
Villa holiday rentals in Grosseto
Find and book unique villas on Airbnb
Top-rated villa rentals in Grosseto
Guests agree: These villas are highly rated for location, cleanliness and more.

Villa dei Gelsomini, Residence in the countryside
Villa dei Gelsomini welcomes you to the peaceful countryside,just 5 km from Viterbo. Close to restaurants, local sites, and the famous Terme dei Papi and Tuscia Terme, it’s ideal for relaxing and exploring. You’ll fall in love with the bright, airy rooms, cozy kitchen, elegant decor, and comfy beds. Outdoor spaces are perfect for dining in the shade, unwinding in the fresh air, or enjoying nature. A charming retreat for couples, families, and friends seeking tranquility and authentic experiences

Cottage in Val d'Orcia Tuscany, Jacuzzi & Hot Tub!
Welcome at Charming Cottage in Tuscan Villa! Immerse in the history of Montepulciano, Pienza, Cortona, Siena, Explore Val d'Orcia, natural hot pools and falls! Fully equipped kitchen, private patio for al fresco dining, magnificent bathroom with large Jacuzzi, and large bedroom with new top quality, Memory foam mattress. Thanks to thick walls, it's very cool in summer! We arrange Winery tours & tasting and cooking class. A/C, Free wifi, comfy sitting and sofas and Hot Tub with great view!

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

A paradise in Montepulciano...
Villa Il Cubo has a large private park and swimming pool and marvellous views on the Tuscan countryside. It is fully air-conditioned and the decoration has been updated with charming details that will make you enjoy the best Tuscany has to offer. We have electric vehicle charging point at a moderate extra contribution. IN JULY AND AUGUST WE LET FOR A MINIMUM OF 7 DAYS FROM SATURDAY TO SATURDAY. Exceptions are possible only if don't create unrentable gaps between one guest and the next.

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.

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

Farmhouse in Chianti
Beautiful portion of a farmhouse immersed in Chianti with a beautiful swimming pool, surrounded by vineyards and olive trees, perfectly furnished with a large garden and parking spaces. It is located 20 minutes from Florence, 40 from Siena and 50 from Pisa, in a few minutes you can reach Certaldo (birthplace of Boccaccio) and Vinci (birthplace of Leonardo Da Vinci). The house is halfway between Montespertoli and San Casciano (7km).

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.
Popular amenities for Grosseto villa rentals
Private villa rentals

Tuscan retreat surrounded by peace and nature

Private villa in Maremma 15 minutes from the sea

Stone villa with pool

Romantic Villa with private pool - "Il Pollaio"

Casa Isabella - Villa with pool and sauna

Villa with garden. The Cardinal's Garden.

Beautiful tuscan country house

Villa Blue Melon - private beach
Luxury villa rentals

Villa Pupì Green Retreat

Country House Lo Spigo 4, Emma Villas

Villa Le Murate

Vakantievilla Farmhouse Dolci Hills

Luxury Villa in the very heart of Chianti

Beach House Giannella w/ direct access to the sea

Villa La Poggerina, private pool and amazing view

Poggio del Fattore-Villa with pool, hilltop, Chianti
Villa rentals with a pool

Charming Chianti Villa | Garden & Panoramic Pool

Lake View Private Villa w Pool

San Giovanni in Poggio, Villa Meriggio 95 sqm

Montemarcoli

CHARMING TUSCANY VILLA PRIVATE POOL

Luxury Tuscany Villa with Pool [La Stellata]

Private Villa with semi-Olympic pool and Tennis

sea view villa with private infinity pool
Quick stats about villa rentals in Grosseto

Nightly prices starting at
Grosseto holiday rentals start at $202 NZD 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!
Destinations to explore
- Condo rentals Grosseto
- Beach house rentals Grosseto
- Family-friendly rentals Grosseto
- Rentals with outdoor seating Grosseto
- Rentals with a washing machine and dryer Grosseto
- Apartment rentals Grosseto
- Smoking-friendly rentals Grosseto
- Rentals with a patio Grosseto
- House rentals Grosseto
- Pet-friendly rentals Grosseto
- Beachfront rentals Grosseto
- Villa rentals Grosseto
- Villa rentals Tuscany
- Villa rentals Italy
- Elba
- Giglio Island
- Lake Bolsena
- Giannutri
- Cala Violina
- Feniglia
- Spiaggia Di Sansone
- Spiaggia Di Barbarossa
- Gulf of Baratti
- Spiaggia di Capo Bianco
- Spiaggia di Marina di Campo
- Le Cannelle
- Cascate del Mulino
- Siena Cathedral
- Palazzo Pubblico
- Parco Regionale Della Maremma
- Valdichiana Outlet Village
- CavallinoMatto
- Santa Maria della Scala
- Saturnia Thermal Park
- Necropolis of Tarquinia
- Terme San Filippo
- Abbey of Sant'Antimo
- Abbey of Monte Oliveto Maggiore





