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Holiday rentals with a pool in Castiglioncello

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Castiglioncello

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

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Guest favourite
A stone cottage is nestled among trees, creating a natural boundary for the property. Soft nighttime lighting highlights the textured facade, while glimpses of a salt-water pool and landscaped garden are visible in the background, suggesting a tranquil outdoor area.
Loft
4.94 out of 5 average rating, 143 reviews

Il Cubetto - Sun Studio: absolute exclusivity

Our little place, Il Cubetto, inaugurated with the 2020 season, stands in full Tuscan country and is particularly distinctive because of its absolute exclusivity: only two studio apartments within our 7000 sqm of garden planted with many fruit trees, with great attention to any detail. Our guests, a maximum of two per studio apartment, have the use of a salt-water infinity swimming pool overlooking the valley. Depending on the car they drive, they can park next to the cottage or beside the road.

Top guest favourite
The rustic stone house features a facade adorned with climbing greenery, offering a blend of natural beauty and architectural charm. Large wooden doors open onto a welcoming terrace, which is surrounded by greenery, providing a serene outdoor space for relaxation.
Home
4.93 out of 5 average rating, 195 reviews

Collina Power

Collina is an ancient stone farmhouse, the house is surrounded by fields and olive groves. It has a large garden with swimming pool and a terrace where you can have pleasant lunches and dinners. A barbecue and garden furniture are available. The road to get to the house in the last stretch is not paved and is therefore not suitable for sports cars or particularly low ones. The route lends itself to pleasant walks during the day, while at night we recommend using a car because it is not lit.

Guest favourite
Flat
5 out of 5 average rating, 5 reviews

Historic fattoria with pool

The property is about 1 km from the sea (only 8-10 minutes' walk) and has about 150 hectares of land in the hinterland with grain fields, maquis and olive trees as well as a small lake. The Fattoria with about 150 square meters of living space was built around 1800 and has since served the family as a summer and country residence. At the front is a classic garden. The 6 x 20 meter pool is also used by 2 other guest families, but offers enough retreat options due to the spacious complex.

Top guest favourite
A traditional stone farmhouse is surrounded by a well-maintained garden. A paved pathway leads to an arched entrance framed by decorative plants. Wooden window shutters add charm, while the bright blue sky complements the earthy tones of the building.
Flat
4.96 out of 5 average rating, 109 reviews

Relax between hills and sea in an ancient farmhouse

Recently renovated apartment in a typical Tuscan farmhouse in the hills, a 20-minute drive from the sea. It has 2 double bedrooms, a cozy entrance to the living room with a comfortable sofa bed, a bathroom with shower and a fully equipped kitchen. In the property's garden there is a swimming pool (from June) and a wooden gazebo with BBQ. The apartment is equipped to accommodate small guests with a crib, high chair, stroller, bottle warmer, and a backpack for walks. Wifi, Satellite TV

Top guest favourite
Home
5 out of 5 average rating, 58 reviews

Design loft with private SPA in Tuscany

Welcome to Loft SPA, your personal refuge in the heart of Massa Marittima, an exclusive accommodation equipped with a private indoor swimming pool. This unique property offers an unparalleled stay experience, combining elegance and comfort, the accommodation has been designed with attention to detail and quality, The highlight is the indoor swimming pool with its accessories, an oasis of relaxation. This exclusive accommodation offers a stay experience you will not easily forget.

Top guest favourite
A historic tower rises prominently against a blue sky dotted with fluffy clouds. Surrounding greenery complements the stone structure, with trees and small buildings visible along the hillside, collectively conveying a sense of tranquility.
Villa
4.99 out of 5 average rating, 132 reviews

Belforti Tower

Torre dei Belforti is the perfect place for people who love beauty, nature and art. Sleeping at the Tower is like traveling trough the time, between knights and princesses. The wonder of this place is enriched by a big garden, with its swimming pool, the cypresses alleys and the olive trees. The village is also a magic place well preserved and still alive. We are Emilia and Luca, we live here and our mission is to give the best to our guests, to fully enjoy this marvelous place.

