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Holiday houses in Sestino

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Top-rated holiday rentals in Sestino

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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, 474 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, 119 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 spacious bedroom is presented featuring two beds, one being convertible, and artwork depicting a mountain landscape. Natural light enters through a nearby window, enhancing the modern decor. A small bedside table and decorative elements, including a plant, add warmth to the space.
Home in San Marino
4.99 out of 5 average rating, 146 reviews

House "Independent" close to the Historic Center

This independent house, located a few steps from the walls surrounding the historic center of the Republic of San Marino, is the top place for those seeking relax, privacy and a breathtaking view of the surrounding mountains. The house, modern and with attention to detail, is perfect for families, couples or small groups who want to live an unforgettable experience. Large and well-organized spaces are designed for your every comfort. Free parking a few steps from the front door. Pets are welcome

Superhost
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, 151 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: a beautiful fireplace that will keep the ambient warm in winter, 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.

Guest favourite
An expansive outdoor deck offers a serene view of rolling hills under a clear sky. An infinity pool transitions seamlessly into the landscape, with two soft seating cushions placed nearby, inviting relaxation and contemplation of the stunning panoramic scenery.
Home in Casale
4.88 out of 5 average rating, 189 reviews

Infinity view

Completamente ristrutturata posizione con vista mozzafiato sul Valdarno. Il piano terra è composto da soggiorno con due vetrate che danno sul patio, camino, divano letto, bagno con grande doccia e cucina moderna con isola in acciaio, con tre porte finestre per accedere alla zona pranzo esterna con bbq. Il primo piano è composto da due camere matrimoniali ognuna dotata del proprio bagno con doccia. Giardino è moto curato,ci sono vari angoli relax, prendisole è una piscina infinity ad idrolisi

Top Guest favourite
An infinity pool sits on a green terrace, surrounded by lush greenery and olive groves. Several loungers are positioned on the lawn, offering views of the expansive valley and distant hills under a clear blue sky.
Villa in Loro Ciuffenna
4.96 out of 5 average rating, 56 reviews

The Lazy Oak

Perched on a hillside above the Valdarno area, between the cities of Florence, Arezzo and Siena, the Lazy Oak villa is surrounded by acres of olive groves. The main house on two level has been fitted with bedrooms, bathrooms and new kitchen whilst retaining its old terracotta floors and beamed ceilings. A dining loggia for al fresco meals enjoys a breathtaking view of the countryside. The infinity pool is set just a few steps from the house on a green terrace furnished with loungers.

Guest favourite
The inviting pool area features clear turquoise water, surrounded by a well-maintained lawn and olive trees. Comfortable lounge chairs are positioned nearby, providing relaxation options. The charming stone building stands in the background, framed by gentle green hills under a partly cloudy sky.
Home in Perugia
5 out of 5 average rating, 19 reviews

Umbrian House with Swimming Pool

Inside the prestigious Antognolla Golf estate, you will find this splendid typical Umbrian farmhouse with swimming pool, with an enchanting landscape surrounded by greenery and panoramic views of the hills of the Green Heart of Italy. Elegant and refined, it offers the possibility of a stay in total relaxation. It is located about 20 minutes from the historic center of Perugia and half an hour from Umbria International Airport. Forget all worries in this spacious oasis of serenity.

Top Guest favourite
A rustic living area features a wooden table surrounded by two elegant armchairs and a beige sofa. A stone fireplace, stocked with logs, stands as a focal point, while wooden beams adorn the ceiling. An inviting atmosphere is created by warm, natural colors and soft furnishings.
Home in Anghiari
4.99 out of 5 average rating, 258 reviews

Casa Rosmarino Eco-Wellness Country Home

Summer 2026 villas w/private pool available : airbnb.com/h/casaflavia10 airbnb.com/h/villaflaviaarezzo Price includes: - Infrared Sauna - Wood for Fireplace - Fire starters - Heating/Air Conditioning - Laundry/Dryer - Shower Gel/Shampoo/Bathrobes - Welcome Appetizer w/Wine - Treats during your stay Pool & parking lot are shared areas. We have 6 units for rent Extra activities (not included) : - Massages, Cooking Classes, Tours & Tasting Please INQUIRE for price & availability.

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, 140 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 stone terrace is framed by arched supports, illuminated by gentle lighting. Wooden furniture is arranged for relaxation, with potted plants adding natural elements. The backdrop showcases the medieval bridge, seamlessly integrating the outdoor space with the historic architecture.
Home in Mercatello sul Metauro
4.96 out of 5 average rating, 51 reviews

The house on the bridge

You will live in a house hundreds of years ago, built on the Romanesque bridge of the village. Large walls, oak beams, terraces under the arches of the bridge and bowls on the road in the warm embrace of a medieval village. Madies, pasta chefs, chests wisely renovated to leave all the flavor of the crafts that still belong to us. Breakfast with the best traditional desserts and pleasant breaks by the lit fireplace. Time will seem to stop with you.

Top Guest favourite
Villa in Castel Rigone
5 out of 5 average rating, 24 reviews

Villa Feronia – Heated Pool & Rooftop Escape

Welcome to Villa Feronia, a contemporary 3-bedroom retreat nestled in a 2-hectare olive grove near Passignano sul Trasimeno. Enjoy refined indoor-outdoor living with 3.5 bathrooms, high-speed Wi-Fi, a smart home system, an infinity saltwater heated pool, and a rooftop terrace with a fire pit. Eco-friendly and elegantly designed, it’s the ideal escape to relax, recharge, and experience authentic Italian beauty.

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 out of 5 average rating, 39 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.&

Popular amenities for Sestino holiday rentals

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Arezzo
  5. Sestino