Vacation rentals in San Leolino

5 out of 5 average rating, 252 reviews

Aerial view showcases the rustic property nestled among the lush vineyards. Sunlight casts a warm glow over the hills, while a sparkling pool is situated near the residences, surrounded by greenery. The tranquil landscape includes gently rolling hills and rows of grapevines.

Condo in Noce

Podere Vergianoni nestled in Chianti with a pool

Podere Vergianoni is an ancient and authentic farmhouse dating back to the 17th century located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional local style of old Tuscany: ancient wooden beams, terracotta floors, and unique furniture. In the large outdoor courtyard, you'll find a large swimming pool on a panoramic terrace at your disposal, overlooking the valley with breathtaking views of vineyards and olive groves, where you can enjoy spectacular sunsets.

4.98 out of 5 average rating, 442 reviews

A quaint terrace is presented with a small round table and two chairs. Potted flowers add natural color, while a beautiful view of rolling hills and vineyards is visible in the background under a clear blue sky.

Home in Panzano

Old Farmhouse near Panzano Castle Abbacìo

The Abbacio apartment is part of an old farmhouse that has been restored respecting the original structure and style. Its location is just on the top of the hill, facing the valley. Surronded by vineyards and olive trees, but also attached to the village. From the house you can easily reach by feet wineries, farms and restaurants. Panzano is halfway between Florence and Siena, easily reached with car. By bus there is a good service from and to Florence, not from and to Siena. A very quiet spot!

4.95 out of 5 average rating, 219 reviews

A spacious terrace features natural wooden beams and panoramic views of the surrounding landscape. Comfortable wooden seating arrangements are placed across the area, creating a welcoming environment. Potted plants add a touch of greenery, enhancing the overall ambiance of the outdoor space.

Villa in Montepulciano

Amazing Tuscany Villa, FREE parking

Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking

Condo in Castelfranco di Sopra

An aerial view captures a rustic stone building with red tiled roofs, surrounded by lush greenery, trees, and manicured gardens. The serene landscape showcases a blend of earth tones and foliage, embodying a peaceful atmosphere in a hillside setting.

4.83 out of 5 average rating, 252 reviews

House between Firenze, Arezzo, chianti e Siena

The House is located in a restored medieval village. There is an atmosphere of peace and tranquility, the gardens are full of flowers and aromatic plants and there is a beautiful panoramic view of the Arno Valley. There is a private terrace outside and two swimming pools to share with other appartraments. Perfect for relaxing and for reaching the main attractions like Florence, Siena, Arezzo, Chianti, Sangimignano. Here you will live a unique experience in the heart of Tuscany ...

4.99 out of 5 average rating, 196 reviews

Castle in Ferrano

The Castle of Ferrano - Castle in Tuscany

Try the experience to stay in a real Castle! Il Castello di Ferrano offers to his hosts the chance of doing an unforgettable experiece:you will be the only guests in the castle and everythig will be for you (private pool from June to September, gardens ecc.)Historical building, surrounded by nature, finely decorated, frescoes/moulding on the ceiling, ample terrace w/ stone and terracotta floor, private outdoor pool.. Good position. Preferably come by car.

4.99 out of 5 average rating, 275 reviews

An outdoor terrace is visible, furnished with several tables and chairs, providing ample seating. Flower pots with colorful blooms adorn the railing, while a panoramic view of the surrounding hills and greenery stretches into the distance under a clear sky.

Apartment in Sinalunga

Resort Panoramic view - Free parking

Appartamento nuovo , potente Wi-Fi, SMART TV, bagno privato , Aria Condizionata, cucina privata , lavanderia , parcheggio privato gratuito . Sala da tea ad uso gratuito . Vista panoramica mozzafiato . Tra le Crete Senesi e la Val D’Orcia , a 800metri dal centro del paese , con ristoranti , bar e supermercati . Posto strategico per visitare le principali località in Toscana : Montalcino , Pienza , Siena , Arezzo , Rapolano Terme , Montepulciano .