Top guest favourite
A spacious outdoor pool surrounded by deck chairs offers a serene view of the countryside. Thatched umbrellas provide shade, while the warm hues of sunset illuminate the rustic buildings in the background, emphasizing the tranquility of the setting.
Flat
4.94 out of 5 average rating, 51 reviews

Michelangelo apt ~ wild Tuscany Hills ~ Le Fraine

Take a break in the wild Tuscan hills, just 15 km from the sea. Agriturismo Le Fraine offers its guests 4 apartments and a large park with a pool overlooking the vineyards. The Michelangelo apartment is the perfect solution for a holiday to enjoy with your loved ones. It features two bedrooms (1 double bed - 2 single beds), a bathroom with a shower, a living room with a kitchen, and a sofa bed. From the private veranda, let your gaze wander over the hills and vineyards.

Top guest favourite
A winding driveway is lined with tall cypress trees on either side. The green landscape stretches into the distance, revealing rolling hills and a distant rustic building surrounded by nature, creating a serene and inviting setting.
Home
4.95 out of 5 average rating, 133 reviews

Cercis - La Palmierina

E' un appartamento facente parte di una tenuta completamente recintata di 60 ettari di natura incontaminata: più di 1000 ulivi, innumerevoli cipressi e foreste profumate creano un ambiente idilliaco per coloro che ricercano tranquillità e silenzi. La tenuta Palmierina è in prossimità di Castelfalfi (un vero gioiello di architettura medievale) e nelle vicinanze di Firenze (50 Km), Siena (50 Km), Pisa (50 Km). Nelle vicinanze ci sono due campi da golf.

Guest favourite
Holiday home in Lajatico
4.93 out of 5 average rating, 29 reviews

Mimosa: Scenic Tuscany Stay, Pool & Walk to town

Welcome to La Lunaria di Lajatico, an elegant residence in the Tuscan hills, just a 7-minute walk from the village of Lajatico, hometown of Andrea Bocelli. With two pools, panoramic terraces overlooking rolling hills, olive groves, BBQ, and full modern comfort, it offers four rustic-chic apartments—ideal for families, couples, or groups seeking authentic Tuscany close to town.

Superhost
An aerial view showcases a rustic property surrounded by olive trees and lush greenery. The structure features a terracotta roof and is complemented by a swimming pool and several outdoor seating areas, enhancing the serene landscape of the Tuscan countryside.
Apartment
4.86 out of 5 average rating, 50 reviews

Apartment in Farmhouse near the Sea

The Agriturismo offers a newly renovated two-room apartment, ideal for 2 people and a child. Comfortable and quiet, furnished in Tuscan style and overlooking the Mediterranean maquis. Equipped with a kitchen, bathroom, bedroom, extra bed, television and heating. The property has an in-house catering service with a fixed menu upon advance booking.

Top guest favourite
The image features a serene infinity pool reflecting the surrounding trees and villa during sunset. Sun loungers are positioned beside the pool, and the well-maintained outdoor area offers a tranquil ambiance enhanced by the natural landscape.
Farm stay
4.99 out of 5 average rating, 328 reviews

Tenuta Chiudendone in Tuscany

Great place in the middle of Tuscan Hills, you will be sorrounded by nature but close to all the beautiful cities of Tuscany! We rent two apartments, one on the upper floor called Balla and one on the ground floor called Modigliani. Tell us which one you prefer. PLEASE NOTE YOU WILL NEED A CAR DURING YOUR STAY.

Top guest favourite
An infinity pool reflects the sky, surrounded by olive trees and well-manicured gardens. Comfortable lounge chairs are placed neatly along the pool deck under shaded umbrellas. A gradual elevation creates a seamless transition between the pool area and scenic countryside views.
Farm stay
4.98 out of 5 average rating, 190 reviews

Countryside Dream farm in Tuscany

Great place in the middle of Tuscan Hills, you will be surrounded by nature but close to all the beautiful cities of Tuscany! We rent two apartments, one on the upper floor called Balla and one on the ground floor called Modigliani. Tell us which one you prefer. PLEASE NOTE YOU WILL NEED A CAR DURING YOUR STAY.

Popular amenities for Castiglioncello rentals with a pool

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Quick stats about holiday rentals with a pool in Castiglioncello

  • Total holiday rentals

    Explore 30 holiday rentals in Castiglioncello

  • Nightly prices starting at

    Castiglioncello holiday rentals start at £22 per night before taxes and fees

  • Verified guest reviews

    Over 370 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Wifi availability

    30 of Castiglioncello holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Castiglioncello rentals

  • 4.8 Average rating

    Castiglioncello stays are highly rated by guests – averaging 4.8 out of 5!

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