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House vacation rentals in Sestino

Find and book unique houses on Airbnb

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Popular amenities for Sestino house rentals

House rentals with a pool

Superhost
A shared swimming pool is surrounded by a fenced area, featuring several sun loungers with striped cushions and umbrellas for shade. Olive trees and lush greenery create a peaceful backdrop, while the clear blue sky adds to the serene atmosphere.
Home in Reggello
4.8 out of 5 average rating, 81 reviews

House with pool among olive trees plantation

KarolinaRating, 5 stars7 months ago
The apartment is located in the picturesque surroundings. It takes quite a while to get there up the hill, but the views reward it! The place was clean and well-prepared for our stay. Good spot if you look for some peace and quiet and want to stay away from the noise!
Top guest favorite
A well-maintained outdoor area features a private pool surrounded by a lush green lawn. A cozy villa can be seen in the background, complemented by tall trees and a relaxing ambiance. Lounge chairs are positioned near the pool, inviting leisure under the partly cloudy sky.
Home in Reggello
5 out of 5 average rating, 44 reviews

Villa in Tuscany - Reggello, with Swimming Pool and WiFi.

MicheleRating, 5 stars1 week ago
Very nice place to stay in the hills of Tuscany. A little remote but we appreciated that. Many restaurants nearby with really very good food and absolutely good prices. Accommodation with large garden, pool, air conditioning and heating. Well-kept and clean. Chickens whose eggs we were allowed to collect. Magena was always available, very friendly and helpful. Many wineries in the area where you can eat and drink. We will be back. Thanks Magena and Eduardo
Superhost
Home in Umbertide
4.81 out of 5 average rating, 37 reviews

Private villa with pool and breathtaking views

SophieRating, 5 stars8 months ago
Anna’s house is stunning and tucked away in such a beautiful quiet location. The people who take care of the house were kind and our two year old loved him. Would highly recommend anyone who wants a quiet get away from the hustle and bustle of life to stay here.
Top guest favorite
The exterior of Villa Pergo is revealed, showcasing a historic stone facade under a clear blue sky. A spacious gravel area is visible, surrounded by lush trees and potted plants, providing ample parking and outdoor space.
Home in Pergaccio
5 out of 5 average rating, 46 reviews

Villa Pergo is an ancient charming country villa

TerriRating, 5 stars6 months ago
Based on the previous wonderful reviews of Antiqua degli D’ulivi, a year ago we booked a three week stay in the outskirts of Cortona in Pergo. We had our kids, grandkids and dear friends with us and as we drove through the gates into the Villa, we entered a magical place filled with generosity, laughter, relaxation, wonderful food, a refreshing pool and golden light. Massi was always there to help us with any questions we had and refill our olive oil bottle with the amazing green liquid made from his olives. We enjoyed the most delicious lunch with his family and they also were such giving, lovely people. We learned so much about Italy and Tuscany from them: porcini mushrooms, Perugia soccer teams, local markets, hot springs near Montepulciano, nearby restaurants, vineyards, hikes and more. We highly recommend an extended stay at this Tuscan home—we were so fortunate to experience it for three glorious weeks. The memories will be long lasting and always treasured. Mille Grazie to Massi
Top guest favorite
A tranquil swimming pool is surrounded by stone decking, complemented by sun loungers in a serene garden setting. Olive trees provide a natural backdrop, while a rustic building and landscaped areas are visible nearby.
Home in Serre di Rapolano
4.97 out of 5 average rating, 74 reviews

L'Olivo - detached villa with swimming pool

MartaRating, 5 stars7 months ago
Amazing place in a quiet area with a beautiful view of the countryside. Climate cottage equipped with everything you need. Together with our dogs we felt like at home. Bruna is an incredibly warm and helpful person. Thank you for a wonderful time.
Guest favorite
A spacious living room features a vaulted ceiling with terracotta tiles. Glass doors open to a scenic outdoor area, inviting natural light. Comfortable seating includes a light-colored sofa with decorative pillows and woven chairs, complemented by framed botanical art on the walls.
Home in Asciano
4.96 out of 5 average rating, 45 reviews

