Vacation rentals in Caggiole

4.96 out of 5 average rating, 164 reviews

A serene swimming pool is surrounded by lush greenery and tall cypress trees. Several lounge chairs are placed along the poolside, offering ample space for relaxation. The water's clear blue hue reflects the bright sky, creating a tranquil outdoor setting.

Guesthouse in Macciano

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.

4.95 out of 5 average rating, 218 reviews

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

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

A panoramic view of a valley unveils rolling hills adorned with clusters of trees and vineyards. Golden autumn foliage frames the foreground, while the distant hills create a tranquil landscape beneath a clear blue sky.

5 out of 5 average rating, 118 reviews

Stuart White Tea Central Panoramic & Garden

Offering ample space, the apartment features two double bedrooms, two full bathrooms, and a living room with a kitchen. The bedroom balconies offer stunning views of the valley and natural light. Its proximity to all town amenities ensures convenience, while a delightful café downstairs provides a delectable gourmet breakfast. It has also access to a secluded, terraced backyard garden. It provides a comfortable retreat perfect for long term stays. A public parking is available nearby.

A dining area features a wooden table adorned with a bowl of fruit, complemented by woven seating. Large glass doors open to a terrace, revealing a view of rolling hills and an evening sky, enhancing the indoor-outdoor connection.

4.97 out of 5 average rating, 392 reviews

A view from the top, Montepulciano

A View From the Top is an apartment in the most peaceful part of Montepulciano. The house with Ac is 250 metres from the piazza and the main street, and has 2 double rooms, 2 bathrooms with shower and a large kitchen-living room with a small terrace overlooking the hills From summer 2025 our wine tasting will be available in the new garden and we have a young private chef for cooking class at home ,not in the weekend. Guests will park close the apartment,in the street 50 mt away.

4.95 out of 5 average rating, 140 reviews

A pergola adorned with blooming wisteria provides shade over a dining area, featuring a round table and red chairs. The vibrant flowers cascade elegantly, enhancing the outdoor space, with the large swimming pool and lush green lawn visible in the background.

Villa in Montepulciano

A paradise in Montepulciano...

Villa Il Cubo is a full centralized air conditioned private house with large private swimming pool placed in the best garden spot for incredible views on the countryside around. Decoration has been updated with charming details that will make you enjoy the best Tuscany has to offer. We have electric vehicle charging point. Supermarkets, restaurants, grocery stores, wineries are just a few minutes away. IN JULY AND AUGUST WE LET FOR A MINIMUM OF 7 DAYS FROM SATURDAY TO SATURDAY!!!!!!

5 out of 5 average rating, 456 reviews

An open kitchen area features a large window that offers a panoramic view of the surrounding landscape. A dining table is set for two, with modern chairs and colorful decor elements. Light reflects off the terracotta floor, highlighting the wooden beams overhead.

Loft in Montepulciano

La Piazzetta - Cozy open space in the historic center of Montepulciano

Pour yourself a glass of wine and sit next to the fireplace of this open space with a warm Tuscan atmosphere: wooden beams, terracotta floors, stone walls. Then go outside and admire the magnificent view of the Valdichiana. Pour yourself a glass of wine and sit next to the fireplace of this open space with a warm Tuscan atmosphere: wooden beams, terracotta floors, and stone walls. Enjoy yourself and relax! Then go out and admire the magnificent view of the Valdichiana Valley.

A view from a window showcases rolling hills and valleys bathed in warm sunset hues. The landscape features distant towns nestled among greenery, while a wrought-iron railing frames the scene. Soft clouds dot the sky, adding depth to the tranquil panorama.

4.93 out of 5 average rating, 197 reviews

Aldo's little house

Typical Tuscan house just renovated while preserving the historical features, such as the wooden beam and brick ceiling, with the addition of a modern touch. From the window, you can admire a breathtaking view and sunset!! Right in the historic center but very close to parking in a truly privileged position!! It has air conditioning, free Wi-Fi, independent heating, double bed, and coffee corner. Self check-in and parking outside the walls 50 m away, free and paid.

A wooden balcony table is set for tea, featuring delicate china cups accompanied by cookies. A simple vase holds fresh flowers. The stunning countryside view stretches across rolling hills under a clear sky, enhancing the serene atmosphere of the outdoor space.

4.94 out of 5 average rating, 191 reviews

I Tramonti di Eramo, Montepulciano city center.

