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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.

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Villa in Chianciano Terme

5 out of 5 average rating, 10 reviews

3 bdr Lux Villa in Montepulciano Tuscany,Top View

Live your own experience as a local at LaVittoria 10 in Val d'Orcia, short driving to Montepulciano, Pienza, Cortona,Siena Huge apt on top floor of the Villa, with 2 magnificent suites, panoramic lounge and professional kitchen, plus The Cottage,for 2+1 pp, with private entrance, kitchen, large bdr and bathroom with Jacuzzi for 2! Hot tub with top view in the garden and relax area with comfy sofas !Your local host arranges priv dinners and Wineries tour & tasting. Ebikes tour with guide. Wifi

Guest favourite

Villa in Sovicille

5 out of 5 average rating, 13 reviews

Exclusive farmhouse, pool, en-suite A/C rooms

Tuscany Villa with privatepool,max 8 pax, SienaView. Siena only 8km driving; less than 5 minutes driving you have supermkt, pizzeria, bank, restaurants. 2 Floors only for you, about 250 sqm 4 bathrooms en suite, Airconditioning, Private pool and garden NO AREAS SHARED WITH OTHER GUESTS Inside an organic Farm, where you can see the real Farm work, to know Farmers and visit their Organic Pasta factory, to have Farm Experience on demand, purchase and taste our organic products ENJOY YOUR TUSCANY!

Guest favourite

Villa in San Leolino

5 out of 5 average rating, 105 reviews

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.

Guest favourite

Villa in Lisciano Niccone

4.85 out of 5 average rating, 41 reviews

Villa San Martino, on the Tuscany/ Umbria border

Villa San Martino is not just another holiday in Tuscany or Umbria - this is a really special place. With spectacular views across the world famous Niccone Valley towards Mercatale di Cortona, relax in the infinity pool, or dine alfresco on the terrace. From the villa you can easily access the enchanting towns of Cortona, Pienza, Montepulciano, Siena, Perugia, Assisi and Florence. The Niccone valley is home to delightful restaurants and you can sample great local Tuscan & Umbrian cuisine.

Guest favourite

Villa in Città della Pieve

5 out of 5 average rating, 33 reviews

Stunning Villa with heated pool

6 BDS + 6 Bathrooms, + 2 kitchen + 3 patios to eat al fresco + Ping pong and swing. + new renovated heated swimming pool!!! Full AC. + barbecue and lounge area. Welcome to our exquisite villa located in Città della Pieve, an area renowned for its rich Tuscan and Umbrian culture, delectable cuisine, and exquisite wines. Immerse yourself in the breathtaking views of the città della Pieve and Cetona hills right from the comfort of your own room. Walking distant to a bio-dinamic cellar.

Guest favourite

Villa in Cortona

5 out of 5 average rating, 69 reviews

Stunning Tuscan Villa & Panoramic Infinity Pool

Stunning Tuscan hilltop Villa, with infinity edge swimming pool, has sweeping 180° panoramic views to Cortona, Lake Trasimeno and the entire Val Di Chiana. The perfect family retreat within ancient sun-drenched olive groves. 5 Double bedrooms; 4 bathrooms; new fully integrated kitchen & dining living space; living room with fireplace; TV snug; stone BBQ & outdoor kitchen within dining terraces and gardens; covered breakfast porch; parking; private infinity pool with sunset views.

Villa in Castelnuovo Berardenga

4.72 out of 5 average rating, 32 reviews

Private Villa: Panoramic Pools and Wellness

la Villa è immersa tra le vigne e gli olivi: Siamo nel cuore del chianti storico ma in posizione strategica per raggiungere Siena , Firenze e San Gimignano. Ideale per riunioni familiari, piccole cerimonie, pizza party nel forno a legna o rilassarsi nella spaziosa piscina con splendida vista.Sempre ad uso esclusivo degli ospiti una suggestiva Spa all'interno di una loggia panoramica, direttamente collegata con la casa, con bagno turco, sauna, Jacuzzi e sala massaggi.

Villa in Radicondoli

4.94 out of 5 average rating, 17 reviews

A Romantic Villa in the heart of Tuscany

The old country villa is the ideal location for an unforgettable vacation, suitable for families and small groups: where you can rest and enjoy the fresh and spacious interiors, the shade of the loggia and the scent of the aromatic herbs in the wide garden. Where you may work, read, write and relax in a peaceful atmosphere, visit the nearby artistic cities, take quiet walks or a gourmet tour through the many trattorias of the area.

