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House holiday rentals in Grosseto

Find and book unique houses on Airbnb

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Popular amenities for house rentals in Grosseto

House rentals with a pool

Guest favourite
Home in Asciano
4.94 out of 5 average rating, 35 reviews

Family Forest - Pool in the Crete Senesi

SylviaRating, 5 stars2 weeks ago
The area is incredible, peaceful and the view spectacular. Asciano has the delightful charm of an Italian village. The people were friendly and welcoming. Even got greeted by their local police who offered up their number in case we needed anything. I felt safe, and it felt as if I lived there for years. I’d say this is a piece of heaven on earth. Bellezza maestosa! Non vedo l'ora di visitare di nuovo la Toscana e la città di Asciano! Grazie!
Guest favourite
Home in Orvieto
4.99 out of 5 average rating, 211 reviews

Vineyards Paradise

KristineRating, 5 stars3 weeks ago
Our stay at Piero’s home was the highlight of our family’s three week Italy trip! It is one of the most beautiful homes we have stayed at and the spectacular vineyards, gardens, and pool really added something special. We plan to definitely return/stay again! Thank you Piero for sharing your special home!
Top guest favourite
Home in Barberino Tavarnelle
4.97 out of 5 average rating, 72 reviews

Podere Tignano, 4-bedroom villa in the Chianti!

MeganRating, 5 stars2 weeks ago
How can we even put into words what an incredible experience this was! Antonella was kind and helpful, and her home is just stunning. She made us feel so at home even with our limited Italian. She prepared us a home cooked, four-course meal one night and it was absolutely delicious. She even gave us the leftovers so we could have them for breakfast the next day. The villa was breathtaking and in a perfect location to visit beautiful towns in Tuscany like Pienza, Montepulciano and San Gimignano. We especially loved the pool and visiting with the animals. This was a bucket list stay for us and worth every penny!
Guest favourite
Home in Lecchi in Chianti
4.96 out of 5 average rating, 138 reviews

Casa di Lyndall - Entire house with exclusive pool

LiannaRating, 5 stars1 week ago
Yet another fabulous stay! Thank you Lyndall for sharing your special space. Getting in on the village pizza night was a surprise bonus and so fantastic to enjoy the local community. Until next time :)
Guest favourite
Home in Pievescola
4.94 out of 5 average rating, 175 reviews

Antico Borgo Ripostena – n. 8 Old House

LucyRating, 5 stars2 weeks ago
This place is something else! The views, the pool, the houses, the interior - it’s something else. We stayed with our 18 month old and had such a happy time - surrounded by nature in such gorgeous accommodation and a kiddy kitchen / toys which were perfect for Otis. It’s simply beautiful and Martina is so helpful - highly recommend with a family or groups of friends for a zen and unique time. Close to lots of gorgeous places and Martina has wonderful recommendations. Only watch out is the 2km dirt track road to get to the location but it’s 100% worth it and quite fun! Enjoy - we can’t wait to come back :)
Superhost
Home in Sorano
4.8 out of 5 average rating, 128 reviews

Lovely home in villa with garden and pool

JoshRating, 5 stars2 weeks ago
A beautiful stay in Tuscany perfect for relaxing on the property and visiting towns.
Superhost
Home in Rietine
4.85 out of 5 average rating, 208 reviews

Gaiole in Chianti Poggio Casabianca

AlexRating, 5 stars1 month ago
Valeria and Simone have a super nice and clean apartment! We felt very comfortable right from the beginning. The apartment offers a great starting point for numerous hikes and excursions. During our stay, we always received good tips and advice from the two. Our dog also felt very comfortable and since the property is completely fenced, he could move freely. We would come back. It was an incredibly beautiful time!
Guest favourite
Home in Rigomagno
4.96 out of 5 average rating, 100 reviews

House Rigomagno Siena

Marco JustusRating, 5 stars1 week ago
We had a wonderful time in this absolutely cute house, which is surrounded by breathtaking nature. The tranquility is unique - you can only hear the chirping of the birds, and every now and then deer appear at the edge of the forest. Simply magical! The pool was well maintained and you had real peace. A real highlight for us was the kitchen: so lovingly furnished and exceptionally well equipped - we have never experienced anything like it! The gas stove and the high-quality oven have made cooking a pleasure. Host Diego was incredibly friendly, attentive and warm. You immediately feel welcome and well cared for. A perfect retreat for those who appreciate nature, tranquility and loving details.

