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Family-friendly holiday rentals in Castiglione della Pescaia

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Castiglione della Pescaia family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Apartment in Montevarchi
4.95 out of 5 average rating, 192 reviews

Art-Design Fienile in the heart of Tuscany

AlisterRating, 5 stars2 weeks ago
Incredible trip. Paola and Michele were so friendly and welcoming. Always there to give advice and make sure you had everything you needed. The little converted hay barn was just beautiful and lovely. Location wise it just couldn’t be beaten. The garden was amazing and we ate outside morning and night, easy access to amazing Tuscany countryside and also a short trip on the train to Florence from Montevarchi. Loved every minute we were there and we were sorry to leave. Would highly recommend.
Superhost
Flat in Monterotondo Marittimo
4.76 out of 5 average rating, 37 reviews

Studio in Farmhouse, Swimming Pool, Restaurant.

ElenaRating, 5 stars2 months ago
We had a lovely time with delicious food and very friendly hosts. The location was beautiful and the time very relaxing. Thank you :)
Guest favourite
Cottage in Radicondoli
4.93 out of 5 average rating, 137 reviews

Beautiful renovated barn in Tuscany

PhilippRating, 5 stars4 weeks ago
We had a wonderful week in Gloria's house. Our four-legged friend also felt totally comfortable in nature. The house is small but nice and has everything you need. The property is a nice size and is perfect for eating outside, relaxing in the hot tub or just lying in the sun. The way to the house is a little challenging, but with a normal car and a little driving experience it can be mastered. Gloria was always available to us and gave us good excursion tips for the area in advance. Even with any inquiries, she always reacted very quickly and helped us. It is perfect for simply getting out and enjoying the nature and tranquility of Tuscany. We will be happy to come back!
Guest favourite
Home in Gaiole in Chianti
4.86 out of 5 average rating, 264 reviews

Charming estate with views

AndrewRating, 5 stars1 week ago
Incredible stay and Bernardino and his family were incredibly welcoming and pleasant. They helped us check in later and were there to help us with any questions we had. Absolutely would recommend to anyone looking for a peaceful Tuscan retreat.
Guest favourite
Home in Catabbio
4.89 out of 5 average rating, 159 reviews

Country house La Meria

AlexRating, 5 stars2 months ago
If you stay here, you will find yourself in a painting, so beautiful is this cottage located in the mountains! Lucca is really super nice and funny. He tells a lot. The restaurant they run is fine too, and good food! The breakfast is very good. We definitely recommend this cottage!
Top guest favourite
Flat in Siena
4.91 out of 5 average rating, 129 reviews

Villa'Colombaiolo di Marciano', 28

HannahRating, 5 stars3 weeks ago
We loved staying here and had the most fantastic time. They were super helpful and responsive to everything and we can’t wait to go back.
Guest favourite
Cottage in Seggiano
4.96 out of 5 average rating, 90 reviews

EcoLodge – modernes Design in ruhiger Panoramalage

ChrisRating, 5 stars1 week ago
Third time at this beautiful place! As always a nice surprise
Guest favourite
Apartment in Casole d'Elsa
4.93 out of 5 average rating, 157 reviews

La Casetta

RalfRating, 5 stars3 weeks ago
We can absolutely recommend it! Everything is as described in the text and as shown in the photos. Located about 2 km outside the totally cute village of Casole de Elsa. Andrea + Barbara provided all the necessary information for the journey and many great tips on site, always with the corresponding links. For example, our arrival was delayed to about 10:15 pm due to traffic. Was no problem, we were in contact and when we arrived, Andrea personally received us. And if we had a question during our stay, an answer always came very quickly. (Where is the best place to park in Siena, how do you best get to Florence, ...)

