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Vacation rentals with a pool in Asciano

Find and book unique homes with a pool on Airbnb

Quick stats about vacation rentals with a pool in Asciano

  • Total vacation rentals

    Explore 480 vacation rentals in Asciano

  • Nightly prices starting at

    Asciano vacation rentals start at G$12,552 GYD per night before taxes and fees

  • Verified guest reviews

    Over 8,050 verified reviews to help you choose

  • Family-friendly vacation rentals

    310 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 260 rentals that welcome pets

  • Rentals with dedicated workspaces

    150 properties have a dedicated workspace

  • Wi-Fi availability

    450 of Asciano vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Asciano rentals

  • 4.8 Average rating

    Asciano stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated rentals with a pool in Asciano

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

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Guest favorite
Home in Asciano

Palazzo Monaci - Piscina nelle crete Senesi

Benvenuti a Palazzo Monaci ! Un' oasi di natura e bellezza unica, nel cuore delle Crete Senesi, in Toscana. Un residence con piscina e vista mozzafiato sulle crete senesi. Perfetta per coppie o famiglie in cerca di una vacanza rilassante. La posizione è perfetta per esplorare le zone limitrofe. Potrete fare escursioni nella campagna toscana, visitare i borghi medievali caratteristici, assaggiare i vini locali prelibati e immergervi nella cultura e nella storia di questa affascinante regione.

ValueFamilyKitchen

4.96 out of 5 average rating, 138 reviews
Guest favorite
A heated mini hydro-massage pool is surrounded by greenery, featuring subtle chromotherapy lighting in shades of purple. In the background, a rustic farmhouse is set against a serene twilight sky, with tall cypress trees lining the space.
Villa in Monteroni d'Arbia

San Giovanni in Poggio, villa Meriggio 95mq

Casa indipendente, due camere da letto matrimoniali, due bagni con doccia, living con cucina completa di tutto (lavastoviglie, lavatrice, forno, microonde), divano letto matrimoniale, giardino privato con pergola attrezzato. Tv Sat e Free wifi. Servizi aggiuntivi in struttura, su prenotazione, biciclette a pedalata assistita marca Focus modello Jarifa2 6.7 e un'area wellness con sauna finlandese da esterni Forest e una minipiscina idromassaggio riscaldata con cromoterapia con vista panoramica.

FamilyValueGetting around

4.98 out of 5 average rating, 128 reviews
Guest favorite
A stone villa surrounded by greenery is featured under a clear blue sky. A large swimming pool reflects the sunlight, complemented by sun loungers and colorful potted flowers along the edges. The outdoor area is perfect for relaxation with scenic views of the Tuscan hills.
Villa in Castiglion Fiorentino

Tuscan charm of villa - countryside - Villa Senaia

Nell’affascinante campagna Toscana,tra ulivi e vigneti una villa in pietra,in posizione strategica per cogliere i segreti di Toscana e Umbria aria condizionata e piscina con area wellness per il vostro relax e confort Villa Senaia è una grande casa con travi in ​​legno, in una splendida posizione in collina con vista idilliaca che affaccia su uno dei luoghi preferiti della campagna toscana, un ambiente attraente per mangiare all'aperto, bevendo vino toscano e ascoltando i grilli e le cicale

ValueLocationBreakfast

4.9 out of 5 average rating, 240 reviews
Top guest favorite
The exterior of a charming farmhouse is visible, featuring stone walls adorned with climbing greenery. Large windows reflect natural light and overlook the landscaped garden. A gravel path leads to the entrance, surrounded by greenery and trees under a clear blue sky.
Home in Rigomagno

House Rigomagno Siena

Apartment with beamed ceilings and terracotta floors, this apartment is set in a 19th-century farmhouse located in the hills of Siena in Rigomagno Toscana. From the solarium next to the swimming pool in the middle of the olive trees, you can admire the panorama of the Sienese hills and the medieval village of Rigomagno ... all this characterizes the ideal holiday for couples or families who want to relax. Solarium, garden, terrace, swimming pool are exclusively for guests of the apartment.

LocationFamilyWalkability

4.96 out of 5 average rating, 122 reviews
Top guest favorite
A serene pool area is showcased with two sun loungers positioned beside a tranquil salt-water pool. The expansive view of the valley and distant cityscape adds to the peaceful ambiance, while greenery surrounds the space, enhancing the sense of privacy and relaxation.
Farm stay in Monte San Savino

LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA

ID Code: 051025 AAT 0017 Wisely renovated 1600 exclusive original tuscanian stone house, superbly positioned up on a hill in total privacy. This villa is placed in a real postcard with a 360˚ view. Just 30 minutes drive from Cortona and less than 10 minutes drive from A1 Monte San Savino motorway exit, the villa is reachable through a boulevard flanked by secular trees and it boasts a stunning view on the Valdichiana valley with its towns and villages such as Monte San Savino and Cortona.

