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Cottage holiday rentals in Grosseto

Find and book unique cottages on Airbnb

Top-rated cottage rentals in Grosseto

Guests agree: these cottages are highly rated for location, cleanliness and more.

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Guest favourite
A sunlit outdoor space features a wooden deck with a dining table and chairs, overlooking lush green fields. A circular stone seating area surrounds a wooden hot tub, providing a tranquil spot to enjoy the serene landscape.
Cottage in Montepulciano
4.94 out of 5 average rating, 31 reviews

Angalia Guesthouse

Una vacanza di relax nell' annesso privato, immerso tra i vigneti del Vino Nobile e circondato da panorami mozzafiato. Ottimo punto di partenza per passeggiate infinite, giri in bicicletta, gite culturali, bagni nelle acque termali, avventure culinarie... e tanto altro! Arredamento in stile tradizionale toscano con tocchi di modernità FAST WIFI ADATTO PER SMART WORKERS che desiderano un ambiente stimolante per concentrarsi sul proprio lavoro, immersi nella bellezza naturale che ci circonda.

Top guest favourite
Cottage in Monticiano
5 out of 5 average rating, 32 reviews

Typical Tuscan Cottage with swimming pool and park

Il Country Cottage è ubicato nel cuore della Toscana autentica, in un territorio incontaminato, con una biodiversità unica. Sito a soli 5 minuti di auto dalla famosa Abbazia di San Galgano e da l'Eremo di Montesiepi, dove è custodita la prestigiosa "Spada nella Roccia". Viene affittata l'intera proprietà: la tipica casa toscana di campagna, la piscina, il giardino e il parco recintato. Una location perfetta per rilassarsi con la massima privacy, senza lo stress ed il logorio della vita moderna

Top guest favourite
A private outdoor jacuzzi is presented in the foreground, with bubbling water inviting relaxation. In the background, a rustic cottage made of stone is framed by flowering plants and a large olive tree, amidst the scenic landscape of Tuscan rolling hills.
Cottage in Castelmuzio
5 out of 5 average rating, 73 reviews

Panoramic view & outdoor jacuzzi - Pienza

‘L’Orto’ sits on a hill facing the 15th century monastery of Sant’Anna in Camprena, which was featured in the Academy Award-winning film ‘The English Patient’. Relax under a vine-covered pergola or in your private outdoor jacuzzi while enjoying panoramic views of idyllic Tuscan countryside, with its rolling hills and winding paths lined with cypress trees. ‘L’Orto’ is ideally located for a visit to the Val d’Orcia, a UNESCO World Heritage site, Pienza, Montalcino, Montepulciano or Siena.

Superhost
A spacious indoor living area features large, retractable glass doors that open to reveal a picturesque outdoor space. Natural stone walls and wooden beams create a rustic charm, while a cozy wood burner and a wooden coffee table add warmth to the serene atmosphere.
Cottage in Monte Argentario
4.81 out of 5 average rating, 101 reviews

Seafront Ecolodge breathtaking view

La Casetta sul Mare Tuscany primes an off the grid experience with all necessary comfort, this romantic ecolodge transpires sensuality, tranquility within walking distance from warm pristine mediterranean sea. A 3-hectare private property sitting on top of a secluded bay in Monte Argentario, Le Cannelle, one of the most exclusive destinations on the italian coast. The ecolodge offers a unique natural experience and a view to die for! You can see more videos IG lacasettasulmare.tuscany

Guest favourite
A cozy bedroom features a large bed framed by elegant wrought-iron headboards. Textured stone walls complement the cream-colored backdrop. A small table displays travel brochures and decorative elements, providing a homely touch.
Cottage in Pari
4.95 out of 5 average rating, 164 reviews

La Casa del Frantoiano - Pari -

We offer our guests a small apartment in Pari, a charming village in the heart of Tuscany, near the Terme di Petriolo and halfway between Siena and the sea, which can be reached in about half an hour. Completely and recently renovated, it consists of a kitchen, large bedroom, bathroom, outdoor relaxation area with table. Equipped with air conditioning and all kinds of comforts, it is ideal for 2/3 people, in the kitchen there is a single bed. Private pool shared with other guests.

Top guest favourite
An outdoor wood-fired hot tub is surrounded by lush green grass, offering a scenic view over the expansive landscape. A stone pathway leads to the hot tub, while the rustic stone cottage is visible in the background under a partly cloudy sky.
Cottage in Castell'Azzara
4.99 out of 5 average rating, 159 reviews

Your Private Tuscan Retreat

This beautiful sheepherder’s stone cottage is equipped with modern comforts and spa facilities free of charge. The large grounds of forest and meadow span a ridge and provide panoramic views of the valley toward Val d’Orcia to the north, the expansive Maremema to the south, and the ancient volcano of Amiata to the west. This is the perfect getaway for those wanting a private retreat from which to explore the rich wine, food, culture, history, and landscape of southern Tuscany.

