We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Some info is shown in its original language. Translate

Villa vacation rentals in Gaiole in Chianti

Find and book unique villas on Airbnb

Top-rated villa rentals in Gaiole in Chianti

Guests agree: these villas are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Top guest favorite

An inviting stone facade of the villa is lit softly by exterior lights, highlighting the rustic architecture. A staircase leads to the upper entrance, flanked by terracotta pots and shrubs, creating an atmospheric approach surrounded by greenery.

Villa in Chianciano Terme

4.96 out of 5 average rating, 112 reviews

Charming Villa in Val d'Orcia Tuscany, Great View

Huge and charming top floor apt in Tuscan Villa with breathtaking view! Visit Montepulciano, Pienza, Siena, explore country side, vineyards and hot springs, hiking or e-biking, strolling or driving! Two roomy suites with top quality beds and bathroom ensuite. Windows walled living room, comfy sofas, professional kitchen at your own use. We can set Winery visit & tasting, Cooking classes and private dinners. NEW Hot tub facing green hilltop! ExperienceTuscany as a local, with your local Host!

A sunlit swimming pool is situated in an expansive landscaped area, surrounded by neatly trimmed grass and lush trees. The charming building stands in the background, showcasing traditional architecture, while cypress trees line the horizon, adding to the tranquil countryside atmosphere.

Villa in Monteroni d'Arbia

4.98 out of 5 average rating, 104 reviews

San Giovanni in Poggio, villa Meriggio 95mq

Casa indipendente, due camere da letto matrimoniali, due bagni con doccia, living con cucina completa di tutto (lavastoviglie, lavatrice, forno, microonde), divano letto matrimoniale, giardino privato con pergola attrezzato. Tv Sat e Free wifi. Servizi aggiuntivi in struttura, su prenotazione, biciclette a pedalata assistita marca Focus modello Jarifa2 6.7 e un'area wellness con sauna finlandese da esterni Forest e una minipiscina idromassaggio riscaldata con cromoterapia con vista panoramica.

A spacious kitchen showcases a large stone fireplace with a wooden mantle as its centerpiece. Light streams through the window, illuminating the wooden beams overhead. A dining table is set for a meal, while traditional utensils adorn the walls, enhancing the inviting ambiance.

Villa in Castellina in Chianti

4.94 out of 5 average rating, 234 reviews

Il Villino Farmhouse

Intero piano superiore della Villa Padronale appena ristrutturata in stile tradizionale toscano.Gli alti soffitti con le travi a vista rendono il posto accogliente e perfetto per famiglie o gruppi di amici.Nella casa si trovano due grandi camini(in salotto e cucina)funzionali.Alloggio privato, non condiviso. La casa ha una ampia terrazza coperta,giardino con divani,bbq,firepit,parking privato. La piscina tra gli ulivi e i vigneti e' ideale per il relax ha un accesso privato alla zona condivisa

Top guest favorite

The exterior of the villa is framed by lush greenery and tall trees, with a stone pathway leading to the entrance. The structure features traditional architecture, characterized by stone walls and wooden accents, set against a backdrop of rolling hills and a blue sky with scattered clouds.

Villa in Montepulciano

4.97 out of 5 average rating, 114 reviews

Wine Experience Villa in Montepulciano

🏡 Villa Talosa è immersa nei vigneti della Fattoria della Talosa, storica azienda vitivinicola di Montepulciano produttrice di Vino Nobile. Un luogo autentico, ideale per rilassarsi con la magia della campagna toscana e una vista incantevole da ogni finestra. A soli 1,5 km dal centro storico, raggiungibile anche a piedi, potrete visitare la nostra Cantina Storica del 1500 sotto Piazza Grande: un’esperienza unica tra storia, passione per il vino. Riscaldamento e aria condizionata sono inclusi.

A stone villa surrounded by greenery is featured under a clear blue sky. A large swimming pool reflects the sunlight, complemented by sun loungers and colorful potted flowers along the edges. The outdoor area is perfect for relaxation with scenic views of the Tuscan hills.

Villa in Castiglion Fiorentino

4.91 out of 5 average rating, 220 reviews

Tuscan charm of villa - countryside

Nell’affascinante campagna Toscana,tra ulivi e vigneti una villa in pietra,in posizione strategica per cogliere i segreti di Toscana e Umbria aria condizionata e piscina con area wellness per il vostro relax e confort Villa Senaia è una grande casa con travi in legno, in una splendida posizione in collina con vista idilliaca che affaccia su uno dei luoghi preferiti della campagna toscana, un ambiente attraente per mangiare all'aperto, bevendo vino toscano e ascoltando i grilli e le cicale

The villa is captured from above, showcasing its spacious gardens filled with greenery and trees. The two-story building is framed by meticulously maintained lawns, with seating areas visible in the garden. The surrounding rolling hills and countryside contribute to a serene landscape.