LocationFamilyKitchen

4.99 out of 5 average rating, 113 reviews
Top guest favorite
Home in Greve in Chianti

Relax e charme tra le colline del chianti

Bellissima colonica in pietra, indipendente, immersa tra gli olivi e le colline del Chianti, con giardino privato e piscina panoramica. Piano terra con ampi saloni, antico camino e forno a legna, soggiorno luminoso e cucina full optional. Al primo piano tre suites composte da camera, studio e bagno privato. Accesso tramite cancello e strada bianca in proprietà privata a soli 500 metri dal paese di Strada in Chianti. Ideale per quiete e relax. Location strategica per visitare la Toscana.

ValueLocationTV

4.99 out of 5 average rating, 113 reviews
Top guest favorite
Aerial view of the agriturismo surrounded by lush green hills and fields. The property includes a swimming pool, framed by rows of tall cypress trees that create a natural boundary. The rural landscape extends into the distance, illustrating the serene environment.
Condo in Asciano

Appartamento Loggiato 3 in toscana vicino Siena

L'appartamento Loggiato 3 per 2 persone si trova nell'agriturismo Santa Lucia (AGRITURISMO DIVISO IN 7 APPARTAMENTI) nelle Crete Senesi vicino Siena ed è situato al primo piano con tavolino privato dinanzi alle vetrate del loggiato. Composto da camera matrimoniale (due letti singoli uniti), bagno e soggiorno con cucina funzionale. E’ dotato di stufa a legna. Spazio esterno con tavolo e sedie a disposizione al piano terreno. L'ARIA CONDIZIONATA in camera è A PAGAMENTO secondo il consumo.

LocationFamilyNearby

4.93 out of 5 average rating, 201 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.

ValueLocationView

4.98 out of 5 average rating, 105 reviews
Top guest favorite
A spacious outdoor area features a swimming pool surrounded by lush green lawns and dotted with comfortable sun loungers. Umbrellas provide shade, and the serene landscape is framed by tall trees and gentle hills in the background.
Farm stay in Greve in Chianti

Typical Tuscan country house

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence just 35 minutes by car This apartment is one level, totally independent with private garden. Restored and furnished with great care to make the guest's stay as comfortable and relaxing as possible, in the full respect of the Tuscan rural style.

ValueLocationCheckout

4.99 out of 5 average rating, 431 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.

LocationValueCondition

4.89 out of 5 average rating, 307 reviews
Guest favorite
An aerial view captures the extensive grounds of the agriturismo, showcasing a swimming pool surrounded by tall cypress trees and lush green fields. The rustic buildings are nestled among the natural landscape, with rolling hills visible in the background.
Apartment in Buonconvento

Appaloosa - Apartment for couples and families

Appaloosa apartment accommodates 4–5 guests and offers air conditioning, Wi-Fi and direct access to the panoramic swimming pool. Ideal for couples or families looking for a relaxing stay in the Tuscan countryside. On the ground floor there is a kitchen, living area, a twin bedroom and a bathroom with shower. Upstairs, reached by a spiral staircase, is the double bedroom with an additional single chair bed.

FamilyValueKitchen

4.86 out of 5 average rating, 122 reviews
Top guest favorite
The outdoor pool area features a light blue water surface complemented by three tiered fountains. A small white table with a glass is placed on the wooden deck, surrounded by two white chairs. The rustic stone buildings create a charming backdrop, adorned with greenery.
Apartment in Montalcino

Castel Brunello - 2 doublebed rooms + terrace

Located in amidst the Tuscan countryside, Castel Brunello is offers an outdoor swimming pool and a garden. This self-catering accommodation features rustic-style furnishings, air condioning and free Wi-Fi. They also offer a satellite TV, and a fully equipped kitchenette with a refrigerator and a dining table. Each apartment has a terrace with an outdoor seating area.

LocationValueGetting around

4.99 out of 5 average rating, 117 reviews

Popular amenities for Asciano rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Guest favorite
A charming stone house with a terracotta roof features a welcoming entryway, shaded by umbrellas and surrounded by colorful flowers. In the background, a serene saltwater infinity pool is framed by landscaped greenery, complementing the tranquil rural setting.
Home in Foiano della Chiana

Conca d'Oro villa with private pool, sleeps 4

FamilyValueLong stay

4.92 out of 5 average rating, 172 reviews
Guest favorite
The image showcases a rustic stone building surrounded by a gravel courtyard. Flower pots with vibrant geraniums decorate the area, and a large tree provides shade. Sunlight illuminates the brick facade, creating a warm and inviting atmosphere in the outdoor space.
Home in Foiano della Chiana

La Lisa: country house surrounded by fields

FamilyLocationSleep quality

4.94 out of 5 average rating, 135 reviews
Top guest favorite
A winding driveway is lined with tall cypress trees on either side. The green landscape stretches into the distance, revealing rolling hills and a distant rustic building surrounded by nature, creating a serene and inviting setting.
Home in Montaione

Cercis - La Palmierina

ValueLocationParks

4.96 out of 5 average rating, 144