Family-friendly vacation rentals in Castiglione della Pescaia

4.93 out of 5 average rating, 294 reviews

A rustic building is seen under a starry night sky, with a partial roof providing shelter. Soft light glows from the interior, illuminating the entrance. Lush greenery and trees surround the scene, adding depth to the serene nighttime landscape.

Farm stay in Simignano

Casa al Gianni - Hut

Hi, we’re Cristina and Carmelo! We look forward to welcoming you to “Casa al Gianni,” our agritourism property in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: just the scent of the earth, the song of the birds, and the warmth of our animals. It is an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It’s not just a vacation; it’s a return to our roots. This peaceful haven will stay in your soul. We look forward to welcoming you!

FamilyIndoor spacesWalkability

Vacation home in Castiglione della Pescaia

A scenic view of the villa's exterior is captured, featuring a terracotta roof and lush greenery. The vibrant colors of blooming flowers are visible alongside a panoramic view of the sea and coastal town below, enhancing the natural beauty of the surroundings.

Panoramic villa with a terrace overlooking the sea

Just an 8-minute walk from the sea, this 150-square-meter villa surrounded by greenery, located on the first floor, offers breathtaking views of the sea and the beach of Castiglione della Pescaia. Bright and spacious, it has 4 bedrooms, 3 bathrooms (2 with shower), a living room, an equipped kitchen, and a washing machine. The highlight is the panoramic terrace and the sea-view attic, perfect for relaxing at sunset. With free Wi-Fi and air conditioning, it is ideal for those looking for nature, comfort and relaxation in Maremma.

FamilyIndoor spacesAir conditioning

4.82 out of 5 average rating, 28 reviews

Condo in Castiglione della Pescaia

A bright and airy dining area features a small table surrounded by four chairs. Natural light enters through two large windows, with scenic views visible outside. A kitchenette is situated nearby, equipped with modern cabinetry and appliances, providing convenience for meal preparation.

The most beautiful apartment in front of the sea

Come see this beautiful and exclusive 5 beds 2 bath seaside. This home features all New recently. Kitchen has Newer Appliances and Cabinets. Spacious light Living Room with 4 windows. Master Suite leads to a private bathroom. Updated Master Bath features Walk-in Shower. All rooms are equipped with TV and air conditioning. High speed WiFi included. City Center, Shopping are close by and easy access by feet or bike. Sailing and Kitesurfing available nearby. Animals and smoking not allowed.

Indoor spacesKitchenWalkability

4.97 out of 5 average rating, 32 reviews

A well-lit kitchen area showcases modern cabinetry and appliances, including a stove and oven. A dining table with four chairs is positioned nearby, set with plates and drinks. A beige sofa with blue accent pillows adds comfort to the open living space.

4.84 out of 5 average rating, 112 reviews

Apartment on Corso di Castiglione 2

Bright apartment on the main street of Castiglione, Piazza della Repubblica 28, in front of the Casty restaurant, 200 meters from the sea. It consists of a double bedroom, a bathroom with a washing machine, and a living room with a kitchenette and a double sofa bed. Finely renovated in 2019 and equipped with soundproofed windows and air conditioning. It is located on the second floor without an elevator. The city tax of €1.20 per night per person is not included.

Indoor spacesKitchenNearby

4.98 out of 5 average rating, 129 reviews

A scenic view features a gentle hillside dotted with wildflowers, leading to the ancient Montemassi Castle perched atop. Olive trees are visible in the background, with a sky presenting a soft blend of clouds and blue hues.

Apartment in Montemassi

Casa Sabina

The apartment, which provides your own private entrance, has been recently renovated and furnished with care. It is located at the foot of the ancient Castle of Montemassi in a historic square in the characteristic medieval village. With only pedestrian access allowed in this square, you can be assured to have a tranquil and peaceful stay. A 5 minute walk from the apartment, the Castle of Montemass provides visitors with a cultural activity during their stay.

