
Villa holiday rentals in Grosseto
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Top-rated villa rentals in Grosseto
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The Farmhouse Cottage
Entire upper floor of the newly renovated Manor House in traditional Tuscan style. High ceilings with exposed beams make the place cozy and perfect for families or groups of friends. In the house, there are two large functional fireplaces (in the living room and kitchen). Private, non-shared accommodation. The house has a large covered terrace, garden with sofas, BBQ, fire pit, private parking. The swimming pool among the olive trees and vineyards is ideal for relaxation and has private access to the shared area

Poggio del Fattore-Villa with pool, hilltop, Chianti
Poggio del Fattore is situated at the eastern edge of the Chianti region in Valdambra, a green valley that joins the lands of Florence, Siena and Arezzo. The farmstead is on the top of an hill and lies at the end of a long private road through a large olive growing estate; therefore you absolutely need a car. The breathtaking landscapes and the location of the villa offer the privacy needed for a peaceful and relaxing holiday and a perfect departure point from which to explore central Tuscany.

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
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

Virgi House
Virgi House is a 160 sqm villa, located 3 km far from Siena’s hystorical center. The villa is distributed over three floors. On the first one there is a double bedroom with bathroom and terrace, a large open space living room, a modern kitchen and a bathroom. Downstairs a double bedroom (or 2 single beds), a large bathroom, a study and a bright living room with a loggia from which you can access the private car park and the garden. The property also provides free wifi, air conditioning.

A paradise in Montepulciano...
Villa Il Cubo is a full centralized air conditioned private house with large private swimming pool placed in the best garden spot for incredible views on the countryside around. Decoration has been updated with charming details that will make you enjoy the best Tuscany has to offer. We have electric vehicle charging point. Supermarkets, restaurants, grocery stores, wineries are just a few minutes away. IN JULY AND AUGUST WE LET FOR A MINIMUM OF 7 DAYS FROM SATURDAY TO SATURDAY!!!!!!

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.

San Giovanni in Poggio, villa Meriggio 95mq
Detached house, two double bedrooms, two bathrooms with shower, living room with fully equipped kitchen (dishwasher, washing machine, oven, microwave), double sofa bed, private garden with equipped pergola. Satellite TV and free Wi-Fi. Additional services at the property, upon reservation, include Focus brand Jarifa2 6.7 pedal-assisted bicycles and a wellness area with a Forest outdoor Finnish sauna and a heated mini-pool with hydromassage and chromotherapy with panoramic views.

Villa Il Diaccio with view of the Tuscan Maremma
Villa in pietra con particolari rifiniture architettoniche immersa in un bosco di castagni. Un grande giardino, in parte pavimentato a pietra, correda la proprietà dal quale si può ammirare un panorama meraviglioso della maremma toscana. Immersi nella natura si nota da una parte il mare con il golfo di Follonica, l'isola d'Elba e la Corsica, dall'altra l'isola del Giglio. E' possibile fare lunghe passeggiate nella natura o raggiungere località balneari o città d'arte.

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.

Private villa in Maremma 15 minutes from the sea
Our private villa is located in the heart of the Tuscan Maremma just a few kilometres from the quiet village of Gavorrano. ‘La Quercia’ consists of a large garden with private veranda and Jacuzzi, two bedrooms, living area with fireplace and kitchen, two private and fully equipped bathrooms and a breathtaking view of the beautiful Maremma. Parking is private and free on site. Pets are allowed at an extra charge.
Popular amenities for villa rentals in Grosseto
Private villa rentals

Stunning Tuscan Villa & Panoramic Infinity Pool

Fabulous Farmhouse with Pool & 360 Panoramic View

Romantic Villa with private pool - "Il Pollaio"

Montemarcoli

Luxury Tuscan countryside villa with pool/WiFi/AC

Beautiful tuscan country house

Capalbio, estate 2026!

[Cortona] Historic Villa with Pool and Park
Luxury villa rentals

Villa with pool in Chianti Area

Villa in Montepulciano with a Pool

Villa with garden. The Cardinal's Garden.

Villa Poggialto: breathtaking views and luxury spa

Villa unesco heritage, Jacuzzi & garden. BB Daria

Villa Capanna, Private Pool, Breathtaking Views

Casa Faraona, villa with private pool

Il Casale Di Manuele 12, Emma, Villas
Villa rentals with a pool

Scacciapensieri. Cottage in Tuscan Country

Charming villa on two levels - Casa Lola

Pasqui Villas : Tribbio private house pool WiFi

Vakantievilla Farmhouse Dolci Hills

Country Charm & Jacuzzi

Sasso Canaldo: Elegant Tuscan farmhouse

Villa Flo' [Private Pool, Relaxation, Privacy]

Villa la Chiusa - with swimming pool and air conditioning
Quick stats about villa rentals in Grosseto

Total holiday rentals
Explore 10 holiday rentals in Grosseto

Nightly prices starting at
Grosseto holiday rentals start at $142 SGD per night before taxes and fees

Verified guest reviews
Over 100 verified reviews to help you choose

Wifi availability
10 of Grosseto holiday rentals include wifi access

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

4.7 Average rating
Grosseto stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
- Smoking-friendly rentals Grosseto
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