
Vacation 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.

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.

Il Frantoio (Hot Tub + 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. 💫

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.

country villa with heated swimming pool
The villa built entirely of stone gives our guests a relaxing stay in complete privacy but also pleasant excursions in the surroundings and the sea. The pool water is heated IMPORTANT: it is heated in the mid-season periods 28° (May-June) (September-November) IMPORTANT: We are immersed in nature and in the woods so there are flying insects! There are mosquito nets in the house. MAX 2 PETS: €5 per day per pet to be paid on arrival. RENT ONLY FROM SUNDAY TO SUNDAY

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.

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.

La Moraiola - Characteristic Tuscan barn
Forget all worries in this oasis of serenity. The house, an old barn, is surrounded by greenery, in a hamlet with a view of the towers of San Gimignano. The entire villa for the exclusive use of guests, with private garden, Jacuzzi and large outdoor area to enjoy a holiday in total relaxation and tranquillity. The historic center is about 1.3 km away, and can also be reached on foot.

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.

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.

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.

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.

Cliffside villa with pool
Villa with swimming pool in an exclusive location on the Tuscan cliffs. It is located in a large private park with direct access to the sea, it can accommodate two people plus two additional guests. A unique setting between sun, sea, food and culture.
Popular amenities for Castiglioncello rentals with a pool
House rentals with a pool

Angela's Nest

Podere La Sterza The barn

CountryHouse immersed in woodland

My home

Podere Livrone with Pool - Tombolo

The Cottage to relax and enjoy

Castor&Pollux House in hillside estate with pool

Lovely house in a scenic and paiceful location
Condo rentals with a pool

Poggio al Casone – Colle

„Toscana Amore Mio“, stunning view, 18min Volterra

Charming apartment with garden, pool and valley view

Tuscany holiday: Pool & garden

Slow Life Apartment with pool and view

Scenic Stilish Country

Sea View and Pool in Tuscany

Limonaia in a 16th century villa
Other vacation rentals with a pool

Viola Suite - La Vitaverde Agriturismo

I 9 Cipressi – Tuscan Retreat with Pool & View

Dream in Tuscany, Villa with pool

Luxury Tuscany Villa on the hill with private pool

Exclusive guests house for wine lovers with AC

Terrace with sea view, swimming pool, and the sea right outside the house

VILLA GIOMA - Completely renovated country house

Villa Montefalcone: Charm, Private Pool, and Chef
When is the best time to visit Castiglioncello?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$41,190 GYD | G$40,772 GYD | G$38,890 GYD | G$30,109 GYD | G$28,854 GYD | G$37,427 GYD | G$48,509 GYD | G$47,045 GYD | G$37,009 GYD | G$31,572 GYD | G$38,890 GYD | G$48,927 GYD |
| 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 vacation rentals with a pool in Castiglioncello

Total vacation rentals
Explore 30 vacation rentals in Castiglioncello

Nightly prices starting at
Castiglioncello vacation rentals start at G$6,273 GYD per night before taxes and fees

Verified guest reviews
Over 370 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Wi-Fi availability
30 of Castiglioncello vacation 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
- Santa Maria Novella
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Salvatore Ferragamo Museum
- Piazza del Duomo (Pisa)
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Cala Violina
- Pisa Centrale Railway Station
- Mercato Centrale
- Fortezza da Basso
- Piazza della Repubblica
- Uffizi Gallery
- Del Chianti
- Gorgona
- Spiaggia Di Sansone
- Piazzale Michelangelo
- Pitti Palace
- Palazzo Vecchio
- Parco delle Cascine
- Boboli's Garden
- Spiagge Bianche
- Spiaggia Di Barbarossa