Villa in Santa Cristina

4.92 out of 5 average rating, 135 reviews

Villa in Chianti near Florence with stunning view

The apartment is part of a 14th-century Tuscan Villa, with a stunning view over Chianti hills and organic vineyards from our family. With its 100 square meters and two gardens can comfortably accommodate 2 people. The villa, while historic and beautiful, is equipped with all the modern amenities you will need. The location is relaxing, yet very close to Florence, Pisa, Siena, and many other Tuscan tourist spots. Read the reviews to understand what you can expect from your stay in our house!

The villa's exterior is highlighted by a modern structure with large glass doors and a gently sloping roof. It is surrounded by lush greenery and features a patio area with steps leading to the entrance. Soft lighting illuminates the garden, creating a serene evening ambiance.

Villa in Montepulciano

4.92 out of 5 average rating, 252 reviews

Amazing Tuscany Villa, FREE parking

Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking

Top guest favorite

A modern villa with a stone exterior features strategically placed windows and a prominent porch area. The surrounding greenery includes an olive tree, while steps lead to a well-maintained garden. An ornamental planter sits at the forefront, adding a decorative touch to the entrance.

4.98 out of 5 average rating, 195 reviews

Virgi House

Virgi House is a 160 sqm villa, located 3 km far from Siena’s hystorical center. The villa is distributed over three floors. On the first one there is a double bedroom with bathroom and terrace, a large open space living room, a modern kitchen and a bathroom. Downstairs a double bedroom (or 2 single beds), a large bathroom, a study and a bright living room with a loggia from which you can access the private car park and the garden. The property also provides free wifi, air conditioning.

Top guest favorite

An inviting villa surrounded by lush greenery and vibrant flowers, featuring blooming rose bushes and olive trees. The gravel pathway leads to the entrance, showcasing a two-story structure with balconies. Sunlight highlights the colorful landscape, creating a serene atmosphere.

Villa in Impruneta

5 out of 5 average rating, 157 reviews

La Torre

Antica villa toscana, bellissima, con giardino privato esclusivo, completamente ristrutturata, immersa nelle splendide e dolci colline toscane. La villa ha una vista mozziafiato, molto soleggiata, ben arredata e dotata di tutti i comfort, silenziosa e non isolata. La casa si trova a Bagnolo, piccola frazione di Impruneta alle porte del Chianti, zona di uliveti, vigneti e pace. La casa si trova a circa 10 km in macchina dal centro di Firenze.

4.89 out of 5 average rating, 292 reviews

Villa Capanna, Private Pool, Breathtaking Views

Ancient restored barn with up to 6 bedrooms and 6 bathrooms, immersed in a historic wine estate, just 6 km from Siena. One of the most beautiful views that the Tuscan panorama can offer, airconditioned bedrooms, exclusive swimming pool, large triple garden, BBQ, poolside table, terrace to enjoy the sunset over the medieval towers on the horizon while sipping the organic wines of the estate, fireplace, parking free, WI-FI internet.

Top guest favorite

A well-maintained garden surrounds a refreshing pool, bordered by manicured grass. A comfortable seating area, featuring two lounger chairs and a shaded umbrella, provides a serene spot for relaxation. Soft greenery and flowering shrubs form a natural backdrop, enhancing the tranquil atmosphere.

Villa in Tignano

4.96 out of 5 average rating, 188 reviews

Villa Isabella

Villa Isabella is a comfortable Tuscan style villa located in the splendid Chianti hills in Tuscany with a large garden and a spectacular breathtaking panoramic swimming pool for exclusive use where you can experience the Tuscan tradition in full local style with the possibility of organizing private shuttles service for reach the property traditional experiences, services and tours only and exclusively for our guests.

Top guest favorite

A well-kept garden features neatly trimmed grass and a variety of trees, including tall pines, providing shade and a natural atmosphere. A subtle hammock is visible between two trees, inviting relaxation in the serene outdoor space.

