Vacation rentals in Gaggioleto

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Top-rated vacation rentals in Gaggioleto

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Top guest favorite

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, 451 reviews

Farmhouse Fattoria La Parita

Provencal style apartment surrounded by vineyard and olive trees. You will enjoy the tranquility of the countryside 10 km from the city and 4 from the highway. The singing of the acorn and cuckoo will be the soundtrack to the living room while the roe deer burn among the olive trees. A basic Italian breakfast (coffee, tea, milk, biscuits, etc.) is included, but if you prefer a richer breakfast served at the table, the cost is €15 per person (€10 for 5 to 15 years, free for children under 5 years). EV wallbox available.

Top guest favorite

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

4.96 out of 5 average rating, 112 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 for all the guests of our 4 apartments We can organize barbecue with paired wines after 7 pm. Large free parking area 100 mt away

Top guest favorite

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, 186 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.

Guest favorite

A stone villa surrounded by greenery is featured under a clear blue sky. A large swimming pool reflects the sunlight, complemented by sun loungers and colorful potted flowers along the edges. The outdoor area is perfect for relaxation with scenic views of the Tuscan hills.

Villa in Castiglion Fiorentino

4.91 out of 5 average rating, 218 reviews

Tuscan charm of villa - countryside

Nell’affascinante campagna Toscana,tra ulivi e vigneti una villa in pietra,in posizione strategica per cogliere i segreti di Toscana e Umbria aria condizionata e piscina con area wellness per il vostro relax e confort Villa Senaia è una grande casa con travi in legno, in una splendida posizione in collina con vista idilliaca che affaccia su uno dei luoghi preferiti della campagna toscana, un ambiente attraente per mangiare all'aperto, bevendo vino toscano e ascoltando i grilli e le cicale

Guest favorite

A bright living space is featured, showcasing a wooden dining table set with dishes and fresh fruit. A comfortable sofa is positioned adjacent to the television on the wall. Natural light filters through a window, illuminating the wooden beams of the ceiling.

Condo in Cortona

4.98 out of 5 average rating, 184 reviews

Chicca: bright and panoramic in the historic center

Bright, delightful and welcoming apartment located right in the heart of the historic center of Cortona with an unforgettable view: the town hall on one side and Lake Trasimeno and the Valdichiana on the other. The apartment has been recently renovated and consists of a living room with sofa bed, a small kitchen, a double bedroom and two bathrooms. The apartment has WiFi, heating and air conditioning, a washing machine, oven, microwave, hairdryer and flat iron.

Top guest favorite

A stone exterior is showcased, with a staircase leading up to the entrance. A shaded area features outdoor seating, including a table and chairs. Potted plants line the pathway, and greenery provides a serene backdrop, enhancing the outdoor living space.

Home in Prato

4.99 out of 5 average rating, 128 reviews

Tofanello Turquoise Luxury 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 orange apartment. Orange: https://www.airbnb.com/rooms/plus/9429730

Top guest favorite

The exterior of the stone annexe is showcased, surrounded by lush greenery. A shaded seating area is highlighted in front, with a small table and chairs beneath an umbrella. A pathway leads up to the entrance, nestled in a serene natural landscape.

Guesthouse in Perugia

4.99 out of 5 average rating, 134 reviews

Ethical house in Umbria

It is a 60 sqm annex suitable for couples who want to visit our region. We don't have a swimming pool but we have the truffle ground, the stream, the roe deer, porcupines, wild boars, our cats and the little dog Moti. In the garden, you will find herbs, fruit, and garden produce. Inside the cottage we rent, you will have our olive oil and helichrysum liqueur that we produce. We also produce saffron, but we sell it! Of course, pets are welcome!

Guest favorite

A spacious living area features a comfortable purple sofa and striped poufs, complemented by a classic wooden sideboard and elegant lamps. Warm colors adorn the walls, and a large artwork adds character. Natural light enters through multiple windows, enhancing the inviting ambiance.

Apartment in Cortona

4.97 out of 5 average rating, 174 reviews

CasaNella: bright, central and panoramic

Cozy, elegant and delightful apartment in the center of Cortona, with an enchanting view that sweeps from Lake Trasimeno to Valdichiana. Carefully furnished, it is the ideal place to spend a few days in this wonderful town. A short walk from the main road, but in a quiet and panoramic location. Free parking is a short distance away. Equipped with heating and air conditioning. High speed WiFi available. Great for smart working.

Guest favorite

A charming rural building is set against a backdrop of lush greenery at dusk. Soft lighting highlights the stone exterior and terracotta roof, while the surrounding trees and landscaped grounds enhance the tranquil environment.

Farm stay in Anghiari

4.95 out of 5 average rating, 104 reviews

Mafuccio Farmhouse - "Casa di Rigo"

Casa di Rigo is the smallest apartment of Agriturismo Mafuccio, a farmhouse immersed in unspoiled nature in the Sovara Valley, a stone's throw from the Rognosi Mountains nature reserve and nestled at the foot of Monte Castello. A quiet and peaceful place like the streams that cross the valley, where you can find peace, and fully experience nature... in the company of the Valley Kids!

Top guest favorite

The bedroom features a spacious double bed adorned with soft linens and cushions, complemented by subtle bedside lamps. Exposed wooden beams highlight the ceiling, while natural light filters through a window, adding warmth to the serene, neutral color palette.

Apartment in Cortona

4.97 out of 5 average rating, 382 reviews

Cortona Shabby Chic House (independent & balcony)

Cortona Shabby Chic con balcone privato e totale privacy, perfetto relax. Il mio alloggio è situato in pieno centro storico a soli pochi passi dalle piazze e vie principali. Questo grazioso appartamento è di recente ristrutturazione e può ospitare fino a 3 persone. Appartamento indipendente con entrata singola tutto in un solo piano. Arredato con cura e dotato di tutti i comfort

Top guest favorite

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, 418 reviews

Old hayloft on the Chianti hills

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence. Hayloft completely independent on two floors connected by an internal staircase. Private garden of 300 mq sorrounded by secolar oaks.

Top guest favorite

Farm stay in Campiglia D'orcia

4.94 out of 5 average rating, 450 reviews

Poggio Bicchieri Holiday Farm - Poesia apartment

Overlooking the Val d 'Orcia, our holiday farm consists of 2 apartments each with a kitchen, bedroom, and bathroom. Large equipped garden. Surrounded by silence, close to Pienza, Montalcino, Bagno Vignoni, and the natural thermal baths of Bagno San Filippo. Getting here is very easy; the last km of the road is unpaved but accessible for all.