Some info has been automatically translated. Show original language

Vacation rentals in Santa Maria alla Rassinata

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Santa Maria alla Rassinata

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

1 of 1 pages1 / 1
Guest favorite
A stone villa surrounded by greenery is featured under a clear blue sky. A large swimming pool reflects the sunlight, complemented by sun loungers and colorful potted flowers along the edges. The outdoor area is perfect for relaxation with scenic views of the Tuscan hills.
Villa in Castiglion Fiorentino
4.9 out of 5 average rating, 240 reviews

Tuscan charm of villa - countryside - Villa Senaia

In the charming Tuscan countryside, among olive trees and vineyards, a stone villa, in a strategic position to grasp the secrets of Tuscany and Umbria air conditioning and swimming pool with wellness area for your relaxation and comfort Villa Senaia is a large house with wooden beams, in a beautiful hillside location with idyllic views overlooking one of the favorite places in the Tuscan countryside, an attractive setting for outdoor dining, drinking Tuscan wine and listening to crickets and cicadas

ValueLocationHot tub

Top guest favorite
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, 525 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.

LocationValueComfort

Top guest favorite
A serene pool area is showcased with two sun loungers positioned beside a tranquil salt-water pool. The expansive view of the valley and distant cityscape adds to the peaceful ambiance, while greenery surrounds the space, enhancing the sense of privacy and relaxation.
Farm stay in Monte San Savino
4.99 out of 5 average rating, 113 reviews

LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA

ID Code: 051025 AAT 0017 Wisely renovated 1600 exclusive original tuscanian stone house, superbly positioned up on a hill in total privacy. This villa is placed in a real postcard with a 360˚ view. Just 30 minutes drive from Cortona and less than 10 minutes drive from A1 Monte San Savino motorway exit, the villa is reachable through a boulevard flanked by secular trees and it boasts a stunning view on the Valdichiana valley with its towns and villages such as Monte San Savino and Cortona.

LocationValueComfort

Top guest favorite
Villa in Arezzo
4.96 out of 5 average rating, 27 reviews

Casa Napoleone - Tuscan Villa w/ pool near Cortona

A villa set on a hill, overlooking a magnificent Tuscan valley, yet only 10 mins drive from Castiglion Fiorentino train station. A 20 min drive from Arezzo and Cortona, a town made famous by the book and movie “Under The Tuscan Sun”. The Villa is the perfect base and within striking distance of Florence, Siena, Assisi and Montepulciano, famous for its Brunello wine, either by car or train. And after all that exploration you’ll return to soak in the pool whilst enjoying the stunning views.

FamilyLocationDecor

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
5.0 out of 5 average rating, 24 reviews

Due Torri, Umbrian elegance

Due Torri oozes rustic Italian elegance and charm amongst the rolling hills of the Umbrian/Tuscan border. A private estate with vineyard, immersed in nature, Due Torri is the perfect place to relax and unwind. Comprising two original watch towers dating back to the 13th century, the property has been painstakingly renovated in a way which preserves the character and features of this historic building, whilst providing a modern level of comfort, style and convenience (air-con throughout).

LocationFamilyKitchen

Guest favorite
Aerial view of a scenic agriturismo surrounded by vineyards and rolling hills. The property features a pool and is framed by tall cypress trees, enhancing the natural landscape of lush green and golden fields under a partly cloudy sky.
Farm stay in Montepulciano
4.96 out of 5 average rating, 115 reviews

Rural Tuscany | Family farmstay with restaurant

Via della Stella is a charming agriturismo with a housing surface of 530m², divided over nine separate apartments. Each apartment has its own living room, kitchen and one or more bath & bedrooms. The farmhouse has a wonderful panoramic swimming pool. Its great position with view over the hills heading up to Montepulciano create a serene atmosphere. The farmhouse has been carefully decorated in rural Tuscan style. Activities such as wine tastings and cooking classes are available onsite.

ValueLocationAmenities

Top guest favorite
A private pool area is surrounded by lush greenery and offers stunning views of the landscape below. Several sun loungers are positioned on the pool deck, with large umbrellas providing shade. The serene ambiance invites relaxation amid nature.
Villa in Castiglion Fiorentino
4.99 out of 5 average rating, 88 reviews

Tuscany Villa Mammi

Large renovated stone villa in the woods of Castiglion Fiorentino, near Cortona, Arezzo, and Siena. A haven of privacy with a swimming pool, a panoramic hot tub with breathtaking views of the valley, and ping pong. Enjoy magical evenings under the stars thanks to the authentic stone barbecue and wood-fired pizza oven. The ideal retreat for those seeking relaxation, nature, and comfort in the heart of Tuscany, perfect for families or groups dreaming of a truly unforgettable vacation.

FamilyValueHospitality

Top guest favorite
Home in Castiglion Fiorentino
5.0 out of 5 average rating, 21 reviews

Villa with Private Pool in the Tuscan Countryside

Modern villa with private pool, waterfall, large garden and relaxation area. Divided into: Suite with hydromassage bathtub, private bathroom and small refreshment corner; Apartment with 2 bedrooms, equipped kitchen and a second bathroom in elegant white faux marble. Perfect for families and groups up to 7. Features American BBQ, panoramic gazebo, ping pong, outdoor dining area and poolside shower. Close to Cortona, Arezzo, Montepulciano, Siena and the Crete Senesi.

FamilyValueCondition

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
4.98 out of 5 average rating, 144 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.

FamilyLocationGetting around

Guest favorite
The traditional stone house is surrounded by a well-maintained lawn, showcasing a multi-level structure with a picturesque roofline. Large arched windows accentuate the façade, providing ample natural light. A clear blue sky serves as a backdrop, highlighting the tranquil rural setting.
Villa in Castiglion Fiorentino
4.95 out of 5 average rating, 19 reviews

Ortaglia di Sotto Farm

Located in the Tuscan countryside, a 10-minute drive from Castiglion Fiorentino, Podere Ortaglia di Sotto offers a private pool with enclosed garden, WiFi and free private parking. The holiday home features 5 bedrooms, 6 bathrooms, a flat-screen TV, a dining area, a fully equipped kitchen and a terrace with mountain and valley views.(The swimming pool is available from 23 May to 17 October, closing and opening dates may vary depending on the weather)

FamilyLocationPets

Top guest favorite
An aerial view showcases the expansive grounds of Villa Pergo, surrounded by lush greenery and fields. The infinity pool is highlighted, surrounded by sunbeds and shaded by cypress and ancient trees. The countryside landscape stretches into the distance, enhancing the villa's serene setting.
Villa in Pergaccio
5.0 out of 5 average rating, 65 reviews

Villa Pergo is an ancient charming country villa

Stay in a piece of Tuscan history at Villa Pergo, a charming countryside estate dating back to 1640. Surrounded by olive groves and rolling hills near Cortona, the villa offers authentic character, panoramic views, and a beautiful infinity pool. With space for up to 11+1 guests in 6 bedrooms, large gardens and peaceful surroundings, it is the perfect retreat for families or groups looking to experience the true charm of Tuscany.

LocationFamilyCondition

Guest favorite
Villa in Arezzo
5.0 out of 5 average rating, 66 reviews

Coaching House

The Villa is situated in an ancient country building located in Arezzo, twenty minutes walk from the historic center and surrounded by shops, supermarkets, restaurants within a few minutes walk. By car you reach the downtown and the treain station in about 10 minutes; moreover, the structure is close to places of interest such as the Equestrian Centre.

FamilyLocationAccuracy

Popular amenities for Santa Maria alla Rassinata vacation rentals