
Villa vacation rentals in Grosseto
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Top-rated villa rentals in Grosseto
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Villa with View for Family & Friends, in Tuscany
Huge and charming top floor apt in Tuscan Villa with breathtaking view! Visit Montepulciano, Pienza, Siena, explore country side, vineyards and hot springs, hiking or e-biking, strolling or driving! Two roomy suites with top quality beds and bathroom ensuite. Windows walled living room, comfy sofas, professional kitchen at your own use. We can set Winery visits & tasting, Cooking classes and private dinners. NEW Hot tub facing green hilltop! ExperienceTuscany as a local, with your local Host!

Exclusive 10 Acre Estate w/ Pool & Olive Grove!
Enchanting, exclusive 10acres estate on a hill, memorable sunsets; large pool framed by lavender&rosemary, open year-round. New air conditioning, Starlink internet. Very private&peaceful 2 floors, 4bedrooms, 4baths, jacuzzibathtub, 55inch smartTV, well-equipped kitchen, porch & pergola for alfresco dining, Weber barbecue, pizza oven, olive grove, fireplace; 20 min. to Orvieto,Todi,Amelia; 10 minutes drive to train station to Rome/Florence, 5min drive to shops in town. Grounds/pool caretaker

Wine Experience Villa in Montepulciano
🏡 Villa Talosa è immersa nei vigneti della Fattoria della Talosa, storica azienda vitivinicola di Montepulciano produttrice di Vino Nobile. Un luogo autentico, ideale per rilassarsi con la magia della campagna toscana e una vista incantevole da ogni finestra. A soli 1,5 km dal centro storico, raggiungibile anche a piedi, potrete visitare la nostra Cantina Storica del 1500 sotto Piazza Grande: un’esperienza unica tra storia, passione per il vino. Riscaldamento e aria condizionata sono inclusi.

Tuscan charm of villa - countryside - Villa Senaia
Nell’affascinante campagna Toscana,tra ulivi e vigneti una villa in pietra,in posizione strategica per cogliere i segreti di Toscana e Umbria aria condizionata e piscina con area wellness per il vostro relax e confort Villa Senaia è una grande casa con travi in legno, in una splendida posizione in collina con vista idilliaca che affaccia su uno dei luoghi preferiti della campagna toscana, un ambiente attraente per mangiare all'aperto, bevendo vino toscano e ascoltando i grilli e le cicale

Amazing Tuscany Villa, FREE parking
Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking

Belforti Tower
Torre dei Belforti is the perfect place for people who love beauty, nature and art. Sleeping at the Tower is like traveling trough the time, between knights and princesses. The wonder of this place is enriched by a big garden, with its swimming pool, the cypresses alleys and the olive trees. The village is also a magic place well preserved and still alive. We are Emilia and Luca, we live here and our mission is to give the best to our guests, to fully enjoy this marvelous place.

Stone farmhouse in Val D'Orcia
19th-century Tuscan farmhouse with exposed stones immersed in the wonderful Tuscan countryside with a splendid view of the Val di Chiana. It is surrounded by a 6-hectare park with an olive grove of 300 plants. It is located in Sarteano, in the village, an ancient medieval village with a dream castle, known for the Music and Jazz Festival that takes place at the end of summer. We are in the beautiful Val d'Orcia, a UNESCO World Natural Heritage Site since 2004.

Grosseto, Casina Girasole
Entire apartment in Grosseto, brand new, in a beautiful villa. Ideal for a relaxing holiday in the heart of the Maremma. Located in a quiet area, rich in greenery, with a large garden and private parking. Equipped with all comforts. A few kilometers from the sea, from the Uccellina Park and from enchanting villages. Perfect location for food tours too. POSSIBILITY of electric car charging, € 0.55 /kw Elena and I are ready to welcome you to Casina Girasole!

Villa in Montepulciano with a Pool
The Villa "I Girasoli" is part of the holiday farm "Il Serraglio" which covers 17 hectares. The Villa has a total area of 220 square meters that includes two bedrooms, two bathrooms, a large living room with an antique fireplace. Free WiFi. Direct access to the pool (which can be used by our other guests too) * Pool open from April to November. Circular warm pool, (36C/97F) from April 1 to October 31. Pool is shared with other guests of our property. *

Villa unesco heritage, Jacuzzi & garden. BB Daria
Carefully renovated and refurbished over a sustained period in order to maintain the original quality of its architecture, San Lorenzo Villa is open to guests. You are invited to enjoy the beauty, comfort and privacy of a beautiful independent villa in the centre of Monticchiello, from where you can have an incredible view on the Val d'Orcia, the UNESCO heritage! Don't forget a delicious breakfast (whatever you like) in our so close typical restaurant

"Villa Daisy" overlooking Siena
Wonderful villa with independent entrance inside the "Caggiolo" farm, brought to light with careful and thorough renovation that has kept intact the typical features of a Tuscan farm. Beautiful panoramic view of Siena. Located in Ville di Corsano, just 14 km from the city. An ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d'Orcia, Crete Senesi etc).

sea view villa with private infinity pool
RENTALS ONLY FROM SATURDAY TO SATURDAY. The house is located within our farm, surrounded by forest is distance from the village of Castagneto Carducci only 3.5 km. Its unique location offers a wonderful view of the sea and the country, ensuring a pleasant tranquility, away from the heat and noise of the country.
Popular amenities for Grosseto villa rentals
Private villa rentals

Fior di Roccia Villa

Gorgeous view on vineyards, Stone Tuscan private V

Case Bianchi

Private villa in Maremma 15 minutes from the sea

Beach House Giannella w/ direct access to the sea

Tuscan Luxury Villa • Natural Pool & Privacy

Country Charm & Jacuzzi

Podere Pereti Vecchi | Stunning Val d'Orcia Views
Luxury villa rentals

Villa Pupì Green Retreat

Luxury Villa in the very heart of Chianti

Villa Il Molinaccio with terrace and private beach

Tuscany Villa With Pool & Magnificent Garden

Villa in Tuscany – private pool – sunsets over Cetona

Poggio del Fattore-Villa with pool, hilltop, Chianti

Villa - Incredible View - Private Beach - Jacuzzi

L'Apparita del Peruzzi | Villa | Private Pool & Air-Con
Villa rentals with a pool

Charming Chianti Villa | Garden & Panoramic Pool

Luxury Villa, Salt water Pool-Orvieto -14 p -Owner

Vakantievilla Farmhouse Dolci Hills

Stone villa with a pool

Stunning house with pool, final summer discounts

Villa on the lake with a pool

Luxury Tuscan Villa with Pool [La Stellata]

The twigs
Quick stats about villa rentals in Grosseto

Nightly prices starting at
Grosseto vacation rentals start at G$25,084 GYD per night before taxes and fees

Verified guest reviews
Over 100 verified reviews to help you choose

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Grosseto rentals

4.8 Average rating
Grosseto stays are highly rated by guests—averaging 4.8 out of 5!
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- Villa rentals Tuscany
- Villa rentals Italy
- Elba
- Giglio Island
- Lake Bolsena
- Giannutri
- Cala Violina
- Feniglia
- Parco Regionale Della Maremma
- Spiaggia Di Sansone
- Gulf of Baratti
- Spiaggia Di Barbarossa
- Cascate del Mulino
- Spiaggia di Capo Bianco
- Le Cannelle
- Spiaggia di Marina di Campo
- Siena Cathedral
- Palazzo Pubblico
- Terme San Filippo
- CavallinoMatto
- Vulci
- Mount Amiata
- Val di Chiana
- Valdichiana Outlet Village
- Abbey of Sant'Antimo
- Necropolis of Tarquinia





