
Family-friendly holiday rentals in Castiglioncello
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Castiglioncello
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is an ancient and authentic farmhouse dating back to the 17th century located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional local style of old Tuscany: ancient wooden beams, terracotta floors, and unique furniture. In the large outdoor courtyard, you'll find a large swimming pool on a panoramic terrace at your disposal, overlooking the valley with breathtaking views of vineyards and olive groves, where you can enjoy spectacular sunsets.

Pieve di Caminino Historic Farm
Solo per amanti della natura. L'antica fattoria Pieve di Caminino, biologica, è un importante sito storico: ex pieve medievale sorta all'incrocio di due strade romane, ospitò due santi (la chiesa del XII secolo è oggi un museo privato, visitabile dagli ospiti, su appuntamento). Oggi copre 200 ettari di proprietà privata recintata, posta su una collina panoramica. Sette alloggi condividono una tenuta con piscina (stagionale), due laghetti, un uliveto centenario, vigneto e una foresta di sughere.

Case nell'aia Arco, apartment in Chianti and pool
L'appartamento Arco si trova in un tipico borgo toscano tra vigneti e oliveti. Appartamento arredato in stile rustico toscano, accogliente per farvi rilassare e visitare la zona. L'appartamento si affaccia sulla grande terrazza dove potete fare pranzi e cene all'aperto o aperitivi. Cucina, divano e punto TV, wifi, due camere matrimoniali, bagno, terrazza, piscina. Parcheggio auto nella proprietà . Ideale come punto di partenza per visitare Siena, Firenze, San Gimignano, sia in auto che in bici.

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.

Il Fienile, Luxury Apartment in the Tuscan Hills
‘Il Fienile’ is in an enchanting position immersed in the beauty of the Tuscan hills, with a breathtaking view of the surrounding countryside. It is located in the hamlet of Catignano in Gambassi Terme, just a few kilometres from San Gimignano. The house sits in a protected oasis surrounded by a beautiful private park with olive trees, a pond, pine trees and woods, where you can walk, relax and enjoy the pleasures of unspoilt nature. A unique experience entirely to be enjoyed.

Casa al Gianni - Hut
Ciao, siamo Cristina e Carmelo! Vi aspettiamo a "Casa al Gianni", il nostro agriturismo tra i boschi della Montagnola Senese a soli 20 minuti da Siena. Qui la vita rallenta: Solo il profumo della terra, il canto degli uccelli e la simpatia dei nostri animali. È un invito a riscoprire la bellezza delle piccole cose, immersi nel verde della Toscana più vera. Non è solo una vacanza, è un ritorno alle origini. Questo angolo di pace vi resterà nell'anima. Vi aspettiamo!

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]Exclusive apartment between downtown and the sea
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.

Villa Isabella
Villa Isabella is a comfortable Tuscan style villa located in the splendid Chianti hills in Tuscany with a large garden and a spectacular breathtaking panoramic swimming pool for exclusive use where you can experience the Tuscan tradition in full local style with the possibility of organizing private shuttles service for reach the property traditional experiences, services and tours only and exclusively for our guests.

Casa Gianguia apartment 100 meters from the sea
Villa such as "viareggina", called "Gianguia", located in an excellent location with respect to the center of Castiglioncello and Rosignano, a short walk from the sea, and the main services. Recently renovated, with practical and modern furnishings but tasteful ; equipped with all the comforts to ensure guests a pleasant and relaxing stay. Great for couples and families who love the sea and relaxation.

Belvedereloft the sea below the house with descent to the sea
Belvedereloft overlooks the beautiful Bay of Quercetano in Castiglioncello, a special location that makes it unique for its breathtaking view. It is part of a property whose access, that is, the gate, is the private descent to the beach, are shared with the owners, the terraces are exclusively for the guests, but the owners can pass through. Only for adults

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 family-friendly rentals
Family-friendly home rentals with a hot tub

Beautiful renovated barn in Tuscany

SuiteLouise.pool, Hot Tub,homeGym & private Garden

Tuscan cottage, sea view and private olive garden

Il Cubetto -Sea Studio: sense of peace and freedom

Japan Apartment Port Area with Balcony and Jacuzzi

"Gigi's House" (GG House)

House for 2/3 people in Fonteregia farmhouse

Farmhouse , pool, 13 px. Lucca 10km
Family- and pet-friendly home rentals

the terrace overlooking the sea

Florence Country Side: Giogoli a place to be!

Antico Borgo Ripostena – n. 5 Garage

country villa with heated swimming pool

Costalmandorlo, a rustic home in the heart of Tuscany

Collina Power

Charming cottage on Lucca hills

Tuscan Cottage with Pool Pet Friendly
Family-friendly home rentals with a pool

Hilltop Views From a Historic Tuscan Home

Infinity pool in Chianti area

Cercis - La Palmierina

Podere La Castellina - No. 3 JUNIPER

Stone House with Exclusive Pool Codilungo in Chianti

Podere Tignano, 4-bedroom villa in the Chianti!

Michelangelo apt ~ wild Tuscany Hills ~ Le Fraine

Tuscan Dream Villa
When is the best time to visit Castiglioncello?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £87 | £89 | £101 | £83 | £87 | £89 | £127 | £127 | £104 | £98 | £128 | £129 |
| 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 that are family-friendly in Castiglioncello

Total holiday rentals
Explore 120 holiday rentals in Castiglioncello

Nightly prices starting at
Castiglioncello holiday rentals start at £15 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
Destinations to explore
- Pet-friendly rentals Castiglioncello
- Rentals with pools Castiglioncello
- Rentals with a washing machine and dryer Castiglioncello
- Smoking-friendly rentals Castiglioncello
- Beachfront rentals Castiglioncello
- Rentals with a patio Castiglioncello
- House rentals Castiglioncello
- Flat rentals Castiglioncello
- Villa rentals Castiglioncello
- Rentals with beach access Castiglioncello
- Rentals with outdoor seating Castiglioncello
- Rentals with a balcony Castiglioncello
- Cottage rentals Castiglioncello
- Apartment rentals Castiglioncello
- Waterfront rentals Castiglioncello
- Family-friendly rentals Tuscany
- Family-friendly rentals Italy
- Elba
- Santa Maria Novella
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Stazione Santa Maria Novella
- Marina di Cecina
- Ponte Vecchio
- Piazza del Duomo (Pisa)
- Basilica of Santa Maria Novella
- Strozzi Palace
- Porta Elisa
- Del Chianti
- Pisa Centrale Railway Station
- Cala Violina
- Mercato Centrale
- Basilica Di San Miniato A Monte
- Uffizi Gallery
- Fortezza da Basso
- Piazza della Repubblica
- Piazzale Michelangelo
- Pitti Palace
- Gorgona
- Spiaggia Di Sansone
- Parco delle Cascine




