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

Nightly prices starting at
Certaldo vacation rentals start at G$10,453 GYD per night before taxes and fees

Verified guest reviews
Over 200 verified reviews to help you choose

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

4.8 Average rating
Certaldo stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated house rentals in Certaldo
Guests agree: these houses are highly rated for location, cleanliness, and more.

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.
ValueLocationComfort
5.0 out of 5 average rating, 143 reviews
Historic house in heart of Tuscany
The apartment is located in a ex-benedectine abbay along the famous Via Francigena. Inside, there are some furniture of the XVIII century and orginal frescoes. There are all confort to make pleasant your holiday: three double bedrooms, a kitchen, a bright living room, a bathroom with shower and a small closet. It’s in the middle of the Tuscan hills, a few kilometers from San Gimignano’s towers and from the medieval country of Certaldo Alto. You can easily reach Siena, Florence, Volterra, Monteriggioni and the picturesque countryside of Chianti.
ValueLocationOutdoor spaces
4.91 out of 5 average rating, 163 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!
FamilyLocationAmenities
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.
LocationValueParking
4.99 out of 5 average rating, 115 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.
ValueLocationLong stay
5.0 out of 5 average rating, 233 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.
FamilyLocationLayout
4.98 out of 5 average rating, 244 reviews
Casa Giulia di Sopra Farmhouse
The CASA GIULIA DI SOPRA apartment, renovated in 2022 and located on the first floor, is a portion of an ancient farmhouse located in the heart of Chianti Classico. It is surrounded by the vineyards of Villa Calcinaia, an estate owned by the Capponi Counts since 1524. The apartment is 130 meters away from the shared swimming pool, open from May to October. The apartment has an outdoor area with a table and chairs where guests can dine and enjoy a glass of wine at sunset.
FamilyLocationAccuracy
4.95 out of 5 average rating, 106 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.
ValueLocationCondition
4.91 out of 5 average rating, 128 reviews
I Limoni Apartment in Tuscany
In the Chianti hills between Florence Siena rich in history and evocative natural sceneries, the cradle of civilizations that have left an artistic and cultural heritage of unparalleled value, surrounded by unspoiled nature luxuriant vineyards cultivated as gardens, centuries-old olive groves, imposing cypresses, is the "VillaBassa" farm is located. easily accessible Florence 30 min Pisa 50 min Siena 50 min S.Gimignano 30 min Monteriggioni 45 min
FamilyValueAccuracy
4.85 out of 5 average rating, 151 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 🌷
ValueLocationOutdoor spaces
4.87 out of 5 average rating, 217 reviews
"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.
ValueLocationWalkability
4.99 out of 5 average rating, 320 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.
LocationValueKitchen
4.96 out of 5 average rating, 147 reviewsPopular amenities for Certaldo house rentals
House rentals with a pool

Ancient Barn in Chianti with Pool
ValueFamilyLayout
4.89 out of 5 average rating, 125 reviews
TREEhouse/casaBARTHEL
FamilyValueSleep quality
4.88 out of 5 average rating, 821 reviews
Lovely house in a scenic and paiceful location
FamilyValueCleanliness
4.93 out of 5 average rating, 124 reviews
Open space surrounded by nature
FamilyLocationBackyard
4.96 out of 5 average rating, 137 reviews
Borgo Ripostena – n. 9 Frantoio
FamilyValueWifi
4.94 out of 5 average rating, 118 reviews
Private villa/swimming pool in Tuscany
LocationFamilyBeach
4.93 out of 5 average rating, 164 reviews
Explore Chianti from a Charming Stone House
FamilyLocationHeating
4.98 out of 5 average rating, 123 reviews
Podere Villetta La Colombaia
FamilyLocationDecor
4.95 out of 5 average rating, 163 reviewsWeekly house rentals

Casa Maurino
ValueLocationKitchen
4.97 out of 5 average rating, 134 reviews
Costalmandorlo, a rustic home in the heart of Tuscany
FamilyLocationCleanliness
4.91 out of 5 average rating, 126 reviewsGorgeous Villa with Postcard Views in Historical Florence
FamilyValueBathroom
4.98 out of 5 average rating, 168 reviews
Romantic Garden in Historic San Gimignano
LocationValueBreakfast
4.99 out of 5 average rating, 216 reviews
Charming converted Hayloft overlooking the Chianti Hills
LocationValueDecor
4.97 out of 5 average rating, 308 reviews
Casa per la Costa – Colle di Val d'Elsa
ValueFamilySleep quality
4.96 out of 5 average rating, 292 reviews
Love in Chianti
FamilyValueComfort
4.96 out of 5 average rating, 247 reviews
Domus Nannini - Loggia Salimbeni SPA
ValueFamilyHot tub
4.96 out of 5 average rating, 156 reviewsPrivate house rentals

Peaceful and Relaxing Tuscan Retreat with Views
LocationValueQuiet
5.0 out of 5 average rating, 90 reviews
Casa Al Cantone
FamilyLocationCleanliness
4.88 out of 5 average rating, 17 reviews
Beautiful villa in Chianti, panoramic garden
FamilyLocationView
4.96 out of 5 average rating, 47 reviews
Villa delle Ortensie
FamilyLocationAccess
4.98 out of 5 average rating, 48 reviews
Japandi apartment with a view!
LocationKitchenHospitality
5.0 out of 5 average rating, 29 reviews
Capanna Frui Ruris, San Gimignano
FamilyValuePool
4.94 out of 5 average rating, 78 reviews
Villa Tirinzano for 14 guests with private pool
ValueFamilyCondition
4.93 out of 5 average rating, 42 reviews
Entire home in San Gimignano
BathroomViewHospitality
5.0 out of 5 average rating, 6 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
- Val di Luce
- Pitti Palace





