Vacation home rentals in Province of Grosseto

Find and book unique vacation home rentals on Airbnb

Top-rated vacation home rentals in Province of Grosseto

Guests agree: these vacation home rentals are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

The exterior of the stone house is featured, showcasing rustic charm with green shutters and a welcoming entrance. The garden area includes tables and chairs, surrounded by lush greenery and potted plants, offering a serene outdoor space for relaxation.

Vacation home in Montisi

4.94 out of 5 average rating, 17 reviews

Unique & Historic Getaway: Dreamy Garden

Questo elegante alloggio è perfetto per viaggi di gruppo o familiari, all'interno di un piccolo, ma prezioso borgo toscano, Montisi, nel Comune di Montalcino, famoso per il vino e per essere nel parco della Val d'Orcia, sito UNESCO. La casa ha un giardino pensile molto tranquillo, dove poter cenare e rilassarsi dopo una giornata passata tra le meraviglie naturali, storiche ed artistiche della zona. Ogni stanza di Umberto121 è differente dall'altra, avendo mantenuto le caratteristiche di ognuna.

Guest favorite

A tranquil pool area is highlighted with sun loungers and thatched umbrellas. In the background, a two-story building is framed by lush greenery and blooming flowers, creating a serene outdoor escape.

Vacation home in Scarlino

4.73 out of 5 average rating, 22 reviews

incantevole casa con piscina - Res. "La Beccanina"

Delizioso appartamento in complesso Turistico "LA BECCANINA"-SCARLINO. Immerso nella splendida Maremma Toscana a pochissimi km dalla spiaggia di Cala Violina, Cala Martina e dalle localita' piu' rinomate della zona. Offre piscina, aree ristoro, barbecue e parcheggio privato. Primo piano, si compone di 2 camere doppie (1 matrimoniale + 1 (2 letti singoli accoppiabili), 2 bagni con doccia, sala con camino, soggiorno con cucina ed ampia terrazza vista piscina.Aria condizionata in tutti gli ambienti

Guest favorite

A rustic stone farmhouse is gently illuminated at dusk, showcasing its architectural details against a twilight sky. Tall cypress trees frame the building, while soft lights outline the windows and entrance, creating a peaceful ambiance amidst the expansive countryside.

Vacation home in Monte Cucco

4.82 out of 5 average rating, 38 reviews

Prachtig huisje in Toscane, Casa di Luca

Genieten op deze stijlvolle plek, deel van drie verbouwde boerderijen aan de rand van het wijngebied Montecucco. Een prachtig wijds uitzicht op de heuvels rondom. Stelt u zich voor met een glaasje Brunello of Montecucco, Italiaanse hapjes bij de hand, kijkend naar de ondergaande zon. Neem een frisse duik in het zwembad, voel de warmte van de zon en ga op in het Italiaanse leven. Maak de mooiste dagtripjes naar de Val D'Orcia, Bagno Vignoni, Siena, Firenze, Montalcino, Montepulciano en naar zee.

Guest favorite

A spacious living area is highlighted by elegant brick arches and soft seating arrangements. A wooden dining table is set for a meal, complemented by stylish tableware. Natural light streams through large windows, illuminating the warm tones of the furnishings.

Vacation home in Torrita di Siena

4.84 out of 5 average rating, 19 reviews

Pian'D'olmo, antico casale nel cuore della Toscana

Nel cuore della Toscana in Val di Chiana, su un crinale circondato da vigneti, si trova Piandolmo - una casa in pietra del 18° secolo. L'appartamento è stato recentemente ristrutturato, proprio grazioso giardino con ampio patio. Grande piscina per condominio. Qui puoi venire come amici, coppie o familiari. Se hai una bicicletta, è un punto di partenza perfetto per molte gite di un giorno. Dista solo 5 minuti di auto dal centro di Montepulciano e dall'accogliente paese di Montefollonico, 15

Top guest favorite

A rustic stone house is set amidst lush greenery, featuring large windows that invite natural light. The structure includes a covered terrace adorned with climbing plants, providing an inviting outdoor space. The surrounding lawn is well-maintained, contributing to a peaceful rural setting.

Vacation home in Monticchiello

5 out of 5 average rating, 22 reviews

Elegant farmhouse overlooking Pienza

Podere Fonte Bernardi is an authentic Tuscan country house. Surrounded by the nature of the Val d'Orcia, an ideal place to relax. Located a few km from the most beautiful places in Tuscany such as Pienza, the medieval village of Monticchiello, the thermal site of Bagno Vignoni and the homeland of Montepulciano wine. Perfect for taking long walks and discovering local wines and food. You will be able to enjoy the most beautiful sunset over Pienza in the silence of the most authentic nature.

Guest favorite

The living and dining area features exposed stone walls and wooden beams, enhancing the rustic charm. A spacious sofa sits adjacent to a wooden dining table, surrounded by four chairs. Natural light filters in through a window, illuminating the tiled flooring.

