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Apartment holiday rentals in Gaiole in Chianti

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Quick stats about apartment rentals in Gaiole in Chianti

  • Total holiday rentals

    Explore 20 holiday rentals in Gaiole in Chianti

  • Nightly prices starting at

    Gaiole in Chianti holiday rentals start at $86 AUD per night before taxes and fees

  • Verified guest reviews

    Over 570 verified reviews to help you choose

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Wi-Fi availability

    10 of Gaiole in Chianti holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Gaiole in Chianti rentals

  • 4.7 Average rating

    Gaiole in Chianti stays receive an average rating of 4.7 out of 5 from guests

Top-rated apartment rentals in Gaiole in Chianti

Guests agree: These apartments are highly rated for location, cleanliness and more.

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Top Guest favourite
A modern dining area features a large wooden table surrounded by sleek black chairs, with expansive glass walls offering views of the surrounding hills and city. The space is well-lit by hanging pendant lights, creating a bright and inviting environment.
Apartment in Florence

Rooftop with Breathtaking Views. Short Walk to The Duomo.

Climb the white marble staircase to the breathtaking rooftop terrace, boasting unforgettable views of the hills surrounding Florence and the historic center. This apartment has been newly renovated, mixing different kinds of architecture and design. In the flat there is plenty of space for your smart-workstation: internet is fast and reliable, accessible from every corner. We take particular care in sanitizing all the critical areas, in particular the space is sanitized by means of ozone generators. The apartment is newly restyled with a very special taste, mixing different styles in the architecture and design. It is a 2 floors apartment at the last floor of a mid 20th century building right outside the historical city center: at the first floor there are the bedrooms (a Suite and a second bedroom) the bathroom and a wardrobe room. The Suite is introduced by an elegant living area with a separè industry in glass and iron dividing it from the double bedroom with balcony and fireplace. The second bedroom has a big wardrobe with mirrors, a fine couch and twin beds to be disposed at one's will. Through an elegant white marble staircase we have access to the brand new rooftop kitchen and the wide terrace with a view on the hills sorrounding Florence and spots of the old buildings of the historic center. The apartment is entirely reserved to our guests, access to it is by the staircase or by elevator with private access to the floor. The rooftop terrace is only for our guests with sole access from inside the apartment by a staircase. At the same floor in a separate flat live the owners, always ready to help! The owner lives next door and is always available if needed. Chez Geraldine is an apartment just outside the historical center. It’s predominantly a residential district, but the cathedral, Galleria dell'Accademia, and Piazza San Marco are a 15-minute walk away. Food stores, restaurants, and bars are close by. AVAILABLE 4 BIKES (adult size) for our guests, included in the price. Please, use it with care and lock it well each and any time you leave them without custody, thank you. IN CASE OF THEFT OR SEVERE DAMAGE DUE TO NEGLIGENCE YOU WILL BE REQUESTED TO PAY THE VALUE OF THE BIKE OF 160€. Thank you WALKING: the city center is at only 15 mins walking. BY BUS: a few steps away from the building there are buses to the city center and the station.

LocationFamilyAccess

4.96 out of 5 average rating, 399 reviews
Top Guest favourite
The elegantly structured Villa di Geggiano is set amidst lush vineyards and well-maintained gardens. Its classic stone facade and terracotta roof harmonize with the surrounding greenery, while neatly manicured pathways and symmetrical garden beds create a picturesque landscape under a partly cloudy sky.
Apartment in Siena

Villa di Geggiano - Alfieri Suite

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.

ValueFamilyQuiet

4.99 out of 5 average rating, 169 reviews
Top Guest favourite
Aerial view of the agriturismo Santa Lucia, showcasing well-maintained grounds surrounded by lush greenery and neatly lined cypress trees. A shared swimming pool is visible at the center, complementing the rustic charm of the old farmhouse and the rolling hills in the background.
Apartment in Asciano

Appartamento Loggiato 2 in toscana con piscina

L'appartamento Loggiato 2 per 2 persone si trova nell'agriturismo Santa Lucia (L'AGRITURISMO è DIVISO IN 7 APPARTAMENTI) nelle Crete Senesi vicino Siena ed è un bilocale situato al primo piano con tavolino privato dinanzi alle vetrate del loggiato d'ingresso. Ci sono una camera matrimoniale (due letti singoli uniti per formare un letto matrimoniale), bagno con doccia e soggiorno con cucina funzionale e televisione. L' APPARTAMENTO HA L'ARIA CONDIZIONATA nella camera ( A PAGAMENTO ).

