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Cottage holiday rentals in San Giovanni d'Asso

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Top-rated cottage rentals in San Giovanni d'Asso

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Top Guest favourite
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

PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

4.99 out of 5 average rating, 155 reviews
Guest favourite
A modern stone house is surrounded by lush greenery, nestled against a hillside. Large glass windows provide ample natural light, showcasing the inviting interior. The roof has a gentle slope, reflecting a blend of traditional and contemporary architecture.
Cottage in Seggiano

EcoLodge – modernes Design in ruhiger Panoramalage

Die moderne, ökologische und komfortable EcoLodge liegt ruhig und für sich inmitten von Olivenhainen, Kastanien- und Obstbäumen, Wein und Wiesen. Vor Ihnen die Hügel des Val d’Orcia, im Rücken der Monte Amiata. Hier treffen drei Welten aufeinander: Val d’Orcia, Monte Amiata und Maremma. Die Vielfältigkeit ist ein idealer Ausgangspunkt für Kultur, Wein, Wandern, Mountainbiken, heiße Quellen und Meer – und zugleich ein Ort, um abseits der Touristenströme das toskanische Landleben zu genießen.

4.94 out of 5 average rating, 111 reviews
Top Guest favourite
Cottage in Castellina in Chianti

Cottage Cappero - Masseto In Chianti

MASSETO IN CHIANTI è un villaggio privato dove potrete rilassarvi nel vostro giardino privato e in piscina, fare sport, o utilizzare come base per visitare città rinascimentali: Firenze, Siena, San Gimignano, Arezzo, Volterra. Offriamo altri tre cottage con accesso indipendente e giardinetto privato: Quinto (2 letti), Vittoria (4 letti), Leccio (6 letti). La piscina è condivisa dai 4 cottage, ciascuno dispone di un gazebo privato, con distanze garantite e sanificazione a norma Covid-19.

4.97 out of 5 average rating, 115 reviews
Top Guest favourite
An aerial view of the historic Monteriggioni Castle showcases its medieval architecture surrounded by lush countryside. The fortified walls encircle the village, which is dotted with trees and buildings, while rolling hills extend into the distance under a sunset sky.
Cottage in Monteriggioni

Monteriggioni Castello, holiday house in Tuscany

Il nostro alloggio è un edificio storico che risale alla costruzione del castello. È stato recentemente restaurato e arredato con cura in tutti i dettagli. È molto accogliente e dispone di tutti i più moderni servizi. I turisti che decideranno di essere nostri ospiti, avranno il vantaggio di vivere nell' ambiente medievale del castello, usufruendo di tutti i confort. Si sentiranno coccolati e avranno l'opportunità di tornare indientro vivendo un' esperienza unica e indimenticabile.

4.95 out of 5 average rating, 298 reviews
Top Guest favourite
The stone house features a welcoming entrance with large arched windows. A vibrant flower box filled with geraniums complements the lush green lawn. A shaded area with wooden seating offers a place to relax, while the infinity pool and surrounding vineyards are visible in the background.
Cottage in Barberino Tavarnelle

Stone House with Exclusive Pool Codilungo in Chianti

Welcome to your Tuscan dream between Florence & Siena. Perfect for families or romantic getaways. • 360° views of iconic Chianti hills. •Huge Exclusive Infinity Pool (17x9m), lit at night (open from May 1st to October 15th) • Total privacy, yet restaurants/shops are 10-15 mins away. • Comfort for 6: 3 bedrooms (2 double, 1 twin) & 3 full baths. • Modern amenities: Fully equipped kitchen area, Smart TV. • Outdoor bliss: Large dining loggia, professional BBQ, poolside porch & bath.

4.98 out of 5 average rating, 218 reviews
Top Guest favourite
A charming stone cottage is set within lush greenery, featuring a covered porch with outdoor seating. Olive trees surround the area, enhancing the natural beauty. A bicycle leans against the wall, inviting exploration of the peaceful countryside.
Cottage in Osteria delle Noci

Your Tuscan oak tree house, enchanting Val d'Orcia

The house enjoys a rare and enchanting view of the Val d’Orcia and Monte Amiata, ensuring maximum privacy. The interiors mirror the charm of the Tuscan style, with antique furniture and finishes made by local artisans. It is equipped with a double bedroom, a large living room with a big table, a fully equipped kitchenette, a double sofa bed in front of the fireplace, in the living room. Outside, the patio will allow you to eat with the colors of the sunset as a backdrop.