Welcome to Montepulciano, the jewel of the Tuscan hills! Our apartment in the heart of the historical center offers a breathtaking view of the surrounding countryside, giving an authentic and unforgettable experience. You can leave the house and taste the historic atmosphere of Montepulciano. Within walking distance you will have the extraordinary Piazza Grande, high quality restaurants and services of all kinds. Tuscany awaits you to experience unique emotions.

A panoramic view is captured from a window, displaying a vibrant landscape of terracotta rooftops transitioning into verdant hills. In the distance, a charming church steeple rises above the picturesque town, set against a bright blue sky with scattered clouds.

4.99 out of 5 average rating, 262 reviews

Montepulciano Downtown Storico

Nice 60 sqm apartment located in the main street of the village. It is located on the second and last floor of a historic palace. The entrance is located on the main street of the town while the windows overlook the outside of the walls offering a breathtaking view. Apartment consists of: entrance hall, living room with double sofa bed, bedroom, kitchen, bathroom with roof window. It is equipped with microwave, large oven, dishwasher, washing machine and wi-fi.

A charming terrace offers a spacious dining setup, complete with a table set for breakfast. The table displays various breakfast items, and the surrounding views feature terracotta rooftops under a clear blue sky, adding to the inviting atmosphere of this outdoor space.

4.91 out of 5 average rating, 127 reviews

Tuscany on the terrace, downtown Montepulciano

Welcome to Montepulciano, the hidden gem of Tuscany, where historical charm blends harmoniously with natural beauty. Our Airbnb in the heart of the historic center embodies the elegance and authenticity of this region. Immersed in the charming labyrinth of cobblestone streets, you will be greeted by the reassuring sound of bell towers announcing the passage of time, while the inviting scent of freshly baked bread mixes with the aromatic notes of our vineyards.

Farm stay in Montepulciano

A cozy sleeping area is presented with natural wood accents and a light-hued headboard. Neatly arranged towels are complemented by a bouquet of dried flowers, creating a serene environment. Subtle wall sconces provide gentle illumination, enhancing the restful atmosphere of the space.

4.94 out of 5 average rating, 126 reviews

Apartment in the Vineyard with Pool

Immersed in wonderful scenery with vineyards as far as the eye can see, this two-room apartment is part of a finely restored farmhouse with a swimming pool. From your private patio, you can access a fully equipped kitchen (crockery, toaster, kettles, microwave, espresso machine, refrigerator), with a modern extra-comfort sofa bed. You then pass to a large double bedroom with a bathroom equipped with a large shower, soft towels and a complete courtesy line.

Condo in Castelnuovo dell’Abate

A balcony is adorned with blooming flowers and greenery, offering a scenic view of the rolling hills and vineyards. Small outdoor furniture is positioned for relaxation, while the sky features scattered clouds, enhancing the tranquil atmosphere of the surrounding landscape.

4.91 out of 5 average rating, 288 reviews

La Casetta di Brunello, very panoramic with terrace

STIAMO LAVORANDO PER VOI! ... WE ARE WORKING FOR YOU! The house is completely renovated and furnished in 2018 with classic-Tuscan style furniture. The colors are warm and enveloping to better rest during your holiday of peace and relaxation. In addition to the two double bedrooms, you have a kitchen with an equipped kitchenette, fridge, induction cooker and a furnished terrace with a beautiful view of the surrounding countryside.

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Popular amenities for Caggiole vacation rentals

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Pool

Free parking on premises

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Other great vacation rentals in Caggiole

Farm stay in San Quirico d'Orcia

4.99 out of 5 average rating, 82 reviews

Podere Pereti Nuovi-modern Tuscan Villa

MichaelRating, 5 stars3 weeks ago

There is no way to accurately describe the views of the Tuscany countryside from this wonderful villa. The updating of the house left nothing to be desired. Indoor and outdoor amenities are perfect for a large group or family. It's a great home base, as it's centrally located. We took day trips to Assisi, Montepulciano, Montalcino, Monticchhiello, Pienza, Siena, and Orvieto. And so close to the hidden gem of Bagno Vignoni - don't skip it. Kathleen was one of the best hosts we have ever had. From recommendations and directions to introductions to chefs and wine tour guides. She was quickly responsive to all of our questions throughout the process. You will love everything about this place. We would definitely go back.

4.93 out of 5 average rating, 28 reviews

An arched wooden door is framed by a rustic brick wall, featuring a circular brass doorknob. A rectangular mailbox with the word 'KEYS' is mounted beside the entrance, which is illuminated by a wall light above.