FamilyIndoor spacesPets

A charming stone cottage is depicted, featuring a dark roof and a welcoming entrance. Vibrant purple flowers in the foreground provide a splash of color against the gravel pathway, while warm sunlight casts a gentle glow, highlighting the serene surroundings.

4.95 out of 5 average rating, 144 reviews

Casetta Venere Tuscan relaxation 3 km from the sea

Casetta Venere: Sea, nature and Pet-Friendly. Just 3 km from the crystal clear sea of Castiglione della Pescaia, Casetta Venere is a small Tuscan jewel among olive trees, perfect for couples, families, and travelers with pets. The house offers well-kept spaces, a beautiful private garden and an intimate and welcoming atmosphere. We look forward to welcoming you for a slow, authentic and beautiful stay in the midst of nature.

KitchenFamilyOutdoor spaces

Townhouse in Castiglione della Pescaia

The exterior of the small house is framed by tall cacti and blooming plants, creating a vibrant setting. A terracotta-tiled roof complements the design, while a clear blue sky provides a bright backdrop. Paved pathways lead to the entrance, enhancing accessibility.

The House of Lemons

It's a small house with 2 bedrooms, a living room, a kitchenette and a bathroom. From the external stairs you can reach the solarium, furnished with a table, chairs, umbrella, and deckchair. Below the house, with access from the external stairs, is my laundry area that I will use with the utmost respect for my guests. The outdoor courtyard is shared and, during high season, will house 2 of our cars.

KitchenFamilyAccuracy

5.0 out of 5 average rating, 30 reviews

Condo in Castiglione della Pescaia

A view from the entrance, featuring a gate leading to a sandy beach. Flanking the pathway are greenery and trees, while the ocean can be seen in the distance under a clear blue sky. The scene captures a peaceful coastal atmosphere.

Beach apartment with private parking space

From the living room to the beach in a leap. From the window overlooking the pedestrian promenade, you can immerse yourself in the sound of the waves while watching the sunset over the Tyrrhenian Sea. In the private back garden, you can spend unforgettable evenings away from prying eyes, perhaps with a nice candlelit dinner, enjoying the scents of wild Maremma nature.

FamilyIndoor spacesParking

4.83 out of 5 average rating, 114 reviews

A cozy bedroom features a spacious bed with a blue patterned coverlet and towels neatly arranged on top. Two bedside lamps illuminate the space, complemented by framed sea-themed art on the wall. A window draped with light blue curtains provides natural light.

4.93 out of 5 average rating, 15 reviews

50m from sea, near center, with garden, AC & WiFi

Very close to the sea and just a stone's throw from the center, this newly furnished apartment is the ideal choice for a relaxing holiday. Its strategic location allows you to enjoy the beaches, the village, and all the services within easy reach. Perfect for families or couples seeking tranquility, immersed in the beauty of the Maremma.

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Apartment in Monteriggioni

An outdoor pool area is surrounded by olive trees and vineyards, with sun loungers and shaded umbrellas arranged on the deck. Soft sunlight bathes the scene, highlighting the peaceful setting. A gravel path leads around the pool, inviting relaxation amid the natural landscape.

Comfort Apartment in the Chianti Vineyards

Apartment on the upper floor of the structure characterized by a wonderful view of the Chianti hills, olive groves or the patio. Renovated while maintaining the charm of their ancient walls but adding every comfort. It includes a living room, kitchenette, a double bedroom, a private bathroom with shower, and air conditioning.

KitchenIndoor spacesHiking

4.93 out of 5 average rating, 455 reviews

5.0 out of 5 average rating, 51 reviews

Alluring Elicriso a few steps from beach & centre

New, cozy, fully equipped, with a private entrance, at the foot of a verdant hill, close to the sea and shops, in a quiet location. Forget about your car because everything is within walking distance. Private terrace surrounded by a charming communal garden. Pets allowed. Accommodates up to 4 people.

