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Vacation rentals with a pool in Castellina in Chianti

Find and book unique homes with a pool on Airbnb

Quick stats about vacation rentals with a pool in Castellina in Chianti

  • Total vacation rentals

    Explore 30 vacation rentals in Castellina in Chianti

  • Nightly prices starting at

    Castellina in Chianti vacation rentals start at ﺩ.ﺇ 367 per night before taxes and fees

  • Verified guest reviews

    Over 790 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Castellina in Chianti vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Castellina in Chianti rentals

  • 4.6 Average rating

    Castellina in Chianti stays receive an average rating of 4.6 out of 5 from guests

Top-rated rentals with a pool in Castellina in Chianti

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite
The image showcases a refreshing pool surrounded by lounge chairs and umbrellas, enhancing the outdoor relaxation area. The pool is framed by lush greenery and a stone wall, with the charming rustic house visible in the background under a clear blue sky.
Home in San Filippo a Ponzano

Infinity pool in Chianti 1

Our house is a part of a stone farmhouse completely independent from the rest of the adjacent property. Arranged on three floors, on the ground floor there is a large entrance hall, a large living room with fireplace, a bedroom with 1 double bed and a bathroom with window. On the first floor there are two bedrooms (2 +2 beds) with a bathroom with window. In the basement, at garden level, there is the kitchen and the dining room. From the kitchen you access the outside where you will find an area for outdoor dining with a large dining table under a pergola. You then go down towards the garden with barbecue area.

5.0 out of 5 average rating, 143 reviews
Top guest favorite
An aerial view captures Podere Vergianoni nestled in the Chianti hills, surrounded by lush vineyards. The property features a clear blue pool, shaded terraces, and carefully landscaped gardens. Rolling hills and rows of grapevines create a serene backdrop, highlighting the natural beauty of the Tuscan countryside.
Condo in Noce

Podere Vergianoni immerso nelChianti con piscina

Podere Vergianoni è un antica proprietà del 1600 a gestione familiare situato nelle splendide colline del Chianti in Toscana con la possibilità di organizzare navetta privata e esperienze locali direttamente con la nostra famiglia . L'appartamento è disponibile per 2 adulti con possibilità aggiunta divano letto per 2 bambini sotto i 12 anni . Nel grande cortile esterno troverete una piscina a sale con area relax su terrazza panoramica con vista su castello e vigneti con tramonti unici.

5.0 out of 5 average rating, 352 reviews
Top guest favorite
A stone wall is adorned with vibrant red climbing roses, creating a striking contrast against the rustic texture. A window with a black grid pattern is visible, framed by the lush greenery of surrounding plants, enhancing the inviting character of the setting.
Home in Castellina in Chianti

Leonardo - Chianti/Siena, Firenze, San Gimignano.

Ancient stone house from the 15th century in a small renovated medieval hamlet in the heart of the Chianti Classico. Located on top of a hill between Florence, Siena and San Gimignano. TENNIS COURT+ SWIMMING POOL Splendid view over the valley. Independent entrance; On the ground floor: large living room with two sofas, dining area and open kitchen. On the 1st floor: 2 bedrooms and 1 bathroom with shower; Private garden with terrace - table and chairs for eating under the gazebo and sun loungers

4.97 out of 5 average rating, 120 reviews
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

4.93 out of 5 average rating, 256 reviews
Top guest favorite
Apartment in Castellina in Chianti

Dolce vita nel Chianti. Piscina e Relax

Appartamento immerso nelle colline del Chianti Classico,nel Borgo di Tregole,a 5 km da Castellina in Chianti. Appartamento privato all'interno di un casale tipico Toscano. Adatto a coloro che desiderano passare una vacanza immersi nella natura all'insegna del completo relax e del silenzio. Ideale punto di partenza per visitare i più importanti luoghi della Toscana. L'appartamento è dotato di tutti i comfort. La biancheria e le pulizie finali sono incluse nel prezzo. I bambini sono i benvenuti