Weekly house rentals

Guest favourite
Home in Giglio Porto
4.94 out of 5 average rating, 18 reviews

Bouganville apartment between "Sky and Sea

MatthewRating, 5 stars9 months ago
Annamaria sent an email with lots of really useful info ahead of our stay and check-in was very easy. She was also responsive to messages and friendly, the perfect Airbnb host - thank you Annamaria. The place itself is almost beyond description - it felt to us like our own piece of paradise. The view from the terrace is breathtaking and having our own private bathing-rock to swim from was really special. We cannot wait to return.
Guest favourite
Home in Castelmuzio
4.93 out of 5 average rating, 42 reviews

Casa Ora d"Oro - Panoramic Views

Jason AllenRating, 5 stars3 weeks ago
first I love his neighbors who checked us in. Cinzia was amazing. She not only showed us our place but took our kids to show us her farm. she also makes her own olive oil and gifted us with some! Wonderful Italian neighbors!! I contacted Rocky in advance and he provided me with specific recommendations for where we should go during a long drive we took. we went where he suggested and was not disappointed! Amazing quiet location with great near by wineries. would 100% recommend to everyone!
Top guest favourite
Home in Montebenichi
5 out of 5 average rating, 59 reviews

[Little Escape] 4 Beds + Private Panoramic Pool

SusanRating, 5 stars3 weeks ago
Our stay in Montebenichi was almost indescribable. Having been to Tuscany before, this time was pure magic. The flat is within the compound of a 12th century fortress village that is mostly inhabited by residents. Tommaso had stocked the kitchen with plenty of coffee, milk, water, juices, snacks and his grandmother's amazing Limoncello! The pool area has the most incredible view with an outdoor kitchen where Tommaso arranged for us to have a traditional Tuscan cooking class. He also made reservations for us at the village Michelin-rated restaurant that is just steps from the flat. One of our favorite things was hearing the wolves of Tuscany howl in the distance - no need to be afraid - it was pure magic. We saw very few tourists which made the experience even better. Moreover, Tommaso was THE BEST HOST we have ever had while staying at an Airbnb. His dedication to ensuring the perfect stay for us was truly a standout. We can not say enough good things about our stay!
Top guest favourite
Home in Rosignano Marittimo
4.95 out of 5 average rating, 79 reviews

Frontemare house with exclusive sea access

YusufRating, 5 stars1 week ago
Really very nice accommodation and a big thank you to Camilla who takes care of everything. For example, with us, to reserve a tennis court. Full recommendation!
Top guest favourite
Home in Bivio di Ravi
4.96 out of 5 average rating, 54 reviews

Casa Elicriso

FrancescoRating, 5 stars1 week ago
We had a fantastic stay thanks to the hospitality and enthusiasm of Barbara and Emmanuele, who were kind enough to spend unforgettable moments with us, despite their work obligations. The apartment is impeccable: clean, tidy and well organized. Their house is well located in southern Tuscany, not far from cultural and archaeological centers such as Vetulonia, Massa Marittima or Grosseto. Beautiful beaches are only 1/4 of an hour, 20 minutes by car, such as Follonica or Castiglione. In short, if you pass through the area, really don't hesitate, go for it! Warmest regards, Brenda & Francesco
Top guest favourite
Home in Montemassi
4.96 out of 5 average rating, 49 reviews

Capezzuolo 33

BenRating, 5 stars1 week ago
This apartment was so beautiful and the views were even better. We had an amazing stay here as our base for exploring Tuscany - visiting the Val d’Orcia and the thermal baths were a highlight! Lucia and Marco met us on arrival and were extremely friendly and gave us plenty of advice and places to visit. There was an issue with the boiler but Lucia was straight on it and it was fixed by the time we were home for the day. Thank you so much!
Guest favourite
Home in Roccastrada
5 out of 5 average rating, 5 reviews

Apartment in the countryside

Dr. SveaRating, 5 stars10 months ago
Exceptionally beautiful apartment furnished with a lot of love and taste in a beautiful, well-kept complex! The beautiful, well-kept pool is the icing on the cake that makes the complex perfect. We really enjoyed the four-course dinner under the stars, but there are also so many good restaurants in the area that you can't try them all. Chiara and Stefano are the perfect hosts, you can learn a lot of interesting things from them! They also attach great importance to sustainability, the facility is self-sufficient and only organic wines are produced in the associated winery.
Top guest favourite
Home in Sasso D'ombrone
5 out of 5 average rating, 29 reviews

Tosco Suite "Solis"

DinaRating, 5 stars1 week ago
Location was perfect and close to fun things to do. The host was very responsive and friendly. 10/10 recommend staying here. Everything was very cleaned and beautiful.

