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Villa vacation rentals in Grosseto

Find and book unique villas on Airbnb

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Popular amenities for Grosseto villa rentals

Private villa rentals

Top guest favorite
Villa in Poggibonsi
4.93 out of 5 average rating, 45 reviews

Villa with pool in Chianti Area

RickRating, 5 stars2 weeks ago
Our stay at Mariella's beautiful home was a highlight of our five week trip throughout Italy. Peacefully situated between Florence and Siena, this villa offers a welcoming respite from the hustle and bustle of the cities. It was also super convenient to the vineyards throughout Chianti. Waking up every morning to the sunrise views over the valley and enjoying a glass of wine in the evening were the perfect beginning and ending to each day. The pool was even larger than we imagined and provided days of entertainment sprinkled in during a week of sightseeing and wine tasting. I cannot recommend this home, location, or host enough. You will NOT be disappointed!
Top guest favorite
Villa in Gaiole in Chianti
4.93 out of 5 average rating, 28 reviews

Sestuccina

RubyRating, 5 stars1 day ago
Beautiful place to stay! • super nice location (a lot of nature and very quiet) • Communication always runs smoothly • Great restaurants and delicious ice cream within 5 minutes' drive • Amenities exactly as indicated I would recommend it again and again! Luciano and Brigitta are great hosts 😊
Superhost
Villa in Castiglione d'Orcia
5 out of 5 average rating, 11 reviews

#1 Luxe Farmhouse, Hilltop Views, Saltwater Pool

MiaRating, 5 stars1 month ago
We were looking for a villa that had plenty of space for my husband and I with our 3 adult kids and this villa was perfect! We all had our own bedrooms and private bathrooms. The villa was in the idyllic peaceful Tuscan countryside surrounded by rolling hills, wine vineyards and olive trees with distant views of castles. It is absolutely gorgeous! Alessandro, the owner of the villa met us upon check in. The property has been in his family for hundreds if years. He was incredibly kind and generous, leaving an abundant amount of fruit, several bottles of wine from his vineyard and beautiful fresh flowers in every room. He was always available to answer any questions and make recommendations. Anke, the property manager, was excellent and responsive. Promptly answering my questions prior to the trip and proactively giving us wonderful recommendations. Highlights were truffle hunting Il Podere Castle, Umbria Olive oil tour and Banfi Castle wine tasting. Memories to last a lifetime! ❤️
Top guest favorite
Villa in Volterra
5 out of 5 average rating, 24 reviews

Romantic Villa with private pool - "Il Pollaio"

ErinRating, 5 stars3 weeks ago
A beautiful home to base ourselves in while exploring Tuscany. Lovely country surrounds. House has everything you need, spacious. Gorgeous terraces and pool. Enjoyed Volterra, San Gimignano and Siena but always great to come back to our Tuscan home! Silvia gave fantastic recommendations - pasta making at Ristorante de Beppino and in house chef Beppe highlights. Also loved Monterosola winery tasting. Very highly recommend. One of the best!
Top guest favorite
Villa in Loro Ciuffenna
4.98 out of 5 average rating, 51 reviews

The Lazy Oak

JordanRating, 5 stars2 weeks ago
The Lazy Oak Villa is everything we dreamed of and more for our honeymoon. The house is beautiful, well furnished and feels so homely and comfortable. The surroundings are simply stunning; the view from the house and pool never get old! Mario and Alessandro were super helpful, offering to help us book restaurants and vineyards if needed. Mario keeps to himself so still feels very private but is happy to help with anything and it was nice to see him around (with his cute little dog!) and know he was about if we needed anything. Couldn’t recommend the Lazy Oak Villa more, and we’re already talking about when we could come back!! Thank you Mario and Alessandro!
Top guest favorite
Villa in Sovicille
4.96 out of 5 average rating, 72 reviews

