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Holiday houses in Masseto

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Top-rated holiday rentals in Masseto

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Guest favourite
A winding pathway leads down through lush greenery and terracotta tiles, surrounded by vibrant foliage. In the background, rolling hills are visible, dotted with vineyards under a partly cloudy sky, evoking a serene atmosphere.
Holiday home in Masseto
4.92 out of 5 average rating, 24 reviews

nel Chianti vicino Firenze

Appartamento nuovo, indipendente, completamente arredato, max 4 persone, dotato di tutti i confort, WiFi/Internet, TV SAT, immerso nel verde della natura della campagna Toscana, un'oasi di pace nel Chianti Rufina a meno di 25 Km da Firenze e vicino al Parco Naz. delle Foreste Casentinesi. parcheggio privato Ideale per relax , trekking , bici, passeggiate, buona cucina 200 mt. Ristorante e fermata Bus 1 Km stazione ferroviaria collegamento diretto con Firenze SMN 1 Km supermercato e altri negozi

Top Guest favourite
The image showcases a vibrant town square surrounded by historic buildings, including the prominent Torre Salvucci Maggiore. The sky is expansive, featuring soft clouds scattered across a blue backdrop. The texture of the stone architecture provides a glimpse into the medieval influence of the area.
Tower in San Gimignano
4.94 out of 5 average rating, 124 reviews

Medieval Tower experience with Panoramic Rooftop

If you are looking for a memorable experience, this is the right place for you! With its 42 mt high, the Salvucci Tower is one of the famous towers of San Gimignano and today the only one turned into a vertically-spread apartment divided into 11 floors, for a total of 143 steps. A unique and timeless place, ideal to experience something never tried before. The tower can hosts couples or small groups up to 3 people. Its panoramic rooftop boasts an incredibly breathtaking view all over the town.

Guest favourite
An expansive outdoor deck offers a serene view of rolling hills under a clear sky. An infinity pool transitions seamlessly into the landscape, with two soft seating cushions placed nearby, inviting relaxation and contemplation of the stunning panoramic scenery.
Home in Casale
4.88 out of 5 average rating, 189 reviews

Infinity view

Completamente ristrutturata posizione con vista mozzafiato sul Valdarno. Il piano terra è composto da soggiorno con due vetrate che danno sul patio, camino, divano letto, bagno con grande doccia e cucina moderna con isola in acciaio, con tre porte finestre per accedere alla zona pranzo esterna con bbq. Il primo piano è composto da due camere matrimoniali ognuna dotata del proprio bagno con doccia. Giardino è moto curato,ci sono vari angoli relax, prendisole è una piscina infinity ad idrolisi

Top Guest favourite
The image showcases a refreshing pool surrounded by lounge chairs and umbrellas, enhancing the outdoor relaxation area. The pool is framed by lush greenery and a stone wall, with the charming rustic house visible in the background under a clear blue sky.
Home in Barberino Tavarnelle
5 out of 5 average rating, 122 reviews

Infinity pool in Chianti

Sulle colline del Chianti, porzione di antica casa colonica in pietra del 1800, situata a S. Filippo una piccola frazione di Barberino Tavarnelle, a metà strada tra Firenze e Siena, a 30 minuti di macchina dall'aeroporto di Firenze, a 1 ora da quello di Pisa. Tre camere da letto, due bagni, ampia sala con camino, cucina abitabile e sala da pranzo. Vista magnifica sulle colline da ogni finestra! Splendida piscina a sfioro con zona idromassaggio, non riscaldata e aperta da Aprile a Ottobre.

Top Guest favourite
A historic tower rises prominently against a blue sky dotted with fluffy clouds. Surrounding greenery complements the stone structure, with trees and small buildings visible along the hillside, collectively conveying a sense of tranquility.
Villa in Montecatini Val di Cecina
4.99 out of 5 average rating, 129 reviews

Torre dei Belforti

Torre dei Belforti is the perfect place for people who love beauty, nature and art. Sleeping at the Tower is like traveling trough the time, between knights and princesses. The wonder of this place is enriched by a big garden, with its swimming pool, the cypresses alleys and the olive trees. The village is also a magic place well preserved and still alive. We are Emilia and Luca, we live here and our mission is to give the best to our guests, to fully enjoy this marvelous place.

