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Villa vacation rentals in Casole d'Elsa

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Quick stats about villa rentals in Casole d'Elsa

  • Nightly prices starting at

    Casole d'Elsa vacation rentals start at ﺩ.ﺇ 881 per night before taxes and fees

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Casole d'Elsa rentals

  • 5 Average rating

    Casole d'Elsa stays are highly rated by guests—averaging 5 out of 5!

Top-rated villa rentals in Casole d'Elsa

Guests agree: these villas are highly rated for location, cleanliness, and more.

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Guest favorite
A spacious kitchen showcases a large stone fireplace with a wooden mantle as its centerpiece. Light streams through the window, illuminating the wooden beams overhead. A dining table is set for a meal, while traditional utensils adorn the walls, enhancing the inviting ambiance.
Villa in Castellina in Chianti

Villa Padronale - IlVillinoFarmhouse

Intero piano superiore della Villa Padronale appena ristrutturata in stile tradizionale toscano.Gli alti soffitti con le travi a vista rendono il posto accogliente e perfetto per famiglie o gruppi di amici.Nella casa si trovano due grandi camini(in salotto e cucina)funzionali.Alloggio privato, non condiviso. La casa ha una ampia terrazza coperta,giardino con divani,bbq,firepit,parking privato. La piscina tra gli ulivi e i vigneti e' ideale per il relax ha un accesso privato alla zona condivisa

FamilyLocationComfort

4.93 out of 5 average rating, 254 reviews
Superhost
The exterior of a charming stone villa is showcased, with a refreshing swimming pool in the foreground. Lush green grass surrounds the pool area, and a shaded gazebo with seating is positioned nearby. Rolling hills and a clear blue sky form a picturesque backdrop.
Villa in Greve in Chianti

Villa La Doccia, Greve in Chianti.

Villa La Doccia si trova a circa 8 minuti di auto dal centro di Greve in Chianti, in Località Casole, nel cuore della splendida campagna del Chianti. La villa è situata in una zona tranquilla e silenziosa, all’interno di una piccola azienda agricola circondata da vigneti e uliveti, dove gli ospiti possono godere della natura e dei tipici paesaggi toscani. La posizione è ideale per chi desidera rilassarsi immerso nella campagna ma allo stesso tempo essere vicino al centro di Greve in Chianti

FamilyValueAccuracy

4.85 out of 5 average rating, 179 reviews
Guest favorite
Villa in Monteriggioni

Villa dei 2 Ulivi (Abbadia Isola)

FULLY AIR CONDITIONED, modern 6BR/4BA VILLA on Via Francigena: an enchanted paradise for friends & families with kids (trampoline, basketball area, soccer & volley/beach tennis nets, fossball, table tennis) & w. pets (fenced garden). Located in the small village Abbadia Isola in the shadow of the medieval castle of Monteriggioni, right on the path the ancient road & pilgrim route running from France to Rome (via Francigena) A.k.A FAMILY GROUPS KIDS FRIENDS dream VILLA Siena 12mn (ABB)

FamilyLocationLong stay

4.97 out of 5 average rating, 174 reviews
Top guest favorite
A historic tower rises prominently against a blue sky dotted with fluffy clouds. Surrounding greenery complements the stone structure, with trees and small buildings visible along the hillside, collectively conveying a sense of tranquility.
Villa in Montecatini Val di Cecina

Torre dei Belforti

Torre dei Belforti is the perfect place for people who love beauty, nature and art. Sleeping at the Tower is like traveling trough the time, between knights and princesses. The wonder of this place is enriched by a big garden, with its swimming pool, the cypresses alleys and the olive trees. The village is also a magic place well preserved and still alive. We are Emilia and Luca, we live here and our mission is to give the best to our guests, to fully enjoy this marvelous place.

LocationFamilyDecor

4.99 out of 5 average rating, 137 reviews
Top guest favorite
A large swimming pool surrounded by a brick patio and manicured lawns is highlighted in this image. Sun loungers are positioned along the pool's edge, with lush greenery and trees creating a serene backdrop. The villa's charming structure is visible in the distance under a partly cloudy sky.
Villa in Barberino Tavarnelle

Podere Tignano, 4-bedroom villa in the Chianti!

Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.

