Some info is shown in its original language. Translate

Vacation rentals in San Leolino

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in San Leolino

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

1 of 1 pages1 / 1
Guest favorite
Villa in Siena
4.8 out of 5 average rating, 295 reviews

XIII Century Tower with Private Panoramic Pool

Ancient country tower property with 5 airconditioned bedrooms for up to 10 guests at the heart of the peaceful Montechiaro organic wine estate. From your private pool, soak in the Tuscan sun and enjoy unforgettable views of the Chianti rolling hills and the medieval towers of Siena. The property also boasts access to the endless olive grove, a large patio area for outside dining in the shade, ping pong table for fun family matches, WIFI & free parking. Silence and time are the real luxury here.

LocationFamilyCleanliness

Top guest favorite
An aerial view showcases the expansive grounds of La settecentesca Villa di Geggiano, surrounded by manicured gardens and lush vineyards. The main villa is prominent, with a circular driveway leading to it, while gentle hills extend into the background.
Cottage in Geggiano
4.99 out of 5 average rating, 155 reviews

Villa di Geggiano - Guesthouse

PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

LocationFamilyQuiet

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, 526 reviews

Agriturismo Fattoria La Parita

Appartamento in stile provenzale immerso tra il vigneto e gli olivi. Godrete della tranquillità della campagna a 10 km dalla città e 4 dall'autostrada. Il canto di ghiandaie e cucù faranno da colonna sonora al soggiorno mentre i caprioli brucano tra gli olivi. E' inclusa una colazione base all'italiana (caffè, tè, latte, biscotti ecc.), se invece preferite una colazione più ricca e servita al tavolo il costo è 15€ a persona (10€ da 5 a 15 anni, gratis meno di 5 anni). Disponibile wallbox EV.

LocationFamilyBathroom

Top guest favorite
The charming farmhouse features a warm yellow exterior and traditional terracotta roof. Tall cypress trees and verdant olive trees surround the property, which sits among rolling hills. A covered patio extends from the house, providing outdoor seating space with a view of the scenic landscape.
Farm stay in Bucine
4.91 out of 5 average rating, 88 reviews

Feriale I. Petrolo Winery. Pool, wi-fi, vineyards

Charming farmhouse of the Petrolo winery in the heart of Tuscany. 5 bedrooms and 4 bathrooms, for 10 guest +2 on sofa bed. Panoramic views over the Valdarno valley, next to Chianti Classico. The house is placed among vineyards and olive trees with the medieval watchtower of Galatrona nearby. The house has wi-fi, private garden with bbq and easy access to the swimming pool shared with 2 of our houses. To access the house climb 20 steps to the first floor, landing on a cute panoramic terrace.

LocationFamilyKitchen

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, 114 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.

FamilyLocationCleanliness

Top guest favorite
An outdoor patio area features rustic furnishings and is framed by gracefully draping curtains. The space is adorned with comfortable seating and a communal dining table, set against a backdrop of tall cypress trees and a clear blue sky, inviting relaxation in a serene environment.
Home in Simignano
4.97 out of 5 average rating, 194 reviews

Casa al Gianni - Il Fienile di Simignano

Trasformato da un antico fienile, questo rifugio lussuoso offre 5 camere, 4 bagni, grande cucina attrezzata, ampio living, un ampio giardino privato con parcheggio, hot tub, patio con divani, BBQ, fire pit e cucina esterna. Ideale per chi cerca un'esperienza unica, unisce fascino rustico a comfort moderni. Perfetto per famiglie o gruppi, promette serate magiche sotto le stelle, tra relax nell'hot tub e cene all'aperto. Una fuga memorabile vi aspetta in questo angolo di paradiso!

