
House vacation rentals in Poggibonsi
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Quick stats about house rentals in Poggibonsi

Total vacation rentals
Explore 10 vacation rentals in Poggibonsi

Nightly prices starting at
Poggibonsi vacation rentals start at G$16,738 GYD per night before taxes and fees

Verified guest reviews
Over 400 verified reviews to help you choose

Wi-Fi availability
10 of Poggibonsi vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Poggibonsi rentals

4.7 Average rating
Poggibonsi stays receive an average rating of 4.7 out of 5 from guests
Top-rated house rentals in Poggibonsi
Guests agree: these houses are highly rated for location, cleanliness, and more.

Domus Nannini - Loggia Salimbeni SPA
Apartment of 200 sqm furnished with precious classical furniture and very spacious rooms: 13 windows overlooking the old town, each window offers a unique view of the city. Big and spacious lounge with peerless view on the begin of Banchi di Sopra, Piazza Salimbeni and the headquarter of the Monte dei Paschi, formed by the noble palaces Tantucci, Salimbeni and Spannocchi. Second lounge with library, sofa-bed and the same exclusive view. 2 large bedrooms with city-views and king-size beds. 3 bathrooms one with jacuzzi and one with shower. A long corridor that crosses the apartment, spacious entrance and private terrace on the internal courtyard. Third lounge with sofa-bed and city-view. Dining room with panoramic views of the Duomo of Siena and Basilica of San Domenico which stand out over the medieval roofs of Siena a few meters from us. Fully equipped kitchen with laundry area. It occupies the entire second floor our 1600's palace and offers unique and privileged views of Siena and its architectural wonders. We are on Banchi sopra Sopra, the main course of the historical center of Siena, below the house you will find the best shops in the center with all the brands of high fashion, lots of restaurants; Wineries, Bars and Supermarkets with typical Tuscan products.
FamilyValueBiking
4.96 out of 5 average rating, 156 reviews
Infinity pool in Chianti 1
Our house is a part of a stone farmhouse completely independent from the rest of the adjacent property. Arranged on three floors, on the ground floor there is a large entrance hall, a large living room with fireplace, a bedroom with 1 double bed and a bathroom with window. On the first floor there are two bedrooms (2 +2 beds) with a bathroom with window. In the basement, at garden level, there is the kitchen and the dining room. From the kitchen you access the outside where you will find an area for outdoor dining with a large dining table under a pergola. You then go down towards the garden with barbecue area.
FamilyValueAccuracy
5.0 out of 5 average rating, 143 reviews
Casa al Gianni - The Simignano Barn
Converted from an old barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large fully equipped kitchen, a spacious living room, 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, including relaxation in the hot tub and outdoor dinners. A memorable getaway awaits you in this slice of paradise!
LocationValueHot tub
4.97 out of 5 average rating, 198 reviews
Relaxation and charm in the Chianti hills
Beautiful stone farmhouse, detached, surrounded by olive trees and the Chianti hills, with private garden and panoramic swimming pool. Ground floor with large living rooms, antique fireplace and wood-burning oven, bright living room and fully equipped kitchen. On the first floor, three suites consisting of a bedroom, study and private bathroom. Access via gate and white road on private property just 500 meters from the village of Strada in Chianti. Ideal for peace and relaxation. Convenient location for visiting Tuscany.
FamilyLocationAccuracy
4.99 out of 5 average rating, 114 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.
ValueFamilyAccess
5.0 out of 5 average rating, 233 reviews
The House in the Alley – Colle di Val d'Elsa
Very central location, house completely renovated in 2023, cozy and quiet, equipped with every comfort. Independent entrance. Located 50 meters from Piazza Arnolfo di Cambio and 300 meters from the historic center (reachable on foot or by elevator), for those traveling by bus the stop is only 100 meters away. Strategic location for visiting Siena, Florence, San Gimignano, Volterra, Chianti Hills and for those who want to travel the Via Francigena or visit the Elsa River Park.
LocationValueDecor
4.99 out of 5 average rating, 135 reviews
The Chianti Classico Sunset
If you are looking for an idyllic location in the heart of Chianti Classico, surrounded by the vineyards and olive groves of the beautiful Tuscan hills, on the estate of a historic 16th-century villa, then come to our barn!! It has a dominant position with a breathtaking view, where you can enjoy stunning sunsets. The total independence of the house, the cozy garden, and the large loggia allow you to spend your stay in total peace of mind. Our reviews are your best guarantee.
FamilyLocationAmenities
4.98 out of 5 average rating, 244 reviews
SuiteLouise.pool, Hot Tub,homeGym & private Garden
SuiteLouise, in the chianti region is the perfect retreat for those seeking design,comfort and authentic tuscan vibes.Relax in the outdoor lounge,enjoy a bbq in the rose garden, or unwind in the private hot tub or home gym. Feel at home embraced by the rolling tuscan hills, whille i help you create tailor-made stays with 10+experiences. Contact me to craft your tuscan escape and create unforgettable memories in this strategic and amazing area between Florence and Siena.
LocationValueView
4.91 out of 5 average rating, 128 reviews
Nada Home
3 comfortable, fully air-conditioned double bedrooms, each with its own private bathroom, in the heart of Chianti, ideally located between Florence, Siena and San Gimignano. A welcoming, well-kept home in the peaceful Tuscan countryside. Fully equipped kitchen with dishwasher, oven and bar area, plus a laundry room with washing machine and dryer. Private garden for your exclusive use with a private hydromassage pool, heated in winter upon request 🌷
LocationValueIndoor spaces
4.87 out of 5 average rating, 217 reviews
Casa Al Poggio in Chianti Shire
Casa al Poggio is a 145 sqm Tuscan country house in the heart of Chianti. The ground floor features a large living area with a kitchen and fireplace. Upstairs are 2 double bedrooms and an open room with a versatile sofa bed (set up as a double or 2 singles). A relaxing bathroom offers a shower, bathtub, and Chianti views. Outside, a terrace in the gravel garden awaits for your evenings. Perfect for experiencing authentic Tuscany!
LocationValueCheck-in
4.96 out of 5 average rating, 330 reviews
Cercis - La Palmierina
The apartment is part of a completely fenced estate of 60 hectares of unspoiled nature: more than 1000 olive trees, countless cypresses and fragrant forests create an idyllic environment for those seeking tranquility and silence. The Palmierina estate is near Castelfalfi (a true jewel of medieval architecture) and close to Florence (50 Km), Siena (50 Km), and Pisa (50 Km). There are two golf courses nearby.
LocationValueLaundry
4.96 out of 5 average rating, 146 reviewsTuscan 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).
ValueFamilyTV
4.9 out of 5 average rating, 292 reviewsPopular amenities for Poggibonsi house rentals
House rentals with a pool