Vacation home in Massa Marittima

4.94 out of 5 average rating, 93 reviews

Design apartment in Massa Marittima, "slow city"

A great 65 m2 - 2 bedroom Apartment, entirely renovated in freestone and exposed beams, with design touch. In the upper, medieval part of Massa Marittima, Siena in miniature, with a superb Romanesque cathedral. Central but quiet area. Many restaurants and oeno-gastronomic specialties. Magnificent freshwater lake, Lago dell'Accesa, 10 minutes by car. Sea at 20 minutes. Siena at 1:15 a.m. Massa, "Citta slow", offers many other activities: museums, wine cellars, horse riding, Bike Park, MTB

Guest favorite

A spacious kitchenette and dining area is presented, featuring wooden cabinets and a gas stove. A wooden table with four chairs occupies the center, while a green sofa sits against the wall. Natural light filters through a nearby window, illuminating the terracotta floor.

Vacation home in Roccastrada

5 out of 5 average rating, 19 reviews

Apartment in a wine estate in Tuscany

Welcome to our 18th century villa in Sticciano, nestled between Florence and Rome, in the Tuscan Maremma! The beautiful villa has been trasformed into a wine estate hostelry, offering ten apartments for an unforgettable stay. Expect to see rolling hills, vineyards, and expansive green landscapes. A traditional Tuscan dinner is served twice a week, and our delicious breakfast is available every morning on request. Enjoy the pool or a wine experience visiting our vineyards and cellars!

Guest favorite

A simple bedroom is presented with a spacious bed, featuring decorative pillows in warm tones. A mirror reflects a clothing rack and a framed photograph adorns the wall. Natural light enters through a window, enhancing the neutral color palette.

Vacation home in Montemerano

4.93 out of 5 average rating, 30 reviews

Casa Monteme, loft moderno con vista sulla Maremma

Tra le colline della Maremma, a solo pochi passi dalle Terme di Saturnia, nell'antico borgo medievale di Montemerano nasce Casa Montemè. Materiali naturali, tecniche tradizionali, artigianato locale e qualche tocco contemporaneo hanno trasformato un'antica casa tradizionale nella casa vacanza dei sogni. La sua posizione la rende ideale per chi cerca un pò di relax e vuole godersi i meravigliosi Borghi della Toscana! Rilassati e ricaricati in quest'oasi di quiete ed eleganza.

Top guest favorite

A balcony view showcases a charming wooden table and two chairs, overlooking the harbor filled with boats. The scene is framed by glass doors and a lush green plant, enhancing the sense of openness and tranquility.

Vacation home in Porto Ercole

4.98 out of 5 average rating, 51 reviews

Casa sul porto - Il Partito

Nel cuore di Porto Ercole, sul lungomare, si affitta questa incantevole casa vacanze di circa 70 mq, situata al primo piano. Il suo balconcino affacciato sul porto offre una vista suggestiva sul mare e sulle barche ormeggiate, facendovi immergere nella magica atmosfera dell’Argentario. Grazie alla posizione privilegiata, bar, ristoranti e negozi sono a pochi passi. Come proprietaria del noleggio gommoni IDROBOAT, sarò lieta di suggerirvi le spiagge più belle.

Guest favorite

The exterior of a multi-story brick building is surrounded by lush greenery and vibrant foliage. Windows with dark shutters are visible, and ornamental plants on the balcony add a touch of color. The building is nestled within a scenic landscape.

Vacation home in Torrenieri

4.96 out of 5 average rating, 67 reviews

CASA VACANZE I DUE CIPRESSI "App. Rosa Canina"

L'appartamento Rosa Canina è situato a Torrenieri (SI) piccola frazione del comune di Montalcino, dotato di ogni confort per trascorrere una rilassante vacanza o per impegni di lavoro. Ottima posizione per visitare gli splendidi borghi della Val d'Orcia, come San Quirico d'Orcia, Pienza, Montepulciano,.. E per chi volesse avventurarsi può percorrere la via Francigena distante da noi 5 minuti a piedi godendo dei meravigliosi paesaggi Toscani.

Top guest favorite

An outdoor seating area features a small table surrounded by two chairs, adorned with a light breakfast setup. The stone facade of the house is complemented by climbing vines and a bright flower arrangement, inviting guests to enjoy the fresh air.

Vacation home in Monticchiello

4.97 out of 5 average rating, 107 reviews

In Toscana Camere

**Your Dream Retreat in the Heart of Val d'Orcia** Welcome to In Toscana Camere, a charming holiday home located in the historic center of Monticchiello, a Tuscan village full of charm and authenticity. Surrounded by stone walls and enhanced by modern, comfortable interiors, this home offers the perfect balance between tradition and contemporary style. Wake up every morning to a breathtaking view of the stunning Val d'Orcia.

Top guest favorite

A spacious sleeping area features a decorative bed with light-colored bedding and plush pillows. Soft towels are neatly arranged at the foot of the bed. Natural light filters through a window adorned with dark curtains, highlighting the room's rustic charm.

Vacation home in Pienza

4.94 out of 5 average rating, 84 reviews

Pienzalettings

Rilassati in questo spazio tranquillo nel piccolo borgo. La nostra casa vacanze PienzaLettings è un'esplosione di unicità e bellezza, dotata di un fascino senza tempo. Dotato di ogni comfort, è pronto ad accogliervi e pronto a farvi vivere un'avventura rilassante ed emozionante in un luogo senza tempo. Non sono inclusi 1€ di tassa di soggiorno per persona a notte, esclusi minori di 15 anni