Apartment vacation rentals in Gaiole in Chianti

Apartment in Montepulciano

An inviting interior features exposed brick walls and a blend of modern and rustic design elements. A staircase leads to the upper floor, while large doors open to reveal a view of the outdoors. A wooden table and a cozy chair enhance the living space.

4.97 out of 5 average rating, 119 reviews

Under the sunset, Montepulciano

In 2023 my son Guglielmo and I decided to restore the old oratory of a church from the 1600s by creating a two floor apartment: upstairs we have 2 bedrooms equipped with AC and 2 en-suite bathrooms with shower; downstairs a spacious living room with stereo Available a table outside with great view and a nice garden 50 mt away where to have a private wine tasting for all the guests of our 4 apartments We can organize barbecue with paired wines after 7 pm. Large free parking area 100 mt away

4.96 out of 5 average rating, 226 reviews

A rustic dining area features a long wooden table set with linens and decorative items. The space is illuminated by a chandelier and has large windows offering views of the surrounding landscape, with a stone fireplace and traditional frescoes adorning the walls.

Apartment in Carmignano

Giglio Blu Loft di Charme

The accommodation is a portion of a historical noble residence dating back to the 14th century, adorned with frescoes and tastefully restored. It is located on the ground floor of a quiet and safe street, with a private and independent entrance and self check-in. The space is cozy, comfortable, and elegant, perfect for guests seeking an authentic Tuscan experience with modern comfort and technology. It is situated just a few kilometers away from Florence, Pisa, Lucca, Vinci, San Gimignano...

The rustic exterior of the stone cottage features a traditional red-tiled roof and large arched windows. Lush greenery and flowering plants surround the building, while the rolling hills of Tuscany are visible in the background under a clear sky.

4.91 out of 5 average rating, 105 reviews

Cottage San Martino con ampia terrazza panoramica

Appartamento di 45 mq a San Martino ai colli, situato lungo la via Cassia e circondato dalla bella campagna toscana. Perfetto per chi ha voglia di visitare le attrazioni della zona: San Gimignano, Monteriggioni, il Chianti, Siena (20 min.), Firenze (30 min.), Volterra (40 min.). A 2 minuti dal raccordo autostradale Firenze-Siena e vicino al centro urbano di Poggibonsi e Barberino-Tavarnelle. La casa è dotata di un'ampia terrazza dove potersi rilassare e ammirare le colline del Chianti.

A scenic view captures a lush landscape with rolling hills, vineyards, and olive trees under a colorful sunset. The traditional Tuscan casolare is visible in the background, surrounded by greenery, while the horizon features soft hues of orange and pink.

4.99 out of 5 average rating, 297 reviews

Laura Chianti Vacanze

Laura Chianti Vacanze è la soluzione ideale per chi cerca pace e tranquillità immerso nelle campagne del Chianti. L'appartamento, a metà strada tra Firenze e Siena, si trova in una posizione strategica per raggiungere velocemente Firenze, Siena, San Gimignano , Volterra, nonché le meravigliose colline del Chianti. L'appartamento dispone di ampio parcheggio privato, due camere, cucina attrezzata, bagno privato, giardino privato, barbecue, ed una stupenda vista sulle colline del Chianti.

Apartment in Castellina in Chianti

A heated pool is surrounded by lush greenery, offering scenic views of the rolling hills. The pool's clear water reflects the sky, while a fenced area provides safety. Flowering plants are positioned along the edges, enhancing the natural beauty of the setting.

4.95 out of 5 average rating, 185 reviews

Visit Chianti,Siena, Florence, S.Gimignano

Apartment into Borgo Sicelle Residence, in Castellina inChianti area (between Florence, Siena, S.Gimignano). Two people. It has a kitchen, a double bedroom, a bathroom with shower. It's on the first floor. Outside, on the ground floor,there are shared tables. Pool heated up to25 degrees in Spring and Autumn In front of the property there is a restaurant (Osteria Uscio e Bottega), only for dinner, closed on Wed. There is no public transport to reach the property Car is required

Apartment in Gaiole in Chianti

A well-equipped kitchen area features light cream cabinetry and modern appliances. A wooden dining table is surrounded by white chairs, with a centerpiece of flowers. Natural light filters through the sheer curtains of the window, enhancing the inviting ambiance of the space.

