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Vacation rentals in Toppole

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Top-rated vacation rentals in Toppole

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favourite
A charming outdoor dining area features a round table set with delicate dishware and a pink tablecloth. Surrounding the table are intricately designed white chairs. A gazebo provides shade, and lush greenery is visible in the background, creating a serene setting for leisurely meals.
Farm stay in Ruscello
4.99 out of 5 average rating, 523 reviews

Farmhouse Fattoria La Parita

Provencal-style apartment nestled between vineyards and olive trees. You will enjoy the tranquility of the countryside 10 km from the city and 4 km from the highway. The song of jays and cuckoos will be the soundtrack to the stay while the roe deer graze among the olive trees. A basic Italian breakfast is included (coffee, tea, milk, biscuits, etc.), but if you prefer a richer breakfast served at the table, the cost is €15 per person (€10 from 5 to 15 years, free under 5 years). EV wallbox available.

Guest favourite
Home in Asciano
4.96 out of 5 average rating, 138 reviews

Palazzo Monaci - Pool in the Crete Senesi

Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

Top guest favourite
A charming cottage is shown with a terracotta facade and a tiled roof. A small table with two chairs is set on a patio, surrounded by potted plants. Lush greenery and trees can be seen in the background under a clear blue sky.
Guesthouse in Macciano
4.97 out of 5 average rating, 244 reviews

Tuscan cottage with an heavenly view

Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

Superhost
A rustic outdoor table is set with a variety of breakfast items, including pastries, fruit, and beverages. A blue chair is positioned nearby under wooden beams, with a backdrop of stone walls and lush greenery. Natural light enhances the inviting ambiance of the setting.
Tiny homes in Anghiari
4.89 out of 5 average rating, 252 reviews

Anghiari. Stay in a Room with a View

The small village of Tortigliano, 5 km from Anghiari, has medieval origins, surrounded by hills where the Etruscans took root for the first great Italian civilization. The yellowed stones of the walls breathe among centuries-old cypresses and the bell tower of a small 17th-century church, you will be the only guests in an enchanted place. The village, abandoned after the war, has been entirely recovered in its original layout. Starting point for discovering the taste of Tuscany at the table.

Top guest favourite
An inviting interior features exposed brick walls and a blend of modern and rustic design elements. A staircase leads to the upper floor, while large doors open to reveal a view of the outdoors. A wooden table and a cozy chair enhance the living space.
Apartment in Montepulciano
4.98 out of 5 average rating, 162 reviews

Under the sunset, Montepulciano

In 2023 my son Guglielmo and I decided to restore the old oratory of a church from the 1600s by creating a two floor apartment: upstairs we have 2 bedrooms equipped with AC and 2 en-suite bathrooms with shower; downstairs a spacious living room with stereo Available a table outside with great view and a nice garden 50 mt away where to have a private wine tasting or barbecue for all the guests of our 4 apartments, after 7pm if booked large in advance Large free parking area 100 mt away

Top guest favourite
The villa's exterior is highlighted by a modern structure with large glass doors and a gently sloping roof. It is surrounded by lush greenery and features a patio area with steps leading to the entrance. Soft lighting illuminates the garden, creating a serene evening ambiance.
Villa in Montepulciano
4.92 out of 5 average rating, 328 reviews

Amazing Tuscany Villa, FREE parking

Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking

Top guest favourite
The exterior of the castle is showcased at sunset, with vibrant orange and purple skies providing a dramatic backdrop. Stone towers rise from the landscape, surrounded by greenery and colorful flora, reflecting the historic charm of the property.
Castle in Ferrano
4.99 out of 5 average rating, 225 reviews

The Castle of Ferrano - Castle in Tuscany

Try the experience of staying in a real Castle! Il Castello di Ferrano offers to its hosts the chance of living an unforgettable experience: you will be the only guests in the castle, and everything will be for you (private pool from June to September, gardens etc..). Historical building, surrounded by nature, finely decorated, frescoes/moulding on the ceiling, ample terrace w/ stone and terracotta floor, private outdoor pool.. Good position. Preferably come by car.

Top guest favourite
The farmhouse entrance is framed by two potted plants and orange pumpkins. A stone facade features a wooden door with gray shutters, complemented by a tiled roof. Natural surroundings are visible in the background, emphasizing the peaceful rural setting.
Home in Prato
4.98 out of 5 average rating, 144 reviews

Tofanello Orange Luxury and Modern Comfort with Outdoor Pool

Escape to the rolling hills of Umbria in this updated farmhouse (90 m2 over 2 floors) that retains its original charm. The home features classic beamed vaulted ceilings, original stone finishes, an indoor wood-burning fireplace, private entrance and a private garden terrace. The shared pool has a large sun lounge area. If your favourite dates aren't available anymore take a look at our turquoise apartment. Turquoise: https://www.airbnb.com/rooms/plus/9430389.

Top guest favourite
A charming stone building surrounded by lush greenery features a wooden terrace with a parasol and flower pots. Two loungers are placed on the well-maintained lawn, providing a relaxing outdoor space.
Farm stay in Greve in Chianti
4.99 out of 5 average rating, 476 reviews

Old hayloft on the Chianti hills

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.

Guest favourite
A rustic dining area features a long wooden table set for eight, with simple tableware and napkins. A large window allows natural light to fill the space, offering a view of the vibrant garden outside, where a hammock is visible in the background.
Home in Anghiari
4.87 out of 5 average rating, 163 reviews

PoggiodoroLoft, Tuscan dream e relax

Welcome to Poggiodoro Loft, 16th century stones' villa located in the countryside of Anghiari. Stunning views, charming and furnished interiors providing all type of comforts, the relaxing sauna, the private garden where you can enjoy the open air and lunch under the pergola, BBQ, fantastic in the warm seasons, lounge with brazier a panoramic swimming pool to spend great moments with friends, to be shared with the hamlet guests.

Top guest favourite
The outdoor pool area is surrounded by neatly trimmed cypress trees and colorful gardens. A gentle slope leads to the pool, with views of the rolling green hills in the background. Sun loungers and umbrellas are placed around the pool, creating a serene atmosphere.
Farm stay in Anghiari
5.0 out of 5 average rating, 56 reviews

Tuscan dream lux 2-bed, pool, private balcony

Explore Tuscany in a beautifully decorated 2-bedroom, 2 bathroom apartment with all amenities & a log fire. Welcome to your luxurious home in the heart of Tuscany, Italy, where every moment will be a new adventure. This beautifully designed and well-furnished apartment is located in a restored farmhouse, surrounded by olive groves, vineyards, and rolling hills, offering you the best of Italian living.

Guest favourite
The exterior of a stone rustic house is presented, featuring large steel structures that frame the outdoor space. Multiple windows are visible, along with a door leading into the building. The surrounding area is paved with gravel, contributing to a natural ambiance.
Home in Tavernelle
5.0 out of 5 average rating, 11 reviews

Palazzolo Resort

We tried to recover everything our grandparents passed on to us, giving a new life to the farmhouse that saw our family grow, we put our heart into it, renovating with the utmost respect for the existing, integrating it with modern materials to ensure comfort and aesthetics. Enjoy a nice book in our garden, relax at sunset in our pool, take all the time you need to give the soul what it needs.

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