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House vacation rentals in Sestino

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Popular amenities for Sestino house rentals

House rentals with a pool

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, 167 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
4.94 out of 5 average rating, 36 reviews

Family Forest - Pool in the Crete Senesi

JánRating, 5 stars1 week ago
The apartment really enchanted us, the rooms are nice, clean with air conditioning, stylish, in the living room a large TV, kitchen with everything that should be here. The "resort" itself was on a hill with beautiful views, a huge garden, a swimming pool, all stylish Tuscan, the surroundings are beautiful, peace, quiet, peace, everything you need here you will find. As the Italians say, it's "Tutto bene" here
Guest favorite
A lush garden area is filled with vibrant hydrangeas in shades of blue and pink, adding color to the outdoor space. Nearby, red geraniums bloom, enhancing the tranquil ambiance. The scene is complemented by a swimming pool and scenic views of the surrounding hills in the background.
Home in Arezzo
4.88 out of 5 average rating, 25 reviews

Colonial house immersed in a natural park.

TomaszRating, 5 stars3 days ago
Ronaldo and Patrizia are great hosts and wonderful people, Bamboo is the best companion. The place itself is full of magic. Beautiful views, wonderful nature, sunrise in your windows. Close to Arezzo with its amazing history and culture. Our stay here was more than holiday. It was like gaining equilibrium in life. And we also tasted the best ever olive oil made by Rolando! We will come back for sure. I told Ronaldo when we were leaving - we left part of our hearts here. Thank you Ronaldo and Patrizia. All the best for you and see you again, Joanna and Tomek
Top guest favorite
A private swimming pool is surrounded by a stone patio, featuring several lounge chairs arranged for sunbathing. Lush greenery and olive trees provide a natural backdrop, while the distant view showcases parts of the historic borgo. A shaded area is available for relaxation.
Home in Montebenichi
5 out of 5 average rating, 61 reviews

[Little Escape] 4 Beds + Private Panoramic Pool

PiretRating, 5 stars4 days ago
We really enjoyed our stay at Tommaso's! The house is located in a lovely small village, very quiet and peaceful, surrounded by beautiful Tuscan nature. We even spotted a wild boar one early morning (so best to be cautious during early mornings and late nights). There’s a charming local restaurant just around the corner where we had a great dinner – Tommaso kindly helped us book a table for our first night, which was much appreciated. Nearest bigger shop is around 20-min drive. The house itself is spacious and well-equipped, we had everything we needed and more. Just a heads-up that the pool area is a short walk from the house (about 3 minutes), but so worth it. Communication with Tommaso was smooth and easy throughout. Thank you for a lovely stay!
Top guest favorite
Home in San Lorenzo
5 out of 5 average rating, 27 reviews

Casa dei Vasi

AlexRating, 5 stars3 weeks ago
Our stay in Tuscany at Lorenzo’s estate was magical! Close to the gorgeous Anghiari, fresh pastry gifts from Lorenzo’s lovely mother every other day and magical firefly displays at night, the pool and wood fired hot tub were an especially nice touch, recommend and would stay again :)
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 stars1 week 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.
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 stars1 month 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.
Guest favorite
A private swimming pool is set against a backdrop of lush hills, displaying clear blue water. Surrounding the pool, a paved area offers space for relaxation, featuring lounge chairs along the perimeter. A wooden fence provides a natural boundary, enhancing the tranquil outdoor atmosphere.
Home in Sogliano Al Rubicone
4.95 out of 5 average rating, 112 reviews

Country house with private pool

AndrewRating, 5 stars1 month ago
What a beautiful little space in the Italian countryside. I am so sad we could not stay longer. We had a wonderful welcome and our stay far exceed our expectations. Our host helped us book dinners every night in local restaurants and we loved the proximity to San Marino and nearby wineries.

Weekly house rentals

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
4.93 out of 5 average rating, 42 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 stars2 weeks 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. :)
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, 20 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 stars4 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!
Guest favorite
A charming outdoor area is framed by a wooden porch, featuring a seating arrangement nestled among greenery. The sunlit space highlights a blend of stone and yellow façade, with nearby structures partially hidden by trees. Pathways of gravel create a welcoming atmosphere.
Home in San Secondo
4.97 out of 5 average rating, 31 reviews

The little house on the garden

MonikaRating, 5 stars1 month ago
A quiet neighborhood with wonderful hosts who make you feel at home from day one. The perfect place for real relaxation. Our dog appreciated the daily company of sweet Memole in the garden. Clean, comfortable, the surroundings of the house are a feast for the senses!Matteo, Marusca and Eva were very friendly and helpful in every matter. I hope we will strengthen this contact in the future!Highly recommended! Monika and Bernd
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.
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
4.83 out of 5 average rating, 41 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
4.93 out of 5 average rating, 67 reviews

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

JohanRating, 5 stars4 days ago
We had an amazing stay at Chianti house, Pamela has allot of good recommendations!

