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House vacation rentals in Sestino

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Popular amenities for Sestino house rentals

House rentals with a pool

Top guest favorite
A private pool is situated amid well-maintained gardens, surrounded by varied greenery and tall trees. Colorful loungers are arranged along the patio, inviting relaxation. The clear water of the pool reflects the sky, enhancing the serene outdoor setting.
Home in Castiglion Fiorentino
5 out of 5 average rating, 35 reviews

Hidden gem in Tuscany

MitchellRating, 5 stars1 month ago
Where to start? I truly can't say enough good things about this property. It exceeded expectations in every way. From start to finish, our time here was a delight. Amanda was responsive, helpful, and accommodating. The location is remote, and a bit of adventure to get to, but Amanda had communicated that and we were prepared with the proper rental car that made it a breeze. The house is beautifully appointed, has every amenity, and lots of perfect spaces for both quiet moments and areas to gather with your group. The outdoor spaces and pool area are lovely, beautifully landscaped, and the views are spectacular. Book this place; you won't be sorry.
Top guest favorite
A clear swimming pool is set against a backdrop of rolling hills, with lush greenery and distant vineyards visible. The water reflects the vibrant blue sky, creating a peaceful scene for relaxation.
Home in Corinaldo
4.97 out of 5 average rating, 136 reviews

For those who love tranquility!

PawelRating, 5 stars1 day ago
We felt at home at Massimo's. Everything was as it should be and even better. The house was large, spacious and very clean. Perfect for our family of four plus a dog. The place is located far from the buildings, so you can relax in peace. The garden was large, perfect for spending time outdoors, and there was a large and clean pool where you could cool off on hot days. The contact with Massimo was without reservations. He always wrote back in a few minutes and if we needed anything, he was always available. There were basic groceries in the kitchen to make coffee and eat something after a long journey. In addition, we received delicious wine, and as soon as it was missing, he always brought new ones. On the last day, we had delicious croissants for breakfast. I highly recommend this home. Everything was perfect. And we hope to return there.
Guest favorite
A modern living area features a beige tufted sofa, complemented by a sleek coffee table and a vibrant area rug. A wood-burning stove stands beside a stacked wood display. Natural light filters through a window, providing a cozy ambience.
Home in Arezzo
4.9 out of 5 average rating, 166 reviews

Italian Interior

LloydRating, 5 stars8 months ago
What a wonderful experience! The description of the home was excelled by the reality. It was very clean and tastefully decorated — Anna has an eye for design and art. the three bedrooms easily accommodated us. The large patio with its charming table and vine screened roof was a charming place to enjoy our morning cappuccino. the home is situated in a agricultural community built in 1788, situated in extensive vineyards. The buildings have been thoroughly renovated into a series of private homes. The community contained renters like us, but also young communities and older retirees. We had a chance to get to know people in the neighborhood, who were uniformly friendly. the AirBnB is about 25 minutes away from Arezzo by car. The best place to park we found was in the short term parking at the train station. From there it was just a short walk to the Old Town. Anna was a wonderful and charming host. We recommend this property highly!
Guest favorite
The image depicts a tranquil swimming pool with sparkling turquoise water, reflecting the surrounding greenery and a distant stone building. Tall cypress trees line the area, enhancing the serene landscape, while sun loungers are arranged neatly near the pool's edge.
Home in Asciano
4.97 out of 5 average rating, 34 reviews

Family Forest - Pool in the Crete Senesi

SylviaRating, 5 stars1 week ago
The area is incredible, peaceful and the view spectacular. Asciano has the delightful charm of an Italian village. The people were friendly and welcoming. Even got greeted by their local police who offered up their number in case we needed anything. I felt safe, and it felt as if I lived there for years. I’d say this is a piece of heaven on earth. Bellezza maestosa! Non vedo l'ora di visitare di nuovo la Toscana e la città di Asciano! Grazie!
Guest favorite
A private pool is set within a well-kept garden, surrounded by lush greenery and gently sloping grass. The octagonal pool is framed by stone pathways and features a small tree at its center. The tranquil outdoor space invites relaxation and enjoyment.
Home in Gaiole in Chianti
4.86 out of 5 average rating, 264 reviews

Charming estate with views

AndrewRating, 5 stars1 week ago
Incredible stay and Bernardino and his family were incredibly welcoming and pleasant. They helped us check in later and were there to help us with any questions we had. Absolutely would recommend to anyone looking for a peaceful Tuscan retreat.
Superhost
A private swimming pool is surrounded by wooden decking and lush greenery, offering expansive views of the rolling hills and valleys in the distance under a clear blue sky. A small ladder is available for easy access to the water.
Home in Rufina
4.86 out of 5 average rating, 104 reviews