4.85 out of 5 average rating, 354 reviews
Top guest favorite
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 favorite
A lush green garden is framed by a rustic pergola made of wooden beams. Grassy paths lead deeper into the garden, where vibrant flowers and trees provide a natural backdrop. Rolling hills and a clear blue sky are visible in the distance, creating a serene outdoor setting.
Home in Castellina in Chianti

Private Chianti Cottage, Garden & Vineyard Views

Set in a picturesque hamlet, overlooking the Chianti hills, this charming country house is just 10 minutes from Siena and Castellina in Chianti. Recently renovated, it blends authentic Tuscan charm with modern comforts. The house features two bedrooms, two bathrooms, a cozy living area and a fully equipped kitchen with a dishwasher, two fridges, and a washing machine. Outside, enjoy a beautiful garden and relax in the outdoor marble hot tub, soaking in the breathtaking views.

4.99 out of 5 average rating, 138 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.

4.98 out of 5 average rating, 107 reviews
Top guest favorite
A charming stone building surrounded by lush greenery features a wooden terrace with a parasol and flower pots. Two loungers are placed on the well-maintained lawn, providing a relaxing outdoor space.
Farm stay in Greve in Chianti

Old hayloft on the Chianti hills

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.

4.99 out of 5 average rating, 481 reviews
Top guest favorite
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.

4.96 out of 5 average rating, 209 reviews
Top guest favorite
A stone facade is viewed from a well-maintained garden, featuring lush green grass and neatly trimmed hedges. A wooden door is visible, leading into a charming interior, while the house's rustic architecture complements the serene landscape under a clear blue sky.
Home in Castellina in Chianti

Explore Chianti from a Charming Stone House

Awaken in a bedroom with beamed ceilings, open doors to a private garden, and take an early morning dip in the pool. Return to a classically designed house with terra cotta floors, wood-burning fireplace, and bathrooms with exuberant tile work. Casa Marinella is the perfect place to discover Chiantishire. Fully equipped kitchen, AC in each bedroom, private garden and barbecue.

4.98 out of 5 average rating, 123 reviews
Top guest favorite
A spacious living area features a modern design, with a prominent stone fireplace and minimalist furniture. Large glass doors open to a serene outdoor view, while natural light brightens the room, highlighting the soft tones of the walls and furnishings.
Tower in Fiesole

A Big Dream in a Little Tower.

The Tower was created in the late 1800s by an illustrious Englishman, Sir John Temple Leader, in one of the oldest and most important stone quarries belonging to the Medici family. From the same quarry were extracted many important works such as the columns of the Medici chapels, the steps of the Laurenziana library .. all just 5 km from the historic center of Florence.

4.95 out of 5 average rating, 222 reviews

Popular amenities for Castellina in Chianti rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Guest favorite
Home in Barberino Tavarnelle

SuiteLouise.pool, Hot Tub,homeGym & private Garden

4.91 out of 5 average rating, 128 reviews
Top guest favorite
Home in Greve in Chianti

Relax e charme tra le colline del chianti

4.99 out of 5 average rating, 115 reviews
Guest favorite
The kitchen area features wooden cabinetry and modern appliances, including a microwave and coffee maker. A round wooden table with simple chairs is surrounded by natural light from large windows, offering views of the surrounding vineyards.
Home in Greve in Chianti

Agriturismo Casa Giulia di Sopra

4.95 out of 5 average rating, 107 reviews
Guest favorite
The image captures a scenic view of a well-maintained garden featuring a private pool and a barbecue area. The stone structure is adorned with a tiled roof, framed by lush greenery and rolling hills in the background. Soft clouds add to the tranquil atmosphere.
Home in Barberino Val d'Elsa

Ancient Barn in Chianti with Pool

4.89 out of 5 average rating, 125 reviews
Guest favorite
Home in Asciano

Palazzo Monaci - Piscina nelle crete Senesi

4.96 out of 5 average rating, 142 reviews
Top guest favorite
Home in Montaione

Cercis - La Palmierina

4.96 out of 5 average rating, 147 reviews
Guest favorite
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

