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Holiday rentals with a pool in Grosseto

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Grosseto

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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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
4.94 out of 5 average rating, 109 reviews

EcoLodge – modern design in a peaceful panoramic location

The modern, ecological and comfortable EcoLodge is in a quiet and secluded location, surrounded by olive groves, chestnut and fruit trees, vines and meadows. In front of you are the hills of the Val d'Orcia, and behind you is Monte Amiata. Three worlds meet here: Val d'Orcia, Monte Amiata and Maremma. The diversity is an ideal starting point for culture, wine, hiking, mountain biking, hot springs and the sea – and at the same time a place to enjoy Tuscan country life away from the crowds of tourists.

Top Guest favourite
Villa in Montepulciano
4.97 out of 5 average rating, 125 reviews

Wine Experience Villa in Montepulciano

🏡 Villa Talosa is immersed in the vineyards of the Fattoria della Talosa, a historic winery in Montepulciano that produces Vino Nobile. An authentic place, ideal for relaxing with the magic of the Tuscan countryside and an enchanting view from every window. Just 1.5 km from the historic center, which can also be reached on foot, you can visit our Historic Winery from the 1500s under Piazza Grande: a unique experience between history and passion for wine. Heating and air conditioning are included.

Guest favourite
The entrance of the building is adorned with lush green vines, climbing its facade. Two light gray doors with glass panels are framed by large windows, reflecting the blue sky. Potted plants are placed on either side of the doors, adding a touch of greenery.
Farm stay in Manciano
4.96 out of 5 average rating, 111 reviews

Casa Mirta art & nature in the heart of Maremma

We welcome you in one of the most beautiful landscapes of Italy, in the countryside between Capalbio and Montemerano. Mirta is an apartment in the casale located in the center of a centuries-old olive grove. The garden offers an incredible view on the Maremma hills with the Argentario coast in the background. Uncontaminated nature & silence and a wide choice of excursions in the surroundings with art, history, borghi and traditions. 20 minutes from Saturnia and 30 from the beaches of Capalbio

Guest favourite
Villa in Montepulciano
4.92 out of 5 average rating, 145 reviews

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) * 2 AirCon units: 1 per bedroom * * 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. *

Top Guest favourite
Home in Pereta
5.0 out of 5 average rating, 73 reviews

Bel Casale with sea view and the mediaeval village

In the Maremma countryside, private panoramic swimming pool, with a 360° !!! View of the Argentario, the island of Giglio and the medieval village. Spectacular sunsets to admire! The villa is on one floor, characterized by exposed wooden beams, verandas, handmade terracotta floors, elegant minimal furniture. It can accommodate up to 6 people. Park of 2 hectares of garden with olive grove and centuries-old oaks. Located 5 minutes from the beautiful village of Pereta.

Top Guest favourite
A rustic stone farmhouse is surrounded by colorful flower pots, adding charm to the entryway. The structure features a mix of wooden shutters and terracotta accents. A gravel driveway leads to the entrance, framed by lush greenery and vibrant blooms.
Apartment in Castiglione d'Orcia
4.99 out of 5 average rating, 111 reviews

Mimosa Apartment - Poggio al Vento

Private apartment in a farmhouse from the 1600s. The same consists of kitchen, double bedroom and bathroom. It has everything you need for a pleasant stay. From the terrace, the breathtaking view, overlooking Mount Amiata, Rocca D'Orcia an ancient fortress and the Castle of Ripa D'Orcia. The swimming pool overlooks the Montalcino side. We are an organic farm, we produce high quality wine and oil. We offer, for a fee, tastings of our red wines. Winery tour etc

Top Guest favourite
A serene outdoor area features well-maintained vineyards and gently sloping hills in the background. A shaded seating area is positioned beneath a large canopy, with rustic seating options visible. The landscape is complemented by a stone wall and lush greenery, creating a calm and inviting environment.
Farm stay in Montalcino
4.96 out of 5 average rating, 80 reviews