Beautiful Country House, near Siena with jacuzzi

DanielRating, 5 stars4 weeks ago
We had a wonderful time at the estate. We were visiting with 4 adults and 2 little babies. The communication with David was always super prompt and he even really quickly helped us out in finding a doctor when our daughter got sick during the stay. The house has everything you need and is well equiped. We cooked every evening in the cosy kitchen and had wonderful breakfasts in the garden. The Jacuzzi overlooking the valley was also a nice spot for relaxing in the warm water. Overall we can just recommend this historic but well modernized house as your idyllic getaway in Tuskany.
Guest favorite
Villa in Lucignano
4.88 out of 5 average rating, 24 reviews

Unique Villa in Tuscany

KeithRating, 5 stars2 weeks ago
A stunning property, completely private and quiet. Large outdoor heated pool was well maintained with perfect outdoor eating and sitting areas. We ate out on the terrace every night. Luc recommended the closest Osteria which we all loved, and also recommended the spot to see those iconic views of Tuscany with the avenues of cypress trees. All 6 of us had joyful experience. Highly recommended.
Superhost
Villa in Civitella in Val di Chiana
4.92 out of 5 average rating, 26 reviews

Casa Quinti, let yourself be surprised by beauty.

BethanyRating, 5 stars1 day ago
Our family of 6 had a wonderful stay in the Tuscan countryside. It was so peaceful! And the pool was a huge hit with the kids (both our teens and little ones). We rented the entire villa which has 2 bedrooms with a shared bath and kitchen and a separate apartment with its own entrance that our teens shared. We were able to find it relatively easily. The kids were welcomed and they have a pack and play crib (which we didn’t use) and a high chair (didn’t use), but we didn’t find kid proofed plates and cups. Thankfully the kids did well, but porcelain and glass over concrete floors definitely made us nervous. The silverware and sharp cutting knives were also easily accessible to our 1.5 year old and 3 year old, which also made us very nervous, but they did fine. The beds were comfortable, but we could have used additional pillows. The bedrooms had air conditioning but the shared spaces did not, but this was not a problem for us, even in 90 degree weather. Overall, we definitely recommend!

Luxury villa rentals

Top guest favorite
Villa in Cortona
5 out of 5 average rating, 76 reviews

Stunning Tuscan Villa & Panoramic Infinity Pool

ChelseaRating, 5 stars1 week ago
This was our second time visiting Mogens and Suzie's beautiful home in Cortona. One reason for coming back was the sheer beauty of the property and the proximity to fantastic medieval towns with incredible history that endures even now. For wine enthusiasts, there are tons of wine tasting opportunities with lunch, dinner or just great wine. Another reason for our return visit was an opportunity to spend time again with Mogens and Suzie, by far the best AIRBNB hosts we have ever encountered. They do everything imaginable to make your time as enjoyable as possible and to say that they go the extra mile would be a gross understatement. We can't wait to come back a third time.
Guest favorite
Villa in Pozzuolo
4.91 out of 5 average rating, 43 reviews

Fabulous Farmhouse with Pool & 360 Panoramic View

Kaidy FendyRating, 5 stars2 weeks ago
Caroline's villa was absolutely stunning. We visited as a family of 8 adults and it was even more beautiful in person. It's completely private with amazing views all around. It's also in a great location to visit other picturesque villages nearby with a car. The pool was a great addition to combat the Tuscan heat. As this is in the countryside, be aware that there will be insects and wildlife. We came across a snake and a scorpion, but that's not an issue with the house, but rather the natural environment. The property manager Bianca greeted us upon arrival. She was super friendly and helpful with tips. And Caroline left us super detailed recommendations for restaurants, itineraries, and wineries. She was always available and friendly. We had an amazing time and would definitely visit again!
Superhost
Villa in Marina di Campo
5 out of 5 average rating, 33 reviews

Casa Pineta Elba, a short walk from the sea

LeighRating, 5 stars1 month ago
We enjoyed a perfect family holiday on Elba Island in the perfect family home. The outdoor kitchen/dinning/sitting area was ideal to unwind after a day or exploring beautiful beaches, trekking amazing mountain trials and of course eating our way the many traditional Italian restaurants. If you want the perfect Italian holiday this is the perfect family home, you will not be disappointed. Claudia is the super host.
Top guest favorite
Villa in Montepulciano
4.9 out of 5 average rating, 21 reviews

