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Vacation home rentals in Casentino

Find and book unique vacation home rentals on Airbnb

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Popular amenities for Casentino vacation home rentals

Family-friendly vacation home rentals

Guest favorite
A charming path winds through lush greenery, leading towards a rustic stone house surrounded by colorful flowers and vines. The scenic landscape features rolling hills and trees, creating a peaceful and inviting atmosphere for guests.
Vacation home in Cortona
4.98 out of 5 average rating, 46 reviews

La Pergola | Farm House with fantastic view

Rasmus RudRating, 5 stars11 months ago
Authentic working home with great views. Lovely location secluded and close to hiking route makes it nice to have a dog with you.
Guest favorite
A small living area features a wooden ceiling with exposed beams. A daybed adorned with patterned cushions sits against the wall. A vintage lamp provides soft illumination beside the daybed, accompanied by a decorative arrangement of sunflowers and a traditional area rug on the floor.
Vacation home in Cortona
4.87 out of 5 average rating, 260 reviews

Wonderful Casa Idilio Cortona

AnnaRating, 5 stars3 weeks ago
Perfectly located apartment in old town - with a gorgeous terrace to enjoy some peace outdoors. Simone was most helpful and kind with his instructions and brought me coffee for the moka when I asked was there any coffee. Excellent restaurants and bars nearby. It was a wonderful weekend medieval festival in Cortona - so memorable. Grazie
Guest favorite
An open living area features two red sofas and a round dining table surrounded by chairs. The space is illuminated by ceiling lights and natural light from windows. A wooden staircase leads to a loft area above, which includes a sleeping space.
Vacation home in Siena
4.85 out of 5 average rating, 78 reviews

"Lisa" apartment with fireplace

BerinRating, 5 stars3 weeks ago
The place is just breathtaking. Lisa was very sweet and had prepared us a little gift. I would definitely recommend! There are lovely dogs which we got used to so much 🥹🧡
Top guest favorite
A dining setup is presented on a terrace, featuring a neatly arranged table with glasses and plates. The scene is enhanced by a sunset that casts warm light over the surrounding hills and trees, creating a peaceful outdoor dining atmosphere.
Vacation home in Siena
4.97 out of 5 average rating, 60 reviews

Apartment in historic Villa in Siena_"LE CONTRADE"

PaulRating, 5 stars4 weeks ago
Located a long walk or very short (5 min) drive outside of Siena. Upon arrival, we had a little difficulty locating the apartment parking lot (small entrance off street), but once we knew where it was it was very easy after that. The apartment was wonderful, big for us, and cozy. Cristina was very communicative with us, and recommended many wineries and restaurants in Siena. We really enjoyed our stay and would stay here again.
Superhost
The exterior of a two-story terraced apartment features warm, rustic brickwork, a private terrace adorned with potted plants, and a wooden dining table surrounded by seating. Lush greenery and scenic hills are visible in the background under a clear blue sky.
Vacation home in Asciano
4.87 out of 5 average rating, 101 reviews

Charming home Crete Senesi

TaraRating, 5 stars1 week ago
We had the most wonderful time here, the host was very kind snd helpful, we even met a few of the neighbours, all really friendly and helpful. The views and peacefulness of this house/area made it so special. Waking up to birdsong and roosters everyday. Everything was perfect, thank you.
Superhost
A stone statue is positioned near a private pool, surrounded by greenery and flowering plants. The pool reflects the blue sky, while tall trees frame the view of the lush landscape beyond. The scene offers a serene atmosphere in a secluded outdoor space.
Vacation home in Arezzo
4.73 out of 5 average rating, 55 reviews

Ancient stone farmhouse with park and pool

SimonRating, 5 stars3 weeks ago
We had a fantastic stay at this beautiful villa in Tuscany. From the moment we arrived, the owner, Stella, made us feel so welcome – she was incredibly friendly and helpful throughout our stay. The villa itself was lovely, and the highlight for us (especially the children!) was the pool. It was perfectly maintained and cleaned daily, which made it a joy to use every day. The pool area could also be shut off when not used to keep the children safe. Stella also gave us some great local restaurant recommendations, all of which served amazing food at very reasonable prices – a real bonus! We did manage to walk out to a few restaurants. Overall, we had a wonderful experience and would absolutely recommend this villa to anyone looking for a relaxing and authentic stay in Tuscany. We would definitely love to return. Thanks for all your help Stella. 👍
Top guest favorite
A well-lit bedroom features a charming window with scenic views of the surrounding countryside. A wooden chair is positioned beside the window, enhancing the serene atmosphere. Warm light is provided by a bedside lamp and a larger ceiling fixture, complementing the rustic furnishings.
Vacation home in Poggibonsi
4.93 out of 5 average rating, 61 reviews

Il Casale di Villore, Poggibonsi, Siena, Tuscany, Cardisco Apt.

