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Holiday houses in Cenaia

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Top-rated holiday rentals in Cenaia

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Top Guest favourite
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, 180 reviews

Casa al Gianni - The Simignano Barn

Transformed from a former barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living room, and a large private garden with parking, a hot tub, a patio with sofas, a BBQ, a fire pit, and an outdoor kitchen. Ideal for those seeking a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, complete with relaxation in the hot tub and al fresco dining. A memorable getaway awaits you in this slice of paradise!

Top Guest favourite
A tea set is arranged on a table, featuring a teapot and two cups with saucers. In the background, the dome of a historic building and the leaning structure of the Torre Pendente can be seen, highlighting the rich architectural heritage of Pisa.
Apartment in Pisa
4.99 out of 5 average rating, 115 reviews

"La Torre al 7 - Leaning Tower View, Pisa"

Private terrace with direct views of the Leaning Tower — just 80 metres away. Wake up, step outside, and find one of the world's most iconic monuments waiting in silence. While other visitors photograph it from below, you take in the view from above, coffee in hand. Original paintings and sculptures by your Tuscan host fill every corner in a dialogue between ancient and contemporary. Not just a place to stay — an experience you carry with you. Pisa is not just a stop. From here, it becomes home.

Top Guest favourite
An aerial view captures Podere Vergianoni nestled in the Chianti hills, surrounded by lush vineyards. The property features a clear blue pool, shaded terraces, and carefully landscaped gardens. Rolling hills and rows of grapevines create a serene backdrop, highlighting the natural beauty of the Tuscan countryside.
Condo in Noce
5 out of 5 average rating, 339 reviews

Podere Vergianoni nestled in Chianti with a pool

Podere Vergianoni è un antica e storica proprietà risalente al 1600 situato nelle splendide colline del Chianti in Toscana con la possibilità di organizzare servizio navetta e esperienze esclusive su misura per voi . L'appartamento è disponibile per 2 adulti con possibilità aggiunta divano letto per 2 bambini sotto i 12 anni . Nel grande cortile esterno troverete una piscina a sale con area relax su terrazza panoramica con vista su castello colline e vigneti con tramonti unici.

Top Guest favourite
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, 221 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.

Top Guest favourite
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, 53 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 favourite
A modern chalet is surrounded by greenery, featuring a spacious covered porch with decorative foliage. Large windows invite natural light, while a cozy seating area is visible. A circular flower bed with vibrant blooms enhances the outdoor aesthetic, creating a calm connection to nature.
Home in Fauglia
4.94 out of 5 average rating, 34 reviews

Chalet i Poggetti,

If you want to surprise the person you love, or experience a relaxing stay, our chalet is an ideal solution allowing you to connect with nature in an elegant and comfortable environment, in total privacy in a unique natural setting, equipped with all comforts, at your disposal a solar greenhouse equipped with a hot tub and sauna... with a forest view. Outside, there is a terrace where you can dine or have breakfast adjacent to the solarium area with deck chairs, etc.

Guest favourite
Castle in Tignano
5 out of 5 average rating, 24 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 favourite
A spacious living area is adorned with intricate frescoes and elegant decor, featuring a comfortable cream-colored sofa and a wooden coffee table. Light filters through large windows, illuminating the room’s artistic details. In the background, a cozy sleeping area with a canopy bed is visible.
Condo in Florence
5 out of 5 average rating, 152 reviews

[SAN LORENZO-DUOMO] Prestigious Historic Residence

Make your stay a unique experience and give yourself an emotion that will last for life. Located in the heart of Florence, this magnificent historic residence is the ideal solution for those looking for an exclusive and prestigious location to combine with a central position, perfect for easily visiting the main sites of interest, reachable in less than 10 minutes on foot. The apartment enjoys exclusive views of the Medici Chapels, offering a unique view.

Top Guest favourite
Casa particular in Florence
5 out of 5 average rating, 46 reviews

Palazzina Maresa - Loft 4

Palazzina Maresa is a 1920s building carefully restored to host eight independent apartments, each shaped by the vision of a different young local designer. The project reflects on early 20th-century aesthetics through a contemporary lens, blending architecture, design, and artistic research. Located in a quiet residential area with private and shared gardens, the building is just a short walk from Florence’s historic center.

Top Guest favourite
Farm stay in Palaia
4.98 out of 5 average rating, 194 reviews

Countryside Dream farm in Tuscany

Have you ever dreamed of experiencing the rolling hills of Tuacany ? This is a berautiful organic farm in the middle of Tuscan Hills, you will be surrounded by nature but close to all the beautiful cities of Tuscany! We rent two apartments, one on the upper floor called Balla and one on the ground floor called Modigliani. Tell us which one you prefer. PLEASE NOTE YOU WILL NEED A CAR DURING YOUR STAY.

Top Guest favourite
Holiday home in Lajatico
5 out of 5 average rating, 34 reviews

Rosa: Tuscan Views & Pool, Walk to Town

Welcome to La Lunaria di Lajatico, an elegant residence in the Tuscan hills, just a 7-minute walk from the village of Lajatico, hometown of Andrea Bocelli. With two pools, panoramic terraces overlooking rolling hills, olive groves, BBQ, and full modern comfort, it offers four rustic-chic apartments—ideal for families, couples, or groups seeking authentic Tuscany close to town.

Top Guest favourite
A spacious living area features a modern design, with a prominent stone fireplace and minimalist furniture. Large glass doors open to a serene outdoor view, while natural light brightens the room, highlighting the soft tones of the walls and furnishings.
Tower in Fiesole
4.95 out of 5 average rating, 214 reviews

A Big Dream in a Little Tower.

The Tower was created in the late 1800s by an illustrious Englishman, Sir John Temple Leader, in one of the oldest and most important stone quarries belonging to the Medici family. From the same quarry were extracted many important works such as the columns of the Medici chapels, the steps of the Laurenziana library .. all just 5 km from the historic center of Florence.

Popular amenities for Cenaia holiday rentals

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Pisa
  5. Cenaia