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Pet-friendly vacation rentals in Gaiole in Chianti

Find and book unique pet-friendly homes on Airbnb

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Popular amenities for Gaiole in Chianti pet-friendly home rentals

Pet-friendly house rentals

Top guest favorite
A charming pathway leads to the entrance of the house, surrounded by lush greenery. Flower pots are positioned along the stone walkway, with a seating area visible to the side, inviting guests to enjoy the serene landscape of rolling hills in the background.
Home in Greve in Chianti
5 out of 5 average rating, 150 reviews

Amore in Chianti

ManueleRating, 5 stars1 week ago
Non posso fare altro spendere buone parole per questa esperienza fantastica e complimentarmi con Riccardo per la gestione che riserva ai suoi clienti che tratta come fossero amici di vecchia data. Tutto perfetto..posizione ottimale a 10 minuti da Greve in Chianti,e circondato da aziende agricole e vigneti,ottima pulizia e alloggio molto molto particolare e curato nel dettaglio,sia all'interno che all'esterno dove si ha a disposizione il parcheggio coperto per la macchina e un grandissimo giardino che offre una visuale mozzafiato e panoramica sulla vallata. Riccardo disponibilissimo a chiarire ogni aspetto non solo riguardo la sua struttura ma anche di tutto ciò che lo circonda,pronto a consigliarvi e a darvi spiegazioni e indicazionii di ogni genere per rendere ottimale il vostro soggiorno. Quando tornerò da quelle parti passerò sicuramente a trovarlo.
Top guest favorite
Well-maintained gardens feature a lush lawn surrounded by mature trees, providing shade. An old stone building is visible in the background, characterized by arched windows and a terracotta roof. A shaded outdoor seating area, under a rustic wooden eave, adds to the inviting exterior.
Home in Figline e Incisa Valdarno
4.96 out of 5 average rating, 105 reviews

Torretta Apartment

DebbieRating, 5 stars4 days ago
I can not say enough about Alessandra and her amazing land! It was the most magical place we have ever been to. We are taking a 3 month trip, hitting up 21 cities in Europe and this is BY far the best! She was so kind and took us shopping and back to our train! She was always there when we needed her.thank you Alessandra we will see you next year!
Guest favorite
An outdoor area features a quaint seating arrangement with a small table and four chairs, nestled under the shade of a rustic covered porch. Surrounding planters hold vibrant flowers, and a brick well adds charm to the lush green lawn.
Home in Cerreto Guidi
4.95 out of 5 average rating, 474 reviews

Casa del Giardino

LoriRating, 5 stars3 weeks ago
My husband and I, plus our French Bulldog, had the pleasure of staying here for just over 3 weeks. Immediately felt like home, and host family had everything to do with that! Highly recommend. stunning views, fabulous location and some of the most gracious people I've ever met.
Top guest favorite
Home in Siena
4.99 out of 5 average rating, 178 reviews

Podere Piazza casa con vista panoramica

NicoleRating, 5 stars1 month ago
Can’t say enough about how great this house was! The views! The house is absolutely adorable! From a story book! Outdoor space was incredible! Loved making dinner in the kitchen (kinda made from local market which Sophia recommended which was amazing! I wish I could stay there for a week!!!
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
4.92 out of 5 average rating, 148 reviews

La Casa di Nada Home

GuillermoRating, 5 stars1 week ago
The main thing is Nada' s attention to every communication you sent, she responds the same day. Anything you asks for within reason, you get from Nada. It was a new experience for us in Tuscany but her property is combiniently located within 40 minutes to an hour and 30 from all the Tuscany turistic places.
Guest favorite
A shaded outdoor area features a table surrounded by several chairs on lush green grass. A reclining sculpture is visible in the background, alongside trees that provide dappled sunlight across the scene. Rolling hills are seen in the distance, enhancing the natural setting.
Home in Casole
4.78 out of 5 average rating, 146 reviews

House in Heart of chianti

MariRating, 5 stars1 day ago
We loved our stay in Pietro’s beautiful, unique and historical place. The house is charming, well-equipped and spacious, the scenery and view are stunning, and the peace of the mountains is soothing. The drive up the mountains is an experience too! Communication with Pietro was easy, fast and kind.
Guest favorite
A charming dining area is illuminated by natural light streaming through large glass doors. A round wooden table is set with a book and tea service, while a patio with seating and an umbrella is visible outside, surrounded by lush greenery.
Home in Certaldo
4.91 out of 5 average rating, 130 reviews