Ancient Tuscan Rural Residence

Jóna BergþóraRating, 5 stars5 days ago
Great house with amazing views. We used the pool a lot as it was very hot during our stay. Francesco and Serena were very nice and helpful. They booked a cooking class for us, which I highly recommend. The location is very convenient for visiting Florence, as it only takes about half an hour by train from Rufina.
Guest favorite
A private pool is surrounded by sun loungers, set on a wooden deck. The pool area features natural stone paving and is enclosed by a child-proof fence. Lush greenery and olive trees outline the space, providing a serene environment for relaxation.
Home in Lecchi in Chianti
4.96 out of 5 average rating, 137 reviews

Casa di Lyndall - Entire house with exclusive pool

LiannaRating, 5 stars1 week ago
Yet another fabulous stay! Thank you Lyndall for sharing your special space. Getting in on the village pizza night was a surprise bonus and so fantastic to enjoy the local community. Until next time :)
Top guest favorite
A private swimming pool is framed by landscaped greenery, with steps leading into the clear water. The expansive water surface reflects the distant view of Lake Trasimeno and the surrounding landscape under a partly cloudy sky.
Home in San Feliciano
4.9 out of 5 average rating, 143 reviews

Casa dei 5 Sensi - Trasimeno view

RobertoRating, 5 stars3 weeks ago
What a beautiful place! Great view of the lake. Sergio was incredibly friendly and responsive. He gave us local recommendations and even made us a fruit salad. I will definitely be booking with Sergio again the next time we are in Umbria.

Weekly house rentals

Top guest favorite
A modern sleeping area features a spacious bed dressed in a textured blanket, complemented by neatly rolled towels. An elegant freestanding bathtub is positioned against a rustic stone wall, while a potted plant adds a touch of greenery to the setting.
Home in San Marino
4.96 out of 5 average rating, 25 reviews

Casa Cicetta Accommodation 1296

BenRating, 5 stars2 weeks ago
Our stay here was amazing! The host was extremely friendly and helped us bring our suitcases in when she saw us struggling to bring them up the hill. She gave us a map of the area along with recommendations for restaurants and things to do. She was super communicative and helpful whenever we needed anything! The airbnb is beautiful and I wish we could’ve stayed longer. The view is amazing and we felt super comfortable and welcome. We fell in love with San Marino and will definitely be back with the same hosts and place!
Guest favorite
A quaint stone building is visible across a rustic bridge surrounded by lush greenery. Colorful flower pots line the railing, enhancing the natural scenery. The bridge leads to a serene setting with trees providing shade, creating a peaceful atmosphere for leisurely walks.
Home in Bibbiena
4.96 out of 5 average rating, 47 reviews

Charming house of the past next to the stream.

NickRating, 5 stars1 week ago
Casa Lisa is a rustic, authentic sanctuary away from the hustle of today’s mayhem yet all the everyday amenities are a short driveway. We had a wonderful few days here our hosts went out of their way to ensure we had a lovely time, hopefully we will return in the future.
Top guest favorite
The image captures a serene outdoor setting with a pathway lined by stepping stones leading to a lush lawn. Glowing sunlight reflects off the glass of the house, enhancing the calmness of the scene, while trees frame the view of the distant lake.
Home in Magione
5 out of 5 average rating, 19 reviews

Beach House, on the shores of Lake Trasimeno

Juan DiegoRating, 5 stars2 weeks ago
To value this property, you have to start with the HOST, a professional in every sense. From the minute 0 of the reservation, until check-out; always attentive, very friendly and very professional. It's a pleasure to meet serious people and this gives the app value. The beach house is a paradise in Italy. Easy access, attention to detail, peace, nature, comfort. Our trip was as a family with our two poodles and I think they were the ones who enjoyed the property the most, seeing them run and jump through the green areas of the property and live with many birds, rabbits is priceless. Our daughter enjoyed her stay studying and with the peace and quiet of the place, it was easy for her to concentrate. We, on the other hand, did some sightseeing in the area, everything is very close and well connected by road. It is a very well-kept, safe property and above all, enjoying its sunset, sitting on a lounger, enjoying a good wine (from the area) is an unrepeatable experience. Thank you Maurizio.
Top guest favorite
A rustic stone building is framed by lush greenery, showcasing wooden shutters and a welcoming arched doorway. A small outdoor table stands nearby, accompanied by planters filled with flowers, all set against a gravel path leading to the home.
Home in Cortona (Pierle)
4.98 out of 5 average rating, 51 reviews