Tuscan farmhouse near Siena + Cortona, heated pool

RobRating, 5 stars7 months ago
We absolutely loved the home and location! There were nine of us and everyone had their own space and bathroom. The home was very clean and decorated beautifully. Amanda was a fabulous host. She was very responsive with all communication and helpful with places to see in the region. The location was excellent for traveling all around Tuscany and it was very peaceful. We can't wait to go back!
Superhost
The outdoor pool area features a rectangular pool surrounded by a spacious wooden deck. Sun loungers and beach umbrellas are placed around the pool, with vibrant flowers adding color to the scene. A panoramic view of the surrounding hills can be seen in the background.
Home in Canneto
4.92 out of 5 average rating, 25 reviews

Elegant Accommodation in Villa with Swimming Pool in Perugia

AndrewRating, 5 stars8 months ago
Wonderful stay. Great layout for us (2A, 2C, 1I) and a fantastic swimming pool. Roberta was lovely and we communicated via messaging app given language differences. Roberta and family were quiet in the ground floor apartment and the upstairs rental were equally nice. We barely had to share the pool. Great location for day trips to Florence, Sienna and Assisi.
Guest favorite
A private pool area is framed by lush greenery and blooming flowers. Two lounge chairs and a small table are arranged on a stone patio under a large umbrella. The bright yellow house is partially visible, showcasing an upper balcony.
Home in Cortona
4.96 out of 5 average rating, 57 reviews

"Casa Elisa", house with swimming pool at the foot of Cortona

AlessandroRating, 5 stars4 months ago
I had an unforgettable stay at Casa Elisa, located at the foot of the beautiful Cortona. The atmosphere is magical: a perfect fusion of Tuscan tradition and modern comfort. The rooms are elegant and quite spacious, tastefully furnished and equipped with all the necessary comforts. The garden with pool is an oasis of tranquility, ideal to relax with a good book or to enjoy an aperitif at sunset. But it's the warmth and hospitality of Elisa's family that makes the stay really special. Their availability in providing information about places to visit and recommended restaurants makes all the difference. I highly recommend Casa Elisa to anyone who wants to discover the beauty of Tuscany, living an authentic and unforgettable experience.

Weekly house rentals

Guest favorite
The living area features wooden beams across the ceiling and a cozy seating arrangement with a sofa and a bench. Large glass doors open to a garden, allowing natural light to fill the space. Decorative items are displayed on the shelves nearby.
Home in Figline e Incisa Valdarno
4.91 out of 5 average rating, 44 reviews

POMEGRANATE CAMPOPINETA

AmandaRating, 5 stars6 months ago
Alessandra’s place was an absolute dream. It’s picturesque with the most gorgeous view of Tuscany hills in a rustic styled rental. She was extremely helpful and attentive during our stay! Would definitely come back here next time we visit!
Superhost
A spacious dining area is illuminated by natural light filtering through open doors. A large wooden table is surrounded by several chairs, and a matching sideboard displays glassware. Soft curtains frame the doorways, enhancing the charming countryside feel.
Home in Lucignano
4.78 out of 5 average rating, 9 reviews

Beautiful property between Siena and Arezzo

TimRating, 5 stars20 months ago
we had a very nice stay. The entire accommodation was very clean. Highly recommend taking something against the mosquitoes. the only criticism was the chairs on the terrace, as 2 have shackled heavily, there should be a replacement here.
Superhost
A stone villa is framed by lush greenery, showcasing a welcoming entrance with an ornate gate. Large windows with green shutters invite natural light into the home. A small balcony is visible on the upper level, adding to the charm of the exterior.
Home in Montefollonico
4.89 out of 5 average rating, 18 reviews

[15 min da Montepulciano] Villa Chiara

JoeRating, 5 stars7 months ago
Great location and the 2 full size bathrooms were nice!
Superhost
A private pool is surrounded by a spacious terrace, featuring two stylish cabana beds and several sun loungers. Lush greenery and rolling hills are visible in the background, offering a serene atmosphere. The pool area is well-lit for enjoyable evenings outdoors.
Home in Pietralunga
5 out of 5 average rating, 11 reviews

