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Vacation rentals in Gaiole in Chianti

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Top-rated vacation rentals in Gaiole in Chianti

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Home in Poggio San Marco

4.97 out of 5 average rating, 265 reviews

Charming converted Hayloft overlooking the Chianti Hills

Inspired by the rustic Tuscan style, this gorgeously refurbished hayloft features ceilings with exposed beams and bricks and thoughtful touches for a stylish and comfortable decor. From the relaxing hammock and the stone made barbecue in a panoramic garden to the cozy fireplace, every space feels open and inviting. Immersed in total peace and tranquillity with a breathtaking view over the Chianti hills, halfway between Florence, Arezzo and Siena, the barn is a perfect homebase to visit Tuscany. The accommodation has 2 floors. The upper floor spaces 2 double bedrooms with wonderful views of the olive trees and a bathroom with window and large masonry shower. On the ground floor a cozy and spacious living area with fireplace and a kitchenette with gas stove a large fridge and oven. The barn has ceilings with exposed beams and bricks. Outside there is a panoramic garden set on its own where, in the shade of a walnut trees, you can relax on a hammock or grill your meal (included an authentic local Fiorentina steak :-) on the stone made barbecue. A garden table is there for romantic dinners 'al fresco'. Immersed in total peace and tranquility halfway between Florence, Arezzo and Siena the barn is a perfect homebase to visit Tuscany. To find the exact location of the house type the following code in GMaps: 8FMHGG25+QV The house is in the countryside. The closest towns are Cavriglia and the small Medioeval villages of Moncioni and Montegonzi. In each town you can find great local restaurants and a small grocery shop. Moncioni is 3 km far away. A big supermarket is located in Montevarchi and you can reach it in 8 minutes by car ( exactly 7 km far away). In Montevarchi you can also find one of the best farmer markets in Tuscany! The station of Montevarchi is 8 km away from the barn. From there you can take train to Florence and Arezzo. Siena can be reached in 30 minutes by car. The easy access to the motorway A1/E35 Milan-Florence-Rome (the Valdarno exit is only at 13 km) allows you to reach numerous interesting spots within a short time, both in Tuscany and Umbria, while few kilometres south of Cavriglia you enter the suggestive territory of the Crete Senesi. Out in the countryside, the home offers an authentic experience of Tuscany. Small towns and villages are a short drive away providing acces to exceptional local restaurants and fantastic farmers markets. A big supermarket is located in Montevarchi (7 km far away). The railway station is 8 km away from the barn. From there you can take train to Florence and Arezzo. Cities of interest like Siena, Montepulciano, Pienza and Monteriggioni can be reached in 40 minutes by car The only way to reach the house is by car. A taxi service is active from Montevarchi You will be provided of blankets and towels. The kitchen is equipped with and kind of pots, pans, bowl, plates and silverware. You are welcome to use them. Free Netflix available

Home in Panzano In Chianti

4.98 out of 5 average rating, 402 reviews

Old farmhouse near Panzano Castle Abbacìo

The Abbacio apartment is part of an old farmhouse that has been restored respecting the original structure and style. Its location is just on the top of the hill, facing the valley. Surronded by vineyards and olive trees, but also attached to the village. From the house you can easily reach by feet wineries, farms and restaurants. Panzano is halfway between Florence and Siena, easily reached with car. By bus there is a good service from and to Florence, not from and to Siena. A very quiet spot!

Villa in Castellina in Chianti

4.93 out of 5 average rating, 196 reviews

The Villino Farmhouse

Entire upper floor of the newly renovated Villa Padronale in traditional Tuscan style. High ceilings with exposed beams make it cozy and perfect for families or groups of friends. In the house there are two functional large fireplaces(in the living room and kitchen). Private accommodation, not shared. The house has a large covered terrace,garden with sofas,bbq,firepit, private parking. The pool among the olive trees and vineyards is ideal for relaxing and has a private access to the shared area

Cottage in Geggiano

4.99 out of 5 average rating, 122 reviews

Villa di Geggiano - Guesthouse

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 idilic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa. 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.

Home in Lecchi in Chianti

4.96 out of 5 average rating, 135 reviews

Casa di Lyndall - Entire house with exclusive pool

Welcome to “Casa di Lyndall” My home is located in the medieval village of Lecchi in Chianti, set in rolling hills, castles, vineyards & olive groves, & provides a view that extends nearly 50 kms. It’s a perfect choice for a family or group of four people. My home is built in typical Tuscan style with exposed chestnut beams, fireplace, and a well appointed kitchen. The 8 metre pool is private & located on the top terrace of the olive grove, has a child proof fence, and 4 sun lounges.