"L'Antico Metato" house in the woods

FriederikeRating, 5 stars3 weeks ago
We stayed 4 days and it was just fantastic. The arrival was hassle-free and Flavia welcomed us very warmly on site. After a short tour of the house and a short briefing, the holiday could begin. A note with restaurant recommendations and excursion destinations was ready on the table. After a short thunderstorm, we had a power outage, but Flavia was immediately available and within 5 minutes we had electricity again. Shopping and restaurants are easily accessible by car. I would recommend this place to anyone who longs for peace and wants to enjoy nature. We will be happy to come back!
Top guest favorite
An outdoor patio area is visible, surrounded by tall trees. A rectangular table is set for dining, accompanied by several chairs. Flower pots with colorful blooms are placed around the space, which is illuminated by natural light filtering through the branches.
Home in Arezzo
5 out of 5 average rating, 12 reviews

Villa Medici Donnini Superior Apartment

RobertRating, 5 stars1 month ago
We had a wonderful week-long visit. I wish we had stayed longer. The villa is beautiful. It is spacious, clean, with modern amenities and appliances but also has some very nice antique furniture and decor. The outdoor patio is really amazing, with views of distant Tuscan hills and farms, olive and cypress trees - a great place to eat and relax outdoors. Nearby Arezzo is a great place to visit. There are many interested museums, churches and places to visit in the older section of the town (including the Basilica di San Francesco with frescoes by Piero della Francesca), but there are also more modern parts of town with shops and restaurants, and ample parking. The villa is also within easy driving distance of many other surrounding towns (such as Cortona) and places to visit. Our hosts were super helpful and friendly, and we especially enjoyed the olive oil that is provided and made from the trees growing on the property. We would definitely stay here again.
Superhost
A warm living area features arched windows allowing natural light to fill the space. A wooden coffee table is positioned in the center, surrounded by a comfortable sofa and a rattan chair. Shelving units display decorative items and a small plant sits atop the table.
Home in Lucignano
4.85 out of 5 average rating, 40 reviews

La Casetta

JonasRating, 5 stars2 weeks ago
Hard to find a place like Maria’s, beautiful place and with such a friendly and helpful staff.
Guest favorite
An outdoor dining area features a wooden table set with green dinnerware. Bright flowers in a vase are displayed at the center. The space is shaded by an awning, surrounded by manicured grass, with a barbecue and a view of nearby greenery.
Home in Pelago
4.92 out of 5 average rating, 65 reviews

Chianti House Garden - 30m Florence center- A/C

DagmarRating, 5 stars3 weeks ago
Nice and spacious place to stay. Plenty of space and quietly located in the middle of a residential complex. Car is necessary. From Pontessieve, Florence is then easily reachable by train. Pamela has made many suggestions for activities and was quick to respond to questions and requests. It was a successful stay for us🍀
Guest favorite
A serene bedroom features a spacious bed with a simple white coverlet. A wooden chair with a striped cushion is placed beside a bench. Natural light filters through the two wooden windows, revealing views of the lush vineyards outside.
Home in Castelnuovo Berardenga
4.91 out of 5 average rating, 89 reviews

The Chianti window

KirstenRating, 5 stars2 weeks ago
This beautiful Tuscan home stole our hearts and we will definitely be back to enjoy this peaceful, spacious and authentic home. Sarah and her family were incredible hosts and made us feel right at home. We are absolutely in love with our experience here and would highly recommend the stay!

Private house rentals

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
5 out of 5 average rating, 51 reviews

Villa Podere Cerretino

Emma KamperRating, 5 stars3 weeks ago
Fabulous place in amazing surroundings. The pool area is wonderful and the garden beautiful. We had an amazing time and enjoyed the entire place - especially the outdoor pizza oven. Nicola was very helpful and fast in his responses.
Top guest favorite
A serene swimming pool is surrounded by lush greenery, with gentle hills visible in the background. Sunlight reflects off the water's surface, enhancing the inviting ambiance. Lounge chairs are positioned beside the pool, offering a comfortable spot to relax and enjoy the panoramic views.
Home in Loc. Casalini - Comune Panicale
4.99 out of 5 average rating, 95 reviews

Cottage surrounded by nature

AlanRating, 5 stars1 week ago
Stayed here last week for 5 days. On arrival we were met with a welcome basket of food a bottle of wine a bottle of homemade olive oil and also bottles of water on arrival. The pictures don’t do it justice it felt like a place out of a fairytale, the property is surrounded by tons of olive trees and greenery. If you want a quiet relaxing holiday this is place to go. Rosella was amazing with quick responses and extremely welcoming, we are definitely going again next year.
Guest favorite
The villa is positioned on a hillside, offering panoramic views of the rolling Tuscan countryside at sunset. Olive trees are scattered throughout the landscaped garden, with a covered terrace visible, inviting outdoor relaxation and dining. Warm light bathes the scene, enhancing the natural beauty.
Home in Castelmuzio
4.98 out of 5 average rating, 40 reviews

