
Family-friendly holiday rentals in Castiglioncello
Find and book unique family-friendly homes on Airbnb
Quick stats about holiday rentals that are family-friendly in Castiglioncello

Total holiday rentals
Explore 120 holiday rentals in Castiglioncello

Nightly prices starting at
Castiglioncello holiday rentals start at $26 SGD per night before taxes and fees

Verified guest reviews
Over 1,430 verified reviews to help you choose

Pet-friendly holiday rentals
Find 60 rentals that welcome pets

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
90 of Castiglioncello holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Castiglioncello rentals

4.7 Average rating
Castiglioncello stays receive an average rating of 4.7 out of 5 from guests
Top-rated family-friendly rentals in Castiglioncello
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

Casa Luna-Splendida vista piscina e natura toscana
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

casa la dori
Casa vacanze situata a 200 mt dal mare in zona centrale molto servita da negozi di vicinato. Piano terra rialzato, dotato di giardino privato dove si può pranzare, cenare o semplicemente riposare al fresco di una piacevole brezza di mare. Completamente ristrutturata, rinnovata e curata nei minimi particolari, ha una zona giorno molto ampia ed elegante con una grande vetrata che permette l'accesso al giardino. Cucina nuova dotata di lavastoviglie, due camere e il bagno totalmente rinnovati.

Museum Suite - Luxurious unit with a River View -
After 13 wonderful years of hosting on Airbnb, the time has come to close this incredible chapter and embrace the next. These upcoming 7 months will be the final season for MuseumSuite, in Jan 2027, the property will be sold and transformed into a private family residence. It has been an absolute honor and a privilege to welcome guests from all walks of life. Each of you has deeply enriched my journey, and I hope that MuseumSuite has left a beautiful, lasting impression on your lives as well.

Renaissance Apartment Touch the Dome
Inspired by the most fascinating artistic era in human history, the Renaissance, each of my homes is a tribute to the elegance, harmony, and craftsmanship that defined that golden age. Step inside and be transported. You’ll not only see the Renaissance — you’ll feel it in the atmosphere, in the light, and in the soul of each space. Discover also The Renaissance & Baroque apartment: https://www.airbnb.it/rooms/30229178?guests=1&adults=1&s=67&unique_share_id=c0087742-7346-4511-9bcd-198bbe23c1b4

Tramonto sul Chianti Classico
Se cercate una location idilliaca nel cuore del Chianti classico, immersi nei vigneti e oliveti delle splendide colline toscane, nel podere di una Villa storica del ‘500, allora venite nel nostro fienile!! Ha una posizione dominante con una vista strepitosa, dove è possibile godersi tramonti mozzafiato. La totale indipendenza della casa, l'accogliente giardino, il grande loggiato permettono di trascorrere soggiorni in totale tranquillità. Le nostre recensioni sono la vostra migliore garanzia.

Historische Fattoria mit Pool
Das Anwesen liegt ca. 1 km vom Meer (nur 8-10 Gehminuten) entfernt und hat im Hinterland noch ca. 150 ha Land mit Getreidefeldern, Macchia und Olivenbäumen sowie einem kleinen See. Die Fattoria mit ca. 150 qm Wohnfläche wurde um 1800 erbaut und dient seitdem der Familie als Sommer- und Landresidenz. An der Vorderseite liegt ein klassischer Garten. Der 6 x 20 Meter grosse Pool wird auch von anderen 2 Gästefamilien genutzt, bietet jedoch durch die grosszügige Anlage genug Rückzugsmöglichkeiten.

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

Casa al Gianni - Il Fienile di Simignano
Trasformato da un antico fienile, questo rifugio lussuoso offre 5 camere, 4 bagni, grande cucina attrezzata, ampio living, un ampio giardino privato con parcheggio, hot tub, patio con divani, BBQ, fire pit e cucina esterna. Ideale per chi cerca un'esperienza unica, unisce fascino rustico a comfort moderni. Perfetto per famiglie o gruppi, promette serate magiche sotto le stelle, tra relax nell'hot tub e cene all'aperto. Una fuga memorabile vi aspetta in questo angolo di paradiso!

