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Holiday houses in Poggibonsi

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Top-rated holiday rentals in Poggibonsi

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

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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, 306 reviews

Podere Vergianoni nestled in Chianti with a pool

Podere Vergianoni is an ancient and authentic farmhouse dating back to the 17th century located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional local style of old Tuscany: ancient wooden beams, terracotta floors, and unique furniture. In the large outdoor courtyard, you'll find a large swimming pool on a panoramic terrace at your disposal, overlooking the valley with breathtaking views of vineyards and olive groves, where you can enjoy spectacular sunsets.

Top Guest favourite
A charming garden area features a round table surrounded by four wrought iron chairs. Vibrant flowers bloom in planters, and lush greenery adds to the tranquil environment. A rustic stone wall and traditional rooftops provide a picturesque backdrop, enhancing the sense of privacy.
Home in San Gimignano
4.99 out of 5 average rating, 202 reviews

Garden House

"Casa del giardino" ...... a blooming oasis within the medieval walls.. The owners Mario and Donella would like to offer you a unique vacation in San Gimignano. You can enjoy the wonderful garden, an extraordinary oasis of peace and silence, in the city center, for the exclusive use of those who rent the apartment. Thus, reading a book, relaxing in the sun, sipping an excellent glass of Chianti or having breakfast surrounded by greenery and among the flowers of this garden will be a memorable experience!

Superhost
A cozy living area is furnished with a black sofa facing a wooden dining table and four chairs. A green accent wall complements the bed area. Natural light filters through sheer curtains on two windows, while a decorative mirror reflects the vibrant space.
Apartment in Poggibonsi
4.74 out of 5 average rating, 195 reviews

"In the heart of Poggibonsi"

Our small apartment is located in the historic center of the city. In a beautiful square with restaurants serving typical Tuscan cuisine. Within walking distance of the bus and train station, just a 5-minute walk away. Immediately next to a small shopping mall. 10 meters away there is a parking lot with a parking disc system and another free parking lot at the station. Excellent location to quickly and conveniently reach the major attractions, San Gimignano, Siena, Florence, Colle di Val d'Elsa

Top Guest favourite
A bright and inviting bedroom features a spacious bed adorned with decorative pillows and neatly arranged linens. Nightstands with lamps flank either side, providing soft illumination. A floral artwork enhances the wall above the bed, while a wooden door adds a warm touch to the space.
Condo in Poggibonsi
4.94 out of 5 average rating, 122 reviews

Gallery Apartment near Chianti

Confortevole e luminoso appartamento in centro di Poggibonsi a 150 mt dalla Clinica Siena Eye Laser e da tutti i servizi necessari. Ampio Parcheggio pubblico adiacente al palazzo. Posizione strategica per raggiungere le città d'arte come Firenze, Siena, San Gimignano, Volterra, Pisa ed i bellissimi borghi del Chianti. Gallery Apartment è dotato di tutti i confort e saprà accogliervi come a casa vostra. Potrete sedervi ai tavolini nelle 2 terrazze e bere un buon chianti o un caffè al mattino.

Top Guest favourite
A stone structure with a tiled roof is framed by greenery, surrounded by rolling hills. A spacious outdoor area features a wooden table, inviting relaxation. Large trees and thriving shrubs enhance the tranquil setting, with a backdrop of a serene sunset illuminating the landscape.
Home in San Casciano In Val di Pesa
4.98 out of 5 average rating, 220 reviews

The Chianti Classico Sunset

Se cercate una location idilliaca nel cuore del Chianti classico, immersi nei vigneti e oliveti delle splendide colline toscane, nel podere di una Villa storica del ‘500, allora venite nel nostro fienile!! Ha una posizione dominante con una vista strepitosa, dove è possibile godersi tramonti mozzafiato. La totale indipendenza della casa, l'accogliente giardino, il grande loggiato permettono di trascorrere soggiorni in totale tranquillità. Le nostre recensioni sono la vostra migliore garanzia.

Top 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
4.95 out of 5 average rating, 185 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
The rustic exterior of the stone cottage features a traditional red-tiled roof and large arched windows. Lush greenery and flowering plants surround the building, while the rolling hills of Tuscany are visible in the background under a clear sky.
Apartment in Poggibonsi
4.92 out of 5 average rating, 107 reviews

San Martino Cottage with large panoramic terrace

45 sqm apartment in San Martino ai Colli, located along Via Cassia and surrounded by beautiful Tuscan countryside. Perfect for those who want to visit the attractions of the area: San Gimignano, Monteriggioni, Chianti, Siena (20 min.), Florence (30 min.), Volterra (40 min.). 2 minutes from the Florence-Siena highway junction and close to the urban center of Poggibonsi and Barberino-Tavarnelle. The house has a large terrace where you can relax and admire the Chianti hills.

