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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!

Villa in Siena

4.8 out of 5 average rating, 263 reviews

XIII Century Tower with Private Panoramic Pool

Ancient country tower property with 5 airconditioned bedrooms for up to 12 guests at the heart of the peaceful Montechiaro organic wine estate. From your private pool, soak in the Tuscan sun and enjoy unforgettable views of the Chianti rolling hills and the medieval towers of Siena. The property also boasts access to the endless olive grove, a large patio area for outside dining in the shade, ping pong table for fun family matches, WIFI & free parking. Silence and time are the real luxury here.

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 Castiglion d'orcia

4.96 out of 5 average rating, 106 reviews

Wp Relais Borgo Vignalunga

Discover Borgo Vignalunga by WP Relais, an charming hamlet set in a 46-hectare estate in the heart of the Val D'Orcia, a UNESCO World Heritage Site. Surrounded by woodland, pastures, a lush vegetable garden, cultivated fields and three olive groves with 1,500 olive trees, Borgo Vignalunga is the ideal place to experience the true essence of Tuscany. The property is close to historical villages, evocative architecture, unspoilt natural landscapes and renowned restaurants, bars and wineries.

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.

Guest favourite

Villa in Barullo-Centoia

4.91 out of 5 average rating, 43 reviews

Bellora: A Perfect Villa in Cortona, Tuscany

Discover the epitome of Tuscan luxury at our exquisite villa, boasting an idyllic location near Cortona. A mere 15-20 minute drive to Cortona and 25 minutes to Montepulciano, it offers unparalleled convenience for exploring Tuscany. Nestled within a private gated estate, this opulent haven showcases 3 bedrooms, 2 pristine bathrooms, and a generously-sized swimming pool exclusively reserved for your indulgence. Youtube: "Villa Bellora Cortona Drone fly by"

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 Castiglione d'Orcia

5 out of 5 average rating, 10 reviews

#1 Luxe Farmhouse, Hilltop Views, Saltwater Pool

With outstanding 360 degree views of vibrant olive groves, cypress trees, and endless vineyards, this outstanding villa sits on top of the world. Surrounded by lush, rolling green hills, one of the most unique getaway experiences awaits. Equipped with a large saltwater pool and a modern interior with just the right amount of Tuscan flair, immerse yourself in the old country with a few added luxuries.

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

Holiday rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Bungalows

Intimate homes, inviting architecture

Houses

A space that's all yours, with room for everyone

Popular amenities for Grosseto villa rentals

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

Villa in Rio Marina

5 out of 5 average rating, 3 reviews

Entire Villa with Private Swimming Pool

Guest favourite

Villa in Orvieto

4.9 out of 5 average rating, 31 reviews

Spectacular view villa and infinity pool

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

Guest favourite

Villa in Gaiole in Chianti

5 out of 5 average rating, 16 reviews

Montemarcoli

Villa in Montalto di Castro

4.93 out of 5 average rating, 28 reviews

La Casa Del Fico Villa with Pool

Villa in Montepulciano

5 out of 5 average rating, 3 reviews

Terra Antica Suite & Ville - Villa Vino - Private Jacuzzi

Villa in Radda in Chianti

4.64 out of 5 average rating, 11 reviews

Tenuta Lo Spugno

Luxury villa rentals

Guest favourite

Villa in Castiglion fiorentino

4.98 out of 5 average rating, 60 reviews

Tuscany Villa Mammi

Guest favourite

Villa in Sodo

4.95 out of 5 average rating, 22 reviews

The House of the Sodo Sun

Guest favourite

Villa in Siena

4.96 out of 5 average rating, 27 reviews

La Capanna di Elfo Independent house with jacuzzi

Guest favourite

Villa in Giglio Porto

5 out of 5 average rating, 11 reviews

Villa exclusive " Cielo e Mare"

Guest favourite

Villa in Montefiascone

4.92 out of 5 average rating, 36 reviews

I Gigli del Belvedere

Guest favourite

Villa in Siena

5 out of 5 average rating, 18 reviews

Panoramic Villa Larniano Private pool 14 max

Guest favourite

Villa in Ambra

4.98 out of 5 average rating, 126 reviews

Chianti Villa in Tuscany near Siena & Arezzo

Villa in Torrita di Siena,

5 out of 5 average rating, 4 reviews

Villa Scianellone

Villa rentals with a pool

Guest favourite

Villa in Località Poggio Olivo

4.98 out of 5 average rating, 57 reviews

Beautiful villa with swimming pool in Tuscany

Villa in Volterra

4.9 out of 5 average rating, 10 reviews

Belvilla by OYO Ulivo

Villa in Monteroni d'Arbia

5 out of 5 average rating, 8 reviews

Villa in Siena with pool x10 guests

Villa in Castiglione del lago

4.78 out of 5 average rating, 9 reviews

A Beautiful Original Villa

Guest favourite

Villa in Paciano

4.98 out of 5 average rating, 40 reviews

Villa Fortuna with Hot-Tub and pool near Tuscany

Guest favourite

Villa in Volterra

4.98 out of 5 average rating, 50 reviews

Villa Casa al Povero

Guest favourite

Villa in Volterra

5 out of 5 average rating, 28 reviews

Detached villa with private pool

Villa in Seggiano

4.92 out of 5 average rating, 12 reviews

A charming 3 bedroom Tuscan villa with pool

Destinations to explore