KitchenFamilyAir conditioning

4.92 out of 5 average rating, 39 reviews

A single-story villa is set within a spacious green garden, featuring a terracotta-tiled roof and sliding glass doors that open to the outdoor space. A patio adorned with a dining area is visible, complemented by a well-maintained palm plant in the foreground.

Home in Pian di Rocca

Villa with a hydromassage pool

Delightful Villa 2 km from the beautiful sea of the Rocchette (choice between free beach or private bath) reachable along a flat road of the typical Maremma countryside, by bike or car. Just a 5-minute drive to the medieval village of Castiglione della Pescaia.

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Popular amenities for Castiglione della Pescaia family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

5.0 out of 5 average rating, 118 reviews

A stone house is positioned on a hillside overlooking the deep blue sea. Lush green terrain surrounds the structure, and a large umbrella provides shade near the entrance. The coastline and distant boats can be seen in the background under a clear sky.

Home in Rio Marina

Casa del Capitano | Monte Grosso, Elba

Indoor spacesKitchenTV

4.96 out of 5 average rating, 142 reviews

Home in Asciano

Palazzo Monaci - Pool in the Crete Senesi

Indoor spacesKitchenQuiet

4.93 out of 5 average rating, 145 reviews

A rustic stone house is set on a green hillside, surrounded by trees. A large pool reflects its surroundings, with steps leading into the water. The garden features well-maintained lawns and a wooden deck nearby, inviting outdoor relaxation.

Home in Poggi del Sasso

LECCIONE RESIDENCE

FamilyIndoor spacesCondition

4.99 out of 5 average rating, 155 reviews

An aerial view showcases the expansive grounds of La settecentesca Villa di Geggiano, surrounded by manicured gardens and lush vineyards. The main villa is prominent, with a circular driveway leading to it, while gentle hills extend into the background.

Cottage in Geggiano

Villa di Geggiano - Guesthouse

Indoor spacesFamilyOutdoor spaces

4.95 out of 5 average rating, 188 reviews

Dome in Volterra

Green Dome @ The Land Before Time Retreats

Indoor spacesFamilyCleanliness

4.93 out of 5 average rating, 197 reviews

A wooden hot tub is positioned against a stone wall, surrounded by lush greenery. Two individuals relax within the tub, illuminated by soft lighting from nearby lanterns, creating a serene evening atmosphere.

Condo in Casole d'Elsa

La Casetta

KitchenIndoor spacesCleanliness

4.96 out of 5 average rating, 156 reviews

An elegantly furnished living room features classic decor, including a chandelier and ornate details. Large windows offer views of the city's architectural highlights. Comfortable seating arrangements, including a tufted sofa and armchairs, are arranged around a glass coffee table, enhancing the room's inviting ambiance.

Home in Siena

Domus Nannini - Loggia Salimbeni SPA

FamilyKitchenHot tub

Vacation home in Castelnuovo Berardenga

A sparkling swimming pool is surrounded by sun loungers and umbrellas, offering a relaxing space for guests. The rustic farmhouse, with its stone exterior, is visible in the background, amidst lush greenery and trees under a partly cloudy sky.

PIERFANTINI private Chianti house ♿️ 🏊‍♂️ 🐶

FamilyKitchenHeating

4.91 out of 5 average rating, 100 reviews

Family- and pet-friendly home rentals

4.94 out of 5 average rating, 118 reviews

A spacious bedroom features a large bed with a neutral bedspread and decorative pillows. A wooden headboard complements the light-coloured walls. A turquoise wardrobe stands against the wall, with a small table and lamp positioned nearby. Natural light fills the room, highlighting the terracotta flooring.

