Vacation rentals in San Regolo

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Top-rated vacation rentals in San Regolo

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Guest favorite

A shaded garden area features a hammock suspended from a tree and a round table with chairs, set against a backdrop of lush greenery and rolling hills. The panoramic view extends under a partly cloudy sky.

Home in Poggio San Marco

4.98 out of 5 average rating, 283 reviews

Charming converted Hayloft overlooking the Chianti Hills

Inspired by the rustic Tuscan style, this gorgeously refurbished hayloft features ceilings with exposed beams and bricks and thoughtful touches for a stylish and comfortable decor. From the relaxing hammock and the stone made barbecue in a panoramic garden to the cozy fireplace, every space feels open and inviting. Immersed in total peace and tranquillity with a breathtaking view over the Chianti hills, halfway between Florence, Arezzo and Siena, the barn is a perfect homebase to visit Tuscany. The accommodation has 2 floors. The upper floor spaces 2 double bedrooms with wonderful views of the olive trees and a bathroom with window and large masonry shower. On the ground floor a cozy and spacious living area with fireplace and a kitchenette with gas stove a large fridge and oven. The barn has ceilings with exposed beams and bricks. Outside there is a panoramic garden set on its own where, in the shade of a walnut trees, you can relax on a hammock or grill your meal (included an authentic local Fiorentina steak :-) on the stone made barbecue. A garden table is there for romantic dinners 'al fresco'. Immersed in total peace and tranquility halfway between Florence, Arezzo and Siena the barn is a perfect homebase to visit Tuscany. To find the exact location of the house type the following code in GMaps: 8FMHGG25+QV The house is in the countryside. The closest towns are Cavriglia and the small Medioeval villages of Moncioni and Montegonzi. In each town you can find great local restaurants and a small grocery shop. Moncioni is 3 km far away. A big supermarket is located in Montevarchi and you can reach it in 8 minutes by car ( exactly 7 km far away). In Montevarchi you can also find one of the best farmer markets in Tuscany! The station of Montevarchi is 8 km away from the barn. From there you can take train to Florence and Arezzo. Siena can be reached in 30 minutes by car. The easy access to the motorway A1/E35 Milan-Florence-Rome (the Valdarno exit is only at 13 km) allows you to reach numerous interesting spots within a short time, both in Tuscany and Umbria, while few kilometres south of Cavriglia you enter the suggestive territory of the Crete Senesi. Out in the countryside, the home offers an authentic experience of Tuscany. Small towns and villages are a short drive away providing acces to exceptional local restaurants and fantastic farmers markets. A big supermarket is located in Montevarchi (7 km far away). The railway station is 8 km away from the barn. From there you can take train to Florence and Arezzo. Cities of interest like Siena, Montepulciano, Pienza and Monteriggioni can be reached in 40 minutes by car The only way to reach the house is by car. A taxi service is active from Montevarchi You will be provided of blankets and towels. The kitchen is equipped with and kind of pots, pans, bowl, plates and silverware. You are welcome to use them. Free Netflix available

Top guest favorite

A sitting room features ornate wooden beams on the ceiling and rich golden walls. A shell-shaped sofa is positioned prominently, surrounded by decorative wooden furnishings and a bookshelf. A classic rug covers the floor, adding warmth. Wooden accents infuse the space with historical charm.

Apartment in Centro Storico

5 out of 5 average rating, 526 reviews

Renaissance Apartment Touch the Dome

Inspired by the most fascinating artistic era in human history, the Renaissance, each of my homes is a tribute to the elegance, harmony, and craftsmanship that defined that golden age. Step inside and be transported. You’ll not only see the Renaissance — you’ll feel it in the atmosphere, in the light, and in the soul of each space. Discover also The Renaissance & Baroque apartment: https://www.airbnb.it/rooms/30229178?guests=1&adults=1&s=67&unique_share_id=c0087742-7346-4511-9bcd-198bbe23c1b4

Top guest favorite

A charming cottage is shown with a terracotta facade and a tiled roof. A small table with two chairs is set on a patio, surrounded by potted plants. Lush greenery and trees can be seen in the background under a clear blue sky.

Guesthouse in Macciano

4.97 out of 5 average rating, 181 reviews

Tuscan cottage with an heavenly view

Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

Guest favorite

A serene bedroom features a spacious bed with a simple white coverlet. A wooden chair with a striped cushion is placed beside a bench. Natural light filters through the two wooden windows, revealing views of the lush vineyards outside.

Home in Castelnuovo Berardenga

4.92 out of 5 average rating, 99 reviews

La finestra del Chianti

Un luogo meraviglioso dove trascorrere alcuni giorni in piacevole compagnia. Un ampio salone con camino dove rilassarsi al rientro da bellissime passeggiate, giri in bicicletta, ed escursioni. L'appartamento indipendente si trova a 15km da Siena, 20 km dai centri Termali e a 40 minuti dai borghi di san Gimignano e Monteriggioni. Nel complesso è presente un'azienda agricola che produce vini e olio con la possibilità di visite guidate e degustazione dei nostri prodotti con cene a tema.

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, 215 reviews

Gaiole in Chianti Poggio Casabianca

We invite you in the heart of Chianti area. Poggio Casabianca is a little family homestead located in the Chianti Classico region exactly in the hearth of Tuscany. The owners live here and they offer at their guests an apartment with a big living room-kitchen with a big door that open directly to the garden, a bathroom with shower and a confortable doublebed room. Outside in the garden ther is a pool, shared with the owner, where you can refreshing and relaxing during the summer.