Private Chianti Cottage, Garden & Vineyard Views
FamilyLocationPool
4.99 out of 5 average rating, 137 reviews
Ancient Barn in Chianti with Pool
FamilyValueIndoor spaces
4.89 out of 5 average rating, 125 reviews
Paluffo Torre House
LocationFamilyIndoor spaces
4.89 out of 5 average rating, 81 reviews
Podere Villetta La Colombaia
LocationFamilyCleanliness
4.95 out of 5 average rating, 163 reviews
Leonardo - Chianti/Siena, Florence, San Gimignano.
FamilyValueGrill
4.97 out of 5 average rating, 120 reviews
I Limoni Apartment in Tuscany
LocationValueWifi
4.85 out of 5 average rating, 151 reviews
Lovely house in a scenic and paiceful location
FamilyValueLaundry
4.93 out of 5 average rating, 123 reviews
Palazzo Monaci - Pool in the Crete Senesi
ValueFamilyAccuracy
4.96 out of 5 average rating, 142 reviewsWeekly house rentals

My country home: garden, quiet, sun, towers view!
ValueFamilyAir conditioning
4.95 out of 5 average rating, 252 reviews
Secret Garden Siena
ValueLocationWifi
4.98 out of 5 average rating, 221 reviews
Charming converted Hayloft overlooking the Chianti Hills
ValueFamilyWifi
4.97 out of 5 average rating, 307 reviews
Casa del Giardino
ValueFamilyBathroom
4.95 out of 5 average rating, 512 reviews
The Chianti window
FamilyLocationHeating
4.9 out of 5 average rating, 135 reviewsGorgeous Villa with Postcard Views in Historical Florence
ValueLocationSleep quality
4.98 out of 5 average rating, 168 reviews
Podere Piazza house with panoramic view
LocationValueNearby
4.97 out of 5 average rating, 197 reviews
Casa Palme
FamilyValueAmenities
4.92 out of 5 average rating, 60 reviewsPrivate house rentals

Casa la Scala
FamilyValueAir conditioning
5.0 out of 5 average rating, 28 reviews
The independent Cottage on the Tuscan hills
FamilyLocationView
4.92 out of 5 average rating, 24 reviews
Ulivi House
LocationFamilyIndoor spaces
4.83 out of 5 average rating, 6 reviews
“At Serena and Lorenzo's apartment"
LocationFamilyWifi
4.8 out of 5 average rating, 69 reviews
Private House for 4P – La Capanna Di Azzurra
FamilyLocationAccuracy
4.96 out of 5 average rating, 27 reviews
The cottage in Chianti with a small breakfast
LocationValueKitchen
4.96 out of 5 average rating, 51 reviews
Luxury Villa Jacuzzi: Iconic Vineyard Views
LocationFamilyAmenities
5.0 out of 5 average rating, 16 reviews
Villa Agnese · Pool · Duomo View · Parking
FamilyValueView
5.0 out of 5 average rating, 19 reviewsDestinations to explore
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Piazza del Duomo (Pisa)
- Stazione Santa Maria Novella
- Cala Violina
- Mugello Circuit
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mercato Centrale
- Spiagge Bianche
- Pisa Centrale Railway Station
- Fortezza da Basso
- Gulf of Baratti
- Uffizi Gallery
- Piazza della Repubblica
- Parco delle Cascine
- Piazzale Michelangelo
- Palazzo Vecchio
- Del Chianti
- Piazza della Signoria
- Pitti Palace
- Boboli's Garden