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.
Guest favorite
A serene outdoor space features a large, clear swimming pool surrounded by carefully manicured hedges and tall trees. The rustic stone house stands in the background, complemented by a few lounge chairs near the pool, offering a peaceful setting for relaxation.
Home in Cavriglia
4.93 out of 5 average rating, 80 reviews

Wonderful country house

MichaelRating, 5 stars1 week ago
We had a brilliant week at Jakob and Margit’s house. Margit was so friendly and helpful (and gave us some wine and fresh eggs!). The views from the gardens are incredible and having the swimming pool was perfect. The local area has lots of great vineyards to visit and the house is close to Florence/Siena/Arezzo for day trips. It had everything we needed like a washing machine etc.
Guest favorite
The exterior of a stone building is surrounded by lush greenery and flowering plants. An awning provides shade over a small seating area. Large glass doors invite natural light into the inviting entryway, while a small staircase leads to the upper level.
Home in Urbino
4.91 out of 5 average rating, 34 reviews

Sant'Eufemia 13 - Farmhouse 4 km from Urbino

LindaRating, 5 stars1 week ago
Beautiful, peaceful location A few minutes from Urbino Well equiped kitchen A place where you can cook, relax and get away from everything. Highly recommended
Guest favorite
The living area features exposed stone walls and wooden beams, creating an inviting space. A traditional fireplace is centered, complemented by a dining table surrounded by chairs. Natural light flows in through a window, illuminating a well-equipped kitchen against the wall.
Home in San Leo
4.92 out of 5 average rating, 24 reviews

18th-century stone house in the historic center

MariusRating, 5 stars6 days ago
Our stay at Jean Philippe's apartment was great, the apartment was very clean and charming and the kitchen had all basic tools and even some basic ingredients for cooking. The location was very central in the village and there were parking options nearby. Jean Philipe was very friendly, very responsive at all times and showed great hospitality. We'd love to come again!
Top guest favorite
A private swimming pool is framed by a sun terrace furnished with several white loungers. A shaded seating area provides a relaxing spot nearby, surrounded by lush greenery and trees. Natural stone steps lead along the edge of the space, enhancing the tranquil outdoor setting.
Home in Montevarchi
5 out of 5 average rating, 25 reviews

Casa San Ripa: Relax Oasis with Private Pool

CarolinaRating, 5 stars6 days ago
We had an amazing time in Casa San Ripa. The house is even nicer than it looks in the pictures, the view is amazing and the outside area is lovely, with all the lights in the trees at night. The whole property was very clean, including the inside and the pool, the instructions were easy and Giulia is super responsive and extremaly nice and helpful. We had a great stay and would highly recommend!
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 stars2 weeks 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
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
4.98 out of 5 average rating, 44 reviews

Villa Piandarca - Tuscany - WIFI - private pool

MelissaRating, 5 stars1 week ago
Absolutely adored this place and can’t recommend it enough. The space and the owners are so welcoming with everything you could need. The grounds were gorgeous and the apartments were so quaint and adorably decorated. We had the pool to ourselves and it was perfect for our kids to play on a really hot day! We opted to have dinner on site one night and it was absolutely fabulous! This family-owned operation is a must-stay and we hope to return! Thank you!
Superhost
A swimming pool with sparkling blue water reflects the surrounding greenery. There are three white canopies positioned alongside the pool, each draped with light fabric. The shaded area behind the pool includes trees, enhancing the tranquil outdoor setting.
Home in Badia Agnano
4.89 out of 5 average rating, 62 reviews

Modern Comforts in a Historic Farmhouse

JuliusRating, 5 stars1 month ago
We were there in April/May together with our friends and a total of three children. The accommodation is fantastically located and perfect especially with toddlers (large private playground, lots of greenery, children's gates on the stairs). We could have breakfast and dinner on the terrace every day and grilled regularly. The accommodation is equipped with everything you need. The facility including pool was cleaned daily by the very nice gardener team. On site you absolutely need a car, as the complex is beautiful but remote. However, there are plenty of restaurants (Perla Nero as a recommendation) and shops for shopping in the surrounding area. Overall definitely a recommendation for all families and couples looking for a quiet place to stay in Tuscany.

Destinations to explore

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