La Strada-Santa Cristina Vacation Rentals from CA $249: Short-Term Rentals for 2026

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Our top choices for La Strada-Santa Cristina vacation rentals

1. San Michele al Borgo

Castiglion Fiorentino

Vern

CA $208 total

includes taxes & fees

Sep 19 - Sep 20

2. iConic Wellness Resort

Arezzo

Rheymarie

CA $143 total

includes taxes & fees

Oct 11 - Oct 12

3. B&B Piccolo Hotel

Cortona Old Town

mansoor

CA $248 total

includes taxes & fees

Sep 23 - Sep 24

Apartment (1 Bedroom) | Front of property

4. Vicolo Della Scala Rooms - La Luna

Cortona Old Town

CA $157 total

includes taxes & fees

Oct 14 - Oct 15

5. CASA AMBRA

Cortona Old Town

CA $222 total

includes taxes & fees

Sep 16 - Sep 17

6. Cameracaffè Centro

Arezzo Centro Storico

Alexandre

CA $135 total

includes taxes & fees

Sep 22 - Sep 23

7. Fontelunga Hotel & Villas

Foiano della Chiana

Shelby

CA $501 total

includes taxes & fees

Sep 19 - Sep 20

Luxury Double or Twin Room, 1 Bedroom, Jetted Tub, City View | View from room

8. B&B 52cento

Arezzo Centro Storico

Tina

CA $110 total

includes taxes & fees

Sep 29 - Sep 30

9. Artisti del Cavallo Tourism

Foiano della Chiana

Heiner

CA $130 total

includes taxes & fees

Oct 13 - Oct 14

Romantic Double Room, 1 Queen Bed, Hot Tub, Ground Floor | Private spa tub

10. DormiVeglia B&B

Monte San Savino

Melissa Hyun Joo

CA $172 total

includes taxes & fees

Oct 14 - Oct 15

11. Castello di Gargonza

Monte San Savino

Ariel

CA $373 total

includes taxes & fees

Sep 15 - Sep 16

12. 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

CA $175 total

includes taxes & fees

Sep 26 - Sep 27

13. Villa La Ginestra

Subbiano

Philippe

CA $161 total

includes taxes & fees

Sep 17 - Sep 18

14. Vicolo Della Scala Rooms - Il Sole

Cortona Old Town

CA $171 total

includes taxes & fees

Sep 16 - Sep 17

15. Palazzo Tarlati Residenza d'Epoca

Civitella in Val di Chiana

"Small family-owned inn located in center of Civitella in Val di Chiana. Room was comfortable and included all we needed. It was cold upon check-in which the co-owner tried to remedy with a space heater. It took a while. The room warmed up after the first night. The other co-owner kindly offered me our first night complimentary. (Thank you again.). The breakfast was simple and included fruit, juice, yogurt, sliced cheese and cold cut, packages sweets, tea, coffee and water. The owners were...

Marco

CA $193 total

includes taxes & fees

Sep 14 - Sep 15

16. Allegra Toscana - Affittacamere Guest house

Arezzo Centro Storico

Justin

CA $148 total

includes taxes & fees

Sep 17 - Sep 18

17. Room-two-room Apartment

Saione

Thelma

CA $195 total

includes taxes & fees

Sep 20 - Sep 21

18. Casale dell'Assiolo

Castiglione del Lago

CA $203 total

includes taxes & fees

Oct 6 - Oct 7

19. Locanda del Viandante

Anghiari

Tatsuya

CA $193 total

includes taxes & fees

Sep 14 - Sep 15

Classic Apartment, 3 Bedrooms | Exterior

20. Rustic Holiday Home in Citta di Castello With Swimming Pool

Città di Castello

CA $359 total

includes taxes & fees

Oct 1 - Oct 2

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Top La Strada-Santa Cristina Hotel Reviews

Monastero di Cortona Hotel & Spa

10/10 Excellent

"Truly a stunning boutique hotel that sits in the perfect place within the walled village of Cortana, Really enjoyed my 3 nights here mid trip. The staff have been trained exceptionally well. Zero pretention, impeccable service. The calm ( so quiet), amenities such as the spa and pool area, the breakfast and restaurants, and staff ( mgt, Eleanora, Matteo, Spa leads), attention to details, views from my window, coupled with the energy of the hotel are stand outs. Do treat yourself to a couple massages or treatments. Very fair pricing, and after all the walking and travel, so worth it. I had a massage my first day and my last, that were sandwiched between two other stays in Tuscany, SO glad I did. Tips: Little micro laundry place right at the bottom of the hill that was perfect to do my laundry for my last leg of my vacation. Day trip to Arezzo was so easy and amazing. Attended mass at 6pm on Sunday at a beautiful church above Cortana at the highest elevation. Lovely. They even have a little gift shop in the church. And the first weekend of the month there is a massive antiques fair in the Grand Piazza. 500 vendors. Recommend. There are other stunning boutique hotels within Cortano. Honestly feel this is your best pick. In off seasons this hotel may consider becoming a school of sorts for family businesses in the area, to act as a training academy of sorts for younger generation family members to ensure success."