Villa in Montespertoli

4.94 out of 5 average rating, 193 reviews

Colonica nel Chianti

Splendida porzione di casa colonica immersa nel Chianti con bellissima piscina, circondata da vigne e olivi, perfettamente arredata con vasto giardino e posti macchina. Si trova a 20 minuti da Firenze, 40 da Siena e 50 da Pisa, in pochi minuti si raggiunge Certaldo (città natale di Boccaccio) e Vinci (città natale di Leonardo Da Vinci). la casa è a metà strada tra Montespertoli e San Casciano (7km).

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Hotels

Stylish accommodations with great services and amenities

Popular amenities for Gaiole in Chianti villa rentals

Free parking on premises

Air conditioning

Private villa rentals

Top guest favorite

An infinity pool is framed by stone decking and wooden lounge chairs, inviting relaxation. Umbrellas provide shade, while terraced gardens with olive trees rise in the background. The surrounding landscape features gently rolling hills and clear blue skies, enhancing the serene outdoor setting.

Villa in Cortona

5 out of 5 average rating, 84 reviews

Stunning Tuscan Villa & Panoramic Infinity Pool

Top guest favorite

Bright pink flowers frame a tranquil infinity pool, with rolling green hills visible in the background. The landscape is dotted with tall trees and stretches toward distant mountains under a clear blue sky.

Villa in Barberino Tavarnelle

5 out of 5 average rating, 41 reviews

Valluccia 51

A serene salt-water pool reflects the surrounding greenery and sky. Lounge chairs line the pool's edge, while an umbrella provides shade to one side. The rustic stone structure is visible in the background, surrounded by olive and pine trees.

Villa in Scandicci

4.95 out of 5 average rating, 20 reviews

Villa con piscina immersa nella natura Fiorentina

Top guest favorite

An outdoor swimming pool is set against a backdrop of rolling green hills. Sun loungers with umbrellas surround the pool, providing shaded areas. A jacuzzi is positioned nearby, with manicured lawns and pathways leading towards the pool area.

Villa in Montepulciano

5 out of 5 average rating, 19 reviews

Terra Antica Suite & Ville - Cervognano

Top guest favorite

An infinity pool sits on a green terrace, surrounded by lush greenery and olive groves. Several loungers are positioned on the lawn, offering views of the expansive valley and distant hills under a clear blue sky.

Villa in Loro Ciuffenna

4.96 out of 5 average rating, 56 reviews

The Lazy Oak

A private pool is featured in the foreground, with clear water inviting relaxation. The villa's stone façade is visible in the background, complemented by arched windows and a shaded outdoor dining area. Sun loungers are arranged beside the pool, set against a backdrop of greenery.

Villa in Badia a Montemuro

4.89 out of 5 average rating, 18 reviews

[Le rondini in Tuscany] Exclusive View Pool Villa

A cozy living area features a warm fireplace set within a stone wall, providing a relaxing ambiance. A large TV is displayed on a wooden shelf filled with decor. Soft lighting enhances the inviting space, furnished with a comfortable leather sofa and an elegantly draped bed.

Villa in Bagno A Ripoli

5 out of 5 average rating, 3 reviews

Villetta dei Fagiani - pools, Jacuzzi in Florence

The rustic two-story house is enveloped in lush green ivy, highlighting its stone façade. Two arched doors are framed by natural greenery, creating a harmonious appearance. An outdoor dining area with a table is partially visible under a shaded patio, providing a serene setting in the garden.

Villa in Sovicille

4.95 out of 5 average rating, 85 reviews

Beautiful Country House, near Siena with jacuzzi

Luxury villa rentals

An aerial view captures the expansive countryside, dotted with vineyards and olive groves. The large swimming pool is framed by lush greenery, while the villa's garden offers a serene atmosphere. Gentle hills roll in the background under a clear, blue sky.

Villa in Poggibonsi

4.93 out of 5 average rating, 55 reviews

Villa with pool in Chianti Area

A panoramic view of a pool set within a serene garden, featuring blooming flowers in the foreground. Olive trees are visible in the background, enhancing the natural beauty of the landscape. The clear blue water of the pool reflects the surrounding greenery.

Villa in Greve in Chianti

4.78 out of 5 average rating, 37 reviews

Romantic Villa with private pool and fabulous view

Top guest favorite

A private swimming pool is surrounded by a spacious stone patio, featuring comfortable sun loungers and shaded seating areas. Potted plants are placed around the pool, enhancing the tranquil outdoor space that is framed by trees and the rustic charm of the stone house.

