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Family-friendly vacation rentals in Santa Fiora

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Top-rated family-friendly rentals in Santa Fiora

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite

An outdoor wood-fired hot tub is surrounded by lush green grass, offering a scenic view over the expansive landscape. A stone pathway leads to the hot tub, while the rustic stone cottage is visible in the background under a partly cloudy sky.

Cottage in Castell'Azzara

4.99 out of 5 average rating, 139 reviews

Your Private Tuscan Retreat

This beautiful sheepherder’s stone cottage is equipped with modern comforts and spa facilities free of charge. The large grounds of forest and meadow span a ridge and provide panoramic views of the valley toward Val d’Orcia to the north, the expansive Maremema to the south, and the ancient volcano of Amiata to the west. This is the perfect getaway for those wanting a private retreat from which to explore the rich wine, food, culture, history, and landscape of southern Tuscany.

Top guest favorite

An aerial view showcases a charming stone cottage surrounded by lush greenery and mature trees. The roof is partially covered with natural foliage, blending the structure harmoniously into the landscape. The area features rocky outcrops and dense vegetation, highlighting the peaceful rural setting.

Farm stay in Seggiano

4.99 out of 5 average rating, 243 reviews

Terra Delle Sidhe, Seggiano, Tuscany, Italy

Terra delle Sidhe is a small organic farm located in southern Tuscany overlooking a beautiful valley located on the slopes of Monte Amiata, between the medieval towns of Castel del Piano and Seggiano. A 250 year old chestnut dryer stone house in use till 30 years ago, the holiday cottage we offer is surrounded by an organic chestnut forest and olive trees that are hundreds of years old. This charming cozy house it has now been lovingly renovated with taste and simplicity.

Top guest favorite

A spacious terrace is showcased with two comfortable armchairs positioned around a glass table. Potted red flowers adorn the railing, overlooking a panoramic view of the rolling hills of the Tuscan countryside under a partly cloudy sky.

Condo in Montalcino

4.99 out of 5 average rating, 114 reviews

"Landscape Notes" Suite

The 80 sqm Suite "Note di paesaggio" is located on the second floor of a historic building where it meets the landscape of the Val d'Orcia. It is divided into several rooms including a furnished double bedroom with air conditioning overlooking the terrace, a living room with a panoramic view, a study with a desk, a marble bathroom with shower, and another double bedroom without air conditioning . You can enjoy a 30sqm terrace and its suggestive view of the countryside.

Top guest favorite

A view from the window reveals a serene landscape of rolling hills and valleys bathed in soft morning light. The garden below is adorned with colorful flowers and greenery, enhancing the tranquil atmosphere of the Tuscan countryside.

Home in San Quirico d'Orcia

4.99 out of 5 average rating, 208 reviews

Alma Vignoni - Vignoni Val d 'Orcia - Bagno Vignoni

Alma Vignoni is an elegant and exclusive holiday house in Vignoni Alto that recalls Tuscan style and is enriched by unusual and personal details. The house consists of an open-space with fireplace in the center. On the one hand the room with stunning views over the surrounding hills (Pienza, Monticchiello and Montepulciano) on the other the kitchen area. Two cozy rooms overlook the ancient Via Francigena and the Orcia river valley. The bathroom has a large shower.

A historic villa is situated amidst lush, rolling hills, surrounded by vineyards. The exterior features a traditional stone facade, large windows, and terracotta roof tiles. Manicured gardens with circular patterns enhance the property's charm, complemented by tall cypress trees framing the serene landscape.

Apartment in Castelnuovo Berardenga

4.93 out of 5 average rating, 161 reviews

Villa di Geggiano - Perellino Suite

The 700 years old Villa di Geggiano, surrounded by our working vineyard and lovingly maintained gardens, is located in Chianti in Tuscany which is one of the most beautiful regions of Italy. Our guesthouse is located in one of the original garden pavilions of the villa. PLEASE NOTE THAT WE ARE IN THE COUNTRYSIDE WITH VERY FEW PUBLIC TRANSPORT OTHER THAN TAXI SO THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A RENTAL CAR.

