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Holiday rentals in Masseto

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Top-rated holiday rentals in Masseto

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

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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
4.93 out of 5 average rating, 30 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

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Guest favourite
A private swimming pool with a distinctive shape is surrounded by green lawns and olive trees. Two white umbrellas and several lounge chairs provide shaded seating. The clear water reflects the bright blue sky with fluffy white clouds, creating a serene outdoor atmosphere.
Villa in Pontassieve
4.92 out of 5 average rating, 61 reviews

Vacanze & Relax in Toscana villa

Our villa is located in a green paradise near Florence, a sanctuary to relax your mind, enjoy nature and embrace slow-living culture. The central part of the house, in stone, derives from the transformation of a medieval watchtower for either Quona or Montefiesole castles both in ruins. Guest can enjoy a ful relax holiday swimming in the private pool, cooking and eating at the special barbecue area, taking a hike or a bike tour in the surrounding hills, booking a Horse trip at the nearby farm!

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Top guest favourite
Home in Greve in Chianti
4.99 out of 5 average rating, 112 reviews

Relax e charme tra le colline del chianti

Bellissima colonica in pietra, indipendente, immersa tra gli olivi e le colline del Chianti, con giardino privato e piscina panoramica. Piano terra con ampi saloni, antico camino e forno a legna, soggiorno luminoso e cucina full optional. Al primo piano tre suites composte da camera, studio e bagno privato. Accesso tramite cancello e strada bianca in proprietà privata a soli 500 metri dal paese di Strada in Chianti. Ideale per quiete e relax. Location strategica per visitare la Toscana.

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Guest favourite
A tranquil outdoor pool area is enclosed by greenery, featuring sun loungers and umbrellas. Clear blue water reflects the surrounding hills under a sunny sky. A rustic shower stands to one side, inviting guests to refresh after enjoying the scenic landscape.
Home in Bagno A Ripoli
5.0 out of 5 average rating, 8 reviews

Casa Spiano

A 14 km da Firenze, Casamaggio è il posto ideale per godere anche della naturale bellezza della campagna fiorentina. Sito alla fine del paese di San Donato in Collina, dove i servizi essenziali sono reperibili anche a piedi, è l'ideale per chi vuole visitare Firenze con trasporti locali/autobus di linea.. Casamaggio è un caratteristico fabbricato rurale, che si affaccia direttamente sul prospiciente oliveto, ed il cui terrazzo rivolto ad est gode della vista panoramica del Valdarno

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Superhost
The exterior of the renovated barn is constructed with natural stone, featuring a large arched window and a sleek glass door. Flower pots filled with colorful blooms line the entrance, enhancing the inviting atmosphere. Olive trees and lush greenery can be seen in the surroundings.
Barn in San Francesco
5.0 out of 5 average rating, 36 reviews

La Capanna - Delightful stay in the renovated barn

Allontanati da tutto e dormi sotto una coltre di stelle! Il nostro alloggio è vicino alla principale città toscana di Firenze, Arezzo, Siena, San Gimignano, Volterra, San Miniato e piccoli paesi ricchi di cultura e tradizioni. Bellissimi sono i panorami e gli ottimi ristoranti nei dintorni con la loro cucina tipica toscana. Il rinnovato fienile ti piacerà per la sua atmosfera tranquilla e per gli spazi all'aperto nel verde. È adatto a coppie o famiglie con bambini. Pet friendly!

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Guest favourite
A serene bedroom is illuminated by two pendant lights, creating a soft ambiance. A spacious bed is dressed in neutral linens, accompanied by a blanket draped over the side. Large windows with light, flowing curtains offer a view of the lush green surroundings.
Flat in San Francesco
4.92 out of 5 average rating, 37 reviews

Elegant riverside retreat near Florence

Welcome to our elegant suite on the banks of the River Sieve, just 20 km from Florence – perfect for guests traveling by car. Enjoy peaceful river views, lush green surroundings, and a newly renovated interior with a cozy living room and spacious terrace. We’re 2 km from Pontassieve (about a 20-minute walk), where frequent trains reach Florence in just 20 minutes. “The Mall” luxury outlet is only a 15-minute drive, making this the ideal base for a relaxing Tuscan getaway.

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Superhost
A private swimming pool is surrounded by wooden decking and lush greenery, offering expansive views of the rolling hills and valleys in the distance under a clear blue sky. A small ladder is available for easy access to the water.
Home in Rufina
4.86 out of 5 average rating, 121 reviews

Ancient Tuscan Rural Residence

An elegant independent peaceful panoramic rustic residence nestled amidts the scenic and gently rolling hills in Tuscany . This beautiful property is the ideal destination for those who want to experience and enjoy true Italian country living, recommended for families. PRIVATE SWIMMING POOL (which is located a few tens of meters from the villa in its own land ) and JACUZZI (located in the garden of the villa ) are open for our guests from June until the end of September.

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Superhost
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, 225 reviews

Il Castello di Ferrano - Castle in Tuscany

Try the experience of staying in a real Castle! Il Castello di Ferrano offers to its hosts the chance of living an unforgettable experience: you will be the only guests in the castle, and everything will be for you (private pool from June to September, gardens etc..). 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.

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Top guest favourite
A large swimming pool surrounded by a brick patio and manicured lawns is highlighted in this image. Sun loungers are positioned along the pool's edge, with lush greenery and trees creating a serene backdrop. The villa's charming structure is visible in the distance under a partly cloudy sky.
Villa in Barberino Tavarnelle
4.98 out of 5 average rating, 104 reviews

Podere Tignano, 4-bedroom villa in the Chianti!

Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.

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Top guest favourite
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, 429 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.

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Top guest favourite
The historic tower-penthouse villa is surrounded by lush greenery and trees. The three-story structure is characterized by its earthy facade and wooden shutters. Well-maintained gardens with various plants create a serene outdoor environment, enhancing the villa's tranquil charm and historical significance.
Castle in Bagno A Ripoli
4.96 out of 5 average rating, 138 reviews

Tower Penthouse in small castle near Florence

900 year old Tower-Penthouse apartment in Chianti Villa, spacious & super-scenic historical home that combines magical atmosphere with space, light, history, convenience. (AC throughout). Painting-like 360° views of Tuscan Hills all the way to Florence; sun-filled, private grounds. Perfect location for an unforgettable family stay. Ample private property (including forest). Walking distance from village shops. Convenient location, Florence in sight.

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Superhost
A charming stone building is seen surrounded by lush greenery, featuring a terracotta roof. The outdoor area includes a stone patio with wooden chairs and tables, accented by blooming purple flowers and potted plants, with rolling hills visible in the background.
Flat in Pelago
5.0 out of 5 average rating, 53 reviews

Fienile

Located in Fontisterni, a small village in Pelago near Pontassieve, the Fienile holiday apartment offers a relaxing stay. The 50 m² property has a living room with sofa bed for 2, a fully equipped kitchen, 1 bedroom, and 2 bathrooms, accommodating up to 4 guests. The open-plan layout uses partial walls to provide some privacy. Amenities include fast Wi-Fi (suitable for video calls) with workspace, TV, washing machine, baby cot, and air conditioning.

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Popular amenities for Masseto holiday rentals