4.94 out of 5 average rating, 118 reviews
Guest favorite
A sunlit sunroom features large windows adorned with sheer curtains, allowing natural light to fill the space. A cozy white sofa is positioned next to a small wooden table with chairs, while indoor plants add a touch of greenery to the inviting atmosphere.
Home in Gaiole in Chianti

Charming estate with views. A/C in the bedrooms

4.86 out of 5 average rating, 296 reviews

Condo rentals with a pool

Top guest favorite
Condo in Panzano in Chianti

Apt.Panzanello-Panzano in Chianti

4.96 out of 5 average rating, 282 reviews
Guest favorite
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

4.93 out of 5 average rating, 197 reviews
Guest favorite
A serene outdoor area features a swimming pool with clear blue water, bordered by wooden decking. Four lounge chairs face a vibrant garden of yellow flowers, offering expansive views of the surrounding hills and sky filled with fluffy clouds.
Condo in Castelfranco di Sopra

House between Firenze, Arezzo, chianti e Siena

4.84 out of 5 average rating, 302 reviews
Superhost
An open space studio with a dining area is visible, featuring a table set for a meal. Above, a loft area houses a spacious bed, while wooden stairs lead to it. Natural light enters through windows, highlighting the rustic decor and inviting ambiance.
Condo in Fiesole

Poggiolieto Studio - on hills 10' from city center

4.85 out of 5 average rating, 214 reviews
Guest favorite
A swimming pool is foregrounded with vibrant red roses, offering a striking contrast against the clear blue water. The panoramic view features rolling hills and the medieval towers of San Gimignano in the distance, with sun loungers arranged around the pool area.
Condo in San Gimignano

Adalberto Apartment inside the Manor of Fulignano

4.95 out of 5 average rating, 152 reviews
Guest favorite
Condo in San Gimignano

Scenic Stilish Country

4.88 out of 5 average rating, 137 reviews
Guest favorite
The exterior of the apartment features a spacious garden with a wooden deck and an elevated pool. A stone pathway leads to the entrance. The structure is surrounded by lush greenery and traditional Tuscan buildings, creating a serene environment.
Condo in Castiglioni

[Ninfea] Ancient House in Tuscany

4.92 out of 5 average rating, 121 reviews
Top guest favorite
A vintage-styled kitchen and dining area feature a small wooden table with colorful chairs, accompanied by a bicycle and a wall-mounted television. Kitchen appliances include a microwave and a minimalist cabinetry design. Natural light filters through a balcony door, opening to a garden view.
Condo in Scandicci

Residenza Vintage con Piscina nel Chianti

4.96 out of 5 average rating, 149 reviews

Home rentals with a private pool

Superhost
A unique treehouse is highlighted among vibrant green grass adorned with clusters of purple flowers. Towering trees provide shade, and the structure features a deck that overlooks the surrounding natural landscape, inviting a sense of tranquility and harmony with nature.
Home in Galluzzo

TREEhouse/casaBARTHEL

4.88 out of 5 average rating, 821 reviews
Top guest favorite
Farm stay in Arezzo

Esplora la natura al centro di Vigneti Chianti

4.97 out of 5 average rating, 265 reviews
Top guest favorite
A bright living area is highlighted by a white sectional sofa, complemented by red throw pillows. An elegant area rug sits on terracotta tiles, with wooden beams and a staircase leading to the upper level visible. Light streams through a window, enhancing the warm atmosphere.
Home in Barberino Tavarnelle

Suite Casa Luigi con piscina esclusiva

4.95 out of 5 average rating, 122 reviews
Guest favorite
A heated outdoor pool is surrounded by terracotta tiles and vibrant landscaping, featuring cypress and pine trees. Sun loungers are positioned around the pool, offering space for relaxation while enjoying views of the surrounding vineyard and countryside.
Villa in Lastra a Signa

Luxe Estate nr Florence. Vineyard, Pool, Privacy

4.97 out of 5 average rating, 73 reviews
Guest favorite
Villa in San Miniato

Historic villa x8 with exclusive pool

4.87 out of 5 average rating, 46 reviews

Destinations to explore