Home in Pievescola

Borgo Ripostena – n. 9 Frantoio

KitchenFamilyGrill

4.98 out of 5 average rating, 294 reviews

Farm stay in Siena

Typical Tuscan Country House WITH A/C

Indoor spacesKitchenCleanliness

Villa in Montecatini Val di Cecina

Torre dei Belforti

FamilyIndoor spacesCleanliness

4.99 out of 5 average rating, 138 reviews

A balcony area is visible, featuring two wicker chairs with yellow cushions. The expansive view of the sea is captured in the background, along with the tranquil scene of rooftops and greenery below, inviting leisurely moments outdoors.

4.87 out of 5 average rating, 31 reviews

Comfortable house and terrace by the sea

Indoor spacesKitchenPets

A comfortable living area features high wooden beams and large windows allowing natural light. A dining table with seating for four, surrounded by flowers, is seen near a cozy seating arrangement with a lamp and artwork adorning the walls.

4.66 out of 5 average rating, 98 reviews

Lovely seasidehouse with new air condition !

Indoor spacesFamilyWifi

4.94 out of 5 average rating, 48 reviews

Country house short distance from the sea

Indoor spacesFamilyLocation

Apartment in San Vincenzo

An outdoor terrace is presented with a circular stone table set for dining, featuring plates and drinks. Comfortable chairs are adorned with striped cushions. A light curtain gently drapes, while a scenic view of the sea is visible in the background.

Antea Blu: beach house in Tuscany-2 bedrooms

Indoor spacesFamilyCheckout

4.95 out of 5 average rating, 93 reviews

4.94 out of 5 average rating, 71 reviews

The terrace of Rosi, houses in the villagge

FamilyKitchenTV

Family-friendly home rentals with a pool

Villa in Castagneto Carducci

A solitary tree stands prominently in the foreground, framed against a vast landscape. Below, the coastline stretches toward the horizon, with the sea shimmering in the distance. The view includes a charming town nestled among the lush greenery of the surrounding hills.

sea view villa with private infinity pool

Indoor spacesFamilyAmenities

4.99 out of 5 average rating, 124 reviews

Home in Rosignano Marittimo

A terrace overlooking the coastline is equipped with a large umbrella, sun loungers, and a small pool. The rocky coastline and clear blue water are visible, while lush greenery frames the outdoor area, creating a serene environment for relaxation.

Frontemare house with exclusive sea access

FamilyKitchenParking

4.96 out of 5 average rating, 112 reviews

4.98 out of 5 average rating, 304 reviews

A rustic terrace features a wooden table and chairs, offering panoramic views of rolling hills and lush greenery. Stone walls support a traditional wooden beam ceiling, while elements like a decorative bell and a sheep silhouette add character to the natural surroundings.

Farm stay in Pari

TUSCANY farm house SWIMMING POOL

Indoor spacesFamilyBreakfast

Vacation home in Sovicille

An aerial view of a rustic complex surrounded by lush greenery. A swimming pool is visible at the center, accompanied by sun loungers. The surrounding landscape features rolling hills and fields, creating a serene atmosphere.

Podere La Castellina - No. 4 FICO

FamilyKitchenAir conditioning

4.96 out of 5 average rating, 110 reviews

Apartment in Castiglione d'Orcia

A rustic stone farmhouse is surrounded by colorful flower pots, adding charm to the entryway. The structure features a mix of wooden shutters and terracotta accents. A gravel driveway leads to the entrance, framed by lush greenery and vibrant blooms.

Mimosa Apartment - Poggio al Vento

KitchenIndoor spacesLong stay

4.99 out of 5 average rating, 112 reviews

4.94 out of 5 average rating, 161 reviews

Aerial view of the agriturismo Santa Lucia, showcasing well-maintained grounds surrounded by lush greenery and neatly lined cypress trees. A shared swimming pool is visible at the center, complementing the rustic charm of the old farmhouse and the rolling hills in the background.

Apartment in Asciano

Loggiato 2 Apartment in Tuscany with pool

Indoor spacesKitchenAir conditioning

4.96 out of 5 average rating, 137 reviews

Home in Montescudaio

Open space surrounded by nature

KitchenFamilyLocation