SteveRating, 5 stars3 weeks ago
We had a wonderful one-week-stay at Casale di Villore. The Airbnb is well located in a small town, 30 minutes away from Siena and 50 minutes from Florence. The accomodation has a welcoming tuscan-style interior and was well equiped for our stay. We were very happy to have stayed there and will certainly come back!
Superhost
A serene outdoor pool area features a rectangular swimming pool surrounded by wooden decking. Several lounge chairs are positioned nearby, along with a large umbrella for shade. Lush greenery and flowering plants enhance the tranquil atmosphere.
Vacation home in Siena
4.86 out of 5 average rating, 14 reviews

Borgo dei Fondi, Apt. Loggia

KimRating, 5 stars12 months ago
David and Vittoria take great care to ensure a positive experience at their beautiful Tuscany home. David welcomed us after our harrowing day in Pisa and we felt at ease and welcomed immediately. Borgo dei fondi is the quintessential Tuscany home, peaceful, beautiful, surrounded by nature, with relaxing and fun amenities like the pool, bbq and outdoor patio. It was the perfect place to come home to and relax after day trips to Florence and Siena and equally wonderful to just stay put for a day and enjoy the tranquility. We highly, highly recommend staying here.

Vacation home rentals with a patio

Top guest favorite
A sunlit outdoor area features wooden decking and lounge chairs, surrounded by trees and greenery. A gravel pathway enhances the natural setting, while the nearby building has large glass doors that provide access to the indoor space.
Vacation home in Greve in Chianti
4.91 out of 5 average rating, 53 reviews

Casa Canaiolo with mini-pool in the center of Greve

MaryRating, 5 stars2 days ago
Alessandro's is something truly special, a little piece of heaven. From the minute you arrive you are so well looked after (by Alessandro and Cristina), and the apartment is beautifully decorated/set up to feel right at home with everything you might need. Location is perfect: incredibly peaceful, but a couple of minutes away from everything, and the outdoor area totally luxurious for afternoons lazing around the pool in a stunning garden setting. Every morning I would take my coffee up the stairs to the top of the garden and sit with a view of the whole town as the sun came up. Alessandro looks after you in La Cantina, which is so welcoming and comes to feel like a second home. Beautiful hosts and an absolutely beautiful place to stay for a truly Tuscan experience.
Guest favorite
A bright bedroom features a spacious bed with light linens and a decorative throw. Natural light enters through open double windows, revealing a private terrace. A television and a small desk with a chair are present, while two bedside tables with lamps offer soft lighting.
Vacation home in Monteroni d'Arbia
4.91 out of 5 average rating, 74 reviews

White lily with a view of Siena

ShufanRating, 5 stars1 day ago
It’s a nice quiet rural place up in a hill. The bedrooms upstairs are more updated, comfortable and the kitchen downstairs is more outdated. Laundry machine and dishwasher are older, same as stove took some time to fully boil eggs like 25-30 minutes. But the location is great if you have a car to go around the places and a nice experience to stay in the area. There are no walkable groceries or restaurants so you need to plan ahead. The host communicates well and responds quickly, also flexible which is great for a more relaxing environment. Would definitely recommend if you would like to stay around Siena area.
Top guest favorite
A cozy living room features rustic stone walls and wooden beams overhead. Two armchairs with ornate upholstery and a coffee table sit centrally, while a lamp provides soft illumination. Large windows with wooden shutters allow natural light to enrich the space, which includes a fireplace in the background.
Vacation home in Umbertide
5 out of 5 average rating, 16 reviews

Casa Torre

JoannaRating, 5 stars8 months ago
We had a magical stay at this house! He surroundings are breathtaking and lots of space for my kids to run around and explore the natural beauty. We felt right at home in this house and it was the perfect base for us to go out exploring everyday. We can only hope to return on our future travels.
Superhost
A serene outdoor pool area is surrounded by lush greenery and tall cypress trees. Sun loungers and umbrellas provide shaded seating options, with a stone wall framing the space. The clear blue sky enhances the tranquil ambiance, creating a relaxing atmosphere for guests.
Vacation home in Ulignano
4.72 out of 5 average rating, 18 reviews