Il Monte

ConstanzeRating, 5 stars9 months ago
Great stay in beautiful house in beautiful house.
Top guest favorite
An appealing stone villa is framed by lush greenery and manicured hedges. A circular stone fountain is centered in a gravel area, surrounded by shrubs and trees. The sky is partly cloudy, providing a gentle light that enhances the natural beauty of the setting.
Home in Castelfranco Piandiscò
4.96 out of 5 average rating, 82 reviews

Villa close to Florence amazing view private pool

Ane ElineRating, 5 stars7 months ago
Had a week here with good friends. Enjoyed the beautiful house and the area. Great for a slow, calm getaway!
Top guest favorite
The living area features a spacious arrangement of seating, including a green-covered sofa and a brown couch, with large windows allowing natural light to fill the room. A small coffee table is situated near the seating, with a dining area visible in the background.
Home in Gabicce Mare
4.96 out of 5 average rating, 26 reviews

independent apartment with private garden

TobiasRating, 5 stars7 months ago
Marcello was very accommodating and friendly. The apartment was exactly as described. Very large and clean. The location is good. Very close to the beach, shops and restaurants. Bicycles are at your disposal
Guest favorite
Home in Montebenichi
4.88 out of 5 average rating, 17 reviews

The Montebenichi Dovecote

StephenRating, 5 stars6 days ago
We had an incredible stay at this beautiful villa in the rolling hills of Tuscany. Perched on a mountain, the property offers stunning views over the countryside, with gorgeous gardens and an authentic Tuscan feel throughout. The villa itself was spacious, comfortable, and full of charm. The location was perfect — peaceful and private, yet central to many of the places we wanted to visit, including Florence, Montepulciano, Siena, and San Gimignano. Christina, our contact person, was a great communicator. She was also on time, very helpful and pleasant to be around. She provided us with great insights about the area and the property. The location was excellent for us to use the e-bikes that we rented. We had breathtaking rides around the area. There was an excellent grocery store, Conrad’s in Bucine with a very tasty restaurant in the same Plaza. It was the perfect rustic home base with lots of charm the Tuscan experience for exploring the region, and we would absolutely stay again
Superhost
A spacious bed is dressed in soft white linens, complemented by decorative pillows. Two bedside tables with lamps stand on either side, providing gentle illumination. The walls feature warm tones and framed artwork, contributing to a calming and serene atmosphere.
Home in Rietine
4.85 out of 5 average rating, 206 reviews

Gaiole in Chianti Poggio Casabianca

MonicaRating, 5 stars5 months ago
What a great getaway!! We hope to make it back soon!

Private house rentals

Guest favorite
The outdoor area features stone walls and a well-maintained garden with various plants. A small deck chair is positioned for relaxing, with a sunny sky overhead. Shade is provided by large awnings, and the serene landscape includes green trees and a distant view of rolling hills.
Home in Urbino
4.9 out of 5 average rating, 31 reviews

Sant'Eufemia 13 - Farmhouse 4 km from Urbino

TeclaRating, 5 stars3 days ago
Mara is an attentive, helpful, generous and welcoming host. The place is beautiful, very quiet away from the chaos of the city. An experience to recommend
A covered terrace features a round dining table with four elegant chairs and a rocking chair. Arched openings frame views of the lush garden and swimming pool, with expansive greenery leading to the lake in the distance. Natural light filters through, enhancing the serene atmosphere.
Home in Le Piagge
5 out of 5 average rating, 4 reviews