Top Guest favourite
A scenic view captures a lush landscape with rolling hills, vineyards, and olive trees under a colorful sunset. The traditional Tuscan casolare is visible in the background, surrounded by greenery, while the horizon features soft hues of orange and pink.
Apartment in Poggibonsi
4.99 out of 5 average rating, 312 reviews

Laura Chianti Holidays

Laura Chianti Vacanze is the ideal solution for those seeking peace and tranquility immersed in the Chianti countryside. The apartment, halfway between Florence and Siena, is conveniently located for quick access to Florence, Siena, San Gimignano , Volterra, as well as the beautiful Chianti hills. The apartment offers private parking, two bedrooms, a fully equipped kitchen, private bathroom, private garden, barbecue, and a wonderful view of the Chianti hills.

Guest favourite
A stylish bedroom features a modern geometric bed frame adorned with two decorative pillows in complementary colors. Nightstands with yellow lamps flank the bed, while an intricate wall art piece adds a touch of elegance above the headboard. The walls are painted white, creating a bright atmosphere.
Apartment in Poggibonsi
4.87 out of 5 average rating, 191 reviews

Casa Luce Modern Urban Chic Apartment in Tuscany

Enjoy Tuscany in our cozy cute apartment, very conveniently located between Florence and Siena and ideal if you want to explore the countryside. The neighborhood is quiet with free parking outside the building. There is a market store, bar, butcher, beauty salon, and cafes all nearby walking distance. Visit our organic farm and get fresh veggies and fruit! Near Campostaggia Hospital & Siena Eye Laser, ideal for medical visits, weddings & Chianti tastings.

Top Guest favourite
A well-equipped kitchen is presented, featuring wooden cabinets and a modern stove. A dining table with colorful floral patterns is set for two. Large windows allow natural light to fill the space, while a small plant adds a touch of greenery.
Condo in Poggibonsi
4.97 out of 5 average rating, 262 reviews

Casa Amaryllis

Delightful two-room apartment located on the first floor in a central area. It consists of a living area with a sofa, kitchen, and laptop; a bedroom with a very comfortable double bed; a bathroom with a spacious and comfortable shower. Suitable for up to 2 people. Has a large terrace. It is a 10-minute walk to the station. Free parking in front of the house or at most within 200 m. Wi-Fi access available. You can walk to Siena Eye Laser in a few minutes.

Top Guest favourite
A charming stone building surrounded by lush greenery features a wooden terrace with a parasol and flower pots. Two loungers are placed on the well-maintained lawn, providing a relaxing outdoor space.
Farm stay in Greve in Chianti
4.99 out of 5 average rating, 446 reviews

Old hayloft on the Chianti hills

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.

Guest favourite
A spacious living area features exposed stone walls and a rustic fireplace with a television positioned nearby. A light-colored sideboard complements the warm tones of the wooden beams above. A dining table with red chairs is set beside large glass doors that open to a green outdoor space.
Home in Poggibonsi
4.89 out of 5 average rating, 274 reviews

Tuscan Counrtry Detached House. Wi-Fi Free

Update: Air conditioning starting June 1st, 2025. Enjoy the summer with a cool breeze! Do you want to spend your holiday in a typical Tuscan barn? This is your place! Charming renovated barn for families / groups. Located in the heart of the Tuscan countryside at 2km from Poggibonsi. Ideal for a relaxing holiday and in a great location for visiting San Gimignano (13km), Siena (25km), Florence (35km).

Popular amenities for Poggibonsi holiday rentals

When is the best time to visit Poggibonsi?

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Avg. price$132 NZD$130 NZD$142 NZD$152 NZD$154 NZD$157 NZD$161 NZD$159 NZD$161 NZD$156 NZD$151 NZD$157 NZD
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Frequently Asked Questions

  • What types of vacation rentals are available in Poggibonsi?

    Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Poggibonsi. From over 40 apartment rentals to over 10 house rentals, we've got you covered.

  • Are there vacation rentals with a dedicated workspace in Poggibonsi?

    Yes! Work meets play with ease at over 40 vacation rentals in Poggibonsi featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Poggibonsi?

    Four-legged friends are welcome in Poggibonsi. Choose from more than 30 vacation rentals for guests traveling with pets.

  • Are there Poggibonsi vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in Poggibonsi, available on Airbnb. Make a splash and soak up the sun in style!

  • How much does it cost to stay in apartment rentals in Poggibonsi?

    Experience the best of Poggibonsi with our apartment rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do apartment rentals in Poggibonsi have air conditioning?

    Absolutely! We offer over 20 apartment rentals with air conditioning in Poggibonsi. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Poggibonsi have free parking?

    Absolutely! We offer over 20 apartment rentals with free parking in Poggibonsi. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Poggibonsi have a kitchen?

    Absolutely! We offer over 40 apartment rentals with a kitchen in Poggibonsi. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly apartment rentals in Poggibonsi?

    Poggibonsi has more than 10 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do apartment rentals in Poggibonsi have wifi?

    Absolutely! We offer over 40 apartment rentals with wifi in Poggibonsi. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Poggibonsi

  • Total holiday rentals

    Explore 110 holiday rentals in Poggibonsi

  • Nightly prices starting at

    Poggibonsi holiday rentals start at $33 NZD per night before taxes and fees

  • Verified guest reviews

    Over 6,080 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 30 rentals that welcome pets

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    100 of Poggibonsi holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Poggibonsi rentals

  • 4.8 Average rating

    Poggibonsi stays are highly rated by guests—averaging 4.8 out of 5!

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