La Strada-Santa Cristina Holiday Rentals from NZ$309: Search Short-Term Rentals

Q: What are some of the best holiday rentals that La Strada-Santa Cristina has to offer?

Holiday Home in Umbria with Pool : This holiday home rental outside of La Strada-Santa Cristina offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Make the most of games in this rental home to help you unwind.

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Our top choices for La Strada-Santa Cristina holiday rentals

A narrow cobblestone street with a rustic stone building featuring a wooden door and arched window.

1. San Michele al Borgo

Castiglion Fiorentino

Vern

includes taxes & fees

29 Sept - 30 Sept

2. iConic Wellness Resort

Arezzo

Rheymarie

includes taxes & fees

11 Oct - 12 Oct

An upper floor view of a courtyard with stone walls, arched doorways, and seating areas with potted plants.

3. B&B Piccolo Hotel

Cortona Old Town

mansoor

includes taxes & fees

22 Oct - 23 Oct

A kitchen with white cabinets, a microwave, a sink, and a window with lace curtains.

4. Happy Nest Tuscany Between Florence and Rome

Castiglion Fiorentino

includes taxes & fees

7 Oct - 8 Oct

A stone house with a swimming pool, outdoor seating, and a well-lit patio area.

5. Villa in Tuscany with Pool and Valley Views

Castiglion Fiorentino

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A narrow stone staircase leading up to a building with a red door, flanked by buildings with balconies and hanging laundry.

6. City / Village Apartment in Cortona with 1 bedrooms sleeps 2

Cortona Old Town

Dawn H.

includes taxes & fees

7 Oct - 8 Oct

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

7. Fontelunga Hotel & Villas

Foiano della Chiana

Shelby

includes taxes & fees

14 Oct - 15 Oct

A view of a historic town with prominent buildings and a church tower.

8. Cameracaffè Centro

Arezzo Centro Storico

Alexandre

includes taxes & fees

27 Sept - 28 Sept

A narrow stone staircase leading up a hillside, flanked by buildings with wooden doors and windows, and hanging laundry.

9. Vicolo Della Scala Rooms - La Luna

Cortona Old Town

includes taxes & fees

26 Sept - 27 Sept

A person sitting at an outdoor table with a drink, a bowl of bread, and a glass of juice.

10. Dolce Casa 2 by Tiny Away

Rigutino

includes taxes & fees

7 Oct - 8 Oct

A balcony with a view of a sunset over a hilly landscape.

11. Stunning Loft nestled in the Tuscan countryside 15 minutes walk from the center.

Toscana

Louis / Jeanne M.

12. Dolce Casa 1 by Tiny Away

Rigutino

includes taxes & fees

29 Sept - 30 Sept

A staircase with two lit lanterns on the wall.

13. Cortona Shabby Chic House<br>(Independent & balcony)

Cortona Old Town

Erin

includes taxes & fees

24 Sept - 25 Sept

A modern hotel room with large windows, a bed, a desk, and a chair.

14. B&B 52cento

Arezzo Centro Storico

Tina

includes taxes & fees

30 Sept - 1 Oct

A balcony with a clear view of a distant landscape, a stone building, and a glass of orange juice.

15. Cortonas Rooftop Nest

Cortona Old Town

Robin F.

includes taxes & fees

28 Sept - 29 Sept

A narrow street with buildings on either side, stone walls, and a clear blue sky.

16. Tolletta 10 e Lode - One Bedroom House, Sleeps 4

Arezzo Centro Storico

Maria Gemma

includes taxes & fees

1 Oct - 2 Oct

A view from a window overlooking a courtyard with stone buildings and a tower.

17. La Finestra sul Teatro

Cortona Old Town

Michelle H.

includes taxes & fees

28 Sept - 29 Sept

A hot tub in a grassy outdoor area with a mountain view.

18. Farmhouse with mountain views hot tub

Cortona

includes taxes & fees

25 Sept - 26 Sept

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

19. Artisti del Cavallo Tourism

Foiano della Chiana

Heiner

includes taxes & fees

3 Oct - 4 Oct

A swimming pool with stone edges, surrounded by greenery and a view of a hill with a castle-like structure in the background.

