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Holiday rentals with a pool in Castiglioncello

Find and book unique homes with a pool on Airbnb

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 $51 NZD per night before taxes and fees

  • Verified guest reviews

    Over 380 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Wi-Fi availability

    30 of Castiglioncello holiday rentals include Wi-Fi 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!

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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Top Guest favourite
A serene plunge pool is set against a backdrop of rolling hills and olive trees. A wooden lounge chair is positioned nearby, inviting relaxation. The surrounding concrete deck offers ample space for sunbathing, with panoramic views of the landscape visible in the distance.
Home in Metato
4.99 out of 5 average rating, 104 reviews

Hilltop Views From a Historic Tuscan Home

Be immersed in the peace and quiet of a Tuscan olive orchard by staying in this stone farmhouse which features traditional architectural elements such as terra cotta floors, vaulted ceilings, and original wood fixtures. Dive into the plunge pool with sweeping views of the Mediterranean Sea. For adventurous travelers who will appreciate the 10-minute panoramic walk to the house (we will transport your luggage and groceries by tractor). The magical view of the world below with the coast on the horizon which can be enjoyed from every room of the house and from the entire olive orchard with its walking paths and plunge pool with waterfall. Being a pedestrian village, Metato is quiet and peaceful. Yet, the beach and many great places to visit are a short drive away- Pisa, Florence, Lucca, the marble quarries of Cararra, Pietrasanta, Viareggio.... Guests have exclusive access to the pool and property. Metato is a friendly litttle village in the hills overlooking the Mediterranean Sea. There is a quaint family-run restaurant in the village that serves local homemade dishes at a very reasonable price. Our pedestrian village tends to attract kind people in search of peace and quiet and a proximity with nature. Time seems to go by more slowly here. It is a perfect base for families who want to explore Tuscany and the beaches of the Versilia coast. The home is in a beautiful, quiet location on a hill surrounded by olive orchards and vineyards just a 10-minute walk from the parking lot. Explore the medieval village of Metato where fireflies and breathtaking views await. Take an invigorating hike or head to the beaches a short drive away. There is a parking lot at the base of the village where you can park the car. The village itself is pedestrian but I am happy to greet guests at the parking lot on their arrival to transport their luggage, groceries and whoever wants to ride to the house with my little Italian tractor! The nearest airport is Pisa (45-minutes by car). All the major car rental places can be found there. The nearest train station is Viareggio.

Top Guest favourite
An inviting kitchen area features a glass dining table surrounded by blue chairs. Stone walls complement modern cabinetry and appliances, illuminated by a contemporary circular light fixture. A warm ambiance is created by the rustic elements and soft lighting throughout the space.
Apartment in Rivalto
4.98 out of 5 average rating, 48 reviews

Il Frantoio (Whirlpool + Swimming Pool)

✨ Romantic retreat in the heart of Tuscany — perfect in every season 🍂 Welcome to Palazzo Riccardi, a historic building in the charming village of Rivalto, where Tuscan authenticity meets modern design. Let yourself be won over by the wood-burning fireplace, the bathroom with a whirlpool tub and a warm and enveloping atmosphere. Ideal for couples looking for relaxation and charm, this apartment is a perfect nest in every season, but it is in autumn and winter that it becomes truly magical. 💫

Guest favourite
Home in Montescudaio
4.96 out of 5 average rating, 131 reviews

Open space surrounded by nature

Casa Namaste is a small stone cottage with well-kept interiors 1 km from the medieval village of Montescudaio. The house is completely surrounded by woods and centuries-old oaks. 150 meters away flows the Cecina river. In the 5000 square meter garden there is a natural spring with a large stone tub to cool off and an outdoor hot shower surrounded by greenery. We have a Vodafone adsl line with download 33 and upload 1.4. Smart TV and air conditioning are also available starting this spring

Superhost
Villa in Rosignano Solvay-Castiglioncello
4.63 out of 5 average rating, 24 reviews

Villa Tenuta Le Case Nuove with pool & garden

Your Tuscany mansion right at the ocean - Villa Le Case Nuove dei Conti Millo is a classical mansion in the heart of Tuscany and offers sleeping accommodation for 12 people (in 2025 you can book an addtional wing and increase capacity to 18 people) With more than 800 sqm the Villa is placed in the midst of the countryside and has a 20 x 10 m pool. The ocean is just 1 km away and can be seen from the residence. The mansion is furnished with antiques, yet provides modern convenience.

Top Guest favourite
Home in Massa Marittima
5 out of 5 average rating, 70 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 in Montecatini Val di Cecina
4.99 out of 5 average rating, 137 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.
Apartment in Santa Luce
4.93 out of 5 average rating, 59 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.

Luxe
Villa in Lucca
4.94 out of 5 average rating, 32 reviews

Villa Lina, Luxury Farmhouse with Pool and Amazing

Lush vegetation invites you to surround to huge stretches of verdant woods. Extensive views towards the city of Lucca and the Tuscan rolling hills on the back are ready to embrace you during lazy summer days. Time can be stopped at Villa Lina, and you will easy forget your busy life left behind. If Stendhal syndrome is known to develop when encountering something overwhelmingly beautiful, then be careful, as you could be subject to it at this magic place.

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 in Montaione
4.96 out of 5 average rating, 140 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.

Top Guest favourite
A terrace overlooking the coastline is equipped with a large umbrella, sun loungers, and a small pool. The rocky coastline and clear blue water are visible, while lush greenery frames the outdoor area, creating a serene environment for relaxation.
Home in Rosignano Marittimo
4.95 out of 5 average rating, 107 reviews

Frontemare house with exclusive sea access

Casa Frontemare is a completely renovated property with direct access to the sea, from which you can enjoy a panoramic view of the sea, the Tuscan islands and wonderful sunsets. It is a perfect place for those who love a relaxing and private vacation. The proximity to the Tuscan art cities and the small typical villages means that it is also possible to discover new places and discover the flavors of Italian cuisine.

Superhost
A communal swimming pool is surrounded by lush greenery and tall pine trees. Sun loungers with blue cushions are positioned around the pool area, providing ample space for relaxation. A few umbrellas offer shade, and a well-maintained residence is visible in the background.
Condo in Rosignano Solvay-Castiglioncello
4.77 out of 5 average rating, 26 reviews

100mt from the sea - apt w/pool, wifi & tv

Enjoy a perfect holiday in our flat! Ideal for those travelling with family or friends, you'll stay less than 100 metres from the sea, in a cosy residence with a beautiful swimming pool, close to all essential services, for a comfortable and relaxing stay! The location is also convenient for visiting much of Tuscany, about an hour and a half's drive from Florence, and less than an hour from Livorno, Pisa and Lucca!

Superhost
Apartment in Chioma
4.73 out of 5 average rating, 15 reviews

Casa Marina - pool and umbrella included

Svegliati con il mare davanti agli occhi, fai colazione in terrazza, poi scendi direttamente allo stabilimento balneare con il tuo ombrellone riservato già incluso nel prezzo. Casa Marina è un appartamento completamente rinnovato con vista mare da ogni angolo, due terrazze private attrezzate e accesso diretto al mare.

Popular amenities for Castiglioncello rentals with a pool

When is the best time to visit Castiglioncello?

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Avg. price$336 NZD$332 NZD$317 NZD$298 NZD$360 NZD$356 NZD$395 NZD$384 NZD$302 NZD$257 NZD$317 NZD$399 NZD
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