
Holiday rentals with a pool in Castiglioncello
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Top-rated rentals with a pool in Castiglioncello
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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.

Villa Cantucci
Traditional architecture blends with modern amenities in this charming 18th century stone villa. Nestled on a quiet hillside just below Volterra, the villa offers a private infinity pool (5m x 10m) equipped with sun loungers and umbrella. There is a large, covered terrace with a comfortable sitting area and dining table to enjoy the panoramic views of the Tuscan hills. Stepping inside, the villa feels sophisticated while maintaining its rustic charm and provides a delightful place to relax.

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

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.

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.

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.

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.

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!

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.

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.

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.

Charming Farmhouse Suite
Tenuta Barosi, Isabella Suite - Experience the charm of Tenuta Barosi, a newly renovated agriturismo in 2024. Perched on a hilltop amidst olive groves, this serene retreat in Malmantile, a medieval village near Florence, offers stunning views and modern comforts.
Popular amenities for Castiglioncello rentals with a pool
House rentals with a pool

Hilltop Views From a Historic Tuscan Home

Sunshine from Anja

Podere Riparossa elegant house with tennis court

Casa Conte Martini

CountryHouse immersed in woodland

Castel San Giorgio

The Cottage to relax and enjoy

Beautiful vacation home with infinity pool
Condo rentals with a pool

Poggio al Casone – Colle

"Toscana Amore Mio", stunning view, 18 min Volterra

Charming apartment with garden, pool and valley view

PINK Farmhouse with panoramic view Infinity pool

Scenic Stilish Country

[JACUZZI\ Private Beach]Modern house in Chioma

Manuela apartment with pool in farmhouse

Apartment in Farmhouse near the Sea
Other holiday rentals with a pool

Rosselmini Agriturismo | Casa Maria

Design loft with private SPA in Tuscany

Flat at 30mt from sea, small pool and parking

Authentic Tuscan Retreat – Bio Pool & Privacy

★ Romantic apartment & stunning view of Tuscany ★

Villa sii felice

Luxury tent in the countryside

Terrace with sea view, swimming pool and the sea right at your doorstep
When is the best time to visit Castiglioncello?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $281 AUD | $278 AUD | $266 AUD | $206 AUD | $197 AUD | $256 AUD | $331 AUD | $321 AUD | $253 AUD | $216 AUD | $266 AUD | $334 AUD |
| Avg. temp | 7°C | 8°C | 10°C | 13°C | 17°C | 21°C | 24°C | 24°C | 21°C | 17°C | 12°C | 8°C |
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 $43 AUD 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 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!
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- Elba
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Piazza del Duomo (Pisa)
- Cala Violina
- Mercato Centrale
- Pisa Centrale Railway Station
- Uffizi Gallery
- Fortezza da Basso
- Stazione Santa Maria Novella
- Del Chianti
- Piazza della Repubblica
- Spiagge Bianche
- Gorgona
- Piazzale Michelangelo
- Spiaggia Di Sansone
- Parco delle Cascine
- Gulf of Baratti
- Pitti Palace
- Piazza della Signoria
- Boboli's Garden





