Santa Maria Holiday Rentals

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Check prices for these dates

Tonight
22 Dec - 23 Dec
Tomorrow
23 Dec - 24 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Santa Maria holiday rentals

View from room
Abbadia Sicille Relais

Residence in Trequanda

Abbadia Sicille Relais
4.0 star property
8.8 out of 10, Excellent, (166)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is NZ$149
includes taxes & fees
11 Jan - 12 Jan 2026
Abbadia Sicille Relais
Classic Double or Twin Room, 1 Double Bed
THE MONNA LISA RESORT

Townhouse in Arezzo

THE MONNA LISA RESORT
9.6 out of 10, Exceptional, (8)
"Massimiliano was a great host, but we were the only guests and the restaurant was closed. The hotel was basically unmanaged. It should not have been listed as a hotel. "
United States
Bart
The price is NZ$293
includes taxes & fees
1 Jan - 2 Jan 2026
THE MONNA LISA RESORT
Exterior
Meublé Il Riccio

Townhouse in Montepulciano

Meublé Il Riccio
9.8 out of 10, Exceptional, (86)
"Staff is great and many good restaurants in short walking distance."
United States
Mark
Meublé Il Riccio
Suite Bernardo, Panoramica al terzo piano senza ascensore
PienzaLettings Suites

Townhouse in Pienza

PienzaLettings Suites
10.0 out of 10, Exceptional, (1)
"Fantastic room in the city center, close to everything in Pienza"
Norway
Tom
The price is NZ$158
includes taxes & fees
23 Dec - 24 Dec
PienzaLettings Suites
Camera Superior, vista città, primo piano senza ascensore
TuscanyLettings Studio&Room

Townhouse in Pienza

TuscanyLettings Studio&Room
10.0 out of 10, Exceptional, (1)
"メイン通りの好立地。 客室は豪華でエレガント。 ウェルカムキットも良く、アメニティも良好。 次回も必ず利用したい。 スタッフの方、いろいろありがとうございました。"
Japan
keita
The price is NZ$189
includes taxes & fees
6 Jan - 7 Jan 2026
TuscanyLettings Studio&Room
Lobby
Residenza Fabroni

Residence in Montepulciano

Residenza Fabroni
8.8 out of 10, Excellent, (94)
"gorgeous historical property, very attentive host, great location"
United States
Sarah
The price is NZ$175
includes taxes & fees
13 Jan - 14 Jan 2026
Residenza Fabroni
Deluxe Double Room | View from room
Affitacamere Maria Gabriella

Townhouse in Pienza

Affitacamere Maria Gabriella
9.8 out of 10, Exceptional, (51)
"This property has a lovely view, great garden, attentive staff with good breakfast. Stayed in the cottage and the patio was very sunny and relaxing. "
United States
Lenise
Affitacamere Maria Gabriella
Balcony
Cameracaffè Centro

Townhouse in Arezzo Centro Storico

Cameracaffè Centro
8.6 out of 10, Excellent, (179)
"Great room and wonderful staff. Loved the breakfast from the veranda with both a view of the mountains and the city center. "
United States
Keith
The price is NZ$186
includes taxes & fees
18 Jan - 19 Jan 2026
Cameracaffè Centro
Casa Gioia, vista città, 2 piano senza ascensore | Private kitchen
Casa Gioia - Casa Olivieri

Apartment in Pienza

Casa Gioia - Casa Olivieri
The price is NZ$182
includes taxes & fees
22 Jan - 23 Jan 2026
Casa Gioia - Casa Olivieri
Bar (on property)
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso

Townhouse in San Quirico d'Orcia

Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
9.0 out of 10, Wonderful, (46)
"Our stay was great. "
United States
Elena
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
Daily buffet breakfast (EUR 10 per person)
DormiVeglia B&B

Townhouse in Monte San Savino

DormiVeglia B&B
10.0 out of 10, Exceptional, (27)
"This was our favourite B&B. The owner Simona was absolutely wonderful. The hot tub in our room was out of this world. If you have the chance to visite this gem…DO IT!!"
Canada
Claude
DormiVeglia B&B
Property grounds
Artisti del Cavallo Tourism