4.88 out of 5 average rating, 129 reviews

Casa Martini nel Chianti Storico

Appartamento con giardino e parcheggio privato a Gaiole in Chianti, a due passi dal centro storico dove troverete numerosi bar ristoranti ed il piccolo supermercato ( coop). l'alloggio è ideale per vacanze con animali perché è dotato di un giardino tutto recintato. Viene richiesta la tassa di soggiorno ( 2 euro a persona a notte per le prime sette notti) minori di 14 anni esclusi ( leggi regolamento completo nel sito internet del Comune di Gaiole in Chianti)

Apartment in Villa a Sesta

The charming stone facade of the historic building is complemented by large green shutters and terracotta pots filled with vibrant plants. Sunlight illuminates the outdoor area, highlighting the welcoming entrance surrounded by steps and a spacious patio.

4.93 out of 5 average rating, 224 reviews

Da Paola nel Chianti

Il mio appartamento è situato nel borgo di Villa a sesta, al pian terreno con accesso diretto al giardino, dispone di due camere, una matrimoniale , l'altra con letti a castello, due bagni, un ampia cucina e un soggiorno. lo spazio esterno è molto grande e il giardino dispone di un grande tavolo e poltrone per il relax, l'auto potrà essere parcheggiata a casa, abbiamo il posto auto privato, arrivati in paese si accede a casa da una piccola strada bianca (30mt).

Apartment in Castelnuovo Berardenga

A historic villa is situated amidst lush, rolling hills, surrounded by vineyards. The exterior features a traditional stone facade, large windows, and terracotta roof tiles. Manicured gardens with circular patterns enhance the property's charm, complemented by tall cypress trees framing the serene landscape.

4.93 out of 5 average rating, 167 reviews

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.

4.94 out of 5 average rating, 183 reviews

A serene outdoor area features a swimming pool surrounded by landscaped gardens. A wooden deck with seating overlooks the pool, while a large umbrella provides shade. The two-story villa is positioned above, framed by vibrant greenery and a clear blue sky.

Apartment in Carpineto

Campagna Toscana, pace e relax a 10 min da Siena

Il nostro alloggio è vicino a Siena, quindi alla vita notturna, al centro città ma anche al piccolo aeroporto di Ampugnano, ai parchi, e al trasporto pubblico. Vi piacerà il nostro alloggio per la luce, la comodità del letto, la cucina, l'intimità e i soffitti alti. Il nostro alloggio è adatto a coppie, avventurieri solitari, a chi viaggia per lavoro, alle famiglie (con bambini) e amici pelosi (animali domestici).

Apartment in Monteroni d'Arbia

An outdoor dining area is surrounded by lush greenery and flowering plants, featuring a circular table with four elegant wrought iron chairs. A cozy blanket is draped over one chair, and a scenic view of rolling hills extends in the background under a muted sky.

4.95 out of 5 average rating, 263 reviews

Appartamento "Red Rose" con vista su Siena.

Caggiolo è un podere completamente ristrutturato composto da più appartamenti, ognuno con ingresso indipendente e giardino privato, con vista panoramica su Siena. Situato alle Ville di Corsano, a soli 14 km dalla città. Luogo ideale per trascorrere giorni in totale relax e godere delle meraviglie che questa zona offre (Chianti, Val d'Orcia, Crete Senesi..).

4.98 out of 5 average rating, 105 reviews

A welcoming entryway features a mural depicting a serene landscape framed by arches. Built-in shelves display decorative items and books. Natural light illuminates the wood flooring, while a small globe and a vase with dried plants add subtle warmth to the space.

Apartment in San Gusmè

Casa Guardiavigna in Chianti

L appartamento Casa Guardiavigna offre la possibilita’ di vivere un esperienza unica e straordinaria, carica di emozioni e di felicita’. Situato a due passi dal piccolo borgo medievale di San Gusme’ e’ circondato da splendide vigne, boschi e prati fioriti. Parcheggio gratuito interno con cancello automatico.

