Vacation rentals in Gaiole in Chianti

Apartment in Centro Storico

A dining area features a light-colored table set with decorative placemats, accompanied by four chairs. A brown leather sofa is positioned nearby, while a lush green plant adds a natural touch. Illuminated wall art complements a textured brick wall, enhancing the space's charm.

4.95 out of 5 average rating, 21 reviews

New MiK HoUsE 2025 with Netflix

Ciao Caro ospite, abbiamo arredato la nostra casa con tutto l'amore possibile per rendere il tuo soggiorno un sogno. Ogni cosa è pensata per il benessere dell'ospite. La zona è super accessibile e centrale ma lontana da locali notturni rumorosi e caos cittadino, parcheggio gratuito a 200 metri, possibilità di arrivare in macchina davanti alla casa, vicinissimo, anche a piedi, alla stazione ferroviaria principale della città. Scoprite tutti confort che abbiamo ideato per i nostri ospiti.

Apartment in Centro Storico

The bathroom features luxurious black marble walls and floors complemented by elegant gold fixtures. A spacious shower with glass doors can be seen alongside a sleek marble vanity. Soft blue light is visible through the doorway leading to the bedroom.

4.92 out of 5 average rating, 51 reviews

David Suite [Florence Centre, Luxury]

In the heart of Florence, David Suite offers a unique experience. Located in a 15th-century historic building, next to Via Tornabuoni and a stone's throw away from the train station, Duomo, Lungarno, and Ponte Vecchio, the accommodation features a king-size bedroom, marble bathroom, modern kitchen and an elegant living room with smart TV and air conditioning. Also available washer, dryer and balcony. With the comfort and luxury of our home, you'll fully enjoy the Florentine atmosphere!

Villa in Figline Valdarno

A charming stone building features a sloped tiled roof and wooden beams. Tall cypress trees rise beside the structure, which is surrounded by lush greenery and vibrant flower pots. Stone steps lead to the entrance, creating an inviting outdoor setting.

4.98 out of 5 average rating, 44 reviews

The Castellaccio of Figline

L'alloggio si trova al PRIMO PIANO di una villa immersa nel verde denominata “Il Castellaccio”, che deve il suo nome alla vicinanza con le rovine del vecchio castello appartenuto alla famiglia degli Uberti. La casa gode di una magnifica vista sulla campagna circostante ed è ideale per una vacanza rilassante per famiglie o gruppi di amici, con la possibilità di visitare città d’arte e godere degli splendidi paesaggi del Chianti, nonché delle specialità enogastronomiche della zona.

4.98 out of 5 average rating, 107 reviews

Loft in Scandicci

Wonderful Loft in Villa with Pool in Chianti

Located on the second and top floor of the "Suites le Valline" complex, the Piazzale Michelangelo loft offers a unique style in an ideal location for exploring Tuscany, a 15-minute drive from Florence and San Casciano! Treat yourself to a moment of relaxation on the beautiful panoramic terrace overlooking Florence, or cool off in the bio pool among the olive trees... and remember that all the vegetables from the Valline vegetable garden are at your disposal!

4.84 out of 5 average rating, 45 reviews

The living area showcases natural light streaming through large open doors, leading to a balcony adorned with wrought iron details. A wooden dining table is set for two, accompanied by a cozy chair and a colorful area rug beneath.

Condo in Centro Storico

[Free Garage] 15 Min. walk from Art

⭐ NEW LISTING! Elegant Central Apartment with BALCONY and GARAGE! &#x1F463 Perfect for exploring the UNESCO center on foot 6 min from the Garden of Gherardesca → another 6 min from the Basilica dell'Annunziata → 3 min from Michelangelo's David → 5 min to Brunelleschi's Dome, Duomo. Nearby, you'll find supermarkets, lounge bars, and typical taverns, yet enjoying a peaceful location. &#x1F9D8 The perfect balance between convenience and tranquility!

4.89 out of 5 average rating, 37 reviews

The image captures the exterior of a renovated farmhouse, set against a clear blue sky. A shimmering pool is visible in the forefront, with several sun loungers positioned around it. The house, framed by trees, features multiple windows and a large terrace surrounded by landscaped garden areas.

