Cottage vacation rentals in Siena

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Top-rated cottage rentals in Siena

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Top guest favorite

Cottage in Città della Pieve

5 out of 5 average rating, 22 reviews

Grove Cottage, Immersed in nature & close to town

Bordering Tuscany with spectacular sweeping views across forests and olive groves through the Tiber Valley towards the Apennine mountains the spacious, luxury cottage and large, landscaped garden are private and tranquil, yet only a short walk from the historic, lively town centre. Famed for its palazzo's, churches, frescos, restaurants, artisan stores, cookery schools & festivals. Here days can be spent relaxing in nature or exploring the regions famed hilltop towns, vineyards or thermal spas.

Guest favorite

A wooden barrel with a vibrant red hue stands on a deck surrounded by lush greenery. Colorful flowering plants and an agave plant add to the vibrant landscape, with rolling hills visible in the background under a clear blue sky.

Cottage in San Bartolomeo a Quarate

4.92 out of 5 average rating, 142 reviews

FAETOLE typical Tuscan country house near FLORENCE

My cottage is hidden in Tuscan countryside among olive groves, vineyards and woodland. Nevertheless, downtown Florence is only 16km away! While away, spend your time by relaxing in the garden, where you will find a barbecue and an outdoor shower to cool down while sunbathing. Discover the beauty of surrounding countryside with a hike and unwind with a view of picture-perfect vineyards! One can also easily go for day trips to many tiny medieval towns scattered on the hills of Tuscany from here!

Top guest favorite

An arched entrance adorned with blooming white flowers leads into a well-maintained garden. Lush greenery surrounds a central flowerbed, while a stately villa with green shutters stands in the background, enhancing the serene atmosphere of the scene.

Cottage in Geggiano

4.99 out of 5 average rating, 129 reviews

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.

Guest favorite

A wood-fired hot tub is positioned on a wooden deck, surrounded by lush greenery. The rustic tub features a round, wooden top and is complemented by a chimney. Views of rolling hills and valleys extend in the background, offering a serene natural setting.

Cottage in Vetulonia

4.89 out of 5 average rating, 101 reviews

La Quercia ~ rustic nature retreat & endless views

Welcome to Il Baciarino! We are a rustic agriturismo in the green hills of Maremma, Toscana's wild and unexplored coastal region. Il Baciarino is a place to come and stay, to escape from the bustle of the city and your busy life, and to unwind in nature; perfect for those who love unspoiled nature, endless views, fresh seafood & good wine. Il Baciarino has various unique rustic cottages nestled in 19 acres of wilderness, on the outskirts of the tiny Etruscan town of Vetulonia.

Guest favorite

A grand living room features stone walls and Tuscan wooden beam ceilings, showcasing comfortable seating arrangements with wicker chairs and a cozy sofa. Natural light flows through large glass doors, providing views of the garden. A decorative rug and a fireplace enhance the room's inviting atmosphere.

Cottage in Lastra a Signa

4.94 out of 5 average rating, 83 reviews

COTTAGE in 17TH CENTURY FARM

Cottage I Cipressi, CIN IT048024C2HIESRD49 rests peacefully in an old Olive and Cypress grove nestled into the hills that overlook Florence. This stone farmhouse has been lovingly and elegantly restored with traditional taste and contemporary comfort. tuscan wooden beams. There is a/c in each room and a fireplace at your disposal. During the winter season the heating gas is on consume. The wood for the fireplace is for free IN THE SUMMER THERE IS AN INFINITY POOL TOO

Superhost

A serene view from the pool area is framed by olive trees, overlooking the expansive hills and the city of Florence in the distance. The water's edge reflects the lush greenery and the vibrant landscape, creating a tranquil outdoor setting.