4.97 out of 5 average rating, 153 reviews

The open-plan living area features a modern kitchen with sleek cabinetry and a dining table with metal chairs. A red sofa adds a pop of color. Natural light enters through the window, illuminating the space and showcasing the neutral-toned walls and ceiling beams.

Apartment in Cavriglia

SOPRA LA BRUMA locazione turistica

Situato alle porte del CHIANTI, in un piccolo borgo medioevale, l'appartamento è stato recentemente ristrutturato in stile moderno. Gode di un'ampia vista sulle verdi colline toscane, silenzioso e confortevole è l'ideale per una vacanza rilassante.

Popular amenities for Gaiole in Chianti apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

4.95 out of 5 average rating, 104 reviews

A spacious living room features intricate wall decorations and a chandelier overhead. Elegant wooden furniture is arranged thoughtfully, including a dining table with chairs and a display cabinet. Large windows allow natural light to fill the room, enhancing the rich colors of the decor.

Apartment in San Marco

Historical mansion in Florence with garden

A cozy living room features two reclined leather chairs and a wooden table, complemented by a decorative rug. A rustic fireplace is positioned against a wall, and framed artworks adorn the space. Natural light streams through two wooden windows, enhancing the warm ambiance.

5 out of 5 average rating, 122 reviews

Villa Mocarello " IL LECCIO"

Apartment in Radda in Chianti

An inviting living area features a wooden door, a round table with a potted plant, and a warm-toned rug. Walls are lined with shelves and artwork, while a backdrop displays a modern kitchen and a spacious archway leading to additional living spaces.

4.92 out of 5 average rating, 96 reviews

La Casina

A scenic view of the surrounding countryside presents rolling hills and lush vineyards. Colorful flowers and greenery frame the pathway leading towards the entrance, under a partly cloudy sky that allows for ample sunlight.

4.97 out of 5 average rating, 263 reviews

APPARTAMENTO ULIVO - CHIANTI

Apartment in San Gimignano

The open-plan living area features wooden beams across the ceiling. Natural light filters through multiple windows, illuminating the cozy seating and dining areas. A rustic stone wall adds character, while a wooden table and light-colored chairs provide a functional dining space.

4.97 out of 5 average rating, 237 reviews

Casa Irene

A panoramic view showcases the charming rooftops of the city, with terracotta tiles and historic buildings. The Torre del Mangia stands prominently in the background, alongside lush greenery and the distant valley. The cloudy sky adds depth to this serene urban landscape.

4.96 out of 5 average rating, 379 reviews

La terrazza sui tetti

4.89 out of 5 average rating, 332 reviews

The expansive view of rolling hills is captured under a dynamic sky filled with scattered clouds. The lush greenery contrasts with the golden fields, creating a serene landscape. In the foreground, the garden area is surrounded by rustic pathways and trees, enhancing the natural setting.

Apartment in Asciano

Podere Le Splandole - Crete Senesi

Apartment in Montepulciano

A small wooden table set for two is adorned with fine china cups and a delicate flower vase. The balcony offers a panoramic view of the rolling hills, as the sun sets, casting warm hues over the landscape.

4.93 out of 5 average rating, 236 reviews

I Tramonti di Eramo , Montepulciano centro.

Private apartment rentals

4.88 out of 5 average rating, 8 reviews

A modern kitchen is shown with sleek cabinetry and an oven beneath a spacious window. Natural light floods the area, illuminating a wooden dining table paired with two chairs. Exposed wooden beams add character to the ceiling, contrasting with the warm tiled floor.

Apartment in Galenda

Apartment Lippi

4.91 out of 5 average rating, 68 reviews

An outdoor terrace is highlighted by a wooden ceiling, featuring a dining table set for six and comfortable seating arrangements. Lush vineyard views extend beyond the railing, complemented by greenery. Subtle outdoor lighting enhances the space, creating an inviting area for relaxation and dining.

Apartment in Bossi

Villino Ersilia, il fascino del Chianti

Apartment in Gaiole in Chianti

A shared pool is featured in the foreground, surrounded by stone buildings with a rustic appearance. Guests are seen enjoying the water and sunbathing on the deck. Lush hills are visible in the background, providing a natural and serene setting.