House with a breathless view in Tuscany
Halfway between Pisa and Florence, this dreamy Tuscan house is your perfect escape. Lounge on the panoramic terrace with sun-kissed views, sip your morning coffee, or enjoy al fresco dinners under the golden sunset. Nestled in the heart of a charming village turned open-air contemporary art museum, every corner feels like a picture-perfect moment. Peccioli is your gateway to Tuscany’s art cities or a serene hideaway to savor the magic of authentic local life.

[LUXURY]Esclusivo appartamento tra centro e mare
New, exclusive luxury home in Castiglioncello’s main square, 500m from the sea and 1.5 km from Cala ’de Medici port. Parking included. Beach service available on request: assistance with reservations, subject to availability. Modern, refined design with elegant arched doors and wood details. Unique, sophisticated atmosphere for a 5-star stay! Perfect location, walking distance to all services, ideal for leaving the car behind and exploring on foot.

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!

Casa Gianguia appartamento a 100 metri dal mare
Villetta tipo "viareggina", dal nome "Gianguia", situata in ottima posizione rispetto al centro di Castiglioncello e Rosignano, a pochi passi dal mare, e dai principali servizi. Di recente ristrutturazione, con arredo pratico e moderno ma di gusto ; dotata di tutti i comfort per garantire agli ospiti un soggiorno gradevole e rilassante. Ideale per le coppie e le famiglie amanti del mare e del relax.
Popular amenities for Castiglioncello family-friendly rentals
Family-friendly home rentals with a hot tub

Splendido fienile ristrutturato in Toscana

SuiteLouise.pool, Hot Tub,homeGym & private Garden

Casa di Delizie - The Medici private leisure house

Il Cubetto - Sun Studio: absolute exclusivity

Japan Apartment Port Area with Balcony and Jacuzzi

Green Dome @ The Land Before Time Retreats

La Casetta

CasaDiManuela:TotallyPrivateChiantiVilla withTub
Family- and pet-friendly home rentals

Florence Country Side: Giogoli a place to be!

Torre dei Belforti

Casa Clarabella

Authentic Tuscan Country House WITH A/C

Lovely apartment with garden and views near Siena

Appartamento con giardino panoramico San Gimignano

Il Sartino

[Very Central] Duomo/Studio - Elegance and Comfort
Family-friendly home rentals with a pool

Agriturismo Rosselmini | Casa Maria

Private Chianti Cottage, Garden & Vineyard Views

Cercis - La Palmierina

Open Space Piscina e Giardino

Un fienile nel Chianti

Stone House with Exclusive Pool Codilungo in Chianti

Tuscan Luxury Villa • Natural Pool & Privacy

Aria condizionata, piscina condominiale
When is the best time to visit Castiglioncello?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $264 SGD | $228 SGD | $222 SGD | $144 SGD | $151 SGD | $156 SGD | $222 SGD | $222 SGD | $180 SGD | $170 SGD | $223 SGD | $225 SGD |
| 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 |
Destinations to explore
- Rentals with pools Castiglioncello
- Waterfront rentals Castiglioncello
- Smoking-friendly rentals Castiglioncello
- Pet-friendly rentals Castiglioncello
- Rentals with a washing machine and dryer Castiglioncello
- Rentals with outdoor seating Castiglioncello
- Flat rentals Castiglioncello
- Villa rentals Castiglioncello
- Rentals with beach access Castiglioncello
- Apartment rentals Castiglioncello
- Beachfront rentals Castiglioncello
- Cottage rentals Castiglioncello
- Rentals with a patio Castiglioncello
- House rentals Castiglioncello
- Rentals with a balcony Castiglioncello
- Family-friendly rentals Tuscany
- Family-friendly rentals Italy
- 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