Family- and pet-friendly home rentals

Guest favourite
Flat in Piombino
4.87 out of 5 average rating, 213 reviews

Cozy apartment in the historic center

Rating, 5 stars5 days ago
I like this apartment very much, it’s in the Main Street. The only problem is shower room is bit too small. And Daria is a very friendly person.
Guest favourite
Earthen home in Pitigliano
4.87 out of 5 average rating, 906 reviews

The cave

SavannahRating, 5 stars6 days ago
One of the most unique, homey and wonderful places on earth. Found Pitigliano with a little research and glad we did - make sure you make your way to Saturnia for the thermal pools as well. Was a little caught off guard with no WiFi for international travel but had WiFi at the cafe upstairs!
Guest favourite
Flat in San Gimignano
4.89 out of 5 average rating, 126 reviews

Apartment Ortensia

DanielaRating, 5 stars2 months ago
Great place! We loved it!
Guest favourite
Apartment in Castiglione della Pescaia
4.88 out of 5 average rating, 99 reviews

Little Jewel in the center of CDP

NadiRating, 5 stars3 weeks ago
We loved the apartment. It was cozy, well equipped and had everything one might need. It is extremely central and you can walk everywhere. Parking is very close. Ingrid was very helpful and gave us tips and suggestions for our stay. All in all a wonderful stay.
Guest favourite
Flat in Pitigliano
4.94 out of 5 average rating, 418 reviews

Panoramic penthouse in the ancient village

BrittanyRating, 5 stars1 week ago
Loved our stay! Great set up, great location, and really responsive host. Check in was easy, we had everything we needed and the views are INCREDIBLE from the house. There’s also a nice coffee place just downstairs that opens early. Highly recommended!
Guest favourite
Castle in Barberino Tavarnelle
4.87 out of 5 average rating, 111 reviews

Suite in Castello di Valle

KapoRating, 5 stars3 weeks ago
We come from Hong Kong, and a building like this is not often seen there. We are very happy to have had the chance to stay at the house. Some of the details in the house really impressed us, especially the antique furniture! Pietro is a great host—very friendly and responsive. I had some pleasant conversations with him. Thanks again!
Guest favourite
Villa in Castagneto Carducci
4.94 out of 5 average rating, 121 reviews

La Conchetta – Bolgheri

JanRating, 5 stars1 month ago
We have been here for the second time and we are thrilled again. We love the house and the surroundings are perfect for us. Gladly again :-)
Top guest favourite
Flat in San Gimignano
4.98 out of 5 average rating, 128 reviews

Apartment at ground floor with garden

CarolineRating, 5 stars1 week ago
Wow! This was just perfect from the beginning to the end. First, Massimo was waiting for us at the gate to bring us to the parking where he took our luggage and brought them to the apartment. Then, he sat down with us to give us some instructions and local recommendations. The apartment was clean and spacious for my family of 4. The location is just perfect. It’s in the heart of San Gimignano so you can walk everywhere from there. Even if San Gimignano is crowded, the apartment is very quiet with a small outdoor to enjoy. Massimo joined us on our last day to bring back the luggage to our car. This is a first-class experience. I don’t want to forget Fabio who has been very responsive on Airbnb as well. I definitely highly recommend Fabio’s place!

Family-friendly home rentals with a pool

Guest favourite
Home in Montaione
4.94 out of 5 average rating, 104 reviews

Cercis - La Palmierina

JenniferRating, 5 stars1 week ago
We had an absolutely amazing time at Daniela’s place - it was clean, had stunning views and was quick access to Pisa, Florence & Siena. Beautiful pool and lovely terrace with amazing views and sunsets. The kitchen also had everything we needed, including local olive oil and pasta & local wine as a welcoming gift. Daniela went above and beyond providing us with lilos and a pump for the pool too. Overall, 10/10 stay!
Guest favourite
Flat in Casole D'Elsa
4.93 out of 5 average rating, 103 reviews

Girasoli apartment with pool in farmhouse

RichardRating, 5 stars1 month ago
Beautiful rustic stay in the heart of Tuscany. Manuela was very friendly and helpful. The farm at night with the fireflies lighting up the bushes and nightingale singing in the trees was absolutely enchanting.
Guest favourite
Farm stay in Cavriglia
4.92 out of 5 average rating, 336 reviews

