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Vacation rentals in Valpiana

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Top-rated vacation rentals in Valpiana

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

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Top guest favorite
A stone house is positioned on a hillside overlooking the deep blue sea. Lush green terrain surrounds the structure, and a large umbrella provides shade near the entrance. The coastline and distant boats can be seen in the background under a clear sky.
Home in Rio Marina
5 out of 5 average rating, 114 reviews

Casa del Capitano | Monte Grosso, Elba

The Casa del Capitano is located on the top of Monte Grosso in the National park of the tuscan archipelago. The location is unique on the island and from here you have a fantastic view of the city of Portoferraio, Piombino, Corsica, Capraia and Gorgona. The house was restored during a project lasting several years, in close collaboration with the National Park and was designed to be self-sufficient and ecological. Here you use purely the energy of the sun, without having to renounce luxury.

Top guest favorite
Home in Siena
5 out of 5 average rating, 21 reviews

Private House for 4P- La Capanna Di Azzurra

Ideale per famiglie, coppie o amici in cerca di una dimora elegante e accogliente, questa casa è pensata per chi vuole vivere la campagna toscana senza rinunciare alla comodità della città. Immaginate una colazione guardando il profilo di Siena, giornate tra arte, vino e natura, e il rientro al tramonto, quando la luce scalda la pietra e il silenzio restituisce il ritmo autentico di questi luoghi. Un rifugio pratico, con charme e scenografico, perfetto per visitare Siena e i suoi dintorni!

Top guest favorite
Condo in Valpiana
4.98 out of 5 average rating, 44 reviews

Infinity Pool nel verde agriturismo vista bosco

Vivi la Toscana autentica tra mare e campagna! A 10 km da Follonica e Massa Marittima si trova la nostra tenuta Casetta Valmora. L'appartamento con patio privato, Wi-Fi, aria condizionata affaccia sul giardino con due lettini prendisole, ideale per coppie, famiglie e amici. Da Giugno 2026 sarà disponibile la nuova piscina a sfioro panoramica con vista sul bosco, per momenti di puro relax. Nei dintorni scopri borghi medievali, Cala Violina, percorsi bike, golf ( a 15 km) e prodotti locali.

Top guest favorite
Home in Massa Marittima
5 out of 5 average rating, 72 reviews

Design loft with private SPA in Tuscany

Welcome to Loft SPA, your personal refuge in the heart of Massa Marittima, an exclusive accommodation equipped with a private indoor swimming pool. This unique property offers an unparalleled stay experience, combining elegance and comfort, the accommodation has been designed with attention to detail and quality, The highlight is the indoor swimming pool with its accessories, an oasis of relaxation. This exclusive accommodation offers a stay experience you will not easily forget.

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
4.98 out of 5 average rating, 189 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!

Top guest favorite
An aerial view of the property reveals a charming red house surrounded by lush greenery. Tall cypress trees and vibrant bushes create a tranquil landscape, while an expansive lawn features relaxing loungers, inviting guests to enjoy the serene atmosphere of the Tuscan countryside.
Home in Gambassi Terme
5 out of 5 average rating, 228 reviews

Il Fienile, Luxury Apartment in the Tuscan Hills

‘Il Fienile’ is in an enchanting position immersed in the beauty of the Tuscan hills, with a breathtaking view of the surrounding countryside. It is located in the hamlet of Catignano in Gambassi Terme, just a few kilometres from San Gimignano. The house sits in a protected oasis surrounded by a beautiful private park with olive trees, a pond, pine trees and woods, where you can walk, relax and enjoy the pleasures of unspoilt nature. A unique experience entirely to be enjoyed.

Guest favorite
An aerial view captures the serene layout of the estate, surrounded by lush greenery and rolling hills. The inviting pool is situated centrally, accompanied by sun loungers. Stone buildings harmonize with the natural landscape, reflecting the tranquil beauty of the Montagnola Senese.
Vacation home in Sovicille
4.97 out of 5 average rating, 160 reviews

Podere La Castellina - N°1 COTTAGE

Cottage indipendente in pietre e mattoni all'interno del "Podere la Castellina" (ex convento 13° secolo), nel magnifico parco naturale della Montagnola Senese. Il cottage può ospitare comodamente 5 persone e comprende: - ampio soggiorno con tv e camino - cucina abitabile con forno - camera matrimoniale - camera con tre letti singoli - bagno con doccia A disposizione degli ospiti piscina panoramica, solarium e terrazza con vista mozzafiato, dotata di forno a legna e barbecue.

Top guest favorite
A spacious living area features exposed brick walls, wooden beams, and warm lighting. A comfortable sofa and a mid-century modern coffee table sit invitingly, while a dining table and chairs are positioned nearby. Large windows enhance the natural light, which complements the earthy tones of the room.
Condo in San Gimignano
5 out of 5 average rating, 63 reviews

AnticaVista, Luxury Apartment with Tower Views

A hidden gem nestled within the ancient walls of a 14th-century tower house, right in the heart of San Gimignano, a UNESCO World Heritage Site. This one-of-a-kind apartment is where history meets contemporary elegance. Look out the window and you’ll feel like you can almost touch the medieval towers. The view is breathtaking: unforgettable glimpses of the majestic Torre Grossa, framed by the iconic skyline that earned San Gimignano its nickname, the “Medieval Manhattan.”

Guest favorite
Apartment in Massa Marittima
5 out of 5 average rating, 22 reviews

Vicolo Porte 21/23, Massa Marittima, Jacuzzi

A pochi passi dalla Piazza Garibaldi, nel cuore medievale di Massa Marittima, Vicolo Porte 21/23 è uno spazioso loft nascosto, dove il fascino della storia incontra il comfort contemporaneo. Relax esclusivo: all'interno troverai una vasca idromassaggio con cromoterapia. Gli spazi, dallo stile minimal ma avvolgente, combinano materiali naturali, colori neutri e dettagli ricchi di personalità. Vicolo Porte 21/23 è il punto di partenza ideale per scoprire la Maremma!

Guest favorite
Castle in Tignano
5 out of 5 average rating, 25 reviews

Luxury Medieval Tower • Exclusive Chianti Stay

Benvenuti in una delle residenze più esclusive del Chianti: una torre medievale trasformata in un raffinato luxury retreat con vista sulle colline toscane. Design contemporaneo, arredi iconici, opere d’arte e comfort di lusso si fondono in un’esperienza unica. Un’oasi di quiete con giardino privato, dependance vetrata, Wi-Fi, area smart working. Servizi extra: chef privato, degustazioni in cantina, trattamenti benessere e tour tra i borghi più belli della Toscana.

Top guest favorite
Home in Barberino Tavarnelle
5 out of 5 average rating, 83 reviews

Authentic Tuscany Experience in our Country House

An amazing experience between nature, flavour and relax in the heart of Chianti. Situated between Barberino Tavarnelle, San Gimignano, Greve in Chianti, and Florence, Belvedere 27/A overlooks the Santa Maria Novella Castle, amidst vineyards and olive groves with an amazing view. A countryside Tuscan home, surrounded by olive’s fields and greenery, equipped with every comfort. Reconnect in this serene, one-of-a-kind stay, for a peaceful and relaxing holiday.

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, 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.

Popular amenities for Valpiana vacation rentals