
Holiday rentals in Santa Maria a Monte
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Top-rated holiday rentals in Santa Maria a Monte
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Florence Sunset Hills • Giogoli
Escape to the peaceful hills of Giogoli where authentic Tuscan charm meets breathtaking views of Florence.Just 15 minutes from the city center and the Chianti countryside, this elegant home is the perfect base for exploring Tuscany while enjoying quiet mornings, unforgettable sunsets, and the beauty of the surrounding landscape. Surrounded by nature but close to the region's most iconic spots, it's the ideal retreat for anyone looking for comfort, tranquility, and a genuinely Tuscan experience

Casa Frediano Holidays
Siamo nella campagna Toscana a 3 Km dall'uscita dell'autostrada A11 Altopascio (Lucca). Abitazione ideale per accogliere anche gli amici più fedeli dell'uomo...i cani, che possono correre liberi nel giardino tutto recintato di oltre 2000 mq con parcheggio. In 15 minuti possiamo raggiungere Lucca e poco dopo Pisa e la Versilia. In 40 minuti si arriva a Firenze. Da vedere Siena, Poggibonsi, Volterra, San Gimignano. A 300 mt passa l'antica Via Francigena. Silenzio e relax. Casa con tutti i confort.

Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is a family-run, historic 17th-century property located in the beautiful Chianti hills of Tuscany, with the option of arranging a private shuttle and local experiences directly with our family. The apartment is available for 2 adults with the option of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard you'll find a saltwater pool with a relaxation area on a panoramic terrace overlooking the castle and vineyards with unique sunsets.

Church of the Vaioni
An ancient deconsecrated church dating back to the early 1900s, originally built as a private chapel of Villa Philipson. Chiesino Dei Vaioni has a loft structure with two double bedrooms on two separate mezzanines. Outside, there is a kitchen with a wood-burning oven, private gardens with a tree-lined avenue and an olive grove. The gates and internal stairs were built by the Antica Fonderia Michelucci. Chiesino Dei Vaioni is immersed in the Tuscan countryside just minutes from the city.

Le Querce, 'Rosmarino' apartment – relaxation in Tuscany!
The new "Le Querce" apartments are located on the ground floor of a villa located on a three-hectare farm with olive grove and orchard, characterized by the presence of groves of tall oaks. The accommodations are apartments of about 60 square meters each, with a front porch for personal use of about 20 square meters overlooking the infinity pool, which is for common use (50 square meters), with sun loungers and umbrella available. Guests can enjoy free, unattended private parking.

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.

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.”

Historic Tuscan Home - Terrace & Private Garage
Scopri il fascino autentico della Toscana soggiornando in un elegante appartamento di 200 m², recentemente ristrutturato, nel cuore del centro storico di San Miniato. Dotato di ingresso indipendente, garage privato collegato all’abitazione, ampia terrazza panoramica con vista sulle colline e sul tramonto, e giardino riservato, è il luogo ideale per vivere un soggiorno tra relax, comfort, storia e i sapori del celebre tartufo bianco, a metà strada tra Firenze e Pisa.

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.

Casale I Lecci – Papavero
75 sqm apartment, first floor, kitchen/living room with sofa bed, bedroom with double bed, triple bedroom with a double bed and a single bed, bathroom with shower. The property, recently renovated, is located on the hill about 1 km from the small medieval historic center of Santa Maria a Monte, in a very favorable position to visit the most important art cities of Tuscany. The farmhouse contains 4 independent apartments, equipped with all the necessary amenities.

Cercis - La Palmierina
E' un appartamento facente parte di una tenuta completamente recintata di 60 ettari di natura incontaminata: più di 1000 ulivi, innumerevoli cipressi e foreste profumate creano un ambiente idilliaco per coloro che ricercano tranquillità e silenzi. La tenuta Palmierina è in prossimità di Castelfalfi (un vero gioiello di architettura medievale) e nelle vicinanze di Firenze (50 Km), Siena (50 Km), Pisa (50 Km). Nelle vicinanze ci sono due campi da golf.

"La limonaia" - Romantic Suite
Romantic Suite immersed in the enchanting hills of Fiesole. It is the ideal place fot those looking for unique and exclusive experience of its kind characterized by suggestive views and unforgettable sunsets. The accommodation is part of an old 19th century Tuscan farmhouse surrounded by its own olive groves and woods. This is an ideal place for a relaxing holiday and privileged base for visiting the major centers of interest in Tuscany.
Popular amenities for Santa Maria a Monte holiday rentals
Other great holiday rentals in Santa Maria a Monte

Fienile Olivo, apartment for 2 people

Enjoy Amazing View in Tuscany in Our Country House

Villa Sunkiss: Luxury Farmhouse with Tuscan Flair

Palazzina Maresa - Loft 4

"The Lost Lake" Family Home The ideal point 0.

‘Il Bosco’ Glamping Cabin with Hot Tub

Nest in the Tuscan woods between Pisa and Lucca

Luxury Villa "Le Rondini" – Peccioli
Destinations to explore
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Piazza del Duomo (Pisa)
- Mugello Circuit
- Stazione Santa Maria Novella
- Mercato Centrale
- Uffizi Gallery
- Pisa Centrale Railway Station
- Spiagge Bianche
- Fortezza da Basso
- Piazza della Repubblica
- Gulf of Baratti
- Parco delle Cascine
- Piazzale Michelangelo
- Gorgona
- Del Chianti
- Pitti Palace
- Boboli's Garden
- Palazzo Vecchio
- Piazza della Signoria
- Medici Chapel