Villa in Foiano della Chiana

Artisti del Cavallo Tourism
8.4 out of 10, Very good, (24)
"Good house for one night. "
Germany
Heiner
The price is NZ$160
includes taxes & fees
30 Dec - 31 Dec
Artisti del Cavallo Tourism
Front of property – evening/night
Sarna Residence

Residence in San Quirico d'Orcia

Sarna Residence
9.6 out of 10, Exceptional, (38)
"We enjoyed our stay. The room was very clean. The staff was helpful."
United States
Bokang
Sarna Residence
Breakfast, lunch, dinner served; local cuisine
Hotel San Gregorio

Residence in Pienza

Hotel San Gregorio
3.0 star property
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 NZ$292
includes taxes & fees
23 Dec - 24 Dec
Hotel San Gregorio
2 bedrooms, iron/ironing board, free WiFi, bed sheets
Dimora del Poggio - cozy Tuscan apartment

Apartment in San Quirico d'Orcia

Dimora del Poggio - cozy Tuscan apartment
10.0 out of 10, Exceptional, (4)
"Our hosts were fantastic, the apartment was clean, roomy, and comfortable, and the location was perfect. Easy walk to enjoy shops and dining."
United States
Joe B.
The price is NZ$342
includes taxes & fees
7 Jan - 8 Jan 2026
Dimora del Poggio - cozy Tuscan apartment
Free daily cooked-to-order breakfast
San Michele al Borgo

Townhouse in Castiglion Fiorentino

San Michele al Borgo
9.8 out of 10, Exceptional, (9)
"Excellent staff and tasty breakfast!"
United States
Vern
The price is NZ$243
includes taxes & fees
11 Jan - 12 Jan 2026
San Michele al Borgo
Deluxe Apartment, 2 Bedrooms, Balcony
Bellarmino Boutique Apartments

Apartment in Montepulciano

Bellarmino Boutique Apartments
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 NZ$263
includes taxes & fees
23 Dec - 24 Dec
Bellarmino Boutique Apartments
Property grounds
Deluxe room Cartazucchero in the heart of Arezzo

Apartment in Arezzo Centro Storico

Deluxe room Cartazucchero in the heart of Arezzo
10.0 out of 10, Exceptional, (2)
"From all the places we stayed during our 13-day trip to Italy, this was by far our favorite. Fabio was incredibly communicative and friendly right from the start, sending us clear instructions on how to get there. He greeted us at the door with such warmth that it truly felt like we were staying with family. The room was spotless, beautifully decorated, and generously stocked with water, cookies, pastries, and other treats. It had the comfort and attention to detail of a hotel, yet the warmth of...
United States
Hector
The price is NZ$145
includes taxes & fees
7 Jan - 8 Jan 2026
Deluxe room Cartazucchero in the heart of Arezzo
1 bedroom, free WiFi, bed sheets
Charming double bedroom in cottage in enchanting Monteaperti with WiFi, AC

Cottage in Monteaperti

Charming double bedroom in cottage in enchanting Monteaperti with WiFi, AC
10.0 out of 10, Exceptional, (1)
"This place was fantastic! What a gem. The bed was comfy, the AC was cold, the bathroom was perfect. We shared the cottage with another couple we were traveling with. The bedroom doors open up to a shared living area, the front entrance is through the main indoor dining area.We had breakfast outside each morning. It was perfect. The staff here is just so nice and considerate, a true family affair. A flight of stairs leads down to a lovely restaurant with plentiful outside dining that shouldn't be...
United States
Cary W.
The price is NZ$344
includes taxes & fees
23 Dec - 24 Dec
Charming double bedroom in cottage in enchanting Monteaperti with WiFi, AC
Exterior
Montecchio di Cortona

Holiday Home in Montecchio

Montecchio di Cortona
9.0 out of 10, Wonderful, (2)
"Tutto estremamente pulito ed ordinato.... Spero di aver modo di poterci tornare presto..."
Italy
Monica S.
The price is NZ$159
includes taxes & fees
31 Dec - 1 Jan 2026
Montecchio di Cortona
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
"Room was beyond expectations. Helpful staff and overall great experience. "
Robert 1-night trip
Posted 2 weeks 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, 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$149 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 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.