Villa Nobile - Private Jacuzzi

MicheleRating, 5 stars3 months ago
Our stay at Villa Nobile was exceptional. The villa provided the perfect balance of privacy, surrounded by olive trees and vineyards, while offering the comforts and services of a resort. From the seamless transfer arrangements coordinated by Mario to the attentive staff who ensured every detail was taken care of, the hospitality was outstanding. The wine tasting upon arrival was a wonderful introduction to the region, and the fresh, thoughtfully prepared breakfasts each morning were a delight. Having dinners prepared for us and placed in the refrigerator after days spent exploring the town and local wineries was an added convenience we truly appreciated. The breathtaking sunrises and sunsets made our time here even more memorable. We are grateful for such a wonderful experience and look forward to returning.
Guest favorite
Villa in Allerona
5 out of 5 average rating, 34 reviews

Vakantievilla Farmhouse Dolci Hills

JeffRating, 5 stars1 month ago
This was the finest AirBNB home that we've ever stayed in. Every room was immaculate, the views were incredible (private and among vineyards, you can see for miles), every appliance and fixture seemed new. Everything was anticipated to make the stay perfect.....a refrigerator, bathroom and shower at the beautiful pool, pool towels in each bedroom, etc. As soon as you walk into this house, you are going to go "wow", and for good reason. Francesca came and cooked us a delicious local dinner and did some light grocery shopping for us.....all for an unreasonably LOW fee. We had another chef team come in on another night. We also visited a local winery where we had a fantastic, private wine tasting tour and lunch (Tenuta Vitalonga) and followed that up with touring Orvieto and having dinner at a very unique restaurant (Le Grotte del Funaro). Make sure you have a car or are using a bus/limo service for your transportation, nothing is walkable from this beautiful private house.
Top guest favorite
Villa in Bolsena
5 out of 5 average rating, 50 reviews

Villa Blue Melon - private beach

AlisonRating, 5 stars1 month ago
What a lovely property and host! Andrea was very friendly and helpful. He gave us a tour of the home and answered any questions we had before leaving us to enjoy the wonderful property. He even sent us restaurant recommendations which turned out to be amazing. The property itself is picturesque and almost felt unreal. My family was in awe and couldn’t stop mentioning how it was the nicest part of our trip (which we stayed in multiple places throughout). It was impeccably clean without a single speck of dust present. The furnishings were all perfectly picked and each added charm to the home. The rooms were cozy and all had wonderful views. We almost didn’t even notice the weather was gloomy the few days we were there because of how much we enjoyed the home itself. I can only imagine when it’s sunny and warm! Thank you for everything Andrea. We definitely plan to come back!
Top guest favorite
Villa in Monticchiello
4.97 out of 5 average rating, 73 reviews

Villa with garden. The Cardinal's Garden.

ShaneRating, 5 stars3 weeks ago
Great place to stay. Excellent communication, went above and being to ensure our stay was exceptional. Deborah even bought a pasta machine for us to use for our evening meal - which was really appreciated. It was a great week.
Guest favorite
Villa in Tignano
4.95 out of 5 average rating, 172 reviews

Villa Isabella

SharonRating, 5 stars2 weeks ago
Christina’s home was beautiful. She was an amazing host, getting us last minute reservations at restaurants and doing a cooking class with us on our last night that was fun and delicious!