FamilyLocationQuiet

4.94 out of 5 average rating, 162 reviews
Guest favourite
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.
Apartment in Gaiole in Chianti

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)

ValueLocationSleep quality

4.88 out of 5 average rating, 154 reviews
Top Guest favourite
A serene garden area is visible, featuring two wooden lounge chairs positioned on lush green grass. Surrounding plants and flowers add a touch of color. The stone house in the background features multiple windows, framed by greenery and terracotta pots.
Apartment in Villa A Sesta

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).

FamilyLocationShared spaces

4.94 out of 5 average rating, 245 reviews
Top Guest favourite
The lounge features elegant walls adorned with intricate frescoes and moldings. A large mirror reflects the refined decor. Two white armchairs and a colorful sofa provide seating, while a coffee table rests on a patterned rug before a decorative fireplace.
Apartment in Siena

Luxury frescoed apartment in the historical center

The Palazzo Pannilini Superior apartment is composed of a bright entrance enriched by an elegant coffered ceiling, a large fully frescoed lounge, a large foyer, a kitchen equipped with a terrace, a dining room topped with a frescoed vault, four bedrooms, three bathrooms, a wardrobe room, and a panoramic terrace where you can sunbathe and relax. The apartment is located at the second floor with no elevator. The apartment has air conditioning.

LocationValueBathroom

4.97 out of 5 average rating, 117 reviews
Top Guest favourite
An aerial view reveals the rustic stone farmhouse surrounded by lush greenery and vineyards. The inviting pool is set within a well-maintained garden, complemented by outdoor seating and barbecue areas, offering a peaceful retreat in the heart of the Tuscan countryside.
Apartment in Gavignano

Poggio Massiccioli

Accogliente appartamento per 4 persone arredato in stile toscano e con travi a vista immerso tra le dolci colline della campagna toscana. A disposizione degli ospiti giardino attrezzato,wi-fi gratuita,piscina condivisa attrezzata,forno a legna e barbecue,lavatrice. L'appartamento è stato ricavato da una graziosa casa colonica in pietra del 1800 recentemente ristrutturata secondo la tradizione toscana e suddivisa in tre comodi appartamenti.

FamilyValueAmenities

4.92 out of 5 average rating, 391 reviews
Guest favourite
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.
Apartment in Monteroni d'Arbia

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..).

LocationFamilyHot tub

4.94 out of 5 average rating, 288 reviews
Top Guest favourite
An outdoor pool area is surrounded by olive trees and vineyards, with sun loungers and shaded umbrellas arranged on the deck. Soft sunlight bathes the scene, highlighting the peaceful setting. A gravel path leads around the pool, inviting relaxation amid the natural landscape.
Apartment in Monteriggioni

Comfort Apartment tra i vigneti del Chianti

Appartamento al piano superiore della struttura caratterizzato da una vista meravigliosa sulle colline del Chianti, uliveti o sul patio. Ristrutturato mantenendo il fascino delle loro antiche mura ma aggiungendo ogni comfort. Comprende soggiorno, angolo cottura, una camera da letto matrimoniale, un bagno privato con doccia, aria condizionata.

FamilyValueLong stay

4.93 out of 5 average rating, 455 reviews
Top Guest favourite
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 | Chianti Hills Vineyard Retreat

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.