FamilyLocationCondition

4.98 out of 5 average rating, 105 reviews
Top guest favorite
Bright seating area features two white armchairs and a patterned ottoman, surrounded by large glass arches that open to a lush garden. Natural light floods the space, enhancing the exposed stone walls and wooden ceiling beams, complemented by a large potted plant.
Villa in San Casciano in Val di Pesa

Luxury Villa in the very heart of Chianti

The views, the views, oh my word the VIEWS! Originating in the early 12th century this spectacular home once served as the bakery for the entire village. Now fully renovated, the entrance and ground level have been opened with glass arches allowing natural light to illuminate the exposed walls, 4 large bedrooms, 3 with ensuite baths ( including a jacuzzi ). Only Minutes away from the famous Wineries of Chianti, this is THE Spot for a glass amongst friends.

FamilyLocationBiking

4.97 out of 5 average rating, 119 reviews
Top guest favorite
An inviting villa surrounded by lush greenery and vibrant flowers, featuring blooming rose bushes and olive trees. The gravel pathway leads to the entrance, showcasing a two-story structure with balconies. Sunlight highlights the colorful landscape, creating a serene atmosphere.
Villa in Impruneta

La Torre

Antica villa toscana, bellissima, con giardino privato esclusivo, completamente ristrutturata, immersa nelle splendide e dolci colline toscane. La villa ha una vista mozziafiato, molto soleggiata, ben arredata e dotata di tutti i comfort, silenziosa e non isolata. La casa si trova a Bagnolo, piccola frazione di Impruneta alle porte del Chianti, zona di uliveti, vigneti e pace. La casa si trova a circa 10 km in macchina dal centro di Firenze.

FamilyLocationNearby

5.0 out of 5 average rating, 188 reviews
Guest favorite
Villa in Monteroni d'Arbia

"Villa Daisy" con vista su Siena

Meravigliosa villa con ingresso indipendente all'interno del podere "Caggiolo", riportato alla luce con curata e profonda ristrutturazione che ha mantenuto intatti i lineamenti tipici di un podere toscano. Splendida vista panoramica su Siena. Situato alle Ville di Corsano, a soli 14 km dalla città. Luogo ideale per trascorrere giorni in totale relax e godere delle meraviglie che questa zona offre (Chianti, Val d'Orcia, Crete Senesi..).

FamilyValueDecor

4.95 out of 5 average rating, 171 reviews
Guest favorite
Villa in Siena

Villa Capanna, Private Pool, Breathtaking Views

Ancient restored barn with up to 6 bedrooms and 6 bathrooms, immersed in a historic wine estate, just 6 km from Siena. One of the most beautiful views that the Tuscan panorama can offer, airconditioned bedrooms, exclusive swimming pool, large triple garden, BBQ, poolside table, terrace to enjoy the sunset over the medieval towers on the horizon while sipping the organic wines of the estate, fireplace, parking free, WI-FI internet.

LocationValueQuiet

4.89 out of 5 average rating, 307 reviews
Top guest favorite
A well-maintained garden surrounds a refreshing pool, bordered by manicured grass. A comfortable seating area, featuring two lounger chairs and a shaded umbrella, provides a serene spot for relaxation. Soft greenery and flowering shrubs form a natural backdrop, enhancing the tranquil atmosphere.
Villa in Tignano

Villa Isabella

Villa Isabella is a comfortable Tuscan style villa located in the splendid Chianti hills in Tuscany with a large garden and a spectacular breathtaking panoramic swimming pool for exclusive use where you can experience the Tuscan tradition in full local style with the possibility of organizing private shuttles service for reach the property traditional experiences, services and tours only and exclusively for our guests.

LocationFamilyGrill

4.96 out of 5 average rating, 207 reviews
Top guest favorite
A well-kept garden features neatly trimmed grass and a variety of trees, including tall pines, providing shade and a natural atmosphere. A subtle hammock is visible between two trees, inviting relaxation in the serene outdoor space.
Villa in Montespertoli

Colonica nel Chianti

Splendida porzione di casa colonica immersa nel Chianti con bellissima piscina, circondata da vigne e olivi, perfettamente arredata con vasto giardino e posti macchina. Si trova a 20 minuti da Firenze, 40 da Siena e 50 da Pisa, in pochi minuti si raggiunge Certaldo (città natale di Boccaccio) e Vinci (città natale di Leonardo Da Vinci). la casa è a metà strada tra Montespertoli e San Casciano (7km).

