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House vacation rentals in Sestino

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Top-rated house rentals in Sestino

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

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Top guest favorite
Home in San Marino

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

4.98 out of 5 average rating, 196 reviews
Guest favorite
The image showcases a rustic stone building surrounded by a gravel courtyard. Flower pots with vibrant geraniums decorate the area, and a large tree provides shade. Sunlight illuminates the brick facade, creating a warm and inviting atmosphere in the outdoor space.
Home in Foiano della Chiana

La Lisa: country house surrounded by fields

La Lisa is a traditional farm house that has been wisely restored. It is surrounded by Tuscan countryside hills, in a quiet, out of time atmosphere. At the same time it is well connected with the A1 motorway and the highway Siena – Perugia (6 km). A large yard with a barbecue and pizza oven, is ideal for evenings under the stars. There's also a tavern with kitchen, living and dining room can host up to 30 people. During warm season enjoy the HEATED POOL equipped with loungers and umbrellas.

4.94 out of 5 average rating, 135 reviews
Guest favorite
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

The house on the bridge

You will live in a house hundreds of years ago, built on the Romanesque bridge of the country. Large walls, oak beams, terraces under the arches of the bridge, and pebbles on the street in the warm embrace of a medieval village. Madie, pastries, wisely renovated chest of drawers to leave all the flavor of the crafts that still belong to us. Breakfast with the best traditional pastries and pleasant breaks by the fireplace. Time will seem to be stopping with you.

4.95 out of 5 average rating, 59 reviews
Top guest favorite
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

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.

4.98 out of 5 average rating, 144 reviews
Guest favorite
The room features a spacious bed with crisp, white bedding and decorative pillows. A large window allows natural light to fill the space, complemented by pale green walls. A small table, adorned with a plant, sits beside the bed, while a comfortable chair adds a pop of color.
Home in Gradara

The Aurora Residence inside the Castle of Gradara

Intimate and charming 90-meter house inside the romantic Castle of Paolo and Francesca, in the hinterland of the Marche and Romagna Riviera. The privileged location: inside the walls of the Castle and in the heart of the charming medieval village, among shops, bars, taverns, restaurants and the convenience of being 10 minutes from the sea. The comfort of a real home inside the castle of the legendary love story. Parking is also available and pet-friendly!

4.95 out of 5 average rating, 155 reviews
Top guest favorite
An aerial view of a rustic villa is framed by lush greenery, showcasing a stone exterior and terracotta roof tiles. A salt-water pool is situated nearby, surrounded by outdoor seating. The tranquil landscape of hills is visible in the background under warm evening light.
Home in Poppi

Villa Podere Cerretino

Podere Cerretino is the perfect place to find and discover your own tranquility and relaxation. A corner of paradise surrounded by the picturesque hills of Tuscany in an enchanting landscape, located in a central and strategic position to visit the most interesting places in Tuscany, such as Florence, Siena, Arezzo. The Villa consists of 4 completely independent apartments and an elegant panoramic veranda where you can gather and enjoy a unique vacation.

5.0 out of 5 average rating, 66 reviews
Guest favorite
A charming stone house with a terracotta roof features a welcoming entryway, shaded by umbrellas and surrounded by colorful flowers. In the background, a serene saltwater infinity pool is framed by landscaped greenery, complementing the tranquil rural setting.
Home in Foiano della Chiana

Conca d'Oro villa with private pool, sleeps 4

Just 2 km from the village, cozy typical Tuscan farmhouse, tastefully furnished and equipped. The farmhouse is located in a panoramic position immersed in the peaceful Tuscan countryside. Guests have access to a beautiful infinity pool for their exclusive use, equipped with sun loungers, and a lovely garden with a patio furnished for outdoor dining and enjoying fantastic sunsets. A strategic location for tourists. Free high-speed satellite Wi-Fi

4.92 out of 5 average rating, 172 reviews
Guest favorite
A spacious bedroom features a king-size bed with neutral bedding, complemented by decorative pillows. Soft lighting is provided by wall sconces, while natural stone walls add texture. A small bedside table and an armchair enhance the inviting ambiance.
Home in Sarsina

Nature Retreat | Peace & Relax in the Hills

A stone house immersed in nature, in the heart of Romagna, between the Apennines and historic villages. A peaceful and quiet place for those seeking slow living, intimacy and relaxation, with a private hot tub. La Cappelletta holds generations of memories and is now a space to live slowly: sleep, cook, taste, meditate and enjoy the silence. Perfect for romantic stays, escapes from the city, retreats with friends or weekends away from the noise.

