
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 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.

Agriturismo Fattoria La Parita
Appartamento in stile provenzale immerso tra il vigneto e gli olivi. Godrete della tranquillità della campagna a 10 km dalla città e 4 dall'autostrada. Il canto di ghiandaie e cucù faranno da colonna sonora al soggiorno mentre i caprioli brucano tra gli olivi. E' inclusa una colazione base all'italiana (caffè, tè, latte, biscotti ecc.), se invece preferite una colazione più ricca e servita al tavolo il costo è 15€ a persona (10€ da 5 a 15 anni, gratis meno di 5 anni). Disponibile wallbox EV.

Podere Vergianoni immerso nelChianti con piscina
Podere Vergianoni è un antica e storica proprietà risalente al 1600 situato nelle splendide colline del Chianti in Toscana con la possibilità di organizzare servizio navetta e esperienze esclusive su misura per voi . L'appartamento è disponibile per 2 adulti con possibilità aggiunta divano letto per 2 bambini sotto i 12 anni . Nel grande cortile esterno troverete una piscina a sale con area relax su terrazza panoramica con vista su castello colline e vigneti con tramonti unici.

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.

Il Castello di Ferrano - Castle in Tuscany
Try the experience of staying in a real Castle! Il Castello di Ferrano offers to its hosts the chance of living an unforgettable experience: you will be the only guests in the castle, and everything will be for you (private pool from June to September, gardens etc..). Historical building, surrounded by nature, finely decorated, frescoes/moulding on the ceiling, ample terrace w/ stone and terracotta floor, private outdoor pool.. Good position. Preferably come by car.

Old hayloft on the Chianti hills
Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.

Casa Dante - Authentic Chianti Stay | Views&Relax
Wake up to breathtaking views over the rolling hills of Chianti and enjoy a glass of wine at sunset from your private terrace. This peaceful home offers the perfect mix of privacy, comfort, and authentic Tuscan charm. Located just minutes from the center of Radda in Chianti, the house is ideally positioned to explore wineries, charming villages, and the surrounding countryside—while still feeling quiet.

Chianti La Pruneta, Raffaello Apartment
Stunning apartment in the heart of Tuscany set in the middle of vines and olives trees. The apartment has been totally refurbished keeping the lovely old features, beamed ceilings, marble floors with antique furniture. Patio doors lead to a private terrace with sun loungers for relaxing and space. With table and chairs you can eat 'Al fresco' enjoying the beautiful views.

A Big Dream in a Little Tower.
The Tower was created in the late 1800s by an illustrious Englishman, Sir John Temple Leader, in one of the oldest and most important stone quarries belonging to the Medici family. From the same quarry were extracted many important works such as the columns of the Medici chapels, the steps of the Laurenziana library .. all just 5 km from the historic center of Florence.

Il Nido - un romantico focolare
Lui non esisteva, è stato ricavato in un angolo della grande casa in cui chissà quante persone della stessa famiglia vivevano. Per questo è diventato il nostro piccolo Nido, la casa da cui partire per scoprire il borgo. Non un piano ma addirittura due, con tanto cotto, legno e colori caldi.

Casa Pieralli nel Chianti Storico
Piccolo ma accogliente bilocale nel cuore di Gaiole in Chianti. Zona assolutamente silenziosa e tranquilla nel centro storico con parcheggio vicino e gratuito. Puo ospitare comodamente 2 persone,disponibile una cucina attrezzata biancheria sapone e shampoo.

Villa Le Miccine w/ Pool - Bello Fresco Unit for 2
Beautiful charming 1 bedroom ground floor apartment in the Le Miccine villa. Surrounded by vines and nature. Ideal location for visiting Tuscany or relaxing by the pool. Wine tasting on site and helpful staff. We are classified as a 4 Sunflower Agriturismo.
Popular amenities for Gaiole in Chianti vacation rentals
Other great vacation rentals in Gaiole in Chianti

AnticaVista, Luxury Apartment with Tower Views

Hidden gem in Tuscany

Old Chianti chapel-style cottage

Sestuccina

Apartment Comfort | Quiet Escape in Tuscany

Happy Stay in a Tuscany Home with Stunning Views

Villa le Scope 5*

Cipressini 2 - piscina e vista mozzafiato
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
- Cathedral of Santa Maria del Fiore
- Lake Trasimeno
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Mugello Circuit
- Mercato Centrale
- Stazione Santa Maria Novella
- Uffizi Gallery
- Fortezza da Basso
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Piazza della Repubblica
- Parco delle Cascine
- Piazzale Michelangelo
- Del Chianti
- Pitti Palace
- Boboli's Garden
- Palazzo Vecchio
- Piazza della Signoria
- Medici Chapel
- Basilica of Santa Croce
- Stadio Artemio Franchi
- Avignonesi Winery Fattoria Le Capezzine