LocationValueLaundry

4.95 out of 5 average rating, 219 reviews
Top guest favorite
The image showcases a rustic stone farmhouse surrounded by lush vineyards and olive trees. The building features a classic roof with terracotta tiles, set against a clear blue sky. Green grass frames the scene, emphasizing the natural beauty of the countryside.
Villa in Impruneta

Agriturismo Podere Scaluccia Chianti, Firenze

L'Agriturismo è situato a 15 minuti (8km) dal centro di Firenze, città di ricca arte e cultura, ed è circondato splendide viste panoramiche collinari, all'ingresso del Chianti. La Casa è antica: i materiali tradizionali quali la pietra, il legno e il cotto fanno da padroni. Il giardino esterno attrezzato è a disposizione di tutti! Per Saperne di più cerca Podere Scaluccia

FamilyLocationCheck-in

4.99 out of 5 average rating, 121 reviews

Popular amenities for Casole d'Elsa villa rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Private villa rentals

Top guest favorite
A charming stone villa is set amidst a lush green lawn. The building features wooden window shutters and a terracotta tile roof. A covered porch, adorned with flower pots, offers a welcoming outdoor space, complemented by a backdrop of blooming plants and trees.
Villa in Barberino Tavarnelle

CasaDiManuela:TotallyPrivateChiantiVilla withTub

FamilyLocationHospitality

4.97 out of 5 average rating, 105 reviews
Top guest favorite
A heated jacuzzi is situated under a shaded pergola, surrounded by lush greenery and colorful flowers. The serene outdoor space is complemented by a gravel path leading towards vineyards in the background, inviting relaxation and privacy.
Villa in San Casciano In Val di Pesa

Il Vichiaccio: Florence Villa with Jacuzzi

FamilyLocationComfort

4.95 out of 5 average rating, 202 reviews
Superhost
Villa in Casole d'Elsa

Panoramic villa & private pool-VacaVilla Exclusive

FamilyLocationAccuracy

4.67 out of 5 average rating, 9 reviews
Top guest favorite
A private swimming pool is surrounded by a spacious stone patio, featuring comfortable sun loungers and shaded seating areas. Potted plants are placed around the pool, enhancing the tranquil outdoor space that is framed by trees and the rustic charm of the stone house.
Villa in Volterra

Romantic Villa with private pool - "Il Pollaio"

LocationFamilyQuiet

5.0 out of 5 average rating, 47 reviews
Guest favorite
An aerial view captures the expansive countryside, dotted with vineyards and olive groves. The large swimming pool is framed by lush greenery, while the villa's garden offers a serene atmosphere. Gentle hills roll in the background under a clear, blue sky.
Villa in Poggibonsi

Villa with pool in Chianti Area

FamilyLocationCheck-in

4.95 out of 5 average rating, 73 reviews
Guest favorite
A crystal-clear swimming pool is framed by a large, well-kept lawn, inviting relaxation. Surrounding the pool are sun loungers, with rustic buildings visible in the distance beneath a clear blue sky, enhancing the serene atmosphere.
Villa in Colle di Val d'Elsa

Villa with pool in the heart of Tuscany

ValueLocationBiking

4.94 out of 5 average rating, 48 reviews
Top guest favorite
A spacious patio area is surrounded by vibrant purple flowers and greenery, creating a serene outdoor environment. The rustic stone house features large glass doors, complemented by a shaded umbrella and seating area. A grassy lawn adds to the charm of this inviting setting.
Villa in Radicondoli

Casa di Leo Romantic House

FamilyLocationCleanliness

5.0 out of 5 average rating, 65 reviews
Top guest favorite
The exterior of the villa is shown against a clear blue sky, featuring textured walls with traditional diamond-shaped brick patterns. Large windows provide natural light, while a shaded patio with seating and table is visible, surrounded by well-maintained greenery and trees.
Villa in San Gimignano

Fabulous 3Br Villa with 360° Views!

ValueFamilyQuiet

4.95 out of 5 average rating, 75 reviews

Luxury villa rentals

Guest favorite
A serene view of a crystal-clear swimming pool is featured, with comfortable lounge chairs arranged around it. In the background, a charming stone villa is set among lush greenery, providing a peaceful ambiance. The area is well-maintained, emphasizing an inviting outdoor setting.
Villa in Orentano

Charming Villa in Stone in Tuscany, Borgo ai Lecci

LocationFamilyLayout

4.97 out of 5 average rating, 116 reviews
Guest favorite
An aerial view showcases the rustic villa surrounded by lush green fields and rolling hills. The exterior features terracotta roofing, a garden area with lounge chairs, and a shaded patio space for outdoor dining, all under a partly cloudy sky.
Villa in Siena

Capanna di Elfo - Capanna Di Elfo

ValueFamilyWalkability

4.97 out of 5 average rating, 60 reviews
Top guest favorite
Villa in Montaione

Private Villa with semi-Olympic pool and Tennis

FamilyLocationCleanliness

4.98 out of 5 average rating, 50 reviews
Top guest favorite
An aerial view captures a charming stone villa surrounded by lush greenery and neatly arranged gardens. A spacious swimming pool is visible, complemented by outdoor seating areas and pergolas, all against the backdrop of rolling hills and cloudy blue skies.
Villa in San Gimignano