★ Relaxing apartment & stunning view of Tuscany ★

Anna-LenaRating, 5 stars10 months ago
We went there for the second time and it was just perfect as the first time. Diego's property is beautiful overlooking San Gimignano, it is quiet and very idyllic so you can really unwind. The apartment was great, is well equipped with everything you need. We felt very comfortable and would love to come a third time next year. Thanks to Giorgia for the good communication and flexible check-in.
Guest favorite
The exterior of a charming stone country house is displayed, surrounded by lush greenery. A well-maintained lawn leads to a terrace with a wooden table and chairs. Climbing plants adorn the facade, and large windows allow natural light to brighten the interior.
Vacation home in Certaldo
4.93 out of 5 average rating, 15 reviews

La Selva , Country house, 130 mq, Stunning views

LindaRating, 5 stars1 month ago
Staying with Carmine is top. We have been to Carmine and Alessandra in Certaldo for a month (mid-April / mid-May) and we can recommend that to everyone. Not only the reception ( in our case very late) was incredibly warm, but throughout our stay we felt very comfortable, this host is always open to questions, is proactive with giving information, tips about everything like where it is nice / tasty/ beautiful to visit. In addition, the house is very nice, it is great in the Tuscan hill country, between the wine and olive farmers, nice beds (we always find important especially if you are staying there longer) and really good Wi-Fi which was important for us to be able to work from here. The location is perfect. You are close to Florence, Siena, Pisa, and many special other villages/towns that are more than worth visiting. The month was over too soon! If we visit Tuscany again for sure with Carmine and Alessandra!
Guest favorite
A traditional kitchen features wooden beams on the ceiling and terracotta tiles on the floor. A rustic wooden table is surrounded by four chairs. Kitchenware is neatly arranged on shelves, and a large window offers natural light and scenic views.
Vacation home in Gaiole in Chianti
4.96 out of 5 average rating, 28 reviews

The Piccola Villa of Borgo Argenina

MeghanRating, 5 stars4 weeks ago
This was our favorite place we stayed in Italy and we went to three other locations. The view is unbeatable and so much to do nearby. We went to a few wineries and ate at Malborghetto (Highly recommend for an authentic experience and small town feel!). We hope to come back! Communication with hosts was great. amenities such as the pool, breakfast, the kitchen, were awesome. Thanks so much for a wonderful stay!
Guest favorite
A spacious room showcases a large bed against a backdrop of earthy tones and original brick ceilings. Natural light filters through a glass door leading to an outdoor space. A wooden table with a decorative vase is positioned nearby, and a well-equipped bathroom is visible in the background.
Vacation home in Bagno A Ripoli
4.91 out of 5 average rating, 35 reviews

Studio apartment in the hills near Florence

GreggRating, 5 stars4 days ago
A beautiful place to stay, very clean and Violetta is a gracious host. She provided excellent information about the local area. My mother was raised in Firenze, so we came many times to visit the family. I picked her place because it was close to where my last Italian family lives. And it's far enough from the touristy Firenze to me beautiful and quiet. Violetta even helped me find info on my cousin. What a beautiful stay! Come and enjoy this beautiful Tuscan hillside area!
Superhost
A spacious bed is presented with neatly arranged towels and a lit candle, creating a serene environment. Soft, peach-colored cushions add subtle warmth. Two bedside lamps provide gentle illumination, enhancing the cozy setting.
Vacation home in Florence
4.85 out of 5 average rating, 40 reviews

Apartment with garden

JeanRating, 5 stars1 week ago
Beautiful place! Very clean and spacious! About 30 min walk from the Duomo. Quiet neighborhood. We would definitely come back!

Vacation home rentals with a washer and dryer

Top guest favorite
Vacation home in Figline e Incisa Valdarno
5 out of 5 average rating, 43 reviews

Farmhouse in the countryside with swimming pool Solatìo

ArnoRating, 5 stars2 weeks ago
We absolutely loved our stay at Marco’s beautiful place! The apartment is stylish, comfortable, and fully equipped with everything you might need. The swimming pool and stunning views of the Tuscan countryside created the perfect setting to relax, read a book, or enjoy a glass of wine. What truly made our stay exceptional, though, was Marco himself—his warm personality and genuine hospitality made us feel incredibly welcome. We highly recommend staying at Marco’s and would love to come back someday!
Top guest favorite
The image captures a panoramic view of Florence at dusk, with the iconic dome of the Cathedral of Santa Maria del Fiore prominently displayed. The softly illuminated cityscape is framed by distant mountains and a winding river, creating a serene setting as evening approaches.
Vacation home in Florence
5 out of 5 average rating, 25 reviews