Top guest favorite

A lush green garden is framed by a rustic pergola made of wooden beams. Grassy paths lead deeper into the garden, where vibrant flowers and trees provide a natural backdrop. Rolling hills and a clear blue sky are visible in the distance, creating a serene outdoor setting.

Home in Castellina in Chianti

4.98 out of 5 average rating, 117 reviews

StageROOM03 -Chianti Idillic Country living

Set in a picturesque hamlet, overlooking the Chianti hills, this charming country house is just 10 minutes from Siena and Castellina in Chianti. Recently renovated, it blends authentic Tuscan charm with modern comforts. The house features two bedrooms, two bathrooms, a cozy living area and a fully equipped kitchen with a dishwasher, two fridges, and a washing machine. Outside, enjoy a beautiful garden and relax in the outdoor marble hot tub, soaking in the breathtaking views.

Top guest favorite

The charming stone facade of the historic building is complemented by large green shutters and terracotta pots filled with vibrant plants. Sunlight illuminates the outdoor area, highlighting the welcoming entrance surrounded by steps and a spacious patio.

Apartment in Villa a Sesta

4.94 out of 5 average rating, 217 reviews

Da Paola nel Chianti

Il mio appartamento è situato nel borgo di Villa a sesta, al pian terreno con accesso diretto al giardino, dispone di due camere, una matrimoniale , l'altra con letti a castello, due bagni, un ampia cucina e un soggiorno. lo spazio esterno è molto grande e il giardino dispone di un grande tavolo e poltrone per il relax, l'auto potrà essere parcheggiata a casa, abbiamo il posto auto privato, arrivati in paese si accede a casa da una piccola strada bianca (30mt).

Top guest favorite

A historic villa is situated amidst lush, rolling hills, surrounded by vineyards. The exterior features a traditional stone facade, large windows, and terracotta roof tiles. Manicured gardens with circular patterns enhance the property's charm, complemented by tall cypress trees framing the serene landscape.

Apartment in Castelnuovo Berardenga

4.93 out of 5 average rating, 165 reviews

Villa di Geggiano - Perellino Suite

The 700 years old Villa di Geggiano, surrounded by our working vineyard and lovingly maintained gardens, is located in Chianti in Tuscany which is one of the most beautiful regions of Italy. Our guesthouse is located in one of the original garden pavilions of the villa. PLEASE NOTE THAT WE ARE IN THE COUNTRYSIDE WITH VERY FEW PUBLIC TRANSPORT OTHER THAN TAXI SO THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A RENTAL CAR.

Top guest favorite

A charming country loft is enveloped in lush green vines, with steps leading from a grassy area to the entrance. Sun loungers are situated on the lawn, providing a serene space for relaxation. This rustic exterior is framed by trees and open skies.

Loft in Siena

4.95 out of 5 average rating, 240 reviews

Siena Country Loft Hideway

Country loft, ideal gateway for a couple looking to experience the flavour of Tuscan countryside 2 bathrooms, one with shower and one with bath tub with unique windows view Fully equipped kitchen Eclectic style with antique accents Endless rolling hills view, modern amenities in typical country side setting Concierge service upon request Wifi Internet connection Only 7km far from Siena town

Guest favorite

A spacious garden is featured, showcasing manicured green grass and pathways lined with stones. A shaded seating area is positioned beneath a gazebo, with metal chairs inviting relaxation. Lush hedges and a view of distant vineyards complete the scene, offering a serene outdoor atmosphere.

Home in Villa a Sesta

4.89 out of 5 average rating, 121 reviews

Casa Nataly Chianti - Jeky Stay

Tipico appartamento toscano nel meraviglioso borgo di Villa a Sesta, immerso nella tranquillità delle colline del Chianti. Parte di Jeky Stay. Punto strategico per uscite in bici, degustazioni in cantine locali e visite a borghi come Pienza, Siena, San Gimignano, Montalcino e Firenze. A pochi km anche i centri termali di Rapolano. Gustate piatti tipici e vini locali nelle trattorie del paese

Top guest favorite

A charming stone building surrounded by lush greenery features a wooden terrace with a parasol and flower pots. Two loungers are placed on the well-maintained lawn, providing a relaxing outdoor space.

Farm stay in Greve in Chianti

4.99 out of 5 average rating, 410 reviews

Old hayloft on the Chianti hills

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. Hayloft completely independent on two floors connected by an internal staircase. Private garden of 300 mq sorrounded by secolar oaks.

Guest favorite

A spacious bedroom features a large bed adorned with soft linens and two neatly rolled towels. Warm terracotta tiles cover the floor, complemented by pale yellow walls and wooden beam ceilings. Natural light fills the room through two windows with dark shutters, creating a calming ambiance.

Farm stay in Gaiole in Chianti

4.93 out of 5 average rating, 239 reviews

Il Nido - un romantico focolare

Lui non esisteva, è stato ricavato in un angolo della grande casa in cui chissà quante persone della stessa famiglia vivevano. Per questo è diventato il nostro piccolo Nido, la casa da cui partire per scoprire il borgo. Non un piano ma addirittura due, con tanto cotto, legno e colori caldi.