5 out of 5 average rating, 111 reviews

A view through a window showcases rolling hills and green fields under a soft sky. The landscape reveals a peaceful outdoor area, highlighted by a table and chairs nestled amongst the natural scenery, inviting relaxation and contemplation.

Condo in Pienza

Mascagni Farmhouse in Val d'Orcia, Pienza

Climb the iconic Tuscan hills to Mascagni Organic Farm, an organic farm where your new home awaits: a finely restored 16th-century barn nestled among olive trees and wheat fields. Relax with a cup of tea, pick rosemary and lavender in the garden with breathtaking views of the Val d'Orcia. Rediscover your true nature among the pristine fields and olive trees: here, walks and bike rides have no limits! Ready to create memories that will last a lifetime?

4.93 out of 5 average rating, 119 reviews

A scenic view of rolling hills and lush greenery is visible from a window. Terracotta roofs and a winding path can be seen below, enhancing the historic charm of the medieval surroundings.

Condo in San Gimignano

Luxury Medieval Tower - Penthouse

Step into the past... San Gimignano Luxury Medieval Tower is right in the heart of the UNESCO town. You will be caught by the sight of San Gimignano's beautiful landscapes and at the same time you will be able to enjoy the luxury amenities of in-town living: walk downstairs to the cafes, bread shop, butcher, restaurants and local shops. Hear the church bells directly from your windows. Walking distance to all of San Gimignano main attractions.

Condo in Castelnuovo dell’Abate

A balcony is adorned with blooming flowers and greenery, offering a scenic view of the rolling hills and vineyards. Small outdoor furniture is positioned for relaxation, while the sky features scattered clouds, enhancing the tranquil atmosphere of the surrounding landscape.

4.91 out of 5 average rating, 288 reviews

La Casetta di Brunello, very panoramic with terrace

STIAMO LAVORANDO PER VOI! ... WE ARE WORKING FOR YOU! The house is completely renovated and furnished in 2018 with classic-Tuscan style furniture. The colors are warm and enveloping to better rest during your holiday of peace and relaxation. In addition to the two double bedrooms, you have a kitchen with an equipped kitchenette, fridge, induction cooker and a furnished terrace with a beautiful view of the surrounding countryside.

Cabin in Gaiole in Chianti

A stone chalet is set among tall pine trees, featuring a wooden deck and outdoor seating. Colorful flowers are placed along the edge, complementing the natural surroundings. A rustic wooden fence defines the outdoor space, inviting relaxation in the serene forested setting.

4.88 out of 5 average rating, 136 reviews

Little Country House "HEART CHAKRA"

Delightful stone chalet immersed in a forest of oaks and pines, ideal for a romantic weekend and/or a relaxing holiday. The environment, new, intimate and cozy, consists of a studio with bathroom and shower, large terrace and wooden pergola. Little country house ideal for a romantic weekend and a relaxing holiday. It includes a studio with kitchen, living room, bedroom and bathroom and equipped with big terrace and pergola.

4.96 out of 5 average rating, 249 reviews

A serene salt-water pool is surrounded by lush greenery and colorful flowers. Sun loungers are positioned around the pool, offering seating for relaxation. Rolling hills and cypress trees create a picturesque backdrop, showcasing the tranquil beauty of the Tuscan countryside.

Condo in Panzano

Apt. Panzanello-Panzano in Chianti

The apartment offers all the comforts and tranquility of the Tuscan countryside. Enjoy the wonderful view that you can admire from your private terrace, a perfect place to spend peaceful and serene moments accompanied by a good glass of Panzanello wine. Access to the apartment is private and free parking is available. The kitchen is equipped with everything you need to prepare delicious meals.

Farm stay in Campiglia D'orcia

4.94 out of 5 average rating, 414 reviews

Poggio Bicchieri Holiday Farm - Poesia apartment

Overlooking the Val d 'Orcia, our holiday farm consists of 2 apartments each with a kitchen, bedroom, and bathroom. Large equipped garden. Surrounded by silence, close to Pienza, Montalcino, Bagno Vignoni, and the natural thermal baths of Bagno San Filippo. Getting here is very easy; the last km of the road is unpaved but accessible for all.