Olindia by Interhome

TimRating, 5 stars19 months ago
I stayed at the adorable place with my family for a week. Upon arrival, the host gave us the key and showed us everything. We especially liked the large pool and the breathtaking view of Lake Trasimeno from the upper floor of the house. We had a very nice week in Umbria and explored the surroundings in day trips. If you have any questions or problems, the host has always been kindly helped. We will be happy to come back.
Superhost
The exterior of the brick house features a rustic wooden door framed by an arched entryway. A bench with cushions is positioned nearby, complementing the green lawn and trees in the background. Soft lighting accents the entrance, creating a welcoming atmosphere.
Home in Foiano della Chiana
4.87 out of 5 average rating, 31 reviews

Casa Walter Valdichiana

OrrRating, 5 stars2 weeks ago
We had a wonderful stay at Julia's villa in Tuscany! The home was beautiful, spotless, and perfectly hosted — Julia made us feel truly welcome. The surroundings were stunning and peaceful, the perfect Tuscan experience. Highly recommend!
The exterior of the rustic stone house features a spacious terrace with tiled flooring and a wooden pergola. Lush greenery surrounds the area, and vibrant flowers add color to the landscape. The entrance is framed by opened double doors, inviting guests to explore.
Home in Cortona
4.87 out of 5 average rating, 15 reviews

Lucia by Interhome

ChristophRating, 5 stars7 months ago
The terrace was great, and the entire place had a quiet and peaceful feeling.
Top guest favorite
A modern kitchen features a central island with an induction cooktop and seating for several guests. Gray cabinetry complements stainless steel appliances, including an oven and refrigerator. Natural light fills the space, highlighting the open-concept layout that connects to the living area.
Home in Castiglion Fiorentino
5 out of 5 average rating, 17 reviews

Volpe by Interhome

MartinRating, 5 stars5 months ago
It was an absolute delight to stay at this gem of a property. We booked for 10 days and had a chance to enjoy and explore the surrounding areas. The house is spotless, comfortable, spacious, and fully equipped with modern appliances. So it has exceeded our expectations and would love to book it again in the future. Our host Alberto, is welcoming and very friendly, making the process of checking in and out quite seamless. My overall impression is 10/10.
Guest favorite
A small covered patio area is presented with a white metal bench complemented by two soft cushions. The wall is painted in a warm orange hue, and a welcome mat is placed in front of the entrance door, enhancing the inviting space.
Home in Cesena
5 out of 5 average rating, 9 reviews

The other house

AkifRating, 5 stars8 months ago
The house is large new and clean, large living room, two bedrooms, good bathroom and practically furnished kitchen. Actually better than description. Host is helpful and kind. Thera are many attractions around, within 10-30 mins drive. Not walking friendly place but quiet and peaceful. Has large garden and terrace.
Superhost
A spacious living area features two comfortable sofas, a wooden desk, and a bookshelf filled with books. Natural light enters through large windows with white curtains, providing a view of the outdoor space. A tasteful floral arrangement decorates the coffee table.
Home in Gabicce Mare
4.93 out of 5 average rating, 14 reviews

The house on the Dolce Colle, within walking distance of the sea

JuergRating, 5 stars7 months ago
We (married couple and three dogs) had a great holiday experience in every respect in the little paradise of Lorenzo & Monica. The house: maintained with a lot of love, care and pride, offers space inside and in the garden as well as privacy. The location: on the small hill enough far away from the hustle and bustle of tourists at the bottom of the promenade, but close enough to the sea (300m, small road down the slope), surrounded by greenery and nature. The hosts: flexible, polite and communicative (Lorenzo, with him the booking was arranged) as well as charming, helpful and host from Passion (Monica, who lives next door with her family). Maybe it is better if we stop with the praise now because we would like to come back next year - and don't want there to be no more space...;-) Grazie mille, Monica e Lorenzo!
Guest favorite
A serene outdoor pool area features a large swimming pool surrounded by green grass. Two orange deckchairs are positioned by the pool, and white umbrellas provide shade. A small stone structure and a potted plant add visual interest to the tranquil landscape.
Home in Terranuova Bracciolini
4.91 out of 5 average rating, 23 reviews

VILLA MARINA, Large Private Villa w/ pool

MathiasRating, 5 stars21 months ago
Friendly host, and the villa looks better in reality than the pictures give impression of.

Destinations to explore

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