
House holiday rentals in Castelfiorentino
Find and book unique houses on Airbnb
Top-rated house rentals in Castelfiorentino
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.
ValueFamilyCheck-in
5.0 out of 5 average rating, 143 reviews
Casa al Gianni - The Simignano Barn
Transformed from a former barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living room, and 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 seeking a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, complete with relaxation in the hot tub and al fresco dining. A memorable getaway awaits you in this slice of paradise!
FamilyValueAir conditioning
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.
FamilyLocationBackyard
4.99 out of 5 average rating, 115 reviews
The Chianti Classico Sunset
If you are looking for an idyllic location in the heart of the Chianti Classico region, 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 commanding position with an amazing view, where you can enjoy breathtaking sunsets. The complete privacy of the house, the cozy garden, and the large loggia allow you to enjoy your stay in total tranquility. Our reviews are your best guarantee.
LocationFamilyBarbecue
4.98 out of 5 average rating, 244 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.
FamilyLocationView
5.0 out of 5 average rating, 233 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.
ValueLocationCheck-in
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
ValueLocationWi-Fi
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 🌷
LocationValueLong stay
4.87 out of 5 average rating, 217 reviews
Lovely house in a scenic and paiceful location
This beautiful house is nestled in a quiet and panoramic location, making it the perfect spot to get away from it all. With three bedrooms, three bathrooms, and room for up to six guests, this is the perfect place for a group of friends or a large family to call home while exploring Tuscany. Spend your days hiking the picturesque landscape, wandering through charming villages, or simply relaxing in the lovely gardens of the house.
ValueFamilyEV charging
4.93 out of 5 average rating, 123 reviews
Costalmandorlo, a rustic home in the heart of Tuscany
Costalmandorlo is your peaceful corner in the center of Tuscany. A charming country cottage restored and furnished with care and with a style that combines ancient and modern. Here you can slow down and relax surrounded by the sounds of nature, admiring beautiful sunsets and having long breakfasts in the garden. A short distance between Florence, Siena and Pisa, it is an excellent base for touring Tuscany.
LocationFamilyDecor
4.91 out of 5 average rating, 126 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.
LocationFamilyQuiet
4.96 out of 5 average rating, 146 reviews
Paluffo Tower House
This is the antic tower of the villa and it is built on three levels and features a private garden and a marvellous view of the Chianti hills and San Gimignano. • Ground-floor: living room with a fireplace, bathroom and dining room with kitchen. • First floor: double bedroom with private bathroom and studio with sofa bed. • Second floor: 2 double bedrooms with bathroom.
LocationValueSleep quality
4.89 out of 5 average rating, 81 reviewsPopular amenities for Castelfiorentino house rentals
House rentals with a pool

Ancient Barn in Chianti with Pool
LocationFamilyNearby
4.89 out of 5 average rating, 125 reviews
Country Rentals - La Canonica
LocationValueCheck-in
4.86 out of 5 average rating, 101 reviews
Podere Villetta La Colombaia
LocationValueParking
4.95 out of 5 average rating, 163 reviews
Borgo Ripostena – No. 8 Casa Vecchia
FamilyLocationCheckout
4.95 out of 5 average rating, 201 reviews
TREEhouse / casaBARTHEL
LocationValueSolo travel
4.88 out of 5 average rating, 821 reviews
Charming house in the hills of Lucca, with a sauna
ValueFamilyPets
4.94 out of 5 average rating, 142 reviews
Open space surrounded by nature
ValueLocationRiver
4.96 out of 5 average rating, 137 reviews
A Home in the Florentine Hills | La Nepitella
ValueFamilyGetting around
4.84 out of 5 average rating, 289 reviewsWeekly house rentals

Podere Solatio - Tuscany Hills next to Florence
LocationFamilyBathroom
4.97 out of 5 average rating, 146 reviews
Sunny Beauty
ValueLocationHiking
4.85 out of 5 average rating, 215 reviews
Casa Al Poggio in Chianti Shire
LocationFamilyBarbecue
4.96 out of 5 average rating, 330 reviews
Tuscan Villa 15 min from Florence, Parking, Garden
LocationFamilyHeating
4.97 out of 5 average rating, 142 reviews
Domus Nannini - Loggia Salimbeni SPA
ValueLocationAir conditioning
4.96 out of 5 average rating, 156 reviews
"La limonaia" - Romantic Suite
ValueLocationIndoor spaces
4.99 out of 5 average rating, 320 reviews
Beautiful villa in Chianti with a panoramic garden
FamilyLocationLong stay
4.96 out of 5 average rating, 47 reviews
Peaceful and Relaxing Tuscan Retreat with Views
ValueFamilyBathroom
5.0 out of 5 average rating, 90 reviewsPrivate house rentals

OttoPini Beautiful villa, Montecatini Terme.
FamilyLocationLong stay
5.0 out of 5 average rating, 23 reviews
Pistoia Hill, charming stone farmhouse
FamilyValueBathroom
4.94 out of 5 average rating, 50 reviews
Margherita: Tuscany views, Pool & Walk to Village
FamilyLocationView
4.89 out of 5 average rating, 36 reviews
Charming Tuscan Villa with pool
FamilyLocationKitchen
5.0 out of 5 average rating, 23 reviews
Redolina House in the Hills with pool 6/8p.
LocationFamilyBiking
5.0 out of 5 average rating, 27 reviews
Villino Isotta (exclusive private villa)
FamilyValueAccuracy
4.99 out of 5 average rating, 70 reviews
700' Villa in the heart of Chianti
ValueLocationIndoor spaces
4.7 out of 5 average rating, 33 reviews
Il Palagio
ValueLocationOutdoor spaces
5.0 out of 5 average rating, 38 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
- 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
- Boboli's Garden





