
Cottage holiday rentals in San Gimignano
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Quick stats about cottage rentals in San Gimignano

Nightly prices starting at
San Gimignano holiday rentals start at $140 NZD per night before taxes and fees

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Over 1,200 verified reviews to help you choose

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

4.9 Average rating
San Gimignano stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated cottage rentals in San Gimignano
Guests agree: These cottages are highly rated for location, cleanliness and more.

Casa del Sole in Chianti
Typical Tuscan country house in stone with fireplace, large garden, with parking. In the garden, there is a barbecue and wood-burning oven for pizza. The house is nestled among the vineyards and olive groves of Chianti Classico in a small country village. It is 4 km from San Casciano Val di Pesa, 20 km from Florence, 22 km from San Gimignano and 40 km from Siena. A1 Impruneta highway exit 8 km, SGC Fi-Siena 3 km. The house has three bedrooms, one of which is in the annex with bathroom and independent access.
LocationFamilyBackyard
4.92 out of 5 average rating, 143 reviews
Cappero Cottage - Masseto In Chianti
MASSETO IN CHIANTI is a private village where you can relax in your private garden and in the pool, play sports, or use it as a base to visit Renaissance cities: Florence, Siena, San Gimignano, Arezzo, Volterra. We offer three other cottages with independent access and a private garden: Quinto (2 beds), Vittoria (4 beds), and Leccio (6 beds). The swimming pool is shared by the 4 cottages, each with a private gazebo, with guaranteed distancing and sanitization in accordance with Covid-19 regulations.
LocationValuePool
4.97 out of 5 average rating, 115 reviews
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.
LocationValueSleep quality
4.95 out of 5 average rating, 297 reviews
Villa di Geggiano – Guesthouse
PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.
ValueFamilyBackyard
4.99 out of 5 average rating, 155 reviews
FAETOLE typical Tuscan country house near FLORENCE
My cottage is hidden in Tuscan countryside among olive groves, vineyards and woodland. Nevertheless, downtown Florence is only 16km away! While away, spend your time by relaxing in the garden, where you will find a barbecue and an outdoor shower to cool down while sunbathing. Discover the beauty of surrounding countryside with a hike and unwind with a view of picture-perfect vineyards! One can also easily go for day trips to many tiny medieval towns scattered on the hills of Tuscany from here!
LocationFamilySleep quality
4.92 out of 5 average rating, 160 reviews
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.
ValueLocationBreakfast
4.98 out of 5 average rating, 218 reviews
Country cottage C&M surrounded by greenery, love Tuscany
Country stone cottage, independent in the Tuscan countryside in the province of Siena, with large garden, porch and gazebo. Our house is located in the countryside of the municipality of Chiusdino, just 5 minutes from the two main towns of Monticiano and Chiusdino and 10 minutes from the beautiful Abbey of Galgano. 30 minutes from Siena, from Monteriggioni, an hour from Florence and 30/40 minutes from the sea. Just 20 minutes from the beautiful Terme del Petriolo.
ValueFamilyParks
4.94 out of 5 average rating, 203 reviews
Il Fienile, Cottage in the country with Jacuzzi
Surrounded by wineyards, close to Florence, a charming accomodation in a cozy cottage with heated jacuzzi at your exclusive use. Perfect starting point to discover Florence and Siena. Kitchen, wide living room, bathroom, two double bedroom (one with an extra single bed). In the living room a sofa bed for other 2 people. Tasteful furniture, Air Conditioning, barbecue, private parking. Partnership for: bike rental, private chef, private driver
FamilyValueCheck-in
4.96 out of 5 average rating, 198 reviews
Lovely apartment with garden and views near Siena
At just 18km from Siena, the apartment is part of a traditional Tuscan farmhouse, Santa Barbara, tucked away in the scenic rolling hills of Tuscany. The uniquely positioned grounds dominate the valley, allowing for stunning views with the most enchanting sunsets, or sunrises for those early birds! The apartment allows for a relaxing and recharging break, as well as being in the perfect location to go out and explore.
ValueFamilyAccess
4.9 out of 5 average rating, 162 reviews
Countryside Cottage With View - Le Papere apt
The cottage is part of a charming traditional Tuscan farmhouse, built in stone and situated in one of the most beautiful areas of Tuscany. A lovely garden surrounds the house and has magnificent views of the medieval town with its famous towers. Warm and cozy atmosphere that makes you feel instantly at home. For those who wish to live the experience of the Tuscan countryside as it is lived by the locals.
FamilyLocationParking
4.88 out of 5 average rating, 139 reviews
Peaceful modern eco house in the Tuscan hills
A private low-impact ecohouse set in a lush garden surrounded by olive trees, flowers and open Tuscan countryside between Florence and Siena. Designed for peace, light and simplicity, this independent home offers complete privacy within a small family-run olive farm. Enjoy a spacious private patio, open views, spectacular sunsets and access to a panoramic swimming pool in a stunning natural setting.
FamilyValueComfort
4.88 out of 5 average rating, 161 reviews
Podere Grignano, beautiful Tuscany.
If the calendar indicates no availability, please check our other advert through the Airbnb map (Podere Grignano, beautiful Tuscany without a dot at the end). The other house can still be free. The houses are semidetached, The 2 houses are practically identical. The reviews are of both houses.
LocationValueCondition
4.94 out of 5 average rating, 108 reviewsPopular amenities for San Gimignano cottage rentals
Cottage rentals with a hot tub

