Holiday houses in Staggia

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Staggia

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

1 of 1 pages1 / 1

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

Casa al Gianni - The Simignano Barn

Transformed from a historic barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living area, 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 looking for a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, with relaxation in the hot tub and outdoor dinners. A memorable getaway awaits you in this little slice of paradise!

LocationValueCheckout

4.97 out of 5 average rating, 194 reviews

Top Guest favourite

Apartment in Staggia

Cozy Apt near Siena, Chianti WiFi A/C Free Parking

Beautiful, newly renovated apartment in the heart of Tuscany, in Staggia, with new furnishings and all the essential amenities. Perfect for couples looking for a cosy, modern and practical option. Strategic location: just a few minutes from Siena and San Gimignano, and in the heart of the Chianti region. It is also a convenient base for visiting the Val d'Orcia (Montalcino, Pienza and Montepulciano) and for getting to Florence in about 45 minutes. Free parking just a short walk from the apartment (about a 3-minute walk).

LocationConditionHospitality

4.96 out of 5 average rating, 26 reviews

Top Guest favourite

Barn in Rigoni

Il Fienile del Borgo – Monteriggioni

This delightful, finely renovated barn combines modernity and Tuscan tradition. It is located in the countryside near Monteriggioni, a short distance from Siena, San Gimignano and Colle Val d'Elsa. The house is an oasis of peace and tranquillity: it has a large private garden with a swimming pool for exclusive use, a barbecue for outdoor dinners under the porch; inside there is a spacious living room with a fully equipped kitchen, a master bedroom, a bathroom and a mezzanine with two single beds and a queen-size bed.

ValueLocationIndoor spaces

4.96 out of 5 average rating, 26 reviews

Top Guest favourite

A private terrace is seen overlooking picturesque Tuscan hills, featuring a tablecloth adorned with decorative patterns. A bottle of wine and several glasses are set on the table, presenting an inviting space for relaxation amidst scenic views.

Apartment in Poggibonsi

Apartment in the heart of Chianti

Charming apartment in a country village less than 20 Km from Siena, 15 from San Gimignano and 45 from Florence. It is located in a XVIII century house in the small village of Lecchi, on the top of a hill in the heart of Elsa valley, surrounded by vineyards, olive trees and oak woods. The apartment is 150 sq. m wide, with a 50 sq.m private terrace that can be used to eat outside, enjoying one of the most beautiful landscapes in Tuscany. It can accommodate up to 6 people in a very comfortable wa

LocationValueNearby

4.92 out of 5 average rating, 156 reviews

Guest favourite

An aerial view of the historic Monteriggioni Castle showcases its medieval architecture surrounded by lush countryside. The fortified walls encircle the village, which is dotted with trees and buildings, while rolling hills extend into the distance under a sunset sky.

Cottage in Monteriggioni

Monteriggioni Castello, holiday house in Tuscany

Our accommodation is a historic building that dates back to the construction of the castle. It has been recently restored and furnished with attention to every detail. It is very welcoming and has all the most modern amenities. Tourists who decide to be our guests will have the advantage of living in the medieval environment of the castle, taking advantage of all the conveniences. They will feel pampered and have the opportunity to return home having lived a unique and unforgettable experience.

FamilyLocationBathroom

4.95 out of 5 average rating, 295 reviews

Guest favourite

An aerial view captures a charming Tuscan farmhouse nestled within lush green vineyards and rolling hills. The property features a rustic stone exterior and a terracotta roof, complemented by surrounding greenery and a clear blue sky.

Holiday home in Poggibonsi

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.