Condo in Montepulciano

Milipano Studio Apt

CaryRating, 5 stars1 week ago

We really enjoyed this place. It exceeded our expectations. It was close to the old town. Pros Shower was excellent. It had Kleenex which was unusual in Italy. It was efficient use of space. Towels/bath sheets were very soft and nice. For an efficiency it had plenty of room for two. Bed was very comfortable. Cons It did not have a comforter..only a blanket. It is close to restaurants and had issue with flies. (Need a fly swatter). Parking—it is VERY limited and plan on paying for it.

An outdoor dining area is presented, featuring a wooden table surrounded by six chairs under a large umbrella. The space is paved with bricks and enclosed by a wooden fence, complemented by lush greenery in the background, enhancing the serene atmosphere.

4.95 out of 5 average rating, 85 reviews

Casa Crociani - Amazing Pool & Free Parking

NatalieRating, 5 stars2 weeks ago

This was the most magical place to call home while in Tuscany. Marco communicated really well from the beginning, and was available for any questions you may have had. The bathrooms were so clean, the kitchen was well stocked, there were enough pillows and blankets if you got cold and the air conditioning was perfect for those hot days and as a bonus the wifi worked really well. The swimming pool was only a few steps away and had a breathtaking view as well and was super clean. The sunsets were to die for on the front patio and they even provide a table with an umbrella if you want to dine outdoors. This place was so beautiful and felt like home, it was our favourite place in all of Italy.

5 out of 5 average rating, 22 reviews

A framed artwork depicting striped deck chairs on a beach is displayed on a neutral-colored wall. Two small boxes, one pink and one blue, are positioned on a light-colored cabinet alongside a decorative wooden container and an essential oil bottle.

Home in Montepulciano

Casa di Mela

BeritRating, 5 stars5 days ago

We loved our visit at the accommodation! Beautiful city, lovely flat, great area. Very clean and nice to live in, the benches in front are perfect for concluding the evening with a glass of vino nobile di montepulciano. Modern stove and kitchen allow for easy cooking, always a blast. 5/5.0

4.95 out of 5 average rating, 19 reviews

A modern kitchen countertop is equipped with a sleek induction cooktop and a coffee machine. A kettle sits nearby, accompanied by jars on the shelf above. Natural stone surfaces and neutral tones create a clean and functional workspace, illuminated by warm under-shelf lighting.

Home in Montepulciano

Hortus Conclusus House

FionaRating, 5 stars2 weeks ago

Amazing place and would definitely be our number one place to stay when we return. Clean and spotless with luxuries like slippers are provided and some breakfast items too. Even a UK-Italy plug converter! Loved it! Thank you to Lucia, Luca and your mum! xx

Farm stay in San Quirico d'Orcia

A serene outdoor area is presented, featuring well-maintained grass and gentle slopes leading to vineyards. The modern structure is partially illuminated, showcasing large windows that create a harmonious connection with the natural surroundings. Silhouetted trees add to the tranquil ambiance against the night sky.

4.98 out of 5 average rating, 44 reviews

Wine Loft in the vineyards

HilaryRating, 5 stars1 week ago

The Wine Loft is incredibly peaceful and beautiful. The modern architecture is gorgeous and the views are magical. We traveled by trains and it was easy to take a taxi (arranged by the Wine Loft) from the station. Additionally, we enjoyed walking the country path through the woods and meadow to Bagno Vignoni. We highly recommend this beautiful property. The wines were a phenomenal addition to the stay.

Cottage in Osteria delle Noci

A dining table is set for a meal, featuring plates and glasses neatly arranged. Large glass doors offer a view of the surrounding landscape, including green hills and distant mountains. Natural light fills the space, enhancing the rustic wooden details.

5 out of 5 average rating, 94 reviews

Your Tuscan oak tree house, enchanting Val d'Orcia

LuziaRating, 5 stars1 week ago

This house with the surrounding garden, nestled in a dreamlike landscape, is an absolute paradise. The garden is huge, beautifully landscaped and very well maintained. The views are stunning and we have daily hiking trips and bike tours directly from the house. The tranquility is unbelievable, you can usually only hear birds and when it gets dark the nightingale. The house itself leaves nothing to be desired. Extremely clean, including in the cabinets and drawers. Everything you need is there, but (despite very tasteful decoration) not overcrowded. Just right and everything very high quality. Super comfortable bed & sofa and beautiful bathroom. Veronica is an outstanding host and her mother (who welcomed us) is very sympathetic. We received gifts directly from the garden and Veronica is responsive and extremely courteous in communication. You can tell from the beginning to the end how much love is in this house.