Poggio Paradiso Resort & Spa

10/10 Excellent

"We LOVED our stay at Poggio Paradiso! The property is absolutely gorgeous and all the staff were amazing! The property is in a great location making it easy to day trip to many different areas in the Tuscan hill country. The onsite restaurant, L’Olivo, has THE most incredible food. The meals we ate there were the best we had in Italy hands down. Marco, the onsite sommelier, was helpful with wine selection at the restaurant and Gabriel, the bartender, was also great. We were also fortunate enough to meet the manager of the property, Chris, and loved hearing more about the history of the property and how it came to be. We will definitely go back!"

Villa Tiberini Wine Relais

10/10 Excellent

"Villa Tiberini is a beautiful place! The chef, staff and owners are wonderful people. The apartment was clean, had all of the necessities and thoughtful touches to make the experience welcoming and comfortable. The shower water pressure and pillow top bed were an extra treat! Breakfast was delicious and we loved the wine. We thoroughly enjoyed our time and would highly recommend this stay for anyone looking to get away from the buzz of tourist destinations. The actual winery is about a 10 minute drive away. We enjoyed our time lounging by the pool and exploring nearby towns by car."

Il Falconiere - Relais e Chateaux

10/10 Excellent

"Il Falconiere treats you as a true guest. Welcoming, courteous and professional were all staff members. Food truly excellent and with the Michelin star, you will enjoy a sumptuous meal, ample portions, amuse bouche at meal's start with a surprise dessert tray with little bites. All staff you interact with are well trained and genuinely friendly and still professional. Our room was in the origjnal residence and had a modern bathroom, lovely size bedroom, anti room with a second desk. In the salon, upon entering the suite, you will find "gifts" left for guests with seating if wishing to entertain. Our group, 4 persons, were very impressed with accommodations, meals and courteous staff. Of course, owner and chef, Silvia Baracchi, too was gracious coming to tables in the evening, welcoming guests and if passed anyone during day, always smiled a buon giorno to one and all. A delightful experience and wonderful to share with good friends."

Find out more about La Strada-Santa Cristina

Everything you need to know about La Strada-Santa Cristina 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 La Strada-Santa Cristina vacation rental for you. At Expedia, you can take your pick from private vacation 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 La Strada-Santa Cristina vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

La Strada-Santa Cristina vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in La Strada-Santa Cristina. 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 La Strada-Santa Cristina vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of La Strada-Santa Cristina vacation rentals we have selected for you start as low as CA $249 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on La Strada-Santa Cristina rentals

At Expedia, we put the best La Strada-Santa Cristina 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 La Strada-Santa Cristina 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 La Strada-Santa Cristina 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 La Strada-Santa Cristina. 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 La Strada-Santa Cristina?

Yes, there are vacation rentals near the most popular local attractions in La Strada-Santa Cristina, or you can select a more remote option if you're looking for a relaxing stay. Visitors to La Strada-Santa Cristina speak positively about the countryside and wineries in this destination. Make sure you have time to check out the churches and musical theater during your trip.

What's the top vacation rental in La Strada-Santa Cristina?

Welcome to Villa Dolce Vita - your private paradise in Tuscany: This vacation home rental near La Strada-Santa Cristina is located in a rural location and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

What’s there to see and do in La Strada-Santa Cristina?

While exploring the area, visit family-friendly sights like Ravagni Oil Mill, or get outside and enjoy nature at Piazza Guido Monaco. Agricola Buccelletti Winery and Tennis Club Castiglionese are a couple of places you'll find in the larger area.

What’s a vacation rental in La Strada-Santa Cristina like?

Vacation rentals are privately owned properties you can stay in for a few weeks or just a few days in La Strada-Santa Cristina. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll have everything you want. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from shared hotel elevators and busy front desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for a family trip.

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Check prices for these dates

Our top choices for La Strada-Santa Cristina vacation rentals

1. San Michele al Borgo

2. iConic Wellness Resort

3. B&B Piccolo Hotel

4. Vicolo Della Scala Rooms - La Luna

5. CASA AMBRA

6. Cameracaffè Centro

7. Fontelunga Hotel & Villas

8. B&B 52cento

9. Artisti del Cavallo Tourism

10. DormiVeglia B&B

11. Castello di Gargonza

12. Locanda Antico Borgo

13. Villa La Ginestra

14. Vicolo Della Scala Rooms - Il Sole

15. Palazzo Tarlati Residenza d'Epoca

16. Allegra Toscana - Affittacamere Guest house

17. Room-two-room Apartment

18. Casale dell'Assiolo

19. Locanda del Viandante

20. Rustic Holiday Home in Citta di Castello With Swimming Pool

Find vacation rentals that suit your style

Top La Strada-Santa Cristina Hotel Reviews

Monastero di Cortona Hotel & Spa

Borgo San Vincenzo

Poggio Paradiso Resort & Spa

Villa Tiberini Wine Relais

Il Falconiere - Relais e Chateaux

Hotel Villa Paradiso

Hotel Minerva

Hotel Continentale

Villa di Piazzano - Small Luxury Hotel of the World

Find out more about La Strada-Santa Cristina

Frequently asked questions

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