A spacious bedroom features a double bed dressed in white linens, with a cozy armchair in the corner. Natural light enters through a window, illuminating the stone wall beside wooden beams above. A wooden table displays snacks and additional seating is available.

Condo in Castelnuovo dell’Abate

4.91 out of 5 average rating, 288 reviews

La Casetta di Brunello, very panoramic with terrace

STIAMO LAVORANDO PER VOI! ... WE ARE WORKING FOR YOU! The house is completely renovated and furnished in 2018 with classic-Tuscan style furniture. The colors are warm and enveloping to better rest during your holiday of peace and relaxation. In addition to the two double bedrooms, you have a kitchen with an equipped kitchenette, fridge, induction cooker and a furnished terrace with a beautiful view of the surrounding countryside.

An outdoor dining area is set on a stone patio, featuring a wooden table with seating for four under a striped umbrella. Scenic views of rolling hills and valleys are visible in the background, framed by greenery and a stone wall.

Apartment in Radicofani

4.91 out of 5 average rating, 146 reviews

"L'Assolata" Cottage in Tuscany

A lovely cottage in the old farmhouse "Podere Maltaia" that overlooks the Unesco's Heritage protected area Orcia Valley, surrounded by large farmyards and 3 hectares of private land that includes an outdoor swimming pool (opened seasonally, based on outside temperature - please ask to know the dates for the upcoming or ongoing summer season), garden, outdoor dining area, BBQ and parking area (not-covered, free of charge).

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

4.89 out of 5 average rating, 198 reviews

Casa al Gianni - Capanna

Hi, we're Cristina & Carmelo! We invite you to live an authentic experience in our farmhouse “Casa al Gianni” located 20 minutes from Siena. Our hallmark is simple life in close contact with nature and the animals of our farm. Immersed in the woods and the beautiful Tuscan countryside, you will spend an unforgettable vacation. This slice of paradise will remain in your heart!

A hammock hangs gently between trees in a spacious garden, surrounded by large volcanic rocks. Sunlight filters through the lush greenery, creating a serene outdoor space ideal for relaxation. Wooden stools and natural landscaping enhance the tranquil atmosphere.

Home in Vivo d’Orcia

4.95 out of 5 average rating, 139 reviews

At the Sassone Holiday Home, Val d'Orcia, Tuscany

Treat yourself to relaxing days in contact with nature! Apartment in villa, large garden with hammocks and large volcanic rocks. Direct access to the woods, with a pond and waterfalls, from which a series of paths and hiking trails lead to the free spas of Bagni San Filippo and the summit of Mount Amiata. DISCOUNTS FOR MEDIUM TO LONG PERIODS!

The bedroom features light-colored walls and wooden flooring. A spacious bed is paired with a smaller bed suitable for a child. Natural light enters through a window adorned with light curtains. A mirror and dark wooden furniture complement the room's decor.

Home in Bagnore

4.93 out of 5 average rating, 177 reviews

La Casa del Valle

La Casa del "Valle" is a romantic 🏡 renovated stone house in the heart of Mount Amiata⛰️. Located in a quiet village, it is perfect for those seeking relaxation and nature🌿. Convenient location for villages, trails and spas🛁. Free Wi-Fi and private parking 100 m away🚗. Ideal for an authentic getaway amidst silence and views.

A spacious bedroom features a large bed adorned with soft linens and two neatly rolled towels. Warm terracotta tiles cover the floor, complemented by pale yellow walls and wooden beam ceilings. Natural light fills the room through two windows with dark shutters, creating a calming ambiance.

Farm stay in Gaiole in Chianti

4.94 out of 5 average rating, 233 reviews

Il Nido - a romantic hearth

Lui non esisteva, è stato ricavato in un angolo della grande casa in cui chissà quante persone della stessa famiglia vivevano. Per questo è diventato il nostro piccolo Nido, la casa da cui partire per scoprire il borgo. Non un piano ma addirittura due, con tanto cotto, legno e colori caldi.

