
House holiday rentals in Poggibonsi
Find and book unique houses on Airbnb
Top-rated house rentals in Poggibonsi
Guests agree: These houses are highly rated for location, cleanliness and more.

Casa al Gianni - The Simignano Barn
Transformed from an old barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, large equipped kitchen, large living room and a large private garden with parking, hot tub, patio with sofas, BBQ, fire pit and 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, between relaxation in the hot tub and outdoor dinners. A memorable getaway awaits you in this slice of paradise!

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!

Palazzo Monaci - Pool in the Crete Senesi
Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

Old Farmhouse near Panzano Castle Abbacìo
The Abbacio apartment is part of an old farmhouse that has been restored respecting the original structure and style. Its location is just on the top of the hill, facing the valley. Surronded by vineyards and olive trees, but also attached to the village. From the house you can easily reach by feet wineries, farms and restaurants. Panzano is halfway between Florence and Siena, easily reached with car. By bus there is a good service from and to Florence, not from and to Siena. A very quiet spot!

House for the Coast
In the center, a completely renovated, cozy and quiet historic house from the 1300s, equipped with every comfort. Independent entrance, kitchen, living room and bathroom and upstairs double bedroom and bathroom. Located 100 meters from Piazza Arnolfo and 200 meters from the historic center, for those traveling by bus the stop is just 200 meters away. Convenient location for visiting Siena, Florence, San Gimignano, Volterra, Chianti and for walking the Via Francigena or taking the Elsa Trail.

House with a breathless view in Tuscany
Halfway between Pisa and Florence this house comes with a large panoramic terrace, equipped with sunchairs and a large table for outdoor dining. Below, an hanging garden on the property overlooks one of the most striking views in Tuscany. The location is strategic, in the beating heart of an ancient medieval village, now home to an open-air contemporary art museum. Peccioli is a great starting point for those who want to visit the art cities of Tuscany, or immerse yourself in local life,

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.

The Chianti Classico Sunset
If you are looking for an idyllic location in the heart of the classic Chianti, immersed in the vineyards and olive groves of the beautiful Tuscan hills, in the farm of a historic Villa of the ‘500, then come to our barn!! It has a dominating position with a stunning view, where you can enjoy breathtaking sunsets. The total independence of the house, the cozy garden, the large loggia allow you to spend stays in complete peace of mind. Our reviews are your best guarantee.

Infinity pool in Chianti area
On the Chianti hills, portion of an old stone farmhouse from the 1800s, located in S. Filippo, a small hamlet of Barberino Tavarnelle, halfway between Florence and Siena, a 30-minute drive from Florence airport, 1 hour from Pisa airport. Three bedrooms, two bathrooms, large living room with fireplace, eat-in kitchen and dining room. Magnificent view of the hills from every window! Beautiful infinity pool with whirlpool area, unheated and open from April to October.

"La limonaia" - Romantic Suite
Romantic Suite immersed in the enchanting hills of Fiesole. It is the ideal place fot those looking for unique and exclusive experience of its kind characterized by suggestive views and unforgettable sunsets. The accommodation is part of an old 19th century Tuscan farmhouse surrounded by its own olive groves and woods. This is an ideal place for a relaxing holiday and privileged base for visiting the major centers of interest in Tuscany.
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).

Casa Al Poggio & Chianti view
Casa al Poggio is a typical country house of Chianti area is spread in 145 square meters on two floors, the ground floor is a large living area, with kitchen and sofa ,fireplace ,up stairs there is 2 large double bedrooms and a sofa bed in the middle open room , always setable as 2 singles or a double bed bed and a relaxing bathroom with shower and bath with Chianti view.
Popular amenities for Poggibonsi house rentals
House rentals with a pool

Ancient Barn in Chianti with Pool

Casa Bada - Barn

House “il colle”.nice house surrounded by vineyard

Private villa/swimming pool in Tuscany

Explore Chianti from a Charming Stone House

Antico Borgo Ripostena – n. 8 Old House

Casa di Lyndall - Entire house with exclusive pool

Leonardo - Chianti/Siena, Firenze, San Gimignano.
Weekly house rentals

Torretta Apartment

Villa in the Hills - San Martino *Chianti*

Casa La Selva

beautiful farmhouse in the Chianti region with panoramic garden

Enjoy Fantastic Tuscany in Our Country House

House in Tuscany: San Gimignano view

casa palme

Agriturismo Podere San Martino (apartment for two)
Private house rentals

Montecatini Alto Art View

House "Il Campanile"

SuiteLouise.pool, Hot Tub,homeGym & private Garden

Podere le Fonti - Casolare 15 min San Gimignano

Chianti House Stunning view 20 min. from Florence

La Cipressina Relax in Tuscany

La Capanna: country house with magnificent view

Boutique house with pool reserved for 2 guests
Quick stats about house rentals in Poggibonsi

Total holiday rentals
Explore 10 holiday rentals in Poggibonsi

Nightly prices starting at
Poggibonsi holiday rentals start at $142 NZD per night before taxes and fees

Verified guest reviews
Over 310 verified reviews to help you choose

Wi-Fi availability
10 of Poggibonsi holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Poggibonsi rentals

4.6 Average rating
Poggibonsi stays receive an average rating of 4.6 out of 5 from guests
Destinations to explore
- Rentals with a washing machine and dryer Poggibonsi
- Rentals with pools Poggibonsi
- Condo rentals Poggibonsi
- Pet-friendly rentals Poggibonsi
- Rentals with outdoor seating Poggibonsi
- Villa rentals Poggibonsi
- Rentals with a patio Poggibonsi
- Family-friendly rentals Poggibonsi
- Apartment rentals Poggibonsi
- House rentals Siena
- House rentals Tuscany
- House rentals Italy
- Santa Maria Novella
- Piazzale Michelangelo
- Duomo di Firenze
- Basilica of Santa Maria Novella
- Ponte Vecchio
- Cala Violina
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mercato Centrale
- Piazza del Duomo (Pisa)
- Uffizi Gallery
- Gulf of Baratti
- Fortezza da Basso
- Piazza della Repubblica
- Pitti Palace
- Parco delle Cascine
- Spiaggia Libera
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- The Boboli Gardens
- Spiagge bianche
- Avignonesi Winery Fattoria Le Capezzine
- Medici Chapels
- Mugello Circuit
- Spiaggia Marina di Cecina
- Palazzo Vecchio