Chianti La Pruneta, Raphael Apartment

KathleenRating, 5 stars1 week ago
Very friendly and helpful host, Massimo made us feel at home. A beautiful apartment overlooking some incredible views. Lovely clean pool. Just a perfect holiday all round!
Guest favourite
Farm stay in San Gimignano
4.89 out of 5 average rating, 209 reviews

Oleandro double room with pool in San Gimignano

EricaRating, 5 stars1 week ago
While Paolo was away, our check-in and communication with Bruno went very smoothly. The property is absolutely stunning. The view of Sam Gimignano as you swim in the pool was something out of a movie scene. The property has surrounding olive trees and vineyards seen right from the window of the airbnb. This particular room is in a tucked away corner of the property and feels very private. Bed was comfy. Washing machine and drying racks, as well as a grill were plusses. Many agriturismos offer a dinner for an added fee, and we were a little disappointed that the dinner (in the past offered by Paolo’s neighbors) was closed during our stay. However, in fending for ourselves, we did appreciate the mini fridge and microwave, and loved eating our dinner right on the private table outside the room door. Also, you do have to clean out your trash at the end of the stay. Price felt right. Overall, would happily stay again and will be forever dreaming of the view.
Superhost
Farm stay in Provincia di Siena
4.87 out of 5 average rating, 117 reviews

Spigo - Independent Cottage Zampugna

FilipRating, 5 stars4 days ago
Beautiful place, everything ready with refreshments, accommodation quiet and clean ... Air conditioning functional, but almost not needed, because it was a beautiful classic Tuscan accommodation, where we definitely were not the last
Guest favourite
Home in Pievescola
4.94 out of 5 average rating, 175 reviews

Antico Borgo Ripostena – n. 8 Old House

LucyRating, 5 stars2 weeks ago
This place is something else! The views, the pool, the houses, the interior - it’s something else. We stayed with our 18 month old and had such a happy time - surrounded by nature in such gorgeous accommodation and a kiddy kitchen / toys which were perfect for Otis. It’s simply beautiful and Martina is so helpful - highly recommend with a family or groups of friends for a zen and unique time. Close to lots of gorgeous places and Martina has wonderful recommendations. Only watch out is the 2km dirt track road to get to the location but it’s 100% worth it and quite fun! Enjoy - we can’t wait to come back :)
Guest favourite
Holiday home in Casole d'Elsa (SI)
4.91 out of 5 average rating, 205 reviews

Charming farmhouse with garden, views & pool

DylanRating, 5 stars3 weeks ago
My stay at Fabio’s farmhouse was delightful. The house was gorgeous and felt right at home. The house felt cozy and comfortable with breathtaking views of the Tuscany country side. The area is very serene and peaceful. There are plenty of beautiful villages around the area to visit via car. Fabio was a delightful host who was very welcoming and responsive. I am looking forward to staying again here in the future.
Top guest favourite
Flat in Barberino Val d'Elsa
4.99 out of 5 average rating, 122 reviews

Apartment in Chianti at Mulino dell 'Argenna

MarkusRating, 5 stars1 week ago
We have now been to Elisa and Alessandro's accommodation for the second time – and it was simply beautiful and absolutely relaxing again! The place is a real oasis where you can switch off perfectly. Elisa and Alessandro are extremely helpful and warm. They provided us with great tips for activities and restaurants, so we could enjoy our stay all around. We'd love to come back and highly recommend this place!

Quick stats about holiday rentals that are family-friendly in Castiglione della Pescaia

  • Total rentals

    230 properties

  • Nightly prices starting at

    ₹3,455 before taxes and fees

  • Total number of reviews

    2.7K reviews

  • Pet-friendly rentals

    130 properties allow pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    140 properties include access to wifi

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