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Popular amenities for San Leolino vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in San Leolino

A stone entrance is framed by a wooden roof, showcasing a wooden door that opens into the home. A potted plant is positioned beside the door, and a welcome mat is laid at the threshold. The surrounding area features a grassy landscape.

Cottage in Bucine

4.84 out of 5 average rating, 148 reviews

Cottage in the Tuscan countryside

CarrieRating, 5 stars1 month ago

Ulisse's was really helpful as he met me at his restaurant and I followed him to the cottage. There is a coop, a butchers, a bakery and a little supermarket in Buccine and a small market on Wednesday mornings, which is really handy as there is not much around the cottage. It is in the middle of the country side surrounded by vineyards and nature, a perfect place for nature lovers. Ulisse, his wife and daughter were all really helpful and quick to resolve issues. For anyone trying to find it, have the petrol station and ristorante di ciccio on your left then continue straight on the SP540 , once you pass ristorante le bottega grassa ( a white building on your right) it is your next right turn ( the dump where you need to dispose of your rubbish from the cottage is on the right of this road) then take your next left signed "Le Mura" you continue down this road until a big yellow and white hse on the left and the big stone house on the right, the cottage is beside the stone house.

4.93 out of 5 average rating, 80 reviews

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

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.

4.87 out of 5 average rating, 30 reviews

A gravel pathway leads to a rustic stone building, showcasing its traditional architecture. The structure features wooden windows and a red-tiled roof. Green trees surround the property, providing shade. In the background, a prominent bell tower rises, adding to the historic ambiance of the setting.

Home in Pergine Valdarno

Loggetta: farmhouse with garden and pool

WouterRating, 5 stars1 month ago

We greatly enjoyed our stay at this beautiful home in Tuscany. The location is truly idyllic – quietly located on the top of a hill, overlooking the beautiful Tuscan landscape. The house fully met our expectations: comfortable, tidy and with everything we needed for a relaxing holiday. Upon arrival we were warmly welcomed by Giovanna, who immediately put us at ease. She took plenty of time to welcome us and also gave us valuable tips for visiting Arezzo and the surrounding area. In short: a wonderful place for those looking for peace, nature and authentic Tuscan charm. We'd love to come back!

Villa in Gaiole in Chianti

A sunlit outdoor area features a lawn bowling green adjacent to a private pool. Scenic views of the rolling Chianti hills are visible. The pool area is fenced, and colorful greenery enhances the serene landscape.

5 out of 5 average rating, 6 reviews

Casanova of Bricciano

PeterRating, 5 stars2 weeks ago

What a fabulous setting and location. Perfect to explore the Chianti region and beyond. It’s roomy, everything you need is there, beautiful pool and a view to cherish. Dining on the terrace is a wonderful experience and with a vinyard with lovely wines available right next door what more do you need from a Tuscan holiday. All hosted perfectly by Fabio and Andrea. Very highly recommended.

Vacation home in Gavignano

4.92 out of 5 average rating, 37 reviews

Charming place in the Silence of Tuscan Chianti

SabineRating, 5 stars1 month ago

Great accommodation, the description is very reliable, everything is done to make you feel on vacation! Close to Buccine where you can take the train to Florence, 1 hour trip (free train station parking). Great location for visiting Tuscany. We loved our vacation. Thanks to Paolo and his family for allowing us to do all this! 🙏🙏🙏🙏

5 out of 5 average rating, 25 reviews

A private pool is framed by lush greenery, with a wooden deck featuring comfortable seating and a sun umbrella. Olive trees dot the landscape, providing a serene view of the surrounding hills under clear blue skies.

Home in Montevarchi

Casa San Ripa: Relax Oasis with Private Pool

CarolinaRating, 5 stars4 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!

4.83 out of 5 average rating, 41 reviews

A person is paddling an orange kayak through calm water surrounded by trees with slender trunks and lush greenery. The reflection of the trees and blue sky on the water creates a serene atmosphere. Sunlight illuminates the scene, highlighting the tranquil environment.

Home in Lucignano

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.