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Holiday home rentals in Siena

Find and book unique holiday home rentals on Airbnb

Top-rated holiday home rentals in Siena

Guests agree: these holiday home rentals are highly rated for location, cleanliness and more.

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Guest favourite
A refreshing swimming pool is nestled in a spacious deck, overlooking rolling hills and vineyards. Lush greenery surrounds the area, complemented by a charming stone path leading to the poolside. The village roofs, framed by nature, create a serene and scenic backdrop.
Holiday home in Dimezzano
4.91 out of 5 average rating, 103 reviews

[Traditional Cozy House] Garden & Viewpool Apt

In the heart of the Chianti countryside, this charming two-bedroom home stands within a medieval hamlet surrounded by vineyards. From the garden’s top terrace, a panoramic pool overlooks the rolling hills, offering an idyllic view of Tuscany’s timeless beauty. Just a few Km from Greve in Chianti and around 30 minutes from Florence and Arezzo, the property is ideally located for exploring the region’s art, wine, and gastronomy. Authentic trattorias and family-run wineries are a short drive away.

Top guest favourite
A bright bedroom features a spacious bed with crisp white linens and a decorative pillow. A vivid landscape painting hangs above, while a window with wooden frames reveals a scenic view of the Tuscan hills, complemented by soft natural light filtering through sheer curtains.
Holiday home in San Gimignano
4.98 out of 5 average rating, 152 reviews

Respira la Toscana: vista a 180° sulle Colline

Please note that the second bedroom is divided from the hallway by a curtain and not by a door. inVivi la tua esperienza a San Gimignano con una splendida vista sulle colline toscane! Nel cuore di San Gimignano, vivi la città con ingresso indipendente, primo piano e panorama mozzafiato sulle colline toscane. Disponibile su richiesta il posto auto privato. Ingresso, salotto, 2 camere matrimoniali, cucina e ampio bagno. city tax da aggiungere al prezzo, 2,5€ per ogni persona per ogni notte.

Guest favourite
An aerial view of a classic Tuscan farmhouse is presented, surrounded by lush vineyards and rolling hills. The property includes a landscaped garden, parking area, and outdoor seating. The warm tones of the rustic structure complement the vibrant green fields, highlighting the serene countryside setting.
Holiday home in Poggibonsi
4.94 out of 5 average rating, 193 reviews

Vittoria Chianti Vacations 🍇🍷

Vittoria Chianti Vacations is the ideal solution for those seeking peace and tranquility in the heart of Chianti, close to all comforts. Typical Tuscan farmhouse halfway between Florence and Siena, is located in a strategic position to quickly reach Florence, Siena, San Gimignano, Monteriggioni, Volterra and the Chianti hills. Siena Eye Laser Clinic 2 min. Private parking, two bedrooms, equipped kitchen, private bathroom, Wi-Fi, private garden, barbecue, a wonderful view of the Chianti hills.

Top guest favourite
An aerial view captures the scenic landscape surrounding an ancient farm complex nestled within lush greenery. A swimming pool is visible at the center, surrounded by sun loungers, while rolling hills stretch into the distance under a soft evening light.
Holiday home in Sovicille
4.93 out of 5 average rating, 123 reviews

Podere La Castellina - N°2 LECCETO

Appartamento in pietre e mattoni all'interno del "Podere la Castellina" (ex convento 13° secolo), nel magnifico parco naturale della Montagnola Senese. L'appartamento situato al piano terra può ospitare comodamente 2 persone e comprende: - soggiorno con tv - cucina con forno e piastre elettriche - camera matrimoniale - bagno con ampia doccia - tavolo esterno privato A disposizione degli ospiti piscina panoramica, solarium e terrazza con vista mozzafiato, dotata di forno a legna e barbecue.

Guest favourite
A bright double bedroom is presented with a spacious bed featuring crisp white linens. Natural light floods the room through an open window, framing a view of the surrounding valley. Wooden beams add character to the ceiling, and bedside tables with lamps are positioned beside the bed.
Holiday home in Montepulciano
4.92 out of 5 average rating, 202 reviews

Stuart Jasmine central, panoramic top location

This abode boasts 1 double and 1 single bedroom, a spacious living room with a fully equipped kitchen, and 1 bathroom with shower. Every window frames a breathtaking view, filling the space with natural light. High-speed Wi-Fi ensures comfort for both work and leisure. Its proximity to all town amenities ensures convenience, while a delightful café downstairs provides a delectable gourmet breakfast. Here, you can unwind and relax, study and learn, discover and explore, or create and dream.