5.0 out of 5 average rating, 116 reviews
Top Guest favourite
An aerial view captures the agriturismo's lush green landscape, featuring neatly arranged cypress trees lining the path. A sparkling swimming pool glimmers amidst the foliage, while sprawling fields extend into the background under a clear sky, showcasing the beauty of the Tuscan countryside.
Cottage in Buonconvento

Tuscan Barn Apartment for 6 with panoramic pool

Panoramic Tuscan apartment converted from an old barn, with direct access to the garden and a shared panoramic swimming pool overlooking the Senese hills. Ideal for families or small groups of friends looking to enjoy for an authentic rural experience, privacy and relax. The apartment features three double bedrooms each with private bathroom, air-conditioning and WI-FI. A perfect place to enjoy nature, silence and unforgettable Tuscan sunsets.

4.89 out of 5 average rating, 100 reviews
Top Guest favourite
The jacuzzi is featured outdoors, illuminated with blue lights, creating a calming atmosphere at night. The surrounding stone walls provide privacy, and a dining table can be seen nearby. Steam rises, indicating the water is warm and inviting.
Cottage in San Casciano In Val di Pesa

Il Fienile, Cottage in the country with Jacuzzi

Surrounded by wineyards, close to Florence, a charming accomodation in a cozy cottage with heated jacuzzi at your exclusive use. Perfect starting point to discover Florence and Siena. Kitchen, wide living room, bathroom, two double bedroom (one with an extra single bed). In the living room a sofa bed for other 2 people. Tasteful furniture, Air Conditioning, barbecue, private parking. Partnership for: bike rental, private chef, private driver

4.96 out of 5 average rating, 198 reviews
Guest favourite
A stone patio is shown, featuring a small table set with two chairs. The entrance to the cottage is visible, accompanied by wooden shutters. Lush greenery surrounds the area, providing a serene environment.
Cottage in Ponte Feccia

Country cottage C&M immerso nel verde love Tuscany

Country cottage in pietra , indipendente nella campagna Toscana in provincia di Siena ,con ampio giardino, portico e gazebo. La nostra casa e' situata nella campagna del comune di Chiusdino, a soli 5 minuti dai due paesi principali Monticiano e Chiusdino e 10 minuti dalla splendida Abbazia di.Galgano . 30 minuti da Siena , da Monteriggioni , un'ora da Firenze e 30/40min minuti dal mare. Soli 20 minuti dalle belle Terme del Petriolo .

4.94 out of 5 average rating, 204 reviews
Guest favourite
A stone exterior is presented, showcasing a well-maintained garden with various plants and flowers. A staircase leads from the garden to an entrance, while a wrought-iron gate opens onto a pathway. The structure is flanked by a neighboring building visible in the background.
Cottage in Vescovado

Casa Roberta: una splendida vista sulle Crete!

Casa in pietra, finemente ristrutturata, collocata sulla collina di Vescovado di Murlo. E' ai limiti del centro storico in zona tranquilla dove si sente solo il suono della natura. Due piani con piccolo giardino con vista splendida. Può accogliere quattro ospiti. La casa non è adatta a persone disabili (presenza di scale, vani porta non idonei). Le automobili devono essere parcheggiate all'esterno, nei molti parcheggi del Borgo.

4.83 out of 5 average rating, 161 reviews
Guest favourite
The charming cottage is set against a backdrop of lush greenery, featuring a natural stone facade and a tiled roof. A swimming pool is visible in the foreground, accompanied by sun loungers and umbrellas, while well-maintained gardens and trees surround the property.
Cottage in Radicofani

Cottage "Girasole" 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).