Private house rentals

Top guest favourite
Home in Castiglion Fiorentino
5 out of 5 average rating, 36 reviews

Hidden gem in Tuscany

MitchellRating, 5 stars1 month ago
Where to start? I truly can't say enough good things about this property. It exceeded expectations in every way. From start to finish, our time here was a delight. Amanda was responsive, helpful, and accommodating. The location is remote, and a bit of adventure to get to, but Amanda had communicated that and we were prepared with the proper rental car that made it a breeze. The house is beautifully appointed, has every amenity, and lots of perfect spaces for both quiet moments and areas to gather with your group. The outdoor spaces and pool area are lovely, beautifully landscaped, and the views are spectacular. Book this place; you won't be sorry.
Superhost
Home in Barberino Tavarnelle
4.76 out of 5 average rating, 55 reviews

7 min Cantina Antinori | Pool | Casa Sala & Pepe

RyanRating, 5 stars1 month ago
Beautiful home near Chianti. Clean and comfortable, with amazing vineyard/sunset views. The hosts were very responsive and friendly, and they gave clear instructions. One thing to note is that the property is listed as "Entire Home", but it is actually a condominium that shares walls and outdoor common areas with the neighbors. There is a divider in the backyard between us and the neighbors, but it is not completely private. Overall, we had a great time here.
Top guest favourite
Home in Sticciano Scalo
4.95 out of 5 average rating, 39 reviews

Villa in Maremma

VickyRating, 5 stars8 months ago
Massimo and his wife were great hosts. His place was ready and clean when we arrived. It had everything we needed. Massimo was always responsive and helpful. We were staying there for a wedding at La Pescaia and Massimo was kind enough to give us rides when needed. He went above and beyond to make us feel at home. I highly recommend Massimo’s place and would love to visit again. Thank you Massimo and Luana!
Guest favourite
Home in Porto Santo Stefano
4.9 out of 5 average rating, 60 reviews

Casa delle Tortore

AnjaRating, 5 stars1 day ago
We enjoyed the stay at Serena so much. The terrace offers a stunning view of the sea, which is not far away and has beautiful beaches. The apartment was perfect for our three children, who had plenty of space and their own bathroom. Everything was very clean and well maintained and very stylishly furnished. The kitchen is very well equipped, with dishwasher, washing machine, WiFi and even a table tennis table, nothing was left to be desired. In addition, Serena and her husband Giulio are incredibly nice and helpful. We hope to come back soon♥️.
Superhost
Home in Sorano
4.86 out of 5 average rating, 43 reviews

Cozy Artist Retreat in the heart of Sorano

EleonoraRating, 5 stars1 week ago
A pleasant and peaceful stay. Special and evocative house, comfortable bed and large and nice terrace. We were accompanied by many cats in the country who made our stay even more pleasant. Caleb was very helpful, especially at early check-in.
Top guest favourite
Home in Magione
5 out of 5 average rating, 20 reviews

Beach House, on the shores of Lake Trasimeno

Juan DiegoRating, 5 stars2 weeks ago
To assess this property, we must start with the HOST, a professional in every sense. From the minute 0 of the reservation, until the departure; always attentive, very kind and very professional. It is a pleasure to meet serious people and this gives value to the application. The beach house is a paradise in Italy. Easy access, attention to detail, peace, nature, comfort. Our trip was as a family with our two poodles and I think they were the ones who enjoyed the property the most, seeing them run and jump through the green areas of the property and live with many birds, rabbits is priceless. Our daughter enjoyed her stay studying and with the peace and tranquility of the place, it was not difficult for her to concentrate. We, on the other hand, did some sightseeing in the area, all very close and well connected by road. It is a very well-kept, safe property and above all, enjoying its sunset, sitting on a lounger, enjoying a good wine (from the area) is a unique experience. Thank you Maurizio.
Superhost
Home in Cala Piccola
4.85 out of 5 average rating, 13 reviews

[cala piccola] peace of mind + reserved beach

SilviaRating, 5 stars1 day ago
A dream location near Cala Piccola. Access to the Cala is definitely a plus for a perfect vacation. The terrace is worth the stay! Very helpful and present host, with valuable advice on the area
Superhost
Home in Lucignano
4.83 out of 5 average rating, 41 reviews

La Casetta

JonasRating, 5 stars2 weeks ago
Hard to find a place like Maria’s, beautiful place and with such a friendly and helpful staff.

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