Jennifer
The price is NZ$1,305
includes taxes & fees
12 July - 13 July
L'Olmo

Villa Fontis Rapolano

Villa Fontis Rapolano
Rapolano Terme
The price is NZ$186
includes taxes & fees
22 June - 23 June
Villa Fontis Rapolano

Holiday home with panoramic terrace ideal for families and couples

Holiday home with panoramic terrace ideal for families and couples
Cortona
The price is NZ$162
includes taxes & fees
24 June - 25 June
Holiday home with panoramic terrace ideal for families and couples

2 Cuori e 1 Yurta Glamping in Toscana

2 Cuori e 1 Yurta Glamping in Toscana
Asciano
The price is NZ$573
includes taxes & fees
23 June - 24 June
2 Cuori e 1 Yurta Glamping in Toscana

iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (37 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
The price is NZ$237
includes taxes & fees
22 June - 23 June
iConic Wellness Resort
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 holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Santa Maria holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Santa Maria. 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 Santa Maria. 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 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 holiday 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 Santa Maria short-term rentals, that won’t be hard to do.

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 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 an electric kettle. 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.