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Popular amenities for Santa Fiora family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A spacious area of well-kept grass is seen in the foreground, with a rustic Tuscan farmhouse in the background. The building features a tiled roof and multiple windows. Bare trees and some greenery surround the property, under a clear blue sky with scattered clouds.

Cottage in Sovicille

4.93 out of 5 average rating, 223 reviews

From Simone, podere santi Lucia and Pietro

The exterior of the property features a rustic stone façade complemented by wrought iron details. A spacious terrace is equipped with a large umbrella and an outdoor dining area, surrounded by lush greenery, enhancing the natural setting.

Cottage in Radicondoli

4.93 out of 5 average rating, 137 reviews

Beautiful renovated barn in Tuscany

The villa is set against a backdrop of rolling hills and gardens. A large pool is visible in the foreground, featuring a circular shape and steps leading into the water. The stone structure with a tiled roof complements the natural surroundings.

Villa in Montepulciano

4.91 out of 5 average rating, 126 reviews

Villa in Montepulciano with a Pool

A living area features a white sofa adorned with striped cushions, complemented by a small ottoman. Shelves display a selection of decor, while a dining table is set with tableware. Natural light enters through a nearby window, illuminating the space.

Apartment in Perugia

4.96 out of 5 average rating, 316 reviews

A Cosy flat

A panoramic view of the countryside reveals a tranquil villa surrounded by rolling hills. The large salt-water pool reflects the sky, while lush greenery and tree-lined paths create a serene atmosphere. The landscape provides a scenic backdrop to the property.

Home in Montebagnolo II

4.92 out of 5 average rating, 107 reviews

B&B "Alle cime"

A serene view of a swimming pool area during sunset, with warm golden light reflecting off the water. Comfortable lounge chairs are positioned around the pool deck, while lush green grass and palm trees frame the scene. A tranquil landscape stretches into the distance.

Villa in Baschi

4.87 out of 5 average rating, 176 reviews

VILLALADOLCEVITA

Top guest favorite

A rectangular swimming pool with a shallow and deep end is surrounded by a stone patio and lush greenery. A villa sits on a hillside in the background, featuring a terrace with windows and shutters. Poolside lights are placed around the pool for evening ambiance.

Apartment in Siena

4.91 out of 5 average rating, 129 reviews

Villa'Colombaiolo di Marciano', 28

A spacious living area features a large wooden table set for a meal, adorned with fresh fruits and glassware. A comfortable red couch is positioned nearby, complemented by framed black and white photographs on the wall and stylish pendant lights above.

Condo in Casole d'Elsa

4.93 out of 5 average rating, 157 reviews

La Casetta

Family- and pet-friendly home rentals

A rustic stone house is set against a backdrop of lush trees, featuring a terrace with sun loungers arranged around a central swimming pool. The building's earthy tones complement the natural surroundings, while a chimney adds a touch of charm to the exterior.

Cottage in Roccalbegna

4.91 out of 5 average rating, 77 reviews

Small cottage, swimming pool entirely private use

A stone house is set against a backdrop of green hills and blue sky. The textured facade features warm colors, complemented by a terracotta roof. Surrounding flowers add a natural touch, while the entrance is framed by lush greenery, enhancing the peaceful atmosphere.

Cottage in Santa Fiora

4.86 out of 5 average rating, 22 reviews

Il Seccatoio – a stone house with a panoramic view

A serene coastal scene displays calm blue waters reflecting the sky. Lush greenery lines the rocky shore, enhancing the natural beauty. A wooden lounge area offers an inviting space to relax, with scenic views of the distant hills across the sea.

Condo in Porto Santo Stefano

4.88 out of 5 average rating, 163 reviews

Villa Rosetta, apt 1, Lovely beach historic house

A stone farmhouse surrounded by lush greenery is visible, with a private pool in the foreground. Tall cypress trees line the property, enhancing the natural setting. The open landscape features well-maintained grass and shrubs, contributing to a peaceful outdoor space.

Apartment in Castiglione d'Orcia

4.96 out of 5 average rating, 47 reviews

La Tana del Bianconiglio - Girasole Apartment

A charming stone farmhouse is set amidst a lush green landscape, framed by tall cypress trees. The building features a welcoming porch with wooden loungers, and climbing vines adorn the walls, emphasizing the natural surroundings and tranquility of the Tuscan countryside.

