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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 $39 SGD 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 & 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!

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, 103 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
A vibrant yellow flower stands prominently in the foreground, with a clear view of a swimming pool beyond. The pool is surrounded by well-maintained green grass and overlooks rolling hills, dotted with trees and distant vineyards.
Apartment in Morrona
4.97 out of 5 average rating, 148 reviews

Casa Luna-Splendida overlooking the pool and Tuscan nature

My husband and I fell in love at first sight with this beautiful place. So we have moved here our whole life. Ideally located on the hill of Morrona,this landscape affords unique views over the hills near Pisa,put us in direct contact with a calm nature and gives us a wonderful spectacle of the fascinating and surprising course of seasons. The location is enhanced by the swimming pool with hydromassage,for those seeking a moment that will remain on their skin and in their hearts for a long time

Guest favourite
A serene coastal view displays glistening water reflecting sunlight. Smooth pebbles and rocky formations line the shore, while gentle waves lap against the beach. A lush, grassy area with wooden railings is positioned in the foreground, contributing to the tranquil landscape.
Home in Rosignano Marittimo
4.85 out of 5 average rating, 20 reviews

MAM house with pool and exclusive beach access

Immerso in un grande parco con discesa privata al mare, piscina e campo da tennis al momento in rifacimento, questo appartamento è perfetto per una vacanza rilassante e indimenticabile a due passi da Castiglioncello. Dotata di parcheggio privato e ingresso indipendente, Casa Mam è composta da una. zona living con divano letto, cucina completa,camera matrimoniale, una seconda camera con due letti singoli ed un bagno con doccia. Un grande giardino privato ti permetterà di cenare con i tuoi amici.

Top guest favourite
A refreshed saltwater pool is surrounded by lush greenery and olive trees. Sun loungers in vibrant colors are positioned along the pool deck. A shaded area with a pergola is visible, providing a relaxing spot for guests to enjoy the serene landscape.
Villa in Monsummano Terme
4.99 out of 5 average rating, 139 reviews

Le Maggioline Your Tuscany country house

Nestled among serene olive groves, this charming, fully renovated Italian home combines rustic elegance with modern amenities, making it the perfect retreat. The house features four en-suite bedrooms with stunning panoramic views, a spacious terrace with a covered veranda for al fresco dining, a BBQ, and a newly updated saltwater pool (2023), open mid-April to October. Guests rave about evenings at the long table, savoring local wines while watching breathtaking sunsets. A true Tuscan escape!

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

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.
Flat 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.

Guest favourite
An inviting outdoor space features a tranquil infinity pool surrounded by manicured lawns and elegant lounge chairs. The scene is enhanced by a backdrop of rolling hills and a colorful sunset, complemented by strategically placed trees and softly glowing outdoor lighting.
Villa in Montecarlo
4.93 out of 5 average rating, 14 reviews

Villa Sunkiss: Luxury Farmhouse with Tuscan Flair

Nestled amidst the rolling hills of Lucca, lies a true haven of luxury and tranquillity: the epitome of Tuscan elegance fused with contemporary opulence. Welcome to Villa Sunkiss, which is part of the bespoke Tenuta Sima Winery where every detail is crafted to elevate your senses and soothe your soul.<br>As you approach the property, a sense of anticipation builds, greeted by the sight of lush, manicured private vineyards stretching as far as the eye can see.

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, 139 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.

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 in Palaia
4.98 out of 5 average rating, 197 reviews

Countryside Dream farm in Tuscany

Have you ever dreamed of experiencing the rolling hills of Tuacany ? This is a berautiful organic farm 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.

Top guest favourite
A well-lit kitchen features a circular wooden dining table surrounded by chairs. Green cabinets complement the pink and white hexagonal floor tiles. A large window allows natural light to flood the space, highlighting the vintage kitchen appliances and decorative items on the counter.
Flat in Rosignano Solvay-Castiglioncello
5 out of 5 average rating, 19 reviews

Fattoria Beletage with rooftop terrace & pool

The Beletage apartment on the first floor of the Fattoria Le Case Nuove is a gem that was reserved for the family until recently and is now offered for rent after a renovation. Once the preferred residence of the Conti Millo family, the Beletage with its roof terrace and stunning views over the pine tops to the sea is the jewel of the estate.

Popular amenities for Castiglioncello rentals with a pool

When is the best time to visit Castiglioncello?

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Avg. price$254 SGD$252 SGD$240 SGD$186 SGD$178 SGD$231 SGD$300 SGD$291 SGD$229 SGD$195 SGD$240 SGD$302 SGD
Avg. temp7°C8°C10°C13°C17°C21°C24°C24°C21°C17°C12°C8°C
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