20. Holiday Apartment "Monastero" with Mountain View, Shared Pool & Wi-Fi

Cortona (AR)

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Top La Strada-Santa Cristina Hotel Reviews

Villa Tiberini Wine Relais

10/10 Excellent

"Property was a bit remote, accessible by a 1K dirt driveway, but definitely worth the trip, and really not far from town and Montepulciano. Beautiful views, rooms were spacious and clean, and owners Nunzia and her husband Luca were helpful and gracious. We were able to spend several hours with Luca walking us through the wine making process, from picking the grapes to tracking the fermenting in oak barrels. Be sure to taste the wine, it is excellent. If you’re looking for a reasonably priced authentic experience in a wonderful location, this is it."

Hotel San Michele

8/10 Good

"This is a charming hotel housed in a 15th century palazzo as close as you can get to the center of Cortona. The staff was pleasant and helpful. Plus you can pull your car up for luggage drop off - a real convenience in a town center where cars are otherwise restricted. Just note this hotel is in an old building. Not all rooms are serviced by elevator - some stairs required. And like any historic property the facilities have charming quirks - rooms but not all public facilities have A/C, lighting is low and there are no amenities on site other than a lovely buffet breakfast you can enjoy inside or in a garden setting. However its location steps from Cortona’s Piazza Republica, restaurants and shops make up for any shortcomings!"

Villa di Piazzano - Small Luxury Hotel of the World

10/10 Excellent

"Stunning little hotel with the most beautiful setting, gardens and pool. The room was exceptionally appointed clean. The best part of the stay was the restaurant. The best meals we had on our entire trip. Definitely recommend hiring e-bikes and riding up to Cortona!"

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!"

Find out more about La Strada-Santa Cristina

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 La Strada-Santa Cristina 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 La Strada-Santa Cristina. 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 La Strada-Santa Cristina. Seeing all the best attractions is bound to make you fall in love with La Strada-Santa Cristina. 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 La Strada-Santa Cristina short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in La Strada-Santa Cristina?

Yes, there are holiday rentals close to the most popular sights in La Strada-Santa Cristina, or you can select a more secluded option if you're looking for a relaxing stay. La Strada-Santa Cristina is known for its wineries.

What are some of the best holiday rentals that La Strada-Santa Cristina has to offer?

Holiday Home in Umbria with Pool: This holiday home rental outside of La Strada-Santa Cristina offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in La Strada-Santa Cristina?

Expedia has 5 holiday rentals for your stay in La Strada-Santa Cristina.

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. In the wider area, you’ll find Agricola Buccelletti Winery and Tennis Club Castiglionese.

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

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in La Strada-Santa Cristina. Holiday rentals offer extras such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from shared hotel lifts and busy reception areas while still allowing you to travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for small groups.

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Check prices for these dates

Our top choices for La Strada-Santa Cristina holiday rentals

1. San Michele al Borgo

2. iConic Wellness Resort

3. B&B Piccolo Hotel

4. Happy Nest Tuscany Between Florence and Rome

5. Villa in Tuscany with Pool and Valley Views

6. City / Village Apartment in Cortona with 1 bedrooms sleeps 2

7. Fontelunga Hotel & Villas

8. Cameracaffè Centro

9. Vicolo Della Scala Rooms - La Luna

10. Dolce Casa 2 by Tiny Away

11. Stunning Loft nestled in the Tuscan countryside 15 minutes walk from the center.

12. Dolce Casa 1 by Tiny Away

13. Cortona Shabby Chic House<br>(Independent & balcony)

14. B&B 52cento

15. Cortonas Rooftop Nest

16. Tolletta 10 e Lode - One Bedroom House, Sleeps 4

17. La Finestra sul Teatro

18. Farmhouse with mountain views hot tub

19. Artisti del Cavallo Tourism

20. Holiday Apartment "Monastero" with Mountain View, Shared Pool & Wi-Fi

Find holiday rentals that suit your style

Top La Strada-Santa Cristina Hotel Reviews

Villa Tiberini Wine Relais

Monastero di Cortona Hotel & Spa

Hotel San Michele

Villa di Piazzano - Small Luxury Hotel of the World

Il Falconiere - Relais e Chateaux

Borgo San Vincenzo

Il Gentiluomo Hotel & SPA

Poggio Paradiso Resort & Spa

Hotel Villa Paradiso

Find out more about La Strada-Santa Cristina

Frequently asked questions

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