Top guest favourite
An aerial view captures the historic castle surrounded by lush green hills and vineyards. The impressive structure features tall towers and ornate architecture, set amid manicured gardens and tree-lined pathways, reflecting the beauty of the Chianti landscape.
Holiday home in Badia a Passignano
5 out of 5 average rating, 118 reviews

Chianti Craft House Badia a Passignano

Ancient house in the historic village of Badia a Passignano, completely and finely restored in 2022. The house is located exactly in the center of the village of Badia a Passignano, overlooking the abbey castle and the Chianti vineyards. The house consists of 2 bedrooms air-conditioned: 1 double bedroom with service bathroom and 1 with 2 single beds and the possibility of a third with sofa chair; a full bathroom with shower, a full kitchen with washing machine and dishwasher, dining area

Top guest favourite
A charming rustic farmhouse is set against a dramatic sky, framed by lush green trees. The exterior features warm-toned walls and a tiled roof, while a spacious yard includes seating arrangements for outdoor relaxation, inviting guests to enjoy the serene countryside.
Holiday home in Simignano
4.92 out of 5 average rating, 228 reviews

Casa al Gianni - Quercia

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 living area features plush burgundy sofas arranged around a coffee table. A sleek black television is positioned against a light wall. A dining table with green chairs is present, complemented by potted plants and light fixtures for additional ambiance.
Holiday home in Florence
4.95 out of 5 average rating, 102 reviews

SMN Luxury Secret Garden View

Welcome to the central part of Florentine charm! This extraordinary apartment, located just 50 meters from Piazza Santa Maria Novella, offers you an unparalleled experience in the historic heart of Florence. Imagine crossing the threshold of a Renaissance Palace, a jewel of inestimable artistic and historical value, and being welcomed by an atmosphere that speaks of history and elegance. Two bedrooms, two complete bathrooms, living room with fully equipped kitchen.

Guest favourite
A rustic stone building features a charming entrance adorned with blooming flowers and lush greenery. The structure showcases traditional architecture with arched doorways and a tiled roof, set against a clear blue sky and surrounded by serene natural beauty.
Holiday home in Casole d'Elsa (SI)
4.91 out of 5 average rating, 222 reviews

Charming farmhouse with garden, views & pool

Agriturismo Timignano is a beautiful farmhouse surrounded by stunning unspoilt countryside. The stone farmhouse has been restored over the years to create 3 totally separate apartments, each with independent entrance , private terraces and garden space. The farm is surrounded by unspoilt countryside with spectacular views and magnificent sunsets. It is a calm, relaxed place, an idyllic retreat away from the crowds ideal for couples.

Guest favourite
Holiday home in Reggello
4.89 out of 5 average rating, 198 reviews

Barrel Suite Tuscany • Hot Tub • Vineyard View

Sleep inside a wine barrel in Tuscany — one of the largest in the world (3.5 m × 8 m) — nestled in an olive grove in Reggello, with panoramic views over the hills and vineyard. Private bathroom, kitchenette, veranda, private courtyard and exclusive hot tub: everything for a total escape from the world. 40 min from Florence, with Siena, Arezzo, The Mall Luxury Outlet and Vallombrosa all within easy reach. Free private parking included.

Top guest favourite
An outdoor seating area features a small table surrounded by two chairs, adorned with a light breakfast setup. The stone facade of the house is complemented by climbing vines and a bright flower arrangement, inviting guests to enjoy the fresh air.
Holiday home in Monticchiello
4.97 out of 5 average rating, 129 reviews

In Toscana Camere

**Your Dream Retreat in the Heart of Val d'Orcia** Welcome to In Toscana Camere, a charming holiday home located in the historic center of Monticchiello, a Tuscan village full of charm and authenticity. Surrounded by stone walls and enhanced by modern, comfortable interiors, this home offers the perfect balance between tradition and contemporary style. Wake up every morning to a breathtaking view of the stunning Val d'Orcia.

Guest favourite
A well-equipped kitchen area features modern appliances and ample cabinetry. A dining table set for four is positioned near a large window that opens to scenic views. Light-colored walls and natural stone flooring create a bright and inviting space.
Holiday home in Pianella
4.9 out of 5 average rating, 192 reviews

AM Apartment

The apartment is 10 km from the center of Siena in a very relaxing and quiet place in Chianti where you can enjoy a beautiful view, take long walks on foot and by bike or taste good wine in local companies. The house includes two bedrooms, two bathrooms, a living room with fireplace, sofa and smart TV and a large equipped kitchen. In addition, there are sheets, towels, hairdryer and free wifi

Popular amenities for holiday home rentals in Siena

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Avg. price$149 SGD$156 SGD$198 SGD$188 SGD$212 SGD$207 SGD$210 SGD$188 SGD$215 SGD$224 SGD$192 SGD$183 SGD
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