Casa Ora d"Oro - Panoramic Views

Jason AllenRating, 5 stars3 weeks ago
first I love his neighbors who checked us in. Cinzia was amazing. She not only showed us our place but took our kids to show us her farm. she also makes her own olive oil and gifted us with some! Wonderful Italian neighbors!! I contacted Rocky in advance and he provided me with specific recommendations for where we should go during a long drive we took. we went where he suggested and was not disappointed! Amazing quiet location with great near by wineries. would 100% recommend to everyone!
Top guest favorite
A spacious bed is centered against a textured white wall, complemented by two wooden nightstands on either side. Each nightstand features a simple lamp and a decorative yellow object. Natural light enters through the window, accentuating the soft bedding and neutral decor.
Home in Savignano sul Rubicone
4.98 out of 5 average rating, 58 reviews

Casa Castelvecchio

ChristinaRating, 5 stars1 week ago
Honestly, Deborah was the perfect host for several reasons. Beyond being incredibly kind and understanding, she really tuned into what I needed. I mentioned that this was my first time in a town like this and that I was hoping to hibernate for a few days, and her place felt like the perfect fit. She went above and beyond to make the check-in process smooth, even offering to pick me up from the train station and take me to the grocery store—on a Sunday, no less, when most places were closed and options were limited. Her home was serene, even more beautiful than the photos, and I immediately felt safe and at ease in the neighbourhood. I also loved how central it was to most things, like a spa, fruit/vegetable store, cafes, restaurants and convenience stores. In a world that often feels like it’s growing less kind, Deborah truly understands the heart of hospitality. :)
Guest favorite
A serene swimming pool reflects the twilight sky, with vibrant hues as the sun sets in the distance. A silhouette of a statue stands gracefully near the pool's edge, while a sun lounger awaits nearby, adding to the tranquil ambiance.
Home in Arezzo
4.88 out of 5 average rating, 24 reviews

Colonial house immersed in a natural park.

MarieRating, 5 stars10 months ago
We spent two weeks at Rolando and Patrizia's with our two one-year-old and three-year-old children. The place is absolutely beautiful with a sublime view. They had a lot of little touches for our children throughout the stay. It was always a pleasure to chat with them. Accommodating, very considerate. The kids were always happy to see them. As for the house, it is very nice and easy to live in. The two terraces are a real plus. And again the views filled us throughout our stay.
Top guest favorite
A rustic bedroom features exposed stone walls and wooden beams. A spacious bed is positioned centrally, surrounded by soft linens. A wooden wardrobe and a small side table complement the space, while a vintage chair adds comfort. Natural light filters through the window, illuminating the room.
Home in Tuoro sul Trasimeno
5 out of 5 average rating, 53 reviews

the oasis of the foxes

AbbyRating, 5 stars2 weeks ago
Beautiful home in a more secluded area overlooking Lake Trasimeno. The trains and a highway are below but not invasive. The views are beautiful. The home was clean and tastefully updated but still clearly old and had a lot of character. We did not have a car and the train station is an hour walk away. There are a couple buses that pass through but not enough to be a reliable means of getting to and from the house. Even the taxi was busy and we had to be flexible on when we went to the train station but it worked out fine. We walked to and from Tuoro for groceries and visited La Puntabella for a great dinner with a view. It was an adventure and we enjoyed it despite our plan not being very good for this location. Sonia was patient and helpful in working out our means of travel and figuring out the bus schedule. Natolino reminded us of home and he is fun to watch and listen to.
Top guest favorite
A charming two-story stone farmhouse is shown surrounded by lush greenery and colorful flowering plants. The building features a mix of natural stone and painted exterior with large windows. A clear blue sky offers a bright backdrop to the inviting landscape.
Home in Chiaveretto
4.98 out of 5 average rating, 45 reviews

Oleandro, cozy studio in Val di Nima

CarolynRating, 5 stars1 week ago
Nicola bnb was amazing! Perfect to relax and such a lovely bnb. Nicola is the perfect host. Highly recommend. So very beautiful with surrounding huge mountains. A great base to explore surrounding areas. And a bonus, the cats are geougous. Thank you
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
4.99 out of 5 average rating, 77 reviews

Casa Carla

DaniloRating, 5 stars2 weeks ago
The experience in Carla's villa is by far the best I've ever had with Airbnb. The house is close to other villas but with a large well-kept garden of roses and medicinal plants and with deck chairs in which to spend moments of absolute calm. Carla waited for us in person to offer us a very welcome tart and explain every detail of the apartment, equipped with TV, wifi and all the kitchen equipment (very very nice), including a kettle, coffee machine and pods and a nice and cozy decor. The bed is the best on Airbnb. Absolute peace. The only regret: having only stayed two nights.

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Arezzo
  5. Sestino
  6. House rentals