FamilyLocationAccuracy

4.98 out of 5 average rating, 130 reviews
Top Guest favourite
A balcony provides a scenic view of Piazza del Campo, showcasing the surrounding historic buildings. A small table and chair invite relaxation, while the colorful sunset casts a warm glow over the area, highlighting the lively atmosphere with people enjoying the space below.
Apartment in Siena

A BALCONY ON THE PIAZZA OF THE PALIO

Three windows with balcony overlooking Piazza del Campo that allows access to an exclusive terrace with breathtaking views of the Piazza del Palio and the Palazzo Pubblico. One bedroom, large super-equipped kitchen. Sofa bed available to comfortably accommodate up to 4 people

LocationFamilyGetting around

4.87 out of 5 average rating, 271 reviews
Top Guest favourite
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.
Apartment in Poggibonsi

APPARTAMENTO ULIVO - CHIANTI

Grazioso appartamento in magnifica posizione collinare nel Chianti a metà strada tra Firenze e Siena da cui è possibile raggiungere e visitare le città d'arte e i borghi più suggestivi della Toscana.

LocationFamilyNearby

4.98 out of 5 average rating, 282 reviews

Popular amenities for Gaiole in Chianti apartment rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Weekly apartment rentals

Top Guest favourite
A spacious terrace is shown, featuring comfortable seating arrangements, including lounge chairs and a small dining table. The area is partially shaded by awnings, with a view of the surrounding landscape. A table is set with fresh strawberries and beverages, inviting relaxation.
Apartment in Siena

Terrazza sulle mura di Siena- Casa Laura

LocationValueGetting around

5.0 out of 5 average rating, 110 reviews
Guest favourite
An outdoor terrace offers seating for four, featuring a table and chairs. The view captures the skyline illuminated against a twilight backdrop, showcasing notable landmarks such as the Torre del Mangia and the Duomo in the distance.
Apartment in Siena

Terrace with a view of Siena

LocationValueAccess

4.87 out of 5 average rating, 203 reviews
Guest favourite
A bright and airy seating area features large glass windows that frame an impressive view of the Duomo and the surrounding cityscape. Potted plants and a lamp add subtle touches to the space, while a comfortable chair invites relaxation.
Apartment in San Marco

The house of Love

ValueFamilyIndoor spaces

4.85 out of 5 average rating, 387 reviews
Guest favourite
The private terrace reveals a panoramic view of the Duomo and the city skyline. Modern lounge seating and a spacious day bed are arranged for relaxation. The entrance to the penthouse is visible, showcasing a contemporary design with clean lines and large windows.
Apartment in Centro

Enjoy a Boutique Penthouse Near the Duomo

FamilyValueCheckout

4.98 out of 5 average rating, 286 reviews
Guest favourite
A serene pool area is highlighted by lounge chairs set along a stone terrace. The water reflects a golden sunset, providing a tranquil atmosphere. Surrounding greenery adds to the natural beauty, creating a peaceful environment for relaxation.
Apartment in La Presura

Countryhouse 9 kms to Florence-3+2,free park, wine

FamilyLocationIndoor spaces

4.86 out of 5 average rating, 275 reviews
Guest favourite
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.
Apartment in Radda in Chianti

La Capannina del Chianti

LocationFamilyBiking

4.96 out of 5 average rating, 67 reviews
Guest favourite
Apartment in Cavriglia

Apartment Comfort | Quiet Escape in Tuscany

ValueFamilyIndoor spaces

4.93 out of 5 average rating, 60 reviews
Top Guest favourite
A panoramic view reveals rolling hills adorned with vineyards and olive groves, stretching under a dramatic sky. The tan-coloured buildings of the property are nestled among lush greenery, while a serene pool reflects the surrounding landscape.
Apartment in Quercegrossa

Tuscany jem: La Casa del Fattore del Chianti

FamilyLocationBreakfast

4.98 out of 5 average rating, 89 reviews

Private apartment rentals

Guest favourite
Apartment in Asciano

Incredible Views & Pool in the Tuscan Hills

FamilyLocationAccess

4.85 out of 5 average rating, 26 reviews
Superhost
A sunny terrace garden is visible, surrounded by flowering plants and greenery. A table is set for dining, with chairs arranged nearby, all overlooking the picturesque hills of Tuscany and the town of Gaiole in the distance.
Apartment in Gaiole in Chianti

