
Vacation rentals in Gaiole in Chianti
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Quick stats about vacation rentals in Gaiole in Chianti

Total vacation rentals
Explore 30 vacation rentals in Gaiole in Chianti

Nightly prices starting at
Gaiole in Chianti vacation rentals start at ﺩ.ﺇ 220 per night before taxes and fees

Verified guest reviews
Over 740 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Vacation rentals with a pool
10 properties feature pools

Wi-Fi availability
30 of Gaiole in Chianti vacation rentals include wi-fi access

Popular amenities for guests
Guests love Gym, BBQ grill, and Laptop-friendly workspace across Gaiole in Chianti rentals

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

Villa Eroica
On the ground floor, a private entrance welcomes guests, leading to a fully equipped kitchen, a bathroom, and an elegantly furnished living/dining room. The spacious spaces and exposed beams create a warm and welcoming atmosphere. Upstairs, the master bedroom boasts high wooden ceilings and a private terrace with a solarium equipped with a table, loungers, and an outdoor hot-water shower. The second bedroom, with a double and single bed, is perfect for families or groups of friends and includes a study corner. Enjoy a spacious apartment spread over two floors, ideal for a comfortable and relaxing stay. You'll have a large furnished porch at your disposal, perfect for spending pleasant moments outdoors. The loggia, with its comfortable sofa, and the large garden offer an oasis of tranquility. Among the common areas, you can relax by the large 14 x 7 meter swimming pool, equipped with a convenient access staircase suitable for both adults and children. The pool is surrounded by a manicured lawn and a paved solarium perfect for sunbathing. Upstairs, an exclusive panoramic terrace with hot and cold shower awaits you, the perfect spot for tanning during the day or enjoying evening moments under a starry sky. You'll fall in love with this home, whose character will allow you to experience Tuscan style.
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Casa Faraona, villa con piscina privata
Imagine the perfect Chianti villa – a secluded house with private pool and fabulous 180-degree views. That’s just what you’ll experience at Casa Faraona. Set down a lane a few meters away from the "Eroica" road and between the wine towns of Radda and Gaiole, this three-bedroom villa is bound to take your breath away at first sight. Typical Tuscan features include terracotta tiles on the floors and beamed ceilings, while soft pastels and stylish furnishings give a light and modern aspect.
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Charming estate with views. A/C in the bedrooms
The estate finely restored in 2016 is accessorized with all the confort you need for an holiday dedicated to the relax or to excursions The Breathtaking view on the Chianti Classico's vineyards give to the estate a unique feature perfect for a romantic holiday, small group of friend or a little family. The estate is provided of external Jacuzzi, private garden and we can arrange for you bike or hike excursions. The Village of Gaiole in Chianti is just 5 minutes away by car.
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Casa Martini nel Chianti Storico
Appartamento con giardino e parcheggio privato a Gaiole in Chianti, a due passi dal centro storico dove troverete numerosi bar ristoranti ed il piccolo supermercato ( coop). l'alloggio è ideale per vacanze con animali perché è dotato di un giardino tutto recintato. Viene richiesta la tassa di soggiorno ( 2 euro a persona a notte per le prime sette notti) minori di 14 anni esclusi ( leggi regolamento completo nel sito internet del Comune di Gaiole in Chianti)
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Sestuccina
Sestuccia Cantina is romantic cottage with two double bedrooms and sofa bed in the living room. The villa is located a few kilometers from Gaiole in Chianti and is surrounded by vineyards, with incredible views of Orchard Castle, The villa is completely built in stone with a beautiful shaded terrace. Guests have access to a relaxing bar area with heated Jacuzzi for 6 persons. Inside the park there is a Chicken Coop with fresh eggs every morning and organic garden.
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Tuscany jem: La Casa del Fattore del Chianti
Questo meraviglioso appartamento appena ristrutturato conserva il fascino dei casolari del Chianti e le comodità di un appartamento moderno. La casa è situata all'interno del complesso della Fattoria di Petroio, azienda vitivinicola del Chianti Classico. Potrete godere della bellezza e della tranquillità delle colline del Chianti, mentre vi immergete nella vita dinamica di un'azienda dedita alla produzione di vini di qualità.
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Villa il Balocco
Antica villa padronale ristrutturata con accesso dalla piazzetta del borgo e immersa nel verde delle colline del Chianti storico nella parte posteriore con ampio giardino e grande terrazza panoramica con piscina e due berso'. Il panorama è magnifico e spazia dai monti del Chianti a Brolio e la Val d'Orcia fino all'Amiata. Facilmente raggiungibile dall'uscita Valdarno della A1 è ideale per famiglie e coppie di amici.
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Casanova di Bricciano
Set on the grounds of a family-run organic winery, this stone-built villa offers a harmonious blend of Tuscan charm and modern comfort. Positioned above a tiny hamlet in the rolling Chianti hills, it enjoys panoramic views over vineyards, olive groves and forested slopes. With a spacious interior and generous outdoor areas, the villa is ideal for a memorable stay with family or friends.
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PIERFANTINI private Chianti house ♿️ 🏊♂️ 🐶
Pierfantini is a rustic farmhouse. It is located on a hill in the middle of a natural park. Isolated from the vitta, the nearest town is the medieval village of San Gusmè. The house is renovated and the ground floor adapted for disabled people or wheelchair users There are three apartments but I never rent them separately. The house rent is for all the property
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Montemarcoli
Immergiti in questo spazio unico nato su una splendida collina a Gaiole in Chianti, una nuovissima villa con piscina situata in un bosco lussureggiante offre un rifugio privato di lusso, stile e amore da cui poter ammirare alba e tramonto. Un progetto realizzato con le ultime tendenze architettoniche, eco sostenibile e con acqua di sorgente naturale.
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Villa le Scope 5*
Villa le scope si trova nel cuore del Chianti, in mezzo alla natura e alla tranquillità, pur essendo a pochi passi dal paese. Potrai degustare un ottimo vino Chianti Classico, sulla bellissima terrazza o in totale relax nel nostro grande giardino. La villa le Scope dista un ora circa da Firenze e mezz'ora da Siena.
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La Pieve - the house next to the church
To the right of the Argenina church, after which it is named, it has the persuasive look of its 2 small arches facing west. Perhaps it was once the parish priest's house, or the one where cooking was done in the large wood-burning oven, who knows?
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Popular amenities for Gaiole in Chianti vacation rentals
Other great vacation rentals in Gaiole in Chianti