Villa rentals with a pool

Guest favorite
Villa in Gambassi Terme
4.96 out of 5 average rating, 54 reviews

Villa Via Francigena

BettyRating, 5 stars1 week ago
Beautiful surroundings, peaceful, beautiful pool! Extremely well-appointed kitchen. Hosts responded immediately if we had any questions.
Top guest favorite
Villa in Sorano
4.98 out of 5 average rating, 97 reviews

Poggio Bronzino, Montebuono – Sorano (Gr)

MarleneRating, 5 stars8 months ago
Very nice and quiet place to stay, perfect for families. The pool was great, the house large enough for 4 adults + toddler, everything very clean, very well equipped kitchen. The pizzeria in the village is very good, the other larger places are a bit far away. All in all, a beautiful place to stay
Guest favorite
Villa in Magione
5 out of 5 average rating, 5 reviews

Villa Polvese Luxury Lake side Villa

YvetteRating, 5 stars9 months ago
The villa is the most beautiful place we stayed at during our 20 day trip through Europe. It’s a bit on a splurge in price but very much worth it. The views from the villa of the pool and the lake are breathtaking. The house is very beautiful, everything was functioning properly and the kitchen is great to cook in. We stayed in and cooked dinner one night and it was great. We also took advantage of the Complimentary olive oil tasting that is included with the stay and that was also of fun. Our guide said was so knowledgeable! I can’t say enough good things about this place. It was a much needed break during our busy vacation.
Superhost
Villa in Baschi
4.87 out of 5 average rating, 176 reviews

VILLALADOLCEVITA

SimonRating, 5 stars1 week ago
Very nice stay for a few days relaxing in summer. Beautiful olive gardens around the house, nice collection of wine. Everything clear, super big house, will come back next year!
Guest favorite
Villa in Paciano
4.98 out of 5 average rating, 45 reviews

Villa Fortuna with Hot-Tub and pool near Tuscany

JenniRating, 5 stars4 weeks ago
A Perfect Holiday – Like Heaven on Earth! This place exceeded all our expectations. A stunning and peaceful location with breathtaking views over the valley, lake, and mountains. The house and garden were beautifully maintained, and the accommodation was very clean and comfortable. A special thank you to Mrs. Lesley, who was an invaluable help throughout our stay. She provided us with plenty of useful tips and advice on various matters, such as train tickets and local attractions. Thanks to her, we were also able to arrange a wonderful dinner at the villa – truly an unforgettable experience. We wholeheartedly recommend this place – if we could give it 150%, we absolutely would!
Top guest favorite
Villa in Cortona
5 out of 5 average rating, 11 reviews

Villa Leopoldina, 6 pax, Private Pool

MaximeRating, 5 stars9 months ago
Gigi’s place is one of the most peaceful places we’ve stayed in in Italy. The location is gorgeous and perfectly located between different towns to explore (Cortona, Arezzo, Montepulciano to name a few). A car is necessary but you can get to the town center for groceries and local produce in 10 minutes. We enjoyed spending our days by the pool, cooking and barbecuing in the garden. The kitchen was the most equipped I’ve ever seen for an Airbnb and the house was spotless. Extra supplies were left for us as well if we needed which was a nice touch. Gigi was always available for recommendations and extremely friendly. If you’re looking for calm and quiet this is your place!!
Guest favorite
Villa in Bagnoregio
4.97 out of 5 average rating, 29 reviews

Sant'Anselmo

ChloeRating, 5 stars2 weeks ago
This Airbnb is amazing. We had a wonderful stay. The scenery is beautiful, it is quite and calming. I would highly recommend to anyone looking to relax. The place was spotless and very comfortable. A bit of a challenge up the driveway but don't let that put you off, the reward is worth it. Jannis is a great host, easy to communicate with as well.
Superhost
Villa in Pierle
4.9 out of 5 average rating, 30 reviews

Historic Villa Getaway with 6BR/9BA, Pool, Views

HaisamRating, 5 stars1 week ago
The villa is located in the heart of the hills, secluded from all the nuisances of today’s world. Check-in was a breeze with extremely straightforward instructions. The host recommended Gimmy for a cooking experience, and that didn’t disappoint. Jackamo was recommended for a trek alongside the property and that too didn’t disappoint. Jackamo was extremely knowledgeable and fun to talk to. To sum it all up, this was one of the most pleasant experiences through Airbnb and we can’t wait to visit again.

Destinations to explore

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  2. Italy
  3. Tuscany
  4. Province of Grosseto
  5. Grosseto
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