Casacorvo Maggiore at Borgo Gaiole

FamilyLocationLaundry

5.0 out of 5 average rating, 4 reviews
Top Guest favourite
Apartment in Pogi

Borgo Iesolana Country Retreat Suite with terrace

FamilyLocationAccuracy

5.0 out of 5 average rating, 36 reviews
Guest favourite
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.
Apartment in Gaiole in Chianti

Idyllic with shared pool in the heart of Chianti

LocationValueWalkability

4.82 out of 5 average rating, 28 reviews
Guest favourite
A well-equipped kitchen features wooden cabinetry and exposed beams. Copper pots are hung on a rack, complementing tile countertops. A doorway opens to outdoor views, allowing natural light to illuminate the space.
Apartment in Castellina in Chianti

Appartamento T4

LocationFamilyGetting around

4.87 out of 5 average rating, 79 reviews
Guest favourite
Apartment in Siena

Pool Escape Just Outside Siena

FamilyLocationGetting around

4.95 out of 5 average rating, 21 reviews
Guest favourite
An outdoor patio area is displayed, featuring a shaded seating space with a table and chairs. Potted plants enhance the green surroundings, while a rustic stone building serves as the backdrop. A large clay pot is positioned on the lawn, contributing to the garden's charm.
Apartment in Montebenichi

Agriturismo I Moraioli app. Parata

FamilyLocationNearby

5.0 out of 5 average rating, 21 reviews
Guest favourite
Apartment in Radda in Chianti

La Terrazza

FamilyLocationGetting around

4.89 out of 5 average rating, 38 reviews

Apartment rentals with a hot tub

Guest favourite
A rectangular swimming pool with a shallow and deep end is surrounded by a stone patio and lush greenery. A villa sits on a hillside in the background, featuring a terrace with windows and shutters. Poolside lights are placed around the pool for evening ambiance.
Apartment in Siena

Villa’Colombaiolo di Marciano',28

LocationFamilySleep quality

4.91 out of 5 average rating, 149 reviews
Superhost
Apartment in Florence

Healthy Home | Duomo • Jacuzzi & Green Oasis

ValueLocationKitchen

4.89 out of 5 average rating, 102 reviews
Top Guest favourite
An expansive terrace features a large table surrounded by black chairs, offering a panoramic view of the city. Bright green lounge chairs provide a spot for relaxation. Decorative tiles enhance the visual appeal against a backdrop of historic architecture and blue skies.
Apartment in Florence

At the top faboulous terrace Florence

ValueLocationRiver

4.83 out of 5 average rating, 166 reviews
Superhost
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

LocationValueBiking

4.88 out of 5 average rating, 105 reviews
Guest favourite
A serene garden scene features a table set with a floral-patterned teapot and matching cups. Lush greenery surrounds the area, with terracotta pots and vibrant flowers enhancing the natural setting. The space is bathed in soft sunlight, providing a tranquil outdoor retreat.
Apartment in Florence

Apartment with garden and parking

LocationValueWalkability

4.89 out of 5 average rating, 371 reviews
Top Guest favourite
A living area is presented with a light-colored sofa and a glass coffee table on a patterned rug. Walls are adorned with framed artwork, and a large television is positioned in a wooden cabinet. Double doors lead to an outdoor space, enhancing natural light.
Apartment in Florence

Fully renovated exclusive apartment in Villa

ValueFamilyAccuracy

4.99 out of 5 average rating, 102 reviews
Top Guest favourite
The living area features a stylish design with a dark gray sofa and two deep red armchairs. A round glass table sits on a marble floor, enhanced by natural light from the two windows with light curtains. A decorative mirror and elegant light fixtures adorn the walls.
Apartment in Siena

Domus Nannini - L' Arco di Matteotti Spa

ValueLocationWi-Fi

4.98 out of 5 average rating, 107 reviews
Superhost
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.
Apartment in Santo Spirito

.2 La Casa sui Tetti dell'Oltrarno

ValueLocationIndoor spaces

4.79 out of 5 average rating, 797 reviews

Destinations to explore