La Casina di Silvia (apartment with terrace), Florence

ShelbyRating, 5 stars4 weeks ago
Silvia’s place was super great. Very quiet safe neighborhood. Easy to get taxis into city center. But plenty of restaurants and bars near by. She was so helpful and even figured out a way to get me in when I forgot the keys. Quick to reply and so kind. Thank you for a great stay in Florence!
Guest favorite
A compact kitchen countertop is displayed, featuring a white espresso machine and a sleek black ventilation hood. Soft lighting illuminates the area, highlighting the natural wood grain of the countertop. A striped fabric curtain adds a subtle touch to the space.
Vacation home in Florence
4.91 out of 5 average rating, 275 reviews

Melarancio Residence

TasneemRating, 5 stars3 weeks ago
We enjoyed our stay at this apartment. Having an elevator was a blessing on days we were exhausted and air conditioning in every room meant we didn’t have to melt the few days we had really hot weather. Location is super convenient with the Mercato Centrale, Firenze SMN station, and the Medici chapel just around the corner from us. The grocery store downstairs was well stocked and there’s also a dollar store, pharmacy, and gym nearby.
Guest favorite
The dining area features a round wooden table surrounded by four upholstered chairs. Natural light fills the space through two large windows and a set of glass doors that open onto a green outdoor area. A small plant sits on the windowsill.
Vacation home in Fiesole
4.87 out of 5 average rating, 53 reviews

[Colline Firenze] Borgo Le Palaie

JuliaRating, 5 stars2 weeks ago
The stay was very nice. The apartment was perfect and beautiful and quiet. We will be happy to come back!
Top guest favorite
A spacious sleeping area features a large bed with soft green pillows and a light blue coverlet. Natural light enters through the sliding doors, which lead to a private courtyard. A circular wall decoration made of foliage adds a touch of nature, complemented by two bedside lamps.
Vacation home in Florence
5 out of 5 average rating, 53 reviews

GREEN like hope in Florence

AmyRating, 5 stars6 days ago
The most wonderful Airbnb we have ever stayed in! Claudia was delightful! The apartment is beautiful and so thoughtfully designed. It is a work of art! The location is perfect - close to everything!
Top guest favorite
A clean and modern bathroom is displayed, featuring a sleek sink with a minimalist faucet. Two neatly rolled white towels rest on a stylish countertop, complemented by a large mirror above. A door in the background leads to the rest of the apartment.
Vacation home in Florence
4.98 out of 5 average rating, 49 reviews

Appartamento Donizetti24 (D24)

WesleyRating, 5 stars1 week ago
One of the best Airbnb’s I’ve stayed at during this trip. Sara was very helpful and responsive. It was very peaceful. The bus station is right around the corner and easy to get anywhere. Very pleased!
Guest favorite
A narrow hallway is depicted with warm terracotta tiles underfoot and soft lighting provided by large lanterns. The walls feature a mix of smooth finish and exposed brick, leading to a wooden door at the end adorned with elegant windows.
Vacation home in Florence
4.93 out of 5 average rating, 179 reviews

TOSCANELLA RUBY STUDIO

BilbaoRating, 5 stars1 month ago
We had an excellent stay at this apartment in Florence! The space is simple yet very practical, comfortable, and equipped with everything needed. The building is old, charming, and authentic — a true piece of the city’s history. Having an elevator was a big plus. The apartment is cozy, well laid out, and perfect for relaxing after a day of exploring. The neighborhood is wonderful, full of life, with many art galleries, bars, and cozy cafes. The neighbors are friendly and the street is especially beautiful — ideal for peaceful walks. Everything combined made our experience in Florence truly special. Highly recommend!
Guest favorite
Vacation home in Poggibonsi
4.92 out of 5 average rating, 53 reviews

App.Cavallo - Megognano,2/A

MattiaRating, 5 stars5 days ago
We stayed at Flaminia's place with our 13-year-old daughter and had a great time. Flaminia is friendly, attentive and very helpful. The beds are really very comfortable and their bio lake is a fabulous surprise. The apartment was in line with the photos and it was a wonderful stay. Thank you, Flaminia 🥰

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Arezzo
  5. Casentino
  6. Vacation home rentals