Superhost
A stone house is set in a lush green landscape, surrounded by mature trees and blooming shrubs. The home features a rustic exterior, with a tiled roof and large windows. An open grassy area leads to the house, offering a serene view of the surrounding hills.
Cottage in Santa Fiora
4.86 out of 5 average rating, 36 reviews

Il Seccatoio - a stone house with panoramic views

Seccatoio is a detached stone house with an area of 60m². It can accommodate 2-4 people and has the bedroom on the first floor, under the antique roof. On the ground floor there is a kitchen, a large bathroom and a spacious living room with a sofa bed for 2 people. It offers a beautiful view of Monte Amiata. From the living you have acces to a terrace with dining table and grill in the shade of a pergola and another small terrace in front of the kitchen to enjoy the sunsets.

Top guest favourite
A covered veranda provides shaded seating with a table and chairs, overlooking expansive green hills dotted with trees and shrubs. A soft breeze can be imagined flowing through the open space, enhancing the serene countryside atmosphere.
Cottage in Osteria delle Noci
5 out of 5 average rating, 109 reviews

Your Tuscan oak tree house, enchanting Val d'Orcia

The house enjoys a rare and enchanting view of the Val d’Orcia and Monte Amiata, ensuring maximum privacy. The interiors mirror the charm of the Tuscan style, with antique furniture and finishes made by local artisans. It is equipped with a double bedroom, a large living room with a big table, a fully equipped kitchenette, a double sofa bed in front of the fireplace, in the living room. Outside, the patio will allow you to eat with the colors of the sunset as a backdrop.

Guest favourite
An aerial view captures the villa surrounded by expansive farmland and lush greenery. An inviting infinity pool is visible in the foreground, complemented by neatly arranged olive trees. The villa's rustic architecture blends harmoniously with the tranquil rural landscape.
Cottage in Provincia di Siena
4.96 out of 5 average rating, 51 reviews

Wonderful Villa for 10 people in Valdorcia

The villa is set in an oasis of tranquillity between the renowned towns of Montepulciano and Pienza that can be reached in only few minutes by drive. Villa Gaeta has four double bedrooms within the main building and an additional double bedroom in the annex by the patio. It can accommodate up to 10 persons, perfectly suitable for families and small parties. This villa is a brilliant example of Tuscan rural 18th century style, well proportioned, carefully renovated.

Guest favourite
A modern stone house is surrounded by lush greenery, nestled against a hillside. Large glass windows provide ample natural light, showcasing the inviting interior. The roof has a gentle slope, reflecting a blend of traditional and contemporary architecture.
Cottage in Seggiano
4.93 out of 5 average rating, 103 reviews

EcoLodge – modern design in a peaceful panoramic location

The EcoLodge, modern, ecological, comfortable, is in the middle of nature in a peaceful, fertile cultural landscape on Monte Amiata in the quiet southern Tuscany. It belongs to an old farmhouse with plenty of space, beautiful views, many old fruit, chestnut, olive trees and our vineyard. It's an ideal location. From here you can explore world-famous sights, do a lot and enjoy the tranquility of Tuscan country life away from the hordes of tourists.

Guest favourite
A rustic two-story building constructed from warm brick is surrounded by lush greenery. Large windows invite natural light, while wooden shutters add charm. The exterior features a gravel path leading to lounge chairs, creating a serene outdoor space for relaxation.
Cottage in Buonconvento
4.87 out of 5 average rating, 83 reviews

Tuscan Barn Apartment for 6 with panoramic pool

Panoramic Tuscan apartment converted from an old barn, with direct access to the garden and a shared panoramic swimming pool overlooking the Senese hills. Ideal for families or small groups of friends looking to enjoy for an authentic rural experience, privacy and relax. The apartment features three double bedrooms each with private bathroom, air-conditioning and WI-FI. A perfect place to enjoy nature, silence and unforgettable Tuscan sunsets.

Guest favourite
A wooden deck offers a serene view of rolling green hills extending into the distance. Two sun loungers are placed on the deck, inviting relaxation amid the natural surroundings. Trees frame the scene, creating a peaceful atmosphere, ideal for enjoying the landscape.
Cottage in Vetulonia
4.96 out of 5 average rating, 130 reviews

La Dolce Vita Romantic Sea-view Cottage. Tuscany

Welcome to Il Baciarino, a rustic agriturismo in the green hills of Maremma, Tuscany’s wild and less-traveled coastal region. Our property offers unique, handcrafted cottages with sea views, privacy, and direct contact with nature. Set within 19 acres of hillside wilderness in the charming Etruscan town of Vetulonia, Il Baciarino is the perfect place to escape the city, slow down, and enjoy unspoiled landscapes, fresh seafood, and good wine.

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