Home in Rietine

4.85 out of 5 average rating, 206 reviews

Gaiole in Chianti Poggio Casabianca

We invite you in the heart of Chianti area. Poggio Casabianca is a little family homestead located in the Chianti Classico region exactly in the hearth of Tuscany. The owners live here and they offer at their guests an apartment with a big living room-kitchen with a big door that open directly to the garden, a bathroom with shower and a confortable doublebed room. Outside in the garden ther is a pool, shared with the owner, where you can refreshing and relaxing during the summer.

Home in Gaiole In Chianti

4.86 out of 5 average rating, 248 reviews

Charming estate with views

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.

Cabin in Gaiole in Chianti

4.88 out of 5 average rating, 135 reviews

Little Country House "HEART CHAKRA"

Delightful stone chalet immersed in a forest of oaks and pines, ideal for a romantic weekend and/or a relaxing holiday. The environment, new, intimate and cozy, consists of a studio with bathroom and shower, large terrace and wooden pergola. Little country house ideal for a romantic weekend and a relaxing holiday. It includes a studio with kitchen, living room, bedroom and bathroom and equipped with big terrace and pergola.

Farm stay in Simignano

4.88 out of 5 average rating, 158 reviews

Casa al Gianni - Hut

Hi, we are Cristina & Carmelo! We invite you to live an authentic experience in our farmhouse “Casa al Gianni” located 20 minutes from Siena. Our brand is simple living in close contact with the nature and animals of our farm. Nestled in the woods and the beautiful Tuscan countryside you will spend an unforgettable holiday. This corner of paradise will remain in your heart!

Farm stay in Gaiole in Chianti

4.94 out of 5 average rating, 225 reviews

Il Piccolo Nido alla Pieve Marsina

Stonewalls and the small romantic fireplace, the iron and wood staircase which brings you to the big double bedroom, the private outdoor area with iron pergola, table and deckchairs characterize the apartment Nido. The best accommodation for couples seeking an unforgettable romantic escape immersed in the Chianti hills. Ideal also for couple with a little baby.

Farm stay in Greve in Chianti

4.99 out of 5 average rating, 358 reviews

Old hayloft on the Chianti hills

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence. Hayloft completely independent on two floors connected by an internal staircase. Private garden of 300 mq sorrounded by secolar oaks.

Farm stay in Gaiole In Chianti

4.97 out of 5 average rating, 100 reviews

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.

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Popular amenities for Gaiole in Chianti vacation rentals

Free parking on premises

Air conditioning

Stay near Gaiole in Chianti's top sights

Eroica 13 locals recommend

Capannelle9 locals recommend

Enoteca La Cantinetta Del Chianti S.A.S. Di Azzato Riccardo Michele8 locals recommend

Lo Sfizio6 locals recommend

I'GALLETTO BRIACO6 locals recommend

Coop Informa6 locals recommend

Other great vacation rentals in Gaiole in Chianti

Home in Radda in Chianti

4.89 out of 5 average rating, 18 reviews

Terraced house in Chianti

Home in Cavriglia

4.95 out of 5 average rating, 76 reviews

Wonderful country house

Villa in Gaiole In Chianti

4.89 out of 5 average rating, 19 reviews

Sestuccin

Home in Cavriglia

4.96 out of 5 average rating, 23 reviews

The House of Briga

Villa in Gaiole in Chianti

5 out of 5 average rating, 10 reviews

L'Agrifoglio

Rental unit in Radda in Chianti

4.91 out of 5 average rating, 65 reviews

La Casina

Home in Gaiole in Chianti

4.8 out of 5 average rating, 99 reviews

loft in the heart of Tuscan Chianti

Cottage in Moncioni

4.95 out of 5 average rating, 83 reviews

Romantic Cottage in Chianti Set in Organic Olive Groves

Quick stats about vacation rentals in Gaiole in Chianti

Total rentals
50 properties
Nightly prices starting at
$40 before taxes and fees
Total number of reviews
920 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
20 properties have a pool

Frequently Asked Questions

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.
Are there Gaiole in Chianti vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in Gaiole in Chianti, available on Airbnb. Make a splash and soak up the sun in style!
How much does it cost to stay in villa rentals in Gaiole in Chianti?
Experience the best of Gaiole in Chianti with our villa rentals, starting at about $130 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do villa rentals in Gaiole in Chianti have wifi?
Absolutely! We offer over 10 villa rentals with wifi in Gaiole in Chianti. Enjoy a tailored experience with all the comforts you desire.
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 vacation rentals with a dedicated workspace in Gaiole in Chianti?
Yes! Work meets play with ease at over 10 vacation rentals in Gaiole in Chianti featuring dedicated workspaces. Stay connected and productive in your home away from home.
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.
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.

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