House vacation rentals in Gaiole in Chianti

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Top-rated house rentals in Gaiole in Chianti

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Guest favorite

A two-story house is visible, featuring a stone facade and a covered terrace. A pathway of stone slabs leads to the entrance, while garden plants and trees surround the property. The sky above displays a mix of clouds, creating a serene backdrop.

Home in Magliano

5 out of 5 average rating, 11 reviews

Tramonto in Chianti

Rilassati con tutta la famiglia in questo alloggio tranquillo, panoramico e immerso nella bellezza della campagna Toscana. Questo appartamento offre una vista che ti lascerà senza fiato. Dotato di un ampio giardino, piscina fuori terra, 2 camere da letto accoglienti, 2 bagni eleganti, una cucina completamente attrezzata, un'area living confortevole e un terrazzo panoramico con un tavolo, perfetto per cene sotto le stelle. Questo luogo è l'ideale per vivere un'esperienza unica e indimenticabile.

Guest favorite

An expansive view of the Cortona landscape is captured, featuring terracotta rooftops of traditional houses and lush greenery. Palm trees are visible in the foreground, while rolling hills extend into the distance, under a clear blue sky.

Home in Cortona

4.91 out of 5 average rating, 85 reviews

Cortona historical centre. Great views and WiFi

Charming apartment on the top floor of a Tuscan mansion house with traditional floor and exposed timber beams. The apartment is located in the heart of Cortona and it has triple exposure, so it is flooded with light and it boasts a stunning view over the valley and the Trasimene lake. Self check-in available. PARKING on the street is available. NO AIR CONDITIONING! This is an environmentally friendly choice. I welcome guests of all backgrounds, faiths, genders, ages and sexual orientations

Guest favorite

A wooden dining table is set with plates and glassware, complemented by a red table runner. A framed artwork hangs on the wall, and a rustic fireplace is visible, adding character to the cozy dining area. The adjacent kitchen is partially seen in the background.

Home in Greve in Chianti

4.88 out of 5 average rating, 115 reviews

La Meridiana a Montefioralle

Nel borgo di Montefioralle, la Meridiana il fascino delle abitazioni storiche. Di fronte ad una delle antiche porte del castello, la casa è parte del castello medievale. Al piano terra troverete la cucina, la sala da pranzo con un grande camino, un salottino e l’antica cantina a volta, al primo piano le due camere matrimoniali, il bagno , un salotto/studio ed il giardino con tavolo e sedie dove trascorrere piacevoli serate. E' disponibile una connessione wi-fi gratuita ad alta velocità.

Superhost

An entrance area is presented with double doors featuring a diamond pattern. A bench and a small round table are positioned nearby, complemented by wall-mounted copper cookware and framed art. The flooring is tiled in warm tones, highlighting the inviting space.

Home in Pratolino

5 out of 5 average rating, 5 reviews

casa nat a 20 minuti da Firenze

Casa di Nat offre un esperienza unica immersa nella natura ma a pochi minuti dal centro di Firenze, una vacanza unica per chi vuole rilassarsi e divertirsi insieme ad amici e famiglia, adatta ad adulti e bambini, con il suo spazio esterno sarà possibile coinvolgere tutti in pranzi o cene, con barbeque e sdraio, il porticato coperto permetterà di poter mangiare all'aperto anche nei mesi più freddi, per facilitare gli spostamenti c'è un parcheggio gratuito in strada e fermata del bus vicino.

Guest favorite

A spacious living room features exposed wooden beams above, with a cozy seating arrangement of soft sofas. A rustic wooden coffee table sits in the center, surrounded by warm, terracotta-tiled floors. A classic fireplace provides a focal point, complemented by thoughtful decorative accents.

Home in San Casciano In Val di Pesa

4.84 out of 5 average rating, 91 reviews

Tuscan Villa Featured Conde Nast Best Villas Italy

Step under archways into a home where the original wood ceilings and tiled floors showcase Tuscan style. Enjoy delicious meals on the terrace with sweeping views of Tuscany, winters curled up in front of a huge fire place or relaxing on warm summer days by the pool. Savour the best of Tuscan food and wine with cooking classes with a Michelin chef, master classes in wine and visits to local artisan cheese and wine makers. Listed by Condé Nast as one of the most beautiful villas in Italy.

Guest favorite

An outdoor dining area is set beneath a wooden pergola, featuring a large stone table surrounded by black chairs. Potted plants line the terrace, and a scenic view of rolling hills and treetops stretches in the background.

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.

Guest favorite

The entrance of a rustic stone house is framed by wooden doors that open outward. Lush greenery surrounds the entrance, enhancing the natural atmosphere. A patio is visible on one side, providing a glimpse of the landscaped garden beyond.