4.85 out of 5 average rating, 140 reviews
Guest favourite
Two rattan chairs are positioned on a lush green lawn, overlooking rolling hills dotted with olive trees. The tranquil scene features views of a medieval town with distinctive towers, under a partly cloudy sky.
Cottage in San Gimignano

Countryside Cottage With View - Le Papere apt

The cottage is part of a charming traditional Tuscan farmhouse, built in stone and situated in one of the most beautiful areas of Tuscany. A lovely garden surrounds the house and has magnificent views of the medieval town with its famous towers. Warm and cozy atmosphere that makes you feel instantly at home. For those who wish to live the experience of the Tuscan countryside as it is lived by the locals.

4.88 out of 5 average rating, 139 reviews

Popular amenities for San Giovanni d'Asso cottage rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Cottage rentals with a hot tub

Top Guest favourite
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

Da Simone, podere santi Lucia e Pietro

4.94 out of 5 average rating, 243 reviews
Top Guest favourite
A shaded pergola adorned with grapevines provides a relaxing spot for outdoor dining. A colorful table features a floral design, surrounded by wrought iron chairs. A private jacuzzi sits nearby, with lush greenery and rolling hills visible in the background.
Cottage in Castelmuzio

Panoramic view & outdoor jacuzzi - Pienza

5.0 out of 5 average rating, 81 reviews
Superhost
A glass-enclosed veranda offers a view of the private garden and pool area. A round dining table with decorative tiles is surrounded by iron chairs. Light filters through the glass, enhancing the rustic charm of the exposed stone walls.
Cottage in Trequanda

"Rosso Poggiolo" casale con piscina.

4.75 out of 5 average rating, 145 reviews
Guest favourite
A stone cottage is surrounded by lush greenery, featuring a rustic facade with wooden accents. Potted plants are placed near the entrance, and the roof is topped with a small chimney. A pathway of stones leads to the door, inviting guests to explore.
Cottage in San Gimignano

Romantic House in Tuscany with jacuzzi

4.96 out of 5 average rating, 85 reviews
Superhost
The two-story country house is surrounded by a spacious garden featuring mature olive trees. Large windows and an inviting porch are visible, blending harmoniously with the natural landscape. The site is well-maintained, showcasing greenery and a fence that marks the property's boundaries.
Cottage in Città della Pieve

Il Picchio Verde

4.97 out of 5 average rating, 65 reviews
Guest favourite
Cottage in Colle di Val d'Elsa

Cottage nel verde con jacuzzi privata e piscina

4.88 out of 5 average rating, 81 reviews
Superhost
A gravel pathway leads through an archway adorned with blooming roses, framed by lush olive trees. The entrance is marked by wooden gates that open into the property, inviting guests to explore the serene surroundings.
Cottage in Paciano

NEW Leccino home pool&Jacuzzi a Fontanaro Property

Top Guest favourite
Cottage in Buonconvento

Capanna at S. Carlo in Buonconvento

4.95 out of 5 average rating, 39 reviews

Pet-friendly cottage rentals

Guest favourite
Cottage in Sovicille

Lovely apartment with garden and views near Siena

4.9 out of 5 average rating, 162 reviews
Superhost
The living/dining area features exposed wooden beams on the ceiling and a terracotta tiled floor. A modern kitchen with wooden cabinetry is complemented by a dining table set for four. Natural light enters through red-framed windows, enhancing the cozy ambiance.
Cottage in Cennina

The Five Oaks Cottage

4.84 out of 5 average rating, 176 reviews
Guest favourite
A dining area features a dark wooden table with black chairs, adorned with a floral centerpiece. Light-colored stone walls and wooden beams create a rustic charm. A blue sofa with floral cushions is positioned against a large window, allowing natural light to fill the space.
Cottage in Quarate

FAETOLE typical Tuscan country house near FLORENCE

4.91 out of 5 average rating, 162 reviews
Guest favourite
A rustic stone building is set amidst a large, green lawn dotted with olive trees. The facade features multiple windows with arched tops, reflecting the characteristic Tuscan architecture. Natural scenery and gentle hills in the background suggest a peaceful, rural atmosphere.
Cottage in Monteriggioni

