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Holiday rentals in Bolgheri

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Top-rated holiday rentals in Bolgheri

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

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Top guest favourite
A bright living area showcases large glass doors leading to an outdoor terrace with scenic views. A colorful area rug lies on the wooden floor, complemented by a modern sofa and decorative artwork on the wall. Natural light fills the space, enhancing its openness.
Home
5 out of 5 average rating, 269 reviews

The MOONLIT & SUNNY COTTAGE near Florence

IL COLLE DI FALTUGNANO: immersed in an olive grove on a Tuscan hills and with an amazing view of the valley, the stone cottage has been remarkably recovered a few months ago, a caravanserai a few century ago. In a strategic position close to Florence and Mugello is a good base for exploring Tuscany and be independent at the same time with supermarkets and restaurants just a few minutes away. Close to a farmhouse you can buy fresh local organic ingredients such as bio vegetables, eggs or cheese.

Top guest favourite
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
5 out of 5 average rating, 107 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 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
4.99 out of 5 average rating, 133 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
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
5 out of 5 average rating, 217 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.
Apartment
5 out of 5 average rating, 49 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
Farm stay
5 out of 5 average rating, 8 reviews

Agriturismo Bolgheri24 - Monti Apartment

Welcome to Bolgheri24, an agriturismo nestled in the stunning countryside of Bolgheri, just 20min from the seaside. Enjoy our finely renovated apartment with a private garden and a charming patio. The house: - 70 sqm of living space - 1 Double Bedroom - 1 Twin Bedroom - 2 Bathrooms - Fully Equipped Kitchen - Air conditioning, Smart TV - Private parking Outdoor: - Private patio with elegant outdoor furniture, ideal for relaxing and soaking in the charm of Tuscany.

Top guest favourite
Castle
5 out of 5 average rating, 22 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 terrace is surrounded by lush greenery, featuring terracotta pots filled with plants. Comfortable wooden chairs are positioned to invite relaxation, overlooking scenic hills in the distance. A soft canopy provides shade, enhancing the tranquil atmosphere of this outdoor space.
Home
4.99 out of 5 average rating, 141 reviews

House with a breathless view in Tuscany

Halfway between Pisa and Florence, this dreamy Tuscan house is your perfect escape. Lounge on the panoramic terrace with sun-kissed views, sip your morning coffee, or enjoy al fresco dinners under the golden sunset. Nestled in the heart of a charming village turned open-air contemporary art museum, every corner feels like a picture-perfect moment. Peccioli is your gateway to Tuscany’s art cities or a serene hideaway to savor the magic of authentic local life.

Guest favourite
Villa
4.89 out of 5 average rating, 18 reviews

Charming Tuscan Villa - "Borgo Il Massera"

Nestled in the Tuscan hills, Borgo Il Massera is a restored luxury estate with independent rooms, jacuzzi, and cypress-lined paths. Exposed stone, wooden beams, and modern comforts create an authentic and relaxing Tuscan charm. The villa offers a private outdoor area and Wi-Fi. Between the sea and towns like Volterra and San Gimignano, it’s the ideal place to enjoy the true essence of Tuscany and explore many destinations nearby.

Guest favourite
A charming outdoor space is featured, set beneath a leafy tree. A small round table with two chairs is positioned on a grassy area, leading to a doorway framed by wooden shutters that open to the interior.
Home
4.96 out of 5 average rating, 90 reviews

Dependance La Bandita

Dependance immersa nel giardino di un tipico podere toscano, siamo nella campagna di Marina di Castagneto Carducci vicina al mare raggiungibile a piedi o in bici percorrendo l’adiacente pista ciclabile per ca. 2 km. Una camera spaziosa con bagno en suite e letto matrimoniale, ingresso indipendente e ampio giardino a disposizione. Rifugio perfetto per viaggiatori che cercano uno spazio tranquillo, romantico e rilassante.

Guest favourite
Flat
4.95 out of 5 average rating, 20 reviews

La casina. Bilocale nel centro storico di Bibbona

Goditi una vacanza all'insegna dello stile in questo spazio in centro. Potrai vivere la realtà di un piccolo borgo toscano, caratterizzato dalla pace in un bilocale completamente ristrutturato. Su richiesta, è possibile organizzare una cena nel piccolo patio della casa completamente preparata dal ristorante Io Cucino. È possibile avere, servizi extra come pulizie aggiuntive e servizi di lavanderia a richiesta.

Guest favourite
The kitchen area features rustic wooden ceiling beams and terracotta floor tiles. A dining table with chairs is set for meals, while modern appliances, including an oven and a refrigerator, are visible in the background. Natural light streams through the window, enhancing the inviting space.
Flat
5 out of 5 average rating, 19 reviews

Tuscan Farmhouse with Pool & Panoramic View

Immersed in Tuscany's pristine nature, this elegant apartment in Podere Bagnoli offers a relaxing getaway with breathtaking views and modern comforts. Located 4 km from the medieval village of Castagneto Carducci, it is the perfect retreat for couples, wine lovers, slow travelers, and those seeking peace and authenticity.

Popular amenities for Bolgheri holiday rentals

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Livorno
  5. Bolgheri