4.95 out of 5 average rating, 64 reviews
Top guest favorite
The rustic exterior of a restored mill is framed by blooming lilac flowers. The two-story building features stone walls with wooden doors and windows, surrounded by lush greenery and a gravel pathway. Sunlight illuminates the quaint structure, reflecting the peaceful rural setting.
Home in Anghiari

Il Vecchio Mulino

Bongiorno! Il Vecchio Mulino is a restored mill in the Anghiari area. Set in the valley surrounded by sunflower fields and a stream behind the villa, Il Vecchio Mulino is a quiet oasis from the metropolitan cities of Florence and Rome. Take a cooling dip in your own private pool (pool opens mid-May and is closed during the winter), stroll about the lawned gardens and enjoy the rural setting – this is the perfect place to relax and unwind.

4.91 out of 5 average rating, 114 reviews
Guest favorite
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

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.

4.87 out of 5 average rating, 164 reviews
Top guest favorite
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

Casa Rosmarino Eco-Wellness Country Home

Price includes: - Infrared Sauna - Wood for Fireplace - 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.

4.99 out of 5 average rating, 271 reviews
Top guest favorite
A rustic stone house is surrounded by lush greenery, featuring wooden shutters and a tiled roof. A shaded outdoor dining area is visible, complemented by potted plants. The serene garden setting invites relaxation and enjoyment of the natural landscape.
Home in Torreone Cortona

Tuscany House | View Breathtaking

Casa Belvedere is 10 minute drive from the center of Cortona. Is located along an old Roman road and enjoys a spectacular view of Cortona. Equipped cooking, 2 double room, 2 bathrooms, sofa bed, large garden with provides all the comforts to relax, sunbathe and have lunch under the pergola, enjoying the view of Cortona and the Val di Chiana.

4.97 out of 5 average rating, 112 reviews

Popular amenities for Sestino house rentals

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Guest favorite
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

Infinity view

4.88 out of 5 average rating, 201 reviews
Top guest favorite
The exterior of a charming farmhouse is visible, featuring stone walls adorned with climbing greenery. Large windows reflect natural light and overlook the landscaped garden. A gravel path leads to the entrance, surrounded by greenery and trees under a clear blue sky.
Home in Rigomagno

House Rigomagno Siena

4.96 out of 5 average rating, 122 reviews
Top guest favorite
The living area features exposed stone walls and wooden beams, creating a rustic ambiance. A spacious sectional sofa is complemented by a round accent chair. A round mirror reflects light from the window, while a decorative fireplace adds warmth to the space.
Home in Castiglion Fiorentino

Hidden gem in Tuscany

5.0 out of 5 average rating, 54 reviews
Top guest favorite
The entrance of Villa Piandarca is framed by lush greenery and decorative pots. A rustic wooden door stands partially open, revealing a white curtain gently flowing in the breeze. The building's warm yellow exterior adds to the inviting atmosphere of the property.
Home in Terranuova Bracciolini

Villa Piandarca - Tuscany - WIFI - private pool

4.98 out of 5 average rating, 57 reviews
Top guest favorite
An aerial view of the estate reveals two distinct swimming pools, surrounded by lush greenery and multiple garden areas. The main building features a rustic design, complemented by a large terrace and ample outdoor seating. Pathways meander through the property, connecting various relaxation zones.
Home in Mondaino

Tenuta Sant'Apollinare

4.96 out of 5 average rating, 50 reviews
Top guest favorite
The rustic stone building is set amidst lush gardens, framed by tall cypress trees. A winding pathway leads through the greenery, guiding towards the entrance. The structure showcases rustic charm with climbing vines and an inviting, well-maintained outdoor space. A small dog is seen wandering nearby.
Home in Città di Castello

Due Torri, Umbrian elegance

5.0 out of 5 average rating, 24 reviews
Guest favorite
The exterior of a spacious villa is displayed, featuring a large garden and a swimming pool in the foreground. Lounge chairs are arranged around the pool area, and the building showcases a combination of stone and plaster finishes under a clear blue sky.
Home in Tavullia

Almifiole

5.0 out of 5 average rating, 20 reviews
Top guest favorite
A serene outdoor swimming pool reflects the surrounding greenery, flanked by lounge chairs and shaded areas. The historic building in the background is surrounded by tall cypress trees, overlooking the gently rolling hills of Tuscany.
Home in Farneta

Podere Bocci residence in Casentino - Entire Villa

5.0 out of 5 average rating, 48 reviews

Weekly house rentals

Guest favorite
A stone house with a rustic exterior is highlighted by a greenery-adorned entrance. The two-story structure features multiple windows and a staircase leading to an upper level. A cozy patio area is visible, surrounded by a lawn and natural landscape.
Home in Sansepolcro