Paluffo Stillo House

LeahRating, 5 stars1 week ago
Don’t hesitate to book this beautiful Airbnb which was thoughtfully restored to reflect the history of the area. You won’t want to leave. We explored Certaldo Alto and Montefioralle- both amazing sites. The pool area was perfection and we couldn’t get enough of the landscape! Couldn’t stayed a week!!!
Top guest favorite
A rustic stone building is surrounded by green grass and vibrant flower pots filled with white and purple blooms. Tall cypress trees are visible in the background, under a clear blue sky, enhancing the peaceful Tuscan landscape.
Home in Castelnuovo Berardenga
4.91 out of 5 average rating, 199 reviews

Bed and Breakfast CASA CERNANO

IngeRating, 5 stars3 weeks ago
Wat een heerlijk verblijf! Een brandschone kamer met een heerlijk bed. De douche was ook fantastisch. Het contact met Catherina was zo ontzettend warm en gezellig! Wat een geweldig verblijf. Dankjewel!

Pet-friendly home rentals with a pool

Guest favorite
A serene outdoor space features a large, clear swimming pool surrounded by carefully manicured hedges and tall trees. The rustic stone house stands in the background, complemented by a few lounge chairs near the pool, offering a peaceful setting for relaxation.
Home in Cavriglia
4.93 out of 5 average rating, 80 reviews

Wonderful country house

MichaelRating, 5 stars2 days ago
We had a brilliant week at Jakob and Margit’s house. Margit was so friendly and helpful (and gave us some wine and fresh eggs!). The views from the gardens are incredible and having the swimming pool was perfect. The local area has lots of great vineyards to visit and the house is close to Florence/Siena/Arezzo for day trips. It had everything we needed like a washing machine etc.
Top guest favorite
A serene outdoor pool area is surrounded by well-maintained gardens, featuring lounge chairs and umbrellas for shade. The historic farmhouse is visible in the background, with trees and colorful flowering plants enhancing the landscape under a clear blue sky.
Apartment in Laviano
4.94 out of 5 average rating, 130 reviews

Farmhouse with swimming pool with wonderful view

BrianRating, 5 stars2 weeks ago
Si vous cherchez un endroit paisible avec une vue incroyable et une très belle piscine en plus n’hésitez pas à séjourner dans cet endroit magnifique. Plusieurs terrasses pour déjeuner/diner seul ou à plusieurs. Ce que nous avons aimé sont les rencontres avec les autres hôtes sur les terrasses ou autour de la piscine et de partager le couché de soleil ensemble à couper le souffle. Merci Flavio
Top guest favorite
The image displays a tranquil outdoor setting featuring a stone swimming pool surrounded by lush greenery. In the background, a historic tower rises among tall trees, while olive trees are seen in the foreground, enhancing the natural beauty of the landscape.
Castle in Montecatini Val di Cecina
4.99 out of 5 average rating, 116 reviews

Torre dei Belforti

CharlieRating, 5 stars4 days ago
This was an incredible and relaxing getaway—we honestly wish we had stayed longer. The tower is just as magical as the photos, and the views, olive grove, and pool were even better than expected. The surrounding town is darling and quiet, with just a couple of small restaurants and markets, which made it feel like a true escape. Luca was kind and responsive throughout our stay. Just a few things to note: there are a lot of stairs, and you’ll want a smaller car to navigate the narrow roads leading up to the tower. It’s a real castle, so it’s older and rustic—but full of charm and clearly loved. The only downside was that the hot tub on the roof no longer works, which was a bit of a letdown. Still, we absolutely loved our time here and would highly recommend it.
Top guest favorite
A serene bedroom space features a spacious bed adorned with soft, neutral-toned linens. Sheer white drapes create a cozy atmosphere, while the open doors offer a view of the lush outdoors, inviting natural light into the room.
Farm stay in Arezzo
4.97 out of 5 average rating, 230 reviews

Esplora la natura al centro di Vigneti Chianti

BaileyRating, 5 stars3 days ago
Staying at Agrigreen La Lama was hands down the best Airbnb experience I’ve ever had. From the moment we arrived, Rita welcomed us with such warmth and hospitality that we felt at home. The property is peaceful, beautifully maintained, and full of charm—surrounded by nature and the kind of quiet that soothes the soul. One of the most memorable parts of our stay was getting to cook in Rita’s own home, which she generously opened to us. It was such a unique and personal experience that made us feel truly connected to the space and the spirit of the farm. If you’re looking for a place to slow down, feel grounded, and enjoy genuine hospitality, Rita’s space is an absolute gem. I’m already looking forward to the day I can return.
Top guest favorite
A tranquil outdoor pool is surrounded by well-maintained gardens and olive trees. Sun loungers are positioned along the poolside, providing space for relaxation. The stone-clad building in the background complements the landscape, contributing to the serene environment.
Apartment in La Presura
4.93 out of 5 average rating, 145 reviews