Home in Castellina in Chianti

4.98 out of 5 average rating, 107 reviews

StageROOM03 -Chianti Idillic Country living

Set in a picturesque hamlet, overlooking the Chianti hills, this charming country house is just 10 minutes from Siena and Castellina in Chianti. Recently renovated, it blends authentic Tuscan charm with modern comforts. The house features two bedrooms, two bathrooms, a cozy living area and a fully equipped kitchen with a dishwasher, two fridges, and a washing machine. Outside, enjoy a beautiful garden and relax in the outdoor marble hot tub, soaking in the breathtaking views.

Guest favorite

A charming stone building is nestled among lush greenery, featuring a pathway lined with potted plants. The warm tones of the building complement the surrounding nature, creating an inviting atmosphere that blends seamlessly with the landscape.

Home in Terranuova Bracciolini

4.96 out of 5 average rating, 24 reviews

Casa Canto alla Luna Piscina WiFi Orto & Giardino

In the center of a small historic village, surrounded by nature and hills. From here, right in front of our houses, the peasants once passed by singing the May song, thus welcoming the arrival of spring. Our vegetable garden is located just above the ancient village, here every season works its magic, we grow the plants and vegetables that we use to prepare the dishes for our cooking classes. Welcome, warmth and comfort are the ingredients of our hospitality.

Top guest favorite

The rustic stone facade of the house features abundant greenery and wisteria blooms cascading from the upper balcony. The entrance is accessible via a stone pathway, and wooden beams frame the windows, enhancing the traditional Tuscan architecture.

Home in San Martino Sopr'Arno

4.94 out of 5 average rating, 104 reviews

Casa Manu

CARATTERISTICA CASA TOSCANA in pietra immersa nelle colline della provincia di Arezzo. Vicino a Siena, Firenze, Cortona, Perugia, il santuario della Verna con la storia di San Francesco di Assisi, Sansepolcro e i dipinti di Piero Della Francesca. Ideale per trekking, turismo enogastronomico (a pochi km si trovano alcune tra le migliori cantine della Toscana), per appassionati di arte e cultura. Vi accoglieremo con un presente di benvenuto.

Guest favorite

A grand staircase adorned with statues leads to an ornate entrance, flanked by manicured hedges and vibrant flower beds. The symmetrical design is complemented by lush greenery and intricate stonework, creating a harmonious outdoor space inviting exploration.

Home in Larciano

4.92 out of 5 average rating, 12 reviews

Stone house

Splendida casa in Toscana perfettamente collegata ai principali luoghi di interesse turistico, per un soggiorno indimenticabile tra storia, arte e natura. &rtrif; Potrai raggiungere: &rtri; Lucca &rtri; Firenze &rtri; Vinci &rtri; Pisa &rtri; Pistoia &rtri; Montecatini Terme • Alcuni servizi: &compfn; WiFi &compfn; Aria condizionata &compfn; Parcheggio &compfn; SmartTV 55 pollici &compfn; Cucina completa, lavastoviglie, lavatrice

Guest favorite

Home in Certaldo

4.87 out of 5 average rating, 62 reviews

Paluffo Torre 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.

Guest favorite

An open-plan kitchen and dining area is showcased, featuring wooden beams overhead. A dining table is surrounded by four chairs, and a cozy seating area includes a gray armchair. Various plants adorn the space, enhancing its warm and inviting ambiance.

Home in Tavarnelle Val di Pesa

4.94 out of 5 average rating, 139 reviews

La Casa di Nada Home

My house is immersed in the Tuscan countryside among olive trees and vineyards in the heart of Chianti, wonderful views, relaxation, I offer cooking schools and exclusive dinners, my garden can be the perfect setting for a wonderful candlelit dinner prepared exclusively for my guests 🤗

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What guests are saying

Casa Fattore - Tuscan countryside house

4.93 out of 5 average rating, 45 reviews7 months ago

Il soggiorno alla tenuta di Capocontro è stato molto soddisfacente. L'intero borghetto antico è un gioiello incastonato nel verde, con vista spettacolare sui boschi della Val di Chiana. L'alloggio in ordine e pulito, pittoresco ed elegantemente retrò. Piero e Lella disponibilissimi nelle comunicazioni e nei suggerimenti di luoghi da visitare e in cui mangiare. Abbiamo amato la pace e il silenzio del luogo, nonchè la piscina con vista. Ci siamo fermati poco e il meteo è stato un po' capriccioso, altrimenti ci saremmo goduti di più gli esterni della fattoria. Unico piccolo neo: le stoviglie e il frigo non erano proprio immacolati, ma nulla che non si possa risolvere con un colpo di spugna. Super consigliato sia per un soggiorno breve che per uno lungo, così da godersi la quiete del luogo e visitare i dintorni.

Home in Civitella in Val di Chiana

What guests are saying

Casa Ora d"Oro - Panoramic Views

4.97 out of 5 average rating, 38 reviewstoday

Rocky's home is incredible. It is so peaceful and relaxing, and the sunsets from the yard are stunning! Our family spent the week here and we loved it. We loved our day trips to Pienza and Montalcino, and a visit to a local farm, but returning to the villa in the afternoon was magical. I would not hesitate to come back or to recommend this place!

Home in Castelmuzio

What guests are saying

Vacanza immersa nella campagna Toscana 'Canaiolo'

4.83 out of 5 average rating, 70 reviews7 months ago

We reached the destination and immediately felt like being at home. Such a nice country-house, quiet surroundings and a most gorgeous and large pool. Gary, who looks after everything, is one of the nicest hosts we have ever met: charming, helpful and making you feel very comfortable. A highly recommendable place to stay! Anne and Werner from Austria

Home in Montespertoli

What guests are saying

Casale La Giara - Enclosed patio, exclusive view

4.82 out of 5 average rating, 17 reviews6 months ago

If you want to have an experience to live in olive garden with a beautiful view of Tuscany's hills and historical city - that's a spot! Peaceful, calm, silent with just a noise of nature (morning birds, owl at night). On ground floor you will find nice kitchen (well equipped) and bathroom (that looks better than on pictures), washing machine, iron, hairdryer, good wifi. On the first floor 2 charming bedrooms with a nice view. Great spot. Truly recommended!

Home in San Miniato

What guests are saying

Casa Cuore Di Mela

4.97 out of 5 average rating, 34 reviews6 days ago

The views are just as good as the pictures! The house was spacious and nicely decorated, clean and tidy. The little town has a couple of small grocery type shops, cafes and restaurants. (Doriane gave recommendations and offered to book restaurants which was great when my phone didn’t work.) It is a great location, in a particularly picturesque part of Tuscany and close to lots of the sites of Tuscany. Would recommend. (If you are a particularly light sleeper and like going to bed very early, I would suggest bringing ear plugs, as the old lady next door has her tv loud, but not late.)

Home in Gambassi Terme

What guests are saying

Casa delle Rose

4.94 out of 5 average rating, 16 reviews3 weeks ago

Lovely home within the city walls, with thought and attention given to the renovation of a historic home. While the weather didn’t cooperate as much as we hoped, the limited time we spent on the amazing terrace was noteworthy. Also rare in Italian rentals was the provision of a dryer, which was appreciated. The only drawback was the antique living room furniture, which was limited in space and comfort. Had we been able to use the terrace, this would have been less of a problem. I would recommend this rental!

Home in Cortona

What guests are saying

Domus Antiqua

4.94 out of 5 average rating, 32 reviews3 months ago

We had an excellent stay at this beautiful home which is very spacious, comfortable and very well furnished. The views are superb even by the high standards of Montalcino. Communication was proactive and very helpful. Nothing to fault. We would definitely stay again and look forward to doing so.

Home in Montalcino

What guests are saying

Tuscan vineyard house, near Florence

5 out of 5 average rating, 13 reviews3 months ago

My husband and I stayed here for 10 days while traveling around Europe. Jane is not only a wonderful host who was always responsive and had wonderful recommendations but was proactive from the beginning, making sure we had clear instructions for arrival and checking in periodically to make sure things were running smoothly. The house itself is perfection. A private farmhouse as described with Jane close by if we needed anything. The views are stunning and the home itself is cozy and inviting with the listed amenities accurate 100%. We used the kitchen to make simple meals and had a perfectly clean kitchen, bathroom, living room and bedroom. Having a car is a must to explore Florence (45 minutes away) Pisa (1 and 1/2 hours away) and surrounding small towns filled with history and the beauty of Tuscany. I’d highly recommend this beautiful stay and look forward to coming back!

Home in San Francesco

What guests are saying

Casa Merli - Le case di Quota

5 out of 5 average rating, 18 reviews4 days ago

Un sogno che diventa realtà, uno dei borghi più belli d'Italia dove regna pace ,tranquillità e semplicità. Borgo di Quota a 10 minuti dal paese Poppi percorrendo una strada di tornanti ben mantenuta accessibile a tutti,tra l'altro nel paese di Poppi puoi trovare tutti i servizi possibili. Una menzione particolare alla Host Claudia , persona stupenda così come l'appartamento. Ma penso che le parole non bastino un posto così bisogna viverlo,e aggiungo che in zona si mangia davvero bene. Dimenticato a Quota troverete anche una bottega rifornitissima gestita da persone speciali.

Home in Quota