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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
Flat
4.97 out of 5 average rating, 63 reviews

Casa Fedora

Casa Fedora era la casa di mia nonna dalla quale prende il nome. Si trova a Sassa un incantevole borgo medievale immerso nelle colline toscane dove regna la tranquillità e l'amore per le proprie origini. Avrete a disposizione 80 mq completamente ristrutturati che godono di una magnifica vista panoramica sulla vallata sottostante. Se cercate la tranquillità nella bellezza Casa Fedora saprà soddisfare le vostre aspettative. Sassa dista 30 minuti dall'etrusca Volterra e 30 minuti da Cecina mare.

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
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.”

Top guest favourite
A rustic building is seen under a starry night sky, with a partial roof providing shelter. Soft light glows from the interior, illuminating the entrance. Lush greenery and trees surround the scene, adding depth to the serene nighttime landscape.
Farm stay
4.92 out of 5 average rating, 269 reviews

Casa al Gianni - Capanna

Ciao, siamo Cristina e Carmelo! Vi aspettiamo a "Casa al Gianni", il nostro agriturismo tra i boschi della Montagnola Senese a soli 20 minuti da Siena. Qui la vita rallenta: Solo il profumo della terra, il canto degli uccelli e la simpatia dei nostri animali. È un invito a riscoprire la bellezza delle piccole cose, immersi nel verde della Toscana più vera. Non è solo una vacanza, è un ritorno alle origini. Questo angolo di pace vi resterà nell'anima. Vi aspettiamo!

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
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
A cozy living area features a light-colored sofa and a small, wooden table with two chairs. An elegant lamp stands nearby, while warm sunlight highlights the natural wooden beams on the ceiling. A fireplace is situated against the white wall, adding a touch of character.
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.

Top guest favourite
Two intricately designed door knockers are mounted on a rich wooden door. Each knocker features a cat's head made of bronze, encircled by ornate metalwork. The warm tones of the wood complement the detailed craftsmanship of the knockers.
Flat
5 out of 5 average rating, 58 reviews

I Gatti (Cats) - holidays and / or smartworking

Our apartment is perfectly equipped to enjoy a peaceful holiday and / or work in smartworking, in fact it is equipped with many comforts and has an excellent wifi connection, which allows you to work as in the office. To relax you can access a balcony from which to admire the sea, which is a few kilometers away; we really appreciate it sitting at sunset with a piece of focaccia and wine or a beer !

Top guest favourite
Holiday home in Lajatico
5 out of 5 average rating, 27 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.

Guest favourite
A spacious living room is presented with terracotta flooring and wooden beams overhead. A comfortable sofa arrangement surrounds a wooden coffee table, with a flat-screen TV positioned nearby. Natural light filters through the windows, enhancing the inviting ambiance.
Home
4.9 out of 5 average rating, 213 reviews

Siena Countryside Colle Ciupi

Countryside Villa apartment. Located in the nearby of Siena (Colle Ciupi, 10 kms away) Ground floor: Kitchen, living room with fireplace, bathroom with shower. First Floor: 3 Double Bedrooms and 2 bathrooms, outdoor with courtyard and huge garden

Guest favourite
A spacious living room is highlighted by a central brick fireplace adorned with decorative plates. Comfortable sofas face a wooden coffee table, while large windows allow natural light to fill the space. Wooden beams enhance the ceiling, and artwork decorates the walls.
Villa
4.95 out of 5 average rating, 137 reviews

La Conchetta - Bolgheri

Located on the Bolgheri road, a dreamlike place where the countryside, climate and nature are absolute master of the scene. Just 10 minutes from Bolgheri and Castagneto Carducci, two beautiful place of Tuscany, famous for wine, food and culture.

Popular amenities for Bolgheri holiday rentals

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