Country house 9 km to Florence-2+1g,free parking

StephanieRating, 5 stars1 week ago
We will definitely be back! The location is about 30-40 minutes from the main city in Florence. Federico recommended we rent a car but we didn’t want to drive in an area we were unfamiliar with. We were provided with the bus schedule which was very easy to take to the city. We planned ahead and bought some groceries in Florence before heading back to the property. We got lucky with getting taxis at the property to eat at a nearby restaurant (Ristorante San Martino) but it wasn’t as convenient as getting one in Florence (had to wait a bit). The place was just as described, very relaxing and just what we wanted! All in all a great experience. We were so sad to leave!
Top guest favorite
A panoramic view of a bright swimming pool surrounded by a lush garden. Comfortable lounge chairs are arranged on the stone patio. Olive trees and shrubs create a natural backdrop, emphasizing the serene outdoor setting under a clear blue sky.
Farm stay in Loro Ciuffenna
4.99 out of 5 average rating, 106 reviews

Il Roseto: your Villa in Tuscan Countryside

ToniRating, 5 stars2 weeks ago
Odina was the perfect spot to relax. Beautiful and comfortable accommodation, wonderful dinners and great communication. Would definitely recommend Odina to people wanting to get away from the city and relax in the countryside.
Guest favorite
Home in Gaiole in Chianti
4.8 out of 5 average rating, 101 reviews

loft nel cuore del chianti toscano

Jean-CharlesRating, 5 stars1 month ago
Très bon séjour passé chez Giulia. Maison agréable et spacieuse. Bon emplacement pour découvrir le Chianti et ses chemins blancs.
Top guest favorite
Villa in San Leolino
4.99 out of 5 average rating, 108 reviews

Poggio del Fattore-Villa with pool,hilltop,Chianti

ElkeRating, 5 stars1 week ago
Unser Aufenthalt bei Marta und ihrer Familie hätte schöner nicht sein können. Wir haben uns vom ersten Moment absolut wohl gefühlt. Das Anwesen ist absolut weitläufig, liebevoll ausgestattet, unglaublich toll gepflegt und mit Liebe geführt. Marta und Ihre Familie sind absolut liebenswert und kümmern sich ganz reizend um ihre Gäste. Es werden einem alle Wünsche erfüllt. Der Pizza-Abend war ganz wunderbar und für uns ein gelungener Abschluss unseres Aufenthaltes. Wer traumhaftes, abgelegenes toskanisches Ambiente und liebevolle Gastgeber sucht ist in "Poggio del Fattore" genau richtig.

Private, pet-friendly home rentals

Guest favorite
A spacious bedroom features a large bed adorned with soft linens. Natural light enters through a window, complemented by warm lamplight. Stone walls and wooden beams add rustic charm. A dresser and side table provide functional decor, and framed images line the walls, enhancing the elegant atmosphere.
Apartment in Pogi
4.94 out of 5 average rating, 89 reviews

Borgo Iesolana Suite Superior

RobertRating, 5 stars2 weeks ago
5 Stars – A Tuscan Dream Come True! Our stay at Francesco’s private resort-style retreat in the hills of Tuscany was absolutely magical. The location is stunning—peaceful, picturesque, and the perfect escape into the beauty of the Italian countryside. The rustic room had so much charm and comfort, and the property itself was amazing, with not one but two beautiful pools to relax by. One of the highlights was the on-site restaurant. The free breakfast was far beyond the typical offering—not just muffins, but a full, authentic Italian breakfast that we looked forward to each morning. Dinner was just as impressive, showcasing delicious local flavors and warm hospitality. It was also a great jumping-off point for exploring the region—we took a lovely day trip to Siena with ease. This place is a hidden gem, and we’d return in a heartbeat. Highly recommended for anyone looking to experience the best of Tuscany!
Guest favorite
A serene bedroom features a spacious bed adorned with a patterned duvet. Natural light filters in through a window, which complements the rustic wooden beams overhead. A blue dresser is positioned nearby, while a sleek bathtub is softly illuminated in the corner.
Condo in Gaiole in Chianti
4.94 out of 5 average rating, 32 reviews

Transito Divino Gaiole

MatteoRating, 5 stars3 weeks ago
Appartamento curato, host disponibile... tutto molto bello! La chicca, la vasca idromassaggio. Consigliatissimo
Guest favorite
A rustic stone house stands with warm lighting illuminating its facade. The building features various window styles and a large, wooden front door. Lush green grass surrounds the property, and a friendly dog is seen resting nearby.
Home in Cavriglia
4.97 out of 5 average rating, 32 reviews