La Capannina del Chianti
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XIII Century Tower with Private Panoramic Pool
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Apartment Comfort | Quiet Escape in Tuscany
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Villa Le Miccine w/ Pool - Bella Vista Unit for 4
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Appartam. 8-9p in villa con piscina
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Wonderful country house
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Cottage indipendente immerso nella natura
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Old Chianti chapel-style cottage
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Frequently Asked Questions
Are there pet-friendly vacation rentals in Gaiole in Chianti?
Four-legged friends are welcome in Gaiole in Chianti. Choose from more than 20 vacation rentals for guests traveling with pets.
Are there Gaiole in Chianti vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Gaiole in Chianti, available on Airbnb. Make a splash and soak up the sun in style!
Are there family-friendly vacation rentals in Gaiole in Chianti?
Gaiole in Chianti has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in apartment rentals in Gaiole in Chianti?
Experience the best of Gaiole in Chianti with our apartment rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do apartment rentals in Gaiole in Chianti have air conditioning?
Absolutely! We offer over 10 apartment rentals with air conditioning in Gaiole in Chianti. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Gaiole in Chianti have wifi?
Absolutely! We offer over 10 apartment rentals with wifi in Gaiole in Chianti. Enjoy a tailored experience with all the comforts you desire.
Destinations to explore
- Lake Trasimeno
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Stazione Santa Maria Novella
- Mugello Circuit
- Mercato Centrale
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Fortezza da Basso
- Uffizi Gallery
- Piazza della Repubblica
- Parco delle Cascine
- Piazzale Michelangelo
- Del Chianti
- Palazzo Vecchio
- Piazza della Signoria
- Pitti Palace
- Boboli's Garden
- Mount Amiata
- Stadio Artemio Franchi
- Basilica of Santa Croce
- Medici Chapel