Top Guest favourite
Two individuals are seated in comfortable chairs on a wooden deck, enjoying a serene moment as the sun sets. A bottle of wine and two glasses are placed on a small table nearby, surrounded by lush greenery and vibrant flowers.
Home in Greve in Chianti
4.99 out of 5 average rating, 70 reviews

Relax e comfort sulle colline di Firenze

Appartamento in tipica casa colonica toscana in pietra : misura 160Mq , è rifinito con materiali tipici toscani , pietra serena e cotto , si compone di un ampio salone all' ingresso , sala da pranzo , cucina , 2 bagni ,ripostiglio , 3 camere da letto , una zona studio.Disposto in posizione est-ovest grazie ad una ampia terrazza , un patio ed un ampio giardino privato vi consente di godere dell' alba per la vostra colazione e del tramonto per un piacevole aperitivo .

Top Guest favourite
A table is set outdoors, featuring a red cloth and a collection of breakfast items, including a coffee cup, croissants, and fruits. The background reveals a scenic view of rolling hills and a charming village, adorned with greenery and colorful flowers.
Apartment in Pelago
4.93 out of 5 average rating, 46 reviews

Bellavista tuscany 2

Ideale per famiglie, coppie e chiunque voglia scoprire l'autentica toscana, tra vigneti ed uliveti e Firenze e le sue bellezze. Guendalina vi accoglierà facendovi sentire a casa vostra, tra suggerimenti di cosa fare e tanti depliants in casa. Troverete un bellissimo giardino per rilassarvi, mangiare e godervi del panorama sul borgo antico di Pelago. A partire da aprile 2026 a disposizione la piscina nello spazio esterno condiviso con il Bellavista Tuscany 1.

Top Guest favourite
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
4.94 out of 5 average rating, 171 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 favourite
The exterior of the castle is showcased at sunset, with vibrant orange and purple skies providing a dramatic backdrop. Stone towers rise from the landscape, surrounded by greenery and colorful flora, reflecting the historic charm of the property.
Castle in Ferrano
4.99 out of 5 average rating, 210 reviews

Il Castello di 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.

Superhost
An outdoor dining area is surrounded by lush greenery, featuring a round table set with tea cups and a small vase containing a pink flower. Wooden chairs are arranged around the table, offering scenic views of the hills and countryside.
Apartment in Vaglia
4.92 out of 5 average rating, 87 reviews

Tuscan Country Home Apt (3 Bedrooms) - Principessa

Principessa is a three-bedroom country apartment beautifully located in the magnificent Villa Ortaglia estate set within the Tuscan rolling hillside and overlooking Florence. It has a shared outdoor pool located under casa anforti complex , esternal, not heated Open from May 2nd to September 30th. And a private external meal area with bbq. We are at 20mn drive from the center of Florence

Superhost
A refreshing swimming pool is set within a stone-paved area, surrounded by well-maintained greenery and mature trees. The charming country house, built with local stones, is positioned on an elevated level, showcasing a rustic design that complements the natural landscape.
Home in Ulignano
4.86 out of 5 average rating, 42 reviews

Cosy Tuscany 2-bedroom home with a private pool

Relax with the whole family or relish romantic elope at this peaceful place. Just 15 min from historical center of Volterra and 20 min from San Gimignano lies this charming Tuscan country house , built of local stones and terracotta, in a most quiet location. Enjoy the refreshing swimming pool during the day and a breeze with a glass of Prosecco on the terrace in the evening.

Top Guest favourite
A stone facade is viewed from a well-maintained garden, featuring lush green grass and neatly trimmed hedges. A wooden door is visible, leading into a charming interior, while the house's rustic architecture complements the serene landscape under a clear blue sky.
Home in Castellina in Chianti
4.98 out of 5 average rating, 111 reviews

Explore Chianti from a Charming Stone House

Awaken in a bedroom with beamed ceilings, open doors to a private garden, and take an early morning dip in the pool. Return to a classically designed house with terra cotta floors, wood-burning fireplace, and bathrooms with exuberant tile work. Casa Marinella is the perfect place to discover Chiantishire. Fully equipped kitchen, AC in each bedroom, private garden and barbecue.

Popular amenities for Masseto holiday rentals

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Metropolitan City of Florence
  5. Masseto