Villa in San Casciano dei Bagni

4.98 out of 5 average rating, 64 reviews

Luxury Tuscan countryside villa with pool/WiFi/AC

A rustic Tuscan farmhouse, restored with care, features a tall tower and expansive windows. Surrounding greenery includes cypress trees and shrubs, complementing the natural landscape. The lawn offers open space for relaxation, enhancing the serene atmosphere of the property.

Villa in Buonconvento

5 out of 5 average rating, 12 reviews

Beautiful tuscan country house

The exterior of a cottage is surrounded by lush greenery and large trees, providing a natural frame. The stone structure features an archway entrance, with a chimney visible above the roof, blending harmoniously into the tranquil landscape.

Farm stay in Provincia di Siena

4.87 out of 5 average rating, 118 reviews

Spigo - Indipendent Cottage Zampugna

Top guest favorite

A spacious living area is showcased with large windows offering panoramic views of the surrounding hills. A dining table sits in the center, accompanied by chairs, while a comfortable seating arrangement is positioned nearby. Natural light fills the space, highlighting the earthy tones and wood accents.

Apartment in Montepulciano

4.97 out of 5 average rating, 392 reviews

A view from the top, Montepulciano

Family-friendly home rentals with a pool

A spacious living area is characterized by high wooden beams and terracotta tiles. A comfortable sofa and a wooden dining table with chairs are present, alongside a cozy fireplace featuring a natural stone surround. Soft lighting fixtures enhance the room's welcoming atmosphere.

Apartment in Pienza

5 out of 5 average rating, 3 reviews

Rocca, elegance in Sorbelle d'Orcia, Pienza

Villa in Buonconvento

4.95 out of 5 average rating, 57 reviews

Bellagatta, an Enchanting spot in Val d'Orcia

An inviting saltwater pool is surrounded by landscaped gardens featuring native greenery. Lounge chairs are placed nearby, offering a comfortable spot to relax. A rustic stone farmhouse is visible in the background, complementing the serene countryside setting.

Villa in Castiglione d'Orcia

5 out of 5 average rating, 11 reviews

#1 Luxe Farmhouse, Hilltop Views, Saltwater Pool

A serene stone pool reflects the clear sky, set against a backdrop of lush trees and rolling hills. The inviting water is framed by a stone deck, with a single umbrella providing shade nearby. The tranquil landscape offers a peaceful escape.

Home in Pievescola

4.94 out of 5 average rating, 175 reviews

Antico Borgo Ripostena – n. 8 Old House

A spacious swimming pool is surrounded by wooden decking, featuring comfortable lounge chairs and shaded areas. Lush greenery marks the perimeter, enhancing privacy. Floatation devices are visible in the water, inviting relaxation in the tranquil environment.

Cottage in Montagnano

4.93 out of 5 average rating, 127 reviews

Charming cottage in Tuscany

A serene infinity pool is surrounded by lush greenery, offering views of rolling hills and trees. Sun loungers provide space for relaxation, while umbrellas offer shade on sunny days. The tranquil landscape invites peaceful outdoor enjoyment.

Cottage in Seggiano

4.96 out of 5 average rating, 90 reviews

EcoLodge – modern design in quiet panoramic location

A tranquil outdoor pool area is surrounded by lush greenery, offering views of the rolling hills and distant mountains. Comfortable sun loungers are arranged around the pool, with large umbrellas providing shade. Colorful flowers border the scene, enhancing the natural beauty of the landscape.

Farm stay in Montepulciano

4.97 out of 5 average rating, 89 reviews

Unique view 3 bdr villa with pool & A/C in Pienza

A private pool is set within a verdant lawn, surrounded by tall cypress trees and leafy shrubs. Sun loungers are arranged for relaxation next to the pool, while a stone house with a terracotta roof stands in the background under a clear blue sky.

Farm stay in Camigliano

4.96 out of 5 average rating, 85 reviews

Tenuta La Fuga – Cottage with private pool

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