From Simone, podere santi Lucia and Pietro
FamilyValueBeach
4.94 out of 5 average rating, 242 reviews
Romantic House in Tuscany with jacuzzi
FamilyLocationHiking
4.96 out of 5 average rating, 85 reviews
Cottage in the countryside with private jacuzzi and swimming pool
FamilyValueCleanliness
4.88 out of 5 average rating, 81 reviews
Tuscan country house with pool+garden by Vacavilla

Detached Cottage with Private Spa
LocationPetsAccuracy
4.94 out of 5 average rating, 16 reviews
Private house with private pool | pet friendly
LocationFamilyAmenities
4.76 out of 5 average rating, 34 reviews
Vintage Cottage in Pescia – Cleaning fee Inc
LocationViewCleanliness
4.67 out of 5 average rating, 3 reviews
Cottage in Pescia with Pool and Garden
LocationFamilyCondition
4.5 out of 5 average rating, 24 reviewsPet-friendly cottage rentals

Chianti Barn with Pool and Vineyard View
LocationValueAir conditioning
4.79 out of 5 average rating, 290 reviews
Countryside, 10 min from Siena
FamilyLocationCondition
4.84 out of 5 average rating, 289 reviews
The Five Oaks Cottage
ValueLocationQuiet
4.83 out of 5 average rating, 175 reviews
Small Cottage in San Gimignano
ValueLocationComfort
4.95 out of 5 average rating, 174 reviews
Casa Valentino, a few km from San Gimignano
FamilyLocationKitchen
4.92 out of 5 average rating, 37 reviews
Villetta Belvedere
LocationFamilyAmenities
4.91 out of 5 average rating, 88 reviews
Private Country House with swimming pool -Chianti
LocationFamilyQuiet
4.95 out of 5 average rating, 57 reviews
The Cottage Florence
FamilyLocationComfort
4.92 out of 5 average rating, 76 reviewsPrivate cottage rentals

Chiantihouse with garden
LocationFamilySleep quality
4.88 out of 5 average rating, 169 reviews
FARMERShouse/casaBARTHEL 15' from the City Center
FamilyValueTV
4.83 out of 5 average rating, 174 reviews
LIKE AT HOME! FAMILY COUNTRY HOUSE!
ValueFamilyWi-Fi
4.96 out of 5 average rating, 114 reviews
Casa Roberta: a beautiful view of the Crete!
FamilyLocationBeach
4.83 out of 5 average rating, 161 reviews
Historic Mill in the Countryside -Chianti Classico
LocationValueBarbecue
4.83 out of 5 average rating, 132 reviews
Cozy villa in Tuscany countryside
FamilyValueWi-Fi
4.83 out of 5 average rating, 112 reviews
Lovely cottage in the park of a Renaissance Villa
LocationFamilyQuiet
4.81 out of 5 average rating, 243 reviews
Stone cottage + private garden near San Gimignano
FamilyLocationGetting around
4.9 out of 5 average rating, 21 reviewsDestinations to explore
- Rentals with a hot tub San Gimignano
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- Cottage rentals Siena
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- Cottage rentals Italy
- 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
- Things to do San Gimignano
- Tastings San Gimignano
- Cooking San Gimignano
- Outdoors San Gimignano
- Food tours San Gimignano
- Things to do Siena
- Tastings Siena
- Museums Siena
- Food tours Siena
- Cultural tours Siena
- Art workshops Siena
- Outdoors Siena
- Dining Siena
- Landmarks Siena
- Wildlife Siena
- Cooking Siena
- Things to do Tuscany
- Water sports Tuscany
- Flying Tuscany
- Cooking Tuscany
- Wildlife Tuscany
- Landmarks Tuscany
- Tastings Tuscany
- Galleries Tuscany
- Outdoors Tuscany
- Museums Tuscany
- Workouts Tuscany
- Art workshops Tuscany
- Food tours Tuscany
- Shopping and fashion Tuscany
- Dining Tuscany
- Performances Tuscany
- Cultural tours Tuscany
- Things to do Italy
- Workouts Italy
- Shopping and fashion Italy
- Cooking Italy
- Cultural tours Italy
- Flying Italy
- Tastings Italy
- Wildlife Italy
- Food tours Italy
- Museums Italy
- Performances Italy
- Wellness Italy
- Art workshops Italy
- Dining Italy
- Galleries Italy
- Landmarks Italy
- Architecture Italy
- Outdoors Italy
- Water sports Italy







