
Holiday houses in Gaiole in Chianti
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Top-rated holiday rentals in Gaiole in Chianti
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Palazzo Monaci - Pool in the Crete Senesi
Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

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.

Casa Martini in Historic Chianti
Apartment with garden and private parking in Gaiole in Chianti, a stone's throw from the historic center where you will find numerous bars, restaurants and the small supermarket (coop). The accommodation is ideal for holidays with animals because it has a fully fenced garden. Tourist tax is required (€2 per person per night for the first seven nights) minors under 14 years excluded (read the complete regulation on the website of the Municipality of Gaiole in Chianti)

The Loggia
Country house located in Radda, the heart of the Chianti, within walking distance from the historical center and other services such as; Coffee shops, Post Office,grocery stores and restaurants. The house is composed of a full equipped kitchen, living room with a sofa bed, bedroom, loggia and bathroom. The property is surrounded by a garden and there is a nice wooden table in the garden to eat in an open space and another lounge spot to enjoy the magnificent landscape.

Villa di Geggiano - Perellino Suite
The 700 years old Villa di Geggiano, surrounded by our working vineyard and lovingly maintained gardens, is located in Chianti in Tuscany which is one of the most beautiful regions of Italy. Our guesthouse is located in one of the original garden pavilions of the villa. PLEASE NOTE THAT WE ARE IN THE COUNTRYSIDE WITH VERY FEW PUBLIC TRANSPORT OTHER THAN TAXI SO THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A RENTAL 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.

đź’ś "Gaia" at Podere Le Fontanelle
Imagine staying in a typical small stone house in the Tuscan countryside, in the middle of Chianti's nature but only 1 km from the historic center of Radda and being able to overlook a breathtaking panorama every day that will give you enchanting sunsets. -55m2 - Private garden area - TV with Netflix -private covered parking - shared pool (June 1st - September 15th) - heating (November 1st - April 1st) - kitchen - Wi-Fi

Chianti La Pruneta, Raphael 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.

Suite in Castello di Valle
A unique experience in a historical dwelling located in the Chianti region. This medieval castle is situated in a strategic position, surrounded by the major Tuscan touristic attractions. The suite is at the entrance floor level: double bedroom with bathroom, sofa bed for two people, kitchenette, fireplace.

Il Nido - a romantic hearth
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.

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.

Casa Dante
Casa Dante is located in the heart of Chianti, a stone's throw from the historic center of Radda in Chianti, an hour from Florence and half an hour from Siena. Located in a panoramic position on the Chianti hills, it allows you to enjoy a beautiful view.
Popular amenities for Gaiole in Chianti holiday rentals
Other great holiday rentals in Gaiole in Chianti

Tuscany jem: The Chianti Farmer's House

Wonderful country house

Divine Transit Gaiole

Casa di Lyndall - Entire house with exclusive pool

Gaiole in Chianti Poggio Casabianca

Podere Erbolino

The Fountain Arch

Independent cottage surrounded by nature
Frequently Asked Questions
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 pet-friendly vacation rentals in Gaiole in Chianti?
Four-legged friends are welcome in Gaiole in Chianti. Choose from more than 10 vacation rentals for guests traveling with pets.
Are there family-friendly vacation rentals in Gaiole in Chianti?
Gaiole in Chianti has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for Apartment Rentals in Gaiole in Chianti?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
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 $70 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 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
- House rentals Gaiole in Chianti
- Apartment rentals Gaiole in Chianti
- Family-friendly rentals Gaiole in Chianti
- Rentals with a washing machine and dryer Gaiole in Chianti
- Rentals with a patio Gaiole in Chianti
- Pet-friendly rentals Gaiole in Chianti
- Rentals with pools Gaiole in Chianti
- Villa rentals Gaiole in Chianti
- Santa Maria Novella
- Cathedral of Santa Maria del Fiore
- Mercato Centrale
- Strozzi Palace
- Ponte Vecchio
- Santa Maria Novella
- Great Synagogue of Florence
- Basilica Di San Miniato A Monte
- Lake Trasimeno
- Marina di Cecina
- Del Chianti
- Basilica of Santa Maria Novella
- Piazza della Signoria
- Eremo Di Camaldoli
- Uffizi Gallery
- Fortezza da Basso
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Piazzale Michelangelo
- Piazza della Repubblica
- Siena Cathedral
- Pitti Palace
- Parco delle Cascine
- Mugello Circuit
- Boboli's Garden