FamilyLocationPool

Top guest favorite
The exterior of a charming villa is surrounded by lush greenery, with vines climbing along the walls. A gravel pathway leads to the entrance, framed by well-kept gardens. Sunlight filters through the trees, creating a peaceful atmosphere ideal for relaxation and outdoor gatherings.
Villa in Pergine Valdarno
4.96 out of 5 average rating, 101 reviews

La Vignaccia (Farmhouse) - villa w/private pool

Nestled amidst the rolling hills of Tuscany, La Vignaccia beckons you to experience the true essence of Italian living. This enchanting villa, set within a sprawling estate, offers a haven of tranquility, where you can unwind and immerse yourself in the beauty of the Tuscan countryside. A secluded garden awaits, providing a serene setting for relaxation and alfresco dining. Take a refreshing dip in the sparkling pool, surrounded by breathtaking views of the Tuscan landscape.

FamilyValueSleep quality

Guest favorite
Home in Pogi
5.0 out of 5 average rating, 10 reviews

Private Cottage with Plunge Pool in Tuscan Estate

A private cottage with garden and plunge pool, set within Borgo Iesolana Estate. Perfect for up to 6 guests, yet equally special for couples. Enjoy total privacy, a fully fenced garden (ideal for dogs), stunning views and an exclusive plunge pool — with breakfast included and full access to the Borgo’s pools, restaurant and bar just a short walk away. Private parking, Wi-Fi, TV, air conditioning, heating and a fully equipped kitchen complete the experience.

LocationConditionComfort

Top guest favorite
A spacious outdoor area features a swimming pool surrounded by lush green lawns and dotted with comfortable sun loungers. Umbrellas provide shade, and the serene landscape is framed by tall trees and gentle hills in the background.
Farm stay in Greve in Chianti
4.99 out of 5 average rating, 431 reviews

Typical Tuscan country house

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence just 35 minutes by car This apartment is one level, totally independent with private garden. Restored and furnished with great care to make the guest's stay as comfortable and relaxing as possible, in the full respect of the Tuscan rural style.

LocationFamilyBiking

Superhost
Home in Bucine
4.83 out of 5 average rating, 6 reviews

villa nel chianti con piscina tenuta lupinari

La Tenuta Lupinari sorge nella Valdambra, uno dei luoghi più suggestivi e incontaminati dell'area del Chianti. I dieci appartamenti sono il frutto di un accurato restauro di un borgo cinquecentesco immerso tra i vigneti e gli oliveti delle colline toscane, in posizione strategica tra Arezzo, Siena e Firenze è luogo ideale sia per trascorrere le giornate all'insegna del relax che per visitare le bellezze artistiche della nostra Terra di Toscana.

LocationFamilyCleanliness

Guest favorite
The exterior of a rustic building is visible, featuring stone archways and blooming flower boxes under windows. Lush greenery surrounds the structure, while a well-maintained lawn provides an inviting outdoor space. A bright blue sky complements the scene, enhancing the serene countryside setting.
Barn in Le Mura
4.88 out of 5 average rating, 103 reviews

Bilocale in fienile toscano

L’alloggio è Immerso tra le splendide colline della Valdambra circondato da torri e castelli medievali e dal silenzio della natura. È ubicato nel triangolo tra Firenze, Siena ed Arezzo, facilmente raggiungibili in auto o treno. L’appartamento è composto da Cucina/soggiorno (con divano letto per una persona), camera con letto matrimoniale e bagno. Ampio giardino con la possibilità di mangiare all’aperto.

FamilyLocationDecor

Superhost
An aerial view showcases a large swimming pool surrounded by well-maintained gardens and lush greenery. Nearby, sun loungers and shaded areas create inviting spots for relaxation. The surrounding landscape includes vineyards and trees, enhancing the serene ambiance of the outdoor space.
Apartment in Bucine
4.77 out of 5 average rating, 78 reviews

Apartment Villa Chianti Pool WiFi Air Cond. (A)

The house is deal for a couple, family with children, or for a group of 5 friends that want to explore Tuscany You can stay in a Tuscan Villa stone hay loft located in Valdarno: from this area you can easily reach Firenze, Arezzo, Siena, Cortona, San Gimignano and the Chianti; after a day spent in our amazing region, you can relax during summer in the private pool that overlook the Tuscan countryside!

FamilyLocationComfort

Popular amenities for San Leolino vacation rentals