FamilyLocationLong stay

4.94 out of 5 average rating, 205 reviews

Guest favourite

Villa in Monteriggioni

Villa of the 2 Olive Trees (Abbadia Isola)

FULLY AIR CONDITIONED, modern 6BR/4BA VILLA on Via Francigena: an enchanted paradise for friends & families with kids (trampoline, basketball area, soccer & volley/beach tennis nets, fossball, table tennis) & w. pets (fenced garden). Located in the small village Abbadia Isola in the shadow of the medieval castle of Monteriggioni, right on the path the ancient road & pilgrim route running from France to Rome (via Francigena) A.k.A FAMILY GROUPS KIDS FRIENDS dream VILLA Siena 12mn (ABB)

LocationFamilyTV

4.97 out of 5 average rating, 174 reviews

Top Guest favourite

The stone house features a welcoming entrance with large arched windows. A vibrant flower box filled with geraniums complements the lush green lawn. A shaded area with wooden seating offers a place to relax, while the infinity pool and surrounding vineyards are visible in the background.

Cottage in Barberino Tavarnelle

Stone House with Exclusive Pool Codilungo in Chianti

Welcome to your Tuscan dream between Florence & Siena. Perfect for families or romantic getaways. • 360° views of iconic Chianti hills. •Huge Exclusive Infinity Pool (17x9m), lit at night (open from May 1st to October 15th) • Total privacy, yet restaurants/shops are 10-15 mins away. • Comfort for 6: 3 bedrooms (2 double, 1 twin) & 3 full baths. • Modern amenities: Fully equipped kitchen area, Smart TV. • Outdoor bliss: Large dining loggia, professional BBQ, poolside porch & bath.

FamilyValueCheckout

4.98 out of 5 average rating, 216 reviews

Guest favourite

Apartment in Staggia

The Optimist's House

Small, fully renovated studio apartment located in the heart of Tuscany, near the Via Francigena: 15 km from Siena, 40 km from Florence, 10 km from San Gimignano and 5 km from Monteriggioni. We are on the 1st floor of a historic building. In our apartment you will find every comfort. A complete kitchen: induction cooktop, microwave oven, toaster, coffee machine, kettle, dishes, washing machine. Bed linen and towels, hairdryer, shampoo are provided. Free public parking nearby.

FamilyLocationAccuracy

4.9 out of 5 average rating, 70 reviews

Top Guest favourite

A living area is seen with a light-colored sofa facing a flat-screen TV on a wooden unit. A glass coffee table is positioned in front of the sofa, and natural light filters through sheer curtains. A black chair and decorative items are present on shelves.

Condo in Castellina Scalo

Above the Post Office

Apartment located in a village in the municipality of Monteriggioni, on the borders of Chianti. The village is located along the ancient Via Francigena. It is about 10 minutes from Siena, Poggibonsi, and Colle di val d'Elsa. It is about 20 minutes from San Gimignano, 40 minutes from Florence, 60 from Pisa and Arezzo. It is possible to move from the village by bus, train, car, bicycle. It is also possible to reach Monteriggioni via a cycle path (20 minutes on foot).

LocationValueCondition

4.98 out of 5 average rating, 125 reviews

Top Guest favourite

A large swimming pool surrounded by a brick patio and manicured lawns is highlighted in this image. Sun loungers are positioned along the pool's edge, with lush greenery and trees creating a serene backdrop. The villa's charming structure is visible in the distance under a partly cloudy sky.

Villa in Barberino Tavarnelle

Podere Tignano, 4-bedroom villa in the Chianti!

Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.

ValueFamilyBreakfast

4.98 out of 5 average rating, 105 reviews

Top Guest favourite

Condo in Colle di Val d'Elsa

Florence & Siena • Terrace • Private Parking • A/C

Imagine waking up to sunlight filling the apartment and enjoying breakfast overlooking the Tuscan hills. Bright top-floor apartment with elevator, panoramic terrace and 180° open views, between Florence and Siena, in a quiet private area with no through traffic. Perfect for families, with parking, air conditioning, fast Wi-Fi, fully equipped kitchen and all the comforts to explore Tuscany’s villages, wineries, art cities and iconic landscapes.

ValueLocationKitchen

5.0 out of 5 average rating, 27 reviews