Tuscan Villa with Pool & Jacuzzi, San Gimignano

LocationFamilyDecor

4.98 out of 5 average rating, 90 reviews
Top guest favorite
A spacious bedroom features a four-poster bed draped with soft fabric. Two bedside lamps create gentle illumination. An arched bookshelf filled with books is visible in the background, alongside a cozy seating area with upholstered chairs, highlighting a mix of comfort and elegance.
Villa in Panzano in Chianti

Luxury Villa on Chianti Wine Estate

FamilyLocationLaundry

4.93 out of 5 average rating, 94 reviews
Top guest favorite
A serene outdoor area features a turquoise swimming pool surrounded by chaise lounges. Vibrant pink roses bloom near the edge, while lush greenery provides a natural backdrop. A stone villa with a tiled roof is visible in the distance, highlighting the tranquil setting.
Villa in Gaiole in Chianti

Sestuccia

LocationFamilyComfort

4.99 out of 5 average rating, 74 reviews
Guest favorite
A charming stone villa stands surrounded by green grass and trees, featuring ivy-covered walls. The exterior is complemented by a pathway made of light-colored stones leading to seating arrangements. Clear blue skies are visible above, enhancing the tranquil outdoor setting.
Villa in Siena

La Villa della Brigata Spendereccia!

LocationFamilyHot tub

5.0 out of 5 average rating, 27 reviews
Guest favorite
Villa in Monteroni d'Arbia

Villa panoramica nelle crete senesi, vista Siena.

FamilyLocationWalkability

5.0 out of 5 average rating, 52 reviews

Villa rentals with a pool

Top guest favorite
A private swimming pool is surrounded by vibrant flowers and lush greenery. Multiple lounge chairs are positioned under umbrellas for shade. A seating area is visible in the background, along with a well-maintained pathway and rustic stone walls, enhancing the serene outdoor setting.
Villa in Poggibonsi

Villa L'Olivo w/Private pool (Close San Gimignano)

LocationFamilyPool

4.99 out of 5 average rating, 98 reviews
Guest favorite
A private swimming pool is framed by manicured lawn and positioned under two large umbrellas. Four lounge chairs are arranged around the pool, offering views of rolling hills and the Tuscan countryside beyond. The pool features a sleek, modern design with clear water reflecting the sky.
Villa in Gambassi Terme

Villa Via Francigena

FamilyValueDecor

4.96 out of 5 average rating, 72 reviews
Top guest favorite
The villa is situated in a lush landscape, surrounded by rolling hills and greenery. A private pool is framed by manicured hedges and lounging areas. The rustic stone structure features a covered patio and is complemented by nearby olive groves and trees, ensuring privacy.
Villa in Montecastelli Pisano

Exclusive villa with pool jacuzzi wifi and green

LocationFamilyPets

4.96 out of 5 average rating, 53 reviews
Guest favorite
Villa in Gambassi Terme

Villa Montignoso - Exclusive villa with Pool

ValueLocationSleep quality

4.87 out of 5 average rating, 30 reviews
Superhost
The villa is set amidst lush greenery, featuring a stone pool terrace that leads to a welcoming swimming pool. Sun loungers are positioned around the pool area. The structure, with multiple windows, showcases a harmonious blend of rustic charm and modern design against a clear blue sky.
Villa in Poggibonsi

Amazing Chianti villa with pool for 12

FamilyLocationBackyard

4.92 out of 5 average rating, 37 reviews
Superhost
The historic stone house, featuring a multi-level design, is surrounded by lush greenery. A spacious outdoor area includes a large lawn and a shaded terrace. The rustic architecture is complemented by details such as wooden shutters and a stone well.
Villa in Volterra

Podere Ulimeto

ValueFamilyAccess

4.9 out of 5 average rating, 77 reviews
Guest favorite
A spacious outdoor area is highlighted by well-maintained greenery and various lounge chairs positioned near a pool. The villa is seen in the background, featuring a terracotta roof and large outdoor seating area, under a bright blue sky dotted with a few clouds.
Villa in Casciana Terme

Villa Le Rocche with pool, breathtaking view

LocationValueView

4.93 out of 5 average rating, 85 reviews
Guest favorite
A heated pool is surrounded by paved stones, offering a relaxing space with loungers nearby. Lush green hills and cypress trees are visible in the background, under a bright sky dotted with clouds.
Villa in Poggibonsi

VILLA TALCIONA

FamilyLocationAir conditioning

4.94 out of 5 average rating, 96 reviews

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