
Villa vacation rentals in Grosseto
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Quick stats about villa rentals in Grosseto

Nightly prices starting at
Grosseto vacation rentals start at ﺩ.ﺇ 477 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!
Top-rated villa rentals in Grosseto
Guests agree: these villas are highly rated for location, cleanliness, and more.

Charming Tuscan Villa in Val d'Orcia with a view
Luxury 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, commercial kitchen at your own use. We arrange Winery visit & tasting, Cooking classes and private dinners. NEW Hot tub facing green hilltop! ExperienceTuscany as a local, with your local Host!
LocationValueLayout
4.97 out of 5 average rating, 130 reviews
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.
FamilyLocationAir conditioning
4.97 out of 5 average rating, 126 reviews
Villa Il Molinaccio con terrazza e spiaggiaprivata
Spacious rustic villa with a terrace overlooking the sea and access via stairs to a small pebbly beach. Ample outdoor and indoor spaces with garden. It has sun beds, sun umbrella, table tennis and barbecue. Recently purchased kitchen and furniture. A 10-minute walk from the harbour and centre, offering privacy but accessibility to all amenities like beaches, windsurfing, diving, and boat hire. Private garage in front of the house on private road. Recently renovated. Vintage and maritime style.
LocationFamilyWalkability
4.9 out of 5 average rating, 96 reviews
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
FamilyLocationBackyard
4.9 out of 5 average rating, 241 reviews
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
ValueLocationCleanliness
4.93 out of 5 average rating, 334 reviews
Villa a Montepulciano con Piscina
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) * 2 AirCon units: 1 per bedroom * * 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. *
FamilyLocationNearby
4.92 out of 5 average rating, 148 reviews
Torre dei Belforti
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.
LocationValueHot tub
4.99 out of 5 average rating, 138 reviews
Casale in pietra in Val D’Orcia
Casale toscano del '800 con pietre a vista immerso nella meravigliosa campagna Toscana con uno splendido panorama sulla Val di Chiana. E' circondato da un parco di 6 ettari con un uliveto di 300 piante. Si trova a Sarteano, nel paese, un antico borgo medioevale con un castello da sogno, conosciuto per il Festival della Musica e del Jazz che si svolge alla fine dell'estate. Siamo nella bellissima Val d'Orcia, patrimonio naturale dell'umanità dall'UNESCO dal 2004.
LocationFamilyAccess
4.97 out of 5 average rating, 159 reviews
Podere Tignano, 4-bedroom villa in the Chianti!
Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.
ValueFamilyKitchen
4.98 out of 5 average rating, 107 reviews
"Villa Daisy" con vista su Siena
Meravigliosa villa con ingresso indipendente all'interno del podere "Caggiolo", riportato alla luce con curata e profonda ristrutturazione che ha mantenuto intatti i lineamenti tipici di un podere toscano. Splendida vista panoramica su Siena. Situato alle Ville di Corsano, a soli 14 km dalla città. Luogo ideale per trascorrere giorni in totale relax e godere delle meraviglie che questa zona offre (Chianti, Val d'Orcia, Crete Senesi..).
FamilyValueTV
4.95 out of 5 average rating, 173 reviews
Villa Capanna, Private Pool, Breathtaking Views
Ancient restored barn with up to 6 bedrooms and 6 bathrooms, immersed in a historic wine estate, just 6 km from Siena. One of the most beautiful views that the Tuscan panorama can offer, airconditioned bedrooms, exclusive swimming pool, large triple garden, BBQ, poolside table, terrace to enjoy the sunset over the medieval towers on the horizon while sipping the organic wines of the estate, fireplace, parking free, WI-FI internet.
ValueFamilyCleanliness
4.89 out of 5 average rating, 309 reviews
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.
ValueFamilyBackyard
4.99 out of 5 average rating, 123 reviewsPopular amenities for Grosseto villa rentals
Private villa rentals

Villa in pietra con piscina
LocationFamilyBiking
5.0 out of 5 average rating, 23 reviews
Beach House Giannella w/ direct access to the sea
FamilyValueComfort
4.82 out of 5 average rating, 99 reviews
Villa Casale "Il Diaccio" con vista sulla Maremma
FamilyValueKitchen
4.94 out of 5 average rating, 18 reviews
"La Capanna di Neri"casale in pietra con piscina
LocationFamilyKitchen
4.96 out of 5 average rating, 56 reviews
Grosseto, Casina Girasole
LocationValueAccuracy
5.0 out of 5 average rating, 28 reviews
Podere Pereti Vecchi | Stunning Val d'Orcia Views
FamilyValueOutdoor spaces
4.97 out of 5 average rating, 68 reviews
Villa Marsiliana
LocationFamilyShared spaces
4.92 out of 5 average rating, 26 reviews
Villetta al mare in Maremma Toscana
LocationValueParking
4.75 out of 5 average rating, 60 reviewsLuxury villa rentals

Villa unesco heritage, Jacuzzi & garden. BB Daria
LocationValueBiking
4.98 out of 5 average rating, 183 reviews
Villa Padronale - IlVillinoFarmhouse
ValueLocationAccuracy
4.93 out of 5 average rating, 255 reviews
Villa Isabella
FamilyLocationDecor
4.96 out of 5 average rating, 209 reviews
La Vignaccia (Farmhouse) - villa w/private pool
FamilyValueHospitality
4.96 out of 5 average rating, 102 reviews
Villa dei 2 Ulivi (Abbadia Isola)
LocationValueCheck-in
4.97 out of 5 average rating, 174 reviews
Villa Castiglioncello - accesso al mare privato
FamilyLocationIndoor spaces
4.91 out of 5 average rating, 35 reviews
Villa con giardino. Il Giardino del Cardinale.
LocationFamilyDecor
4.97 out of 5 average rating, 97 reviews
Villa - Incredible View - Private Beach - Jacuzzi
LocationFamilyHospitality
4.88 out of 5 average rating, 43 reviewsVilla rentals with a pool

la Balza
LocationValueNearby
4.93 out of 5 average rating, 128 reviews
Luxury Tuscan countryside villa with pool/WiFi/AC
ValueLocationIndoor spaces
4.99 out of 5 average rating, 81 reviews
Villa with pool in Chianti Area
ValueFamilyShared spaces
4.95 out of 5 average rating, 73 reviews
Coaching House
FamilyLocationAccuracy
5.0 out of 5 average rating, 67 reviews
Luxury Villa in Chianti • Private Natural Pool
FamilyLocationCondition
5.0 out of 5 average rating, 31 reviews
Villa in Toscana con piscina privata panoramica
FamilyLocationOutdoor spaces
5.0 out of 5 average rating, 35 reviews
Charming villa on two levels - Casa Lola
LocationFamilyAccuracy
4.9 out of 5 average rating, 10 reviews
Fabulous Farmhouse with Pool & 360 Panoramic View
LocationFamilyWifi
4.92 out of 5 average rating, 61 reviewsDestinations to explore
- Elba
- Giglio Island
- Lake Bolsena
- Giannutri
- Cala Violina
- Parco Regionale Della Maremma
- Feniglia
- Gulf of Baratti
- Spiaggia Di Sansone
- Le Cannelle
- Spiaggia di Marina di Campo
- Spiaggia di Capo Bianco
- Mount Amiata
- Cascate del Mulino
- Siena Cathedral
- CavallinoMatto
- Vulci
- Val di Chiana
- Necropolis of Tarquinia
- Palazzo Pubblico
- Valdichiana Outlet Village
- Saturnia Thermal Park
- Rimigliano Natural Park
- Riserva Naturale Diaccia Botrona