4.81 out of 5 average rating, 26 reviews

Idyllic with shared pool in the heart of Chianti

Apartment in San Gimignano

An open-concept living area is presented, featuring a hanging chair and stylish black furnishings. Arched doorways lead to the dining space, which is brightened by natural light. Potted plants add greenery to the environment, alongside a cozy rug on the tiled floor.

4.98 out of 5 average rating, 59 reviews

Herons Superior Apartment - Splendid view!

Two sun loungers are positioned on a well-maintained green lawn under a white umbrella. In the background, a stone building is visible, accompanied by potted plants and trees, creating a serene outdoor space.

4.94 out of 5 average rating, 104 reviews

Suite Il Tinaio. A former cellar

5 out of 5 average rating, 14 reviews

An open space layout is showcased, featuring a cozy living area with a light grey sofa and decorative cushions. The kitchen, equipped with modern appliances, transitions into a dining area with a table surrounded by chairs. Natural light floods in through a large window.

Apartment in Cavriglia

Appartamento Cantuccio e VinSanto

Apartment in Radda in Chianti

A serene bedroom features two single beds that can be combined into a double, complemented by soft pillows and warm bedding. Natural light filters through the window, adorned with patterned curtains. Rustic decor includes wooden accents and artwork on the walls, enhancing the inviting atmosphere.

5 out of 5 average rating, 40 reviews

La Capannina del Chianti

4.97 out of 5 average rating, 91 reviews

An aerial view showcases the agriturismo, surrounded by rolling hills and lush fields. The landscaped grounds encapsulate a central building with a pool, bordered by neatly arranged cypress trees leading towards the property. The tranquil natural setting emphasizes a peaceful rural atmosphere.

Apartment in Asciano

Alloggio Melograno nelle colline senesi in Toscana

Apartment rentals with a hot tub

4.96 out of 5 average rating, 101 reviews

A modern kitchen area is featured, complete with sleek cabinets and a dining table for four. A Smart TV with Netflix is positioned in the corner, while large windows provide natural light. The marble floor adds an elegant touch to the space.

Apartment in Rifredi

Iris apartment [5 min centro] Suite con Jacuzzi

4.93 out of 5 average rating, 420 reviews

An outdoor terrace features a small wooden table with two chairs, adorned with potted pink flowers. Lanterns with candles provide ambient lighting. In the background, a clock tower is visible against a bright blue sky, framed by historic rooftops.

Apartment in Centro

Casa Gori - Palazzo Vecchio - p.Za della Signoria

4.88 out of 5 average rating, 105 reviews

A sunlit outdoor area features comfortable lounge chairs in vibrant colors beside a hot tub. Olive trees and shrubs surround the space, providing a serene backdrop. A gentle slope of green grass continues toward distant hills, enhancing the tranquil atmosphere.

Apartment in Montevarchi

Apartment with garden in the heart of Tuscany

4.88 out of 5 average rating, 180 reviews

A view of Palazzo Vecchio is visible through an open window, framed by sheer curtains. The clock tower and architectural details of the building can be seen against a clear blue sky.

Apartment in Centro

Love Honeymoon Jacuzzi Piazza Signoria View Ac WiF

4.91 out of 5 average rating, 571 reviews

The luxurious bedroom features a stunning ceiling adorned with a captivating fresco. A spacious bed is placed in the center, accompanied by a state-of-the-art TV nearby. A hydromassage tub situated at the foot of the bed complements the elegant decor, with soft lighting and decorative elements enhancing the ambiance.

Apartment in Florence

Casa di Delizie - The Medici private leisure house

Apartment in Santo Spirito

An open living area is shown, featuring a spacious wooden dining table surrounded by light-colored chairs. The modern kitchen, equipped with sleek appliances, is visible in the background. The space is enhanced by wooden beams on the ceiling and a large window allowing natural light.

4.81 out of 5 average rating, 735 reviews

.2 La Casa sui Tetti dell'Oltrarno

4.94 out of 5 average rating, 123 reviews

Domus Nannini - L' Angolo di Paradiso Spa

The spacious living area features a dining table set for four, surrounded by wooden chairs. A cozy seating arrangement of two light-colored couches is visible, with decorative pillows. The elegant archway above connects the living space to the mezzanine, enhancing the open layout.