Cottage in Bagno A Ripoli

4.88 out of 5 average rating, 42 reviews

The Cottage

The Cottage Florence .. così si realizzano i sogni. La cornice è dorata, la posizione dominante, centrale, indispensabile a volte per trovarsi emozionalmente sopra alla quotidianità e vivere un ambiente che pone la propria persona ed il proprio spirito come su di un altipiano. Vedere ad occhi aperti il paesaggio e le sensazioni di pace e di controllo che questo evoca con tutto il necessario ed il superfluo a portata di mano e tutto è panoramico sulla città di Firenze

Guest favorite

The country cottage is surrounded by tall trees and lush greenery, softly illuminated at dusk. The rustic stone exterior features warm light emanating from the windows, highlighting the tranquil setting in the Tuscan countryside. A wooden fence outlines the property, enhancing its privacy.

Cottage in Ponte Feccia

4.95 out of 5 average rating, 164 reviews

Country cottage C&M surrounded by greenery, love Tuscany

Country stone cottage, independent in the Tuscan countryside in the province of Siena, with large garden, porch and gazebo. Our house is located in the countryside of the municipality of Chiusdino, just 5 minutes from the two main towns of Monticiano and Chiusdino and 10 minutes from the beautiful Abbey of Galgano. 30 minutes from Siena, from Monteriggioni, an hour from Florence and 30/40 minutes from the sea. Just 20 minutes from the beautiful Terme del Petriolo.

Superhost

A scenic view of the Orcia Valley is presented, displaying rolling hills adorned with greenery and neatly trimmed cypress trees. The landscape transitions into soft earth tones that blend with the horizon, creating a serene backdrop under a clear sky.

Cottage in Radicofani

4.84 out of 5 average rating, 127 reviews

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).

Guest favorite

The exterior of a rustic two-story house is framed by lush olive trees and greenery. A simple bench sits on a stone pathway, inviting relaxation. The wall displays a neutral tone, complementing the natural surroundings.

Cottage in Capannori

4.81 out of 5 average rating, 204 reviews

Lovely cottage in the park of a Renaissance Villa

Classica casa colonica di due piani totalmente indipendente inserita nel parco di una villa lucchese del '500, villa Galliani. La casa è stata interamente ristrutturata e ha a disposizione un parcheggio con un giardino privato. Si trova nella zona della ville lucchesi, tra i vigneti con le uve per la produzione del vino Doc delle Colline Lucchesi e gli oliveti da cui si ricava l'olio extravergine d'oliva Dop di Lucca.

Guest favorite

Cottage in Casole d'Elsa (SI)

4.85 out of 5 average rating, 132 reviews

Eco-house, pool & garden on beautiful olive farm

New independent eco-house in rural setting, away from the crowds between Florence and Siena. This is an annex building on a family run olive farm surrounded by unspoilt Tuscan countryside. Plenty of shaded outdoor space, barbecue, stunning views, fantastic sunsets and big night skies. We are an official agriturismo, there are two other independent apartments on the olive farm that share the pool and private parking.

Guest favorite

An archway adorned with greenery frames a clear view of a spacious pool, surrounded by manicured grass. A variety of lounge chairs are positioned nearby, inviting relaxation under the bright blue sky with scattered clouds.

Cottage in Montagnano

4.93 out of 5 average rating, 125 reviews

Charming cottage in Tuscany

Charming cottage located on a hill with 360-degree views. An oasis of peace and quiet. Surrounded by greenery. Large swimming pool BBQ Area Inside there is a bedroom with a French bed, a living room with a sofa bed, a bathroom, a kitchenette and an indoor and outdoor dining area. Ideal for couples and families with one/two children. Crib available

Guest favorite

The image captures a serene outdoor space with well-maintained green lawns and a gravel pathway. Two rustic buildings are visible, set against a backdrop of trees and rolling hills. A large terrace with dining furniture invites for outdoor meals, while colorful flowers add a touch of vibrancy.

Cottage in Montespertoli

4.97 out of 5 average rating, 39 reviews

COTTAGE for up to 9 people/WIFI/AIR-CO/SWIM-POOL

The cottage is made of 2 units that may sleep all together up to 9 people in 4 bedrooms, 4 bathrooms, 2 kitchens fully equipped, 2 large livingrooms with freplace, 2 private gardens with table and chairs to relax or eat open-air. Internet WIFI. FREE AIR-CONDITIONING everywhere inside the cottage!!!