Villa in Volterra

5 out of 5 average rating, 35 reviews

Romantic Villa with private pool - "Il Pollaio"

A rustic Tuscan farmhouse, restored with care, features a tall tower and expansive windows. Surrounding greenery includes cypress trees and shrubs, complementing the natural landscape. The lawn offers open space for relaxation, enhancing the serene atmosphere of the property.

Villa in Buonconvento

5 out of 5 average rating, 14 reviews

Beautiful tuscan country house

A private swimming pool is set on a wooden deck surrounded by lush greenery. Comfortable cushions are placed around the pool area, enhancing the serene outdoor environment. A charming villa is visible in the background, blending harmoniously with the natural landscape.

Villa in Galluzzo

4.75 out of 5 average rating, 12 reviews

Tenuta del Podestà villa di charme a Firenze

A private pool is nestled among vibrant pink flowers, with a whimsical float positioned in the water. Sun loungers line the poolside, surrounded by lush greenery and olive trees, offering expansive views of the rolling Tuscan hills in the distance.

Villa in La Poggerina

4.98 out of 5 average rating, 41 reviews

Villa La Poggerina, private pool and amazing view

Top guest favorite

A serene garden area features a lounging chair with a folded towel placed neatly on it. Stone planters and lush greenery surround a small hot tub, complemented by flowering plants and trees. The backdrop includes rustic architecture under a clear sky.

Villa in Monticchiello

4.98 out of 5 average rating, 165 reviews

Villa unesco heritage, Jacuzzi & garden. BB Daria

Top guest favorite

Two large arched windows provide a view into a cozy living space featuring soft, warm lighting. The interior displays bookshelves, comfortable seating, and decorative accents. Greenery from the surrounding area gently frames the scene, adding a natural touch to the inviting atmosphere.

Villa in San Casciano In Val di Pesa

5 out of 5 average rating, 13 reviews

A Charming Country House in the Tuscan Chianti

Villa rentals with a pool

The pool area features a rectangular swimming pool surrounded by meticulously landscaped gardens. Olive trees, rosemary, and rose bushes complement the scenic views of rolling hills and distant mountains under a clear blue sky.

Villa in Pozzuolo

4.91 out of 5 average rating, 53 reviews

Fabulous Farmhouse with Pool & 360 Panoramic View

The villa is set against a backdrop of rolling hills and gardens. A large pool is visible in the foreground, featuring a circular shape and steps leading into the water. The stone structure with a tiled roof complements the natural surroundings.

Villa in Montepulciano

4.91 out of 5 average rating, 133 reviews

Villa a Montepulciano con Piscina

A serene outdoor space features a sparkling pool bordered by a well-maintained lawn and vineyards. Lounge chairs are positioned alongside the pool, and a table is set with snacks and cups, inviting relaxation. A cloudy sky adds depth to the tranquil atmosphere.

Villa in Campogialli

4.72 out of 5 average rating, 29 reviews

VILLA DI CHARME NEL CHIANTI

Top guest favorite

A refreshed saltwater pool is surrounded by lush greenery and olive trees. Sun loungers in vibrant colors are positioned along the pool deck. A shaded area with a pergola is visible, providing a relaxing spot for guests to enjoy the serene landscape.

Villa in Monsummano Terme

4.98 out of 5 average rating, 133 reviews

Le Maggioline Your Tuscany country house

A spacious dining area is featured with a long table set for a meal. Natural light enters through arched openings, illuminating the rustic stone walls and wooden beams. Extra seating and decorative elements create a warm, inviting environment for shared meals.

Villa in San Giovanni d'Asso

4.94 out of 5 average rating, 78 reviews

Villa "La memoria del tempo "

Top guest favorite

A cozy living area is characterized by terracotta tiled flooring and exposed wooden ceiling beams. A large brick fireplace serves as a focal point, surrounded by comfortable seating and decorative artwork. Natural light fills the room through a window, complemented by colorful wall decors.

4.93 out of 5 average rating, 82 reviews

Villa "La Scuola" "The Charming School"

A shaded dining area is presented under a canopy, featuring a large table set for meals. In the background, a private swimming pool is visible, with sun loungers placed nearby and olive trees dotting the landscape beyond.

Villa in San Donato

4.95 out of 5 average rating, 88 reviews

Casa Colombaia, in the Chiantishire

A dining table is set outdoors, surrounded by olive trees. It features white plates, glasses filled with red wine, and a selection of cheese. In the background, sweeping views of the Valdichiana and the medieval village of Scrofiano are visible under a partly cloudy sky.

Villa in Scrofiano

4.87 out of 5 average rating, 100 reviews

SacroFanum Villa

Destinations to explore