Countryside, 10 min from Siena

4.84 out of 5 average rating, 289 reviews
Guest favourite
A well-maintained garden features a green lawn surrounded by olive trees. Colorful flower pots with red blooms accent the space. A shaded seating area under a canopy provides a cozy spot for relaxation, with additional garden ornaments and a path leading through the landscape.
Cottage in Montespertoli

Casa del Sole nel Chianti

4.92 out of 5 average rating, 143 reviews
Superhost
Cottage in Montespertoli

Chianti Barn with Pool and Vineyard View

4.79 out of 5 average rating, 290 reviews
Guest favourite
A wooden deck offers a serene view of rolling green hills extending into the distance. Two sun loungers are placed on the deck, inviting relaxation amid the natural surroundings. Trees frame the scene, creating a peaceful atmosphere, ideal for enjoying the landscape.
Cottage in Vetulonia

La Dolce Vita Romantic Sea-view Cottage. Tuscany

4.96 out of 5 average rating, 130 reviews
Guest favourite
A cozy bedroom features a large bed framed by elegant wrought-iron headboards. Textured stone walls complement the cream-colored backdrop. A small table displays travel brochures and decorative elements, providing a homely touch.
Cottage in Pari

Affittacamere La Casa del Frantoiano -Pari-

4.94 out of 5 average rating, 179 reviews

Private cottage rentals

Guest favourite
A rustic stone building is framed by lush greenery and seasonal flowers. Outdoor seating is arranged on a grassy area, including a table and chairs. A swimming pool partially visible in the background invites relaxation. The sky is clear, suggesting a bright day.
Cottage in Fabro

dependance mandriola

4.9 out of 5 average rating, 106 reviews
Guest favourite
An open space design features a vaulted brick arch, creating a warm atmosphere. Two spacious beds are positioned under wooden beams, accompanied by a compact seating area and a desk. Natural light filters through the windows, enhancing the rustic charm of the room.
Cottage in Chiusdino

Casa rurale openspace a San Galgano

4.93 out of 5 average rating, 174 reviews
Guest favourite
A charming cottage is surrounded by lush green grass and decorative plants. The rustic brick exterior features large windows framed with climbing vines. A cozy seating area on a tiled porch offers a relaxing view of the garden and the inviting countryside.
Cottage in Montagnano

Affascinante cottage in Toscana

4.94 out of 5 average rating, 141 reviews
Guest favourite
The stone building features arched windows and a terracotta roof, nestled among green trees. A lavender-filled pathway leads to a patio with outdoor furniture. A parasol and sun loungers are visible, adding to the tranquil setting against a backdrop of rolling hills and a blue sky.
Cottage in Volterra

Podere Grignano, beautiful Tuscany.

4.94 out of 5 average rating, 108 reviews
Guest favourite
A modern eco-house features a wooden exterior with slatted design, surrounded by vibrant greenery and blooming flowers. A small patio is visible at the front, furnished with outdoor seating, complemented by a serene natural landscape under a clear blue sky.
Cottage in Casole d'Elsa

Peaceful modern eco house in the Tuscan hills

4.88 out of 5 average rating, 161 reviews
Superhost
A quaint outdoor dining area features a round table with rust-colored cushions and wooden chairs set on a grassy patch. The backdrop includes a charming brick structure with green-framed windows and warm lighting, surrounded by lush vines and greenery.
Cottage in Galluzzo

FARMERShouse/casaBARTHEL 15' from the City Center

4.83 out of 5 average rating, 175 reviews
Guest favourite
The exterior of a charming yellow farmhouse is featured, with large arched windows framed by wrought iron. A spacious lawn is set with lounge chairs and a wooden table surrounded by trees, creating a serene outdoor space ideal for relaxation.
Cottage in Montespertoli

Chiantihouse with garden

4.88 out of 5 average rating, 169 reviews
Guest favourite
A charming stone villa is surrounded by lush greenery, featuring a shaded terrace with a wooden awning. Six outdoor chairs are arranged on a stone patio overlooking a well-kept lawn. A staircase leads to the upper level of the villa, framed by olive trees.
Cottage in Montisi

Il Villino

4.95 out of 5 average rating, 59 reviews

Destinations to explore