Vacation rentals in Caggiole

4.96 out of 5 average rating, 164 reviews

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.

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.

4.92 out of 5 average rating, 125 reviews

A private terrace is visible, adorned with vibrant flowers and a small table set for two. A bottle of wine and two glasses are elegantly placed, inviting relaxation with a view of the terracotta rooftops and the distant landscape under a pastel sky.

Condo in Montepulciano

"Dimora Valinda" Montepulciano Piazza Grande +A/C

🏠 Ideal location: within walking distance of stores, restaurants and attractions in the historic center. ❄️ Air conditioning for maximum comfort during hot days. 🛁 Washing machine for extended stays or simply for traveling light. 🌅 Private terrace for relaxing moments outdoors. 🍴 Full kitchen with dishwasher, perfect for those who love to cook even on vacation. 🌐 Ultra-fast 150 Mb/s Wi-Fi, ideal for smart working ☕ Well-stocked coffee station for a perfect start to the day.

4.97 out of 5 average rating, 106 reviews

Villa in Montepulciano

Wine Experience Villa in Montepulciano

Villa Talosa è una residenza immersa tra i vigneti di "Fattoria della Talosa",Azienda vitivinicola di Montepulciano ove produciamo il Vino Nobile di Montepulciano d.o.c.g . Un luogo per godere di relax con una fantastica vista da ogni finestra della Villa. Distiamo 1.5 km dal centro storico,dove sarà possibile visitare la ns Cantina Storica risalente al 1500 A.D. e collocata sotto piazza Grande . Nota: Riscaldamento ed l’Aria condizionata sono dei costi aggiuntivi, in base al consumo.

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.

Guesthouse in Montefollonico

A wine bottle is being poured into a glass, catching the warm hues of a sunset. The landscape of rolling hills and trees is visible in the background, creating a serene atmosphere enhanced by the vibrant colors of dusk.

4.97 out of 5 average rating, 103 reviews

Casale Santa Barbara - Exclusive Apartment

At a glance: • Location: perfect entry door to the Val d’Orcia between Pienza (8,5 km) and Montepulciano (8,5 km). • Charming warm old stones Tuscan house – completely restored in 2016 • Big apartment (100m2), designed for 2 persons, completely independent, fully furnished, Tuscan style with modern equipment. • Exclusivity: we are living on the 1st floor; the ground floor is yours. You are our only guests. • Spacious private garden (+ 300m2) • Stunning view on the Tuscan hills.

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.

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.

Apartment in Monticchiello

4.97 out of 5 average rating, 152 reviews

Casa Bonari - a paradise for the eyes

Casa Bonari is a single-level independent apartment inside a villa at the foot of Monticchiello. It consists of 3 bedrooms, 2 bathrooms, an equipped kitchen and a living room. The rooms are bright and furnished in Tuscan style, with old restored family furniture combined with contemporary elements. The kitchen is fully equipped and the apartment is surrounded on all sides by a large garden, so that all rooms boast a beautiful view of the countryside.

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.

An inviting entrance showcases a rustic wooden door, leading to a stone pathway lined with greenery. Open shelves display white dishware and a small flower arrangement, complementing the earthy tones of the surrounding walls.

4.82 out of 5 average rating, 103 reviews

Il Segreto di Agnaresi, 30 meters from Caffè Poliziano

Welcome to the beating heart of Montepulciano, where your stay becomes an unforgettable experience. Our newly renovated apartment, designed to accommodate two people, is located in the center of town, just 200 meters from Montepulciano's majestic Piazza Grande, one of the most beautiful squares in Italy, and only 30 meters from the famous Caffè Poliziano, Montepulciano's most historic bar and the third most beautiful bar in Italy.

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Popular amenities for Caggiole vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Caggiole

Superhost

A gravel path leads through tall cypress trees on either side, guiding towards a gated entrance. Lush greenery and rolling hills are visible in the background under a clear blue sky.

Vacation home in Torrita di Siena

4.82 out of 5 average rating, 17 reviews

Pian'D'olmo, an ancient farmhouse in the heart of Tuscany

AnnieRating, 5 stars8 months ago

We had a vision and dream of staying in a Tuscan villa in the country and it exceeded all our expectations.

A charming cobblestone street winds down between buildings, adorned with potted plants and blooming flowers. Vibrant colors are seen in the hydrangeas and other greenery, creating a picturesque scene. An arched gateway in the distance leads to another pathway, inviting exploration.

5 out of 5 average rating, 16 reviews

WiFiFiberCozyStudioMontepulciano

KenRating, 5 stars1 month ago

Great location! Centrally located near Piazza Grande. Steps away from shopping, restaurants, and incredible views of the countryside. Apartment was very comfortable. Perfect for a solo traveler. Updated bathroom and shower was great. Overall, the entire apartment was clean and well appointed. Elias was awesome. Incredibly responsive and helpful. Provided several recommendations of things to do within Montepulciano but also gave insights on other nearby towns. He texted me a few times during my stay to see how I was doing and if I needed anything. Very gracious. Overall great experience.

A private terrace is showcased with a small wooden table and two black chairs. Potted flowers add a touch of color, while the surrounding rooftops of Montepulciano and distant hills are visible under a clear blue sky.

5 out of 5 average rating, 83 reviews

Appartamento dell'Erbe (Apartment of Herbs)

BruceRating, 5 stars1 week ago

Wow! What a great place. Francy is a wonderful host. She went above and beyond to help us make our time in Montepulciano comfortable and memorable. This remodeled gem in the heart of Montepulciano was created in a very thoughtful way. Two separate bedroom suites with view, great air conditioning, comfortable beds. And the kicker is the upstairs roof-top balcony with breath taking views over the town and beautiful countryside. Well done Francesca! Thank you!

Farm stay in San Quirico d'Orcia

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.

An aerial view reveals a charming Tuscan landscape, with a rustic building nestled among lush greenery. Rolling hills and vineyards stretch into the distance, suggesting a serene countryside atmosphere. The warm tones of the stone structure harmonize with the natural surroundings.

5 out of 5 average rating, 59 reviews

Luxury Attic in Tuscany+Incredible view and A/C

EugenioRating, 5 stars3 weeks ago

Staying at this apartment was truly magical. Every time I looked out the window or stepped onto the balcony, I was left in awe. The views were absolutely breathtaking, and the town of Montepulciano was every bit as beautiful—charming, historic, and full of character. Leaving was the hardest part, and I’m already counting down the days until I can return. From the incredible local restaurants to the stunning wineries nestled in the Tuscan hills, every moment felt like a dream. Photos simply can’t capture the beauty—you have to experience it for yourself.

4.85 out of 5 average rating, 33 reviews

A charming street in Montepulciano features stone pavements and beautifully preserved historic buildings. Wooden doors with intricate designs and plants in pots are visible, adding a touch of greenery to the scene.

Home in Montepulciano

Stunning Tuscany Villa in Montepulciano

LaurenRating, 5 stars1 week ago

We had a wonderful stay! The location was perfect. We especially enjoyed the flexibility to use the kitchen for cooking after much eating out and lived mornings and evenings on the roof top terrace!

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.