Little house in the woods, Il Palazzo – peace and tranquility

4.97 out of 5 average rating, 62 reviews
Top guest favorite
An aerial view presents a charming stone farmhouse surrounded by lush greenery and a vineyard. The inviting pool area features loungers and a covered seating space, offering a serene spot for relaxation. The spacious garden complements the tranquil countryside landscape.
Home in San Giustino

Le Murce

5.0 out of 5 average rating, 19 reviews
Guest favorite
A serene pool is bordered by a stone patio, inviting relaxation. The surrounding lawn features green grass and several trees. In the background, the restored stone farmhouse stands prominently, with steps leading up to it, framed by lush greenery.
Home in Monte Santa Maria Tiberina

Casale S. Stefano

4.9 out of 5 average rating, 41 reviews
Guest favorite
The exterior of the villa is showcased, featuring a stone facade and a red-tiled roof. A staircase leads to a covered entrance with arched columns. Lush greenery surrounds the building, and large windows with wooden shutters enhance its rustic charm.
Home in Chiusi della Verna

Villa dei Macchini

5.0 out of 5 average rating, 15 reviews
Top guest favorite
A cozy living room is presented with a comfortable sofa facing a television, situated near a fireplace. The space is enhanced by decorative wall plates and a small side table, creating a warm atmosphere for relaxation and entertainment.
Home in Chiusi della Verna

Casa Carla

4.99 out of 5 average rating, 92 reviews
Top guest favorite
A serene sleeping area features a spacious bed with neutral bedding, complemented by a rustic stone wall. A small bedside table with a lamp is positioned next to the bed, while soft natural light fills the room from a window adorned with light curtains.
Home in Mercato Saraceno

Casa del Moro

4.97 out of 5 average rating, 35 reviews
Top guest favorite
Home in Umbertide

Farmhouse with incredible view with pool

5.0 out of 5 average rating, 12 reviews
Guest favorite
A serene outdoor area features two wooden lounge chairs positioned beside a modern infinity pool. The pool reflects the landscape of rolling hills and distant historic structures, with lush greenery surrounding the space, creating a tranquil setting for relaxation.
Home in Poppi

Casentino Villa Antonella

4.95 out of 5 average rating, 19 reviews

Private house rentals

Superhost
A charming stone house is surrounded by lush greenery and a wooden fence. The outdoor area features a vine-covered terrace, with ample natural light highlighting the serene setting. Windows overlook the peaceful landscape, creating an inviting environment for relaxation.
Home in Chiusi della Verna

The house in the paradise of Serra.

4.86 out of 5 average rating, 43 reviews
Guest favorite
A private swimming pool is surrounded by lush greenery, with a smooth stone wall bordering the area. Wooden lounge chairs are positioned nearby, offering shaded comfort under a wooden pergola. The turquoise water reflects the sky, creating a serene outdoor space.
Home in Città di Castello

Country house with pool in northern Umbria bordering Tuscany

4.98 out of 5 average rating, 60 reviews
Guest favorite
A serene outdoor view showcases a large swimming pool surrounded by vibrant greenery and blooming yellow flowers. Rolling hills and the expansive countryside are visible in the background, with clear blue skies enhancing the peaceful atmosphere.
Home in Città di Castello

Acadirospi

4.9 out of 5 average rating, 42 reviews
Guest favorite
A large heated swimming pool is surrounded by a stone patio, featuring a wooden gazebo with seating and sun loungers. Lush greenery and trees frame the pool area, providing natural shade, while expansive views of rolling hills and valleys stretch out in the background.
Home in Umbertide

Casa Maestra, Umbria hills, AC, large heated pool

4.96 out of 5 average rating, 23 reviews
Guest favorite
A scenic view showcases rolling hills and a tranquil private pool surrounded by greenery. The landscape features a mix of trees and open fields, with a distant medieval village visible on the hillside.
Home in Borgo alla Collina

luxury villa in centre of tuscany

4.77 out of 5 average rating, 99 reviews
Guest favorite
Home in Caprile

Montana House in Stone-Garden-Panorama-Jacuzzi

4.95 out of 5 average rating, 43 reviews
Guest favorite
A charming exterior view of the house is presented, featuring a pastel-colored facade complemented by wooden shutters. Floral arrangements in terracotta pots enhance the entryway, while a shaded patio area with a table and chairs invites relaxation under a large umbrella.
Home in Monterchi

Terrace on the Borghetto

5.0 out of 5 average rating, 16 reviews
Top guest favorite
Home in Venere

Vacation home

4.98 out of 5 average rating, 40 reviews

Destinations to explore