Villa in Montescudaio

4.8 out of 5 average rating, 10 reviews

PRIVATE VILLA BERTI TUSCANY FOREVER Montescudaio

Villa Berti TUSCANY FOREVER. This is standalone, new villa with private swimming pool and 3 bedrooms and 2 bathrooms. WE KNOW WHERE HAPPY KIDS ARE ! TUSCANY FOREVER featuring unique family friendly properties. Berti is located 2km from the center of Montescudaio town with magnificent views. Etruscan coast , the sea is about 10km away. If you’re facing an issue that requires a personal touch, please contact us.

Villa in Asciano

5 out of 5 average rating, 4 reviews

Villa Le Liscaie [Crete Senesi]

Private Villa in the Crete Senesi - Stunning swimming pool surrounded by olive grow - 4 bedrooms: one master bedroom, one room with two single beds, one with a single bed and another room with a comfortable double sofa bed - large outdoor space and private forest - 5 minutes from the highway

Guest favourite

Villa in Terricciola

4.9 out of 5 average rating, 52 reviews

Villa Donna Camilla

Imagine your Tuscan dreams home, the big iron gate opening to your cypress driveway up to your home, big windows, amazing tuscan views, big pool and plenty of space to spend time with your family and friends. Come and experience Villa Donna Camilla, a real journey Under The Tuscan Sun!

Holiday rentals for every style

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Houses

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Bungalows

Intimate homes, inviting architecture

Flats

Convenient locations with everyday essentials

Popular amenities for villa rentals in Grosseto

Free parking on premises

Air conditioning

Private villa rentals

Villa in Fornaci

5 out of 5 average rating, 15 reviews

Villa with pool,tennis court,village walk distance

Guest favourite

Villa in Orvieto

4.9 out of 5 average rating, 31 reviews

Spectacular view villa and infinity pool

Guest favourite

Villa in Celleno

5 out of 5 average rating, 17 reviews

Cilenia, a beautiful Villa in the heart of Tuscia

Guest favourite

Villa in Cortona

5 out of 5 average rating, 6 reviews

Villa Pietrenta

Villa in Montepulciano

5 out of 5 average rating, 3 reviews

Terra Antica Suite & Ville - Villa Vino - Private Jacuzzi

Villa in Provincia di Arezzo

4.91 out of 5 average rating, 43 reviews

Villa near Florence: Pool, AC, Vast natural garden

Guest favourite

Villa in Seccheto

4.82 out of 5 average rating, 39 reviews

Villa in Solana, Elba Island - Seccheto

Guest favourite

Villa in Gaiole in Chianti

5 out of 5 average rating, 9 reviews

Casa Faraona, villa with private pool

Luxury villa rentals

Guest favourite

Villa in Sodo

4.95 out of 5 average rating, 22 reviews

The House of the Sodo Sun

Guest favourite

Villa in Castiglion Fiorentino

5 out of 5 average rating, 18 reviews

Villa Degli Olivi

Villa in Radda in Chianti

5 out of 5 average rating, 5 reviews

Villa Montemaggio

Guest favourite

Villa in Arezzo

4.94 out of 5 average rating, 18 reviews

Villa Leopoldina in the heart of Tuscany

Villa in Montalto di Castro

4.93 out of 5 average rating, 28 reviews

La Casa Del Fico Villa with Pool

Villa in Paciano

5 out of 5 average rating, 4 reviews

Villa Lidia - Independent luxury farmhouse

Villa in Colle di Val D'Elsa

4.95 out of 5 average rating, 19 reviews

Villa L'Elsa, amazing view, pool always open

Guest favourite

Villa in Marina di Bibbona

4.97 out of 5 average rating, 31 reviews

Casa Rosa - Villa with private access to the beach

Villa rentals with a pool

Guest favourite

Villa in Greve in Chianti

4.95 out of 5 average rating, 37 reviews

Villa San Martino 6-8 people

Villa in Rio Marina

5 out of 5 average rating, 4 reviews

Entire Villa with Private Swimming Pool

Guest favourite

Villa in Montevarchi

4.91 out of 5 average rating, 43 reviews

Villa Pongina - Tuscany - private pool - air con

Guest favourite

Villa in Montepulciano

4.91 out of 5 average rating, 119 reviews

Villa in Montepulciano with Pool

Villa in Monteroni d'Arbia

5 out of 5 average rating, 8 reviews

Villa in Siena with pool x10 guests

Guest favourite

Villa in Castiglion Fiorentino

4.95 out of 5 average rating, 39 reviews

Villa Il Sogno di Pietro, private swimming pool and AC

Villa in Castiglione del lago

4.78 out of 5 average rating, 9 reviews

A Beautiful Original Villa

Villa in San Gimignano

4.79 out of 5 average rating, 24 reviews

Elisa Villa

Destinations to explore