La Casa del Briga

TomRating, 5 stars1 week ago
Uno de los mejores lugares en los que nos hemos quedado y explicó porqué: Monia y su hija Giusy han sido muy amables, buenas anfitrionas y responden rápido. El lugar nos ha encantado: perfecto para desconectar y pasar rodeados por naturaleza en una casa grande, limpia y cómoda. Además, la casa ha venido muy bien abastecida, sobre todo la cocina: nos dejaron muchas cosas para desayunar y también para la cena, que nos alcanzó para más de un día sin tener que ir. hacer la compra del supermercado! También como padres valoramos mucho que la cuna para nuestra bebé haya sido de las de madera, con su colchón y todo, como en casa. No era una cuna de viaje, así que resultó súper cómodo para nuestra bebé. Asimismo, tenían un cambiador y trona, que nos vinieron genial. En una futura oportunidad, seguro repetiremos!
Guest favorite
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.
Apartment in Radda in Chianti
4.91 out of 5 average rating, 79 reviews

La Casina

StephanRating, 5 stars1 week ago
The stay at Paola’s place was great. It was clean, easy to get to by car, and has a small parking lot right next to the door. Everything was as described and Paola responded quickly. Would recommend! You should bring earplugs and be prepared for a slow internet connection. The WiFi is slow and sometimes breaks apart completely, while mobile service isn’t much better. So this is great for a digital detox.
Guest favorite
A rustic living area is showcased with exposed wooden beams and terracotta flooring. A floral sofa complements a wooden dining table surrounded by chairs. Natural light fills the space, highlighting a wall-mounted clock and framed artwork. An inviting atmosphere is created by the warm color palette.
Farm stay in Ville di Corsano
4.96 out of 5 average rating, 119 reviews

Archi, Appartamento rustico in Toscana

Jiayi (Loretta)Rating, 5 stars3 weeks ago
We had a great time staying at Sara's, the hosts are very friendly and kind. The house and the neighborhood are beautiful and quiet, we were able to relax. The apartment had everything we needed. Sara's father also gave us a tour to their museum, we absolutely loved it and great conversation together. Highly recommend!
Top guest favorite
A spacious bedroom features a double bed adorned with a yellow bedspread. Natural light floods in from wide glass doors leading to a balcony with views of the valley. A cozy seating area includes two armchairs and a small table, complemented by decorative curtains.
Apartment in Montepulciano
5 out of 5 average rating, 118 reviews

Stuart White Tea Central Panoramic & Garden

MarkRating, 5 stars4 weeks ago
My wife, brother-in-law, and I had an incredible time in Montepulciano, and Giacomo’s apartment was the perfect place from where we started out daily adventures, took afternoon naps, and then headed out for fantastic dinners. Giacomo’s apartment was excellent, making it easy to get settled after a long day of travel. Giacomo guided us into the temporary parking spot when we got lost for a few minutes, and was quick to assist with any questions we had during our stay. The restaurant recommendations were all excellent, as well as the other activities he suggested. We will definitely stay here again when we visit Montepulciano!
Top guest favorite
A charming stone villa is framed by lush greenery and tall trees. Natural stone pathways lead to the entrance, where wooden shutters are seen beside arched windows. Shadows from the surrounding foliage create a tranquil ambiance, reflecting the serene countryside setting.
Home in Radda in Chianti
5 out of 5 average rating, 20 reviews

Villa le Scope 5*

ColeRating, 5 stars1 week ago
Beautiful home. Extremely clean. Riccardo was extremely responsive and made our check in process very easy. Definitely would stay again!
Top guest favorite
The kitchen area features wooden cabinetry and modern appliances, including a microwave and coffee maker. A round wooden table with simple chairs is surrounded by natural light from large windows, offering views of the surrounding vineyards.
Farm stay in Greve in Chianti
4.98 out of 5 average rating, 58 reviews

Agriturismo Casa Giulia di Sopra

DarioRating, 5 stars2 weeks ago
What a great winery! The location is really unique, the accommodation is in the middle of the vineyard and very quiet. Alessandro our host was very nice, gave us a warm welcome and took a lot of time to show us everything (including the wines). We were also very happy with the accommodation, which was beautifully furnished and had everything we needed.

Quick stats about vacation rentals that are pet-friendly in Gaiole in Chianti

  • Total rentals

    20 properties

  • Nightly prices starting at

    G$12,539 GYD before taxes and fees

  • Total number of reviews

    520 reviews

  • Wifi availability

    10 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

  • Local attractions

    Comune Di Gaiole In Chianti, Castello di Spaltenna, and Osteria Al Ponte

Destinations to explore