Cappella - farmhouse surrounded by vineyards

The Cappella apartment is part of the Le Chiuse farm, an 1840 structure immersed in the vineyards. It is made from a small deconsecrated church, consisting of a living room with kitchenette, armchairs and fireplace, a large double bedroom, a bathroom with shower, a small room and a loft with a double bed. Equipped with air conditioning. The window of the master bedroom is equipped with a mosquito net. Aperture pool June-October

Guest favourite
The image depicts a serene swimming pool surrounded by sun loungers and umbrellas, set against a backdrop of lush greenery and the distant Monte Amiata. The clear water reflects the sky, offering a tranquil atmosphere for relaxation and enjoyment.
Farm stay in Montepulciano
4.95 out of 5 average rating, 102 reviews

Unique view 3 bdr villa with pool & A/C in Pienza

Nestled within the picturesque Val d'Orcia National Park and the enchanting Natural Reserve of Lucciola Bella, this apartment sits perched on a natural terrace, offering unparalleled views of Mount Amiata. Immerse yourself in the untouched beauty of this protected oasis, where the ever-changing play of sunlight and the rhythm of the seasons paint a constantly shifting panorama across the rolling hillsides.

Top Guest favourite
A rustic agriturismo is framed by vibrant greenery and blooming flowers. Outdoor seating is provided by several light-colored chairs and a patterned table. The stone building showcases large windows, which invite natural light into the space, while a welcoming atmosphere is suggested by the well-maintained garden.
Farm stay in Pienza
4.97 out of 5 average rating, 181 reviews

Spedaletto Castle, Val d'Orcia, Pienza

The Castello di Spedaletto farmhouse is located in the building that once housed the granary of the ancient medieval castle and has been recently renovated in perfect balance between modernity and tradition: stone, bricks, exposed beams blend with the characteristic crystal and wrought iron staircase. The farmhouse consists of 5 double bedrooms with bathrooms and 2 apartments. Come, See, Live...

Top Guest favourite
The outdoor pool area features a light blue water surface complemented by three tiered fountains. A small white table with a glass is placed on the wooden deck, surrounded by two white chairs. The rustic stone buildings create a charming backdrop, adorned with greenery.
Apartment in Montalcino
4.99 out of 5 average rating, 117 reviews

Castel Brunello - 2 doublebed rooms + terrace

Located in amidst the Tuscan countryside, Castel Brunello is offers an outdoor swimming pool and a garden. This self-catering accommodation features rustic-style furnishings, air condioning and free Wi-Fi. They also offer a satellite TV, and a fully equipped kitchenette with a refrigerator and a dining table. Each apartment has a terrace with an outdoor seating area.

Guest favourite
An infinity pool extends into the horizon, revealing sweeping views of the Tuscan landscape. Surrounding greenery and a paved patio are visible, with two lounge chairs positioned for relaxation. Soft natural light casts a tranquil ambiance across the scene.
Apartment in Campagnatico
5.0 out of 5 average rating, 67 reviews

Suite

A 45sqm house, separated from the main complex. Ideal for romantic getaways. It consists of: one bedroom, bathroom and living room with an open space kitchen. It includes: A sofa bed in the living room, which can be used as an extra bed. Bed linen, bathroom towels and beach towels Cleaning services halfway through the week.

Guest favourite
The villa's exterior showcases a charming Mediterranean-style design, featuring a terracotta roof and soft pink walls. The surrounding well-maintained lawn is bordered by tall trees, providing a serene backdrop, while outdoor seating is positioned on the patio, inviting relaxation.
Villa in Grosseto
5.0 out of 5 average rating, 27 reviews

Podere la Pompa

Villa with three bedrooms with ensuite bathroom, large kitchen and living room. External loggia for outdoor dining and possibility of using the shared swimming pool. Piccola Pompa is located a short drive from Grosseto and less than 20 minutes from the beaches of Castiglione della Pescaia

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