Apartment in Peccioli

Jasmine - Podere Cornacchino

Podere Cornacchino is a newly renovated Tuscan farmhouse, where the owners live and where they have decided to welcome guests. The property consists of only two apartments, "Il Leccio" and "Il Gelsomino," thus offering a relaxing and intimate setting. The property includes the main house, the duck pond, a large garden and a beautiful swimming pool overlooking the vineyards and olive groves of the Tuscan countryside.

4.91 out of 5 average rating, 23 reviews

The image depicts a panoramic view of a tranquil landscape featuring a private swimming pool surrounded by sun loungers. The rolling hills of the Valdarno valley stretch into the distance, dotted with olive trees, while a charming farmhouse is visible on the hillside.

Villa in Loro Ciuffenna

Villa with pool & view near Florence and Arezzo

Tuscan 1700 farmhouse in dominant position with a stunning view over the Valdarno valley. Features six separate apartments with 1 or 2 bedrooms each (total 7 bedrooms plus added beds), private gardens, private swimming pool (open May - September), common lounge and kitchen, WI-FI in every apartment. For groups up to 20 persons.

Apartment in San Gimignano

The historic skyline of San Gimignano is visible against a clear blue sky. The image showcases a collection of medieval towers and buildings set atop gently rolling hills, surrounded by patches of lush greenery and olive trees.

4.93 out of 5 average rating, 107 reviews

"Il Nespolo" Apartment - Girasole Location

The apartment "Il Nespolo", location "Girasole", is located in the historic center of San Gimignano, just 150 meters from Piazza del Duomo, in a side street of the main street. The property is in the immediate vicinity of all points of interest and at the same time away from the noise of the busiest street in the town.

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Popular amenities for Gaiole in Chianti vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

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

Apartment in Centro Storico

A cozy living area is presented with a plush green sofa facing a set of glass doors that open to a small balcony. A table and two chairs on the balcony provide a space for enjoying views of the surrounding architecture.

4.98 out of 5 average rating, 220 reviews

Art Apartment Luxury Por Santa Maria

4.8 out of 5 average rating, 5 reviews

The image depicts a spacious green lawn surrounded by vibrant flowers and shrubs. Two charming stone buildings with terracotta roofs are visible in the background, complemented by a variety of trees and under a partly cloudy sky, creating a serene outdoor atmosphere.

Villa in Poppi

Villa for 22 people w/private pool

Apartment in Mercatale Valdarno

A private outdoor space features a serene swimming pool surrounded by stone tiles. Comfortable lounge chairs are positioned near the pool. A gazebo provides shade, furnished with seating, and overlooks lush greenery, enhancing the tranquil atmosphere of the area.

4.98 out of 5 average rating, 80 reviews

Panoramic view from stone Apartment- Pool and A/C

4.9 out of 5 average rating, 179 reviews

A charming stone exterior features large windows and arched details, surrounded by lush greenery. A path lined with lavender leads to the entrance, with outdoor seating visible under shaded umbrellas. The tranquil setting is complemented by nearby trees and rolling hills in the background.

Cottage in Volterra

Podere Grignano, beautiful Tuscany

5 out of 5 average rating, 5 reviews

A living area features a gray sofa adorned with pink cushions, complemented by a colorful striped rug. A dining table is set for four, while framed portraits line the wall, adding character to the space. Arched doorways lead to adjacent areas.

Condo in Centro Storico

Mercutio 3 Rooms & 2 Bathrooms

4.88 out of 5 average rating, 40 reviews

The villa is surrounded by lush greenery and tall trees, providing shade to a spacious outdoor seating area with a pergola. Steps lead up to the entrance, framed by well-manicured hedges, while a stone barbecue area is positioned nearby.

Villa in San Miniato

Historic home with exclusive pool

5 out of 5 average rating, 5 reviews

A sunny outdoor area is framed by trees and shrubs, featuring a stone pathway lined with potted plants. A subtle stone wall borders the space, while a wooden railing provides a view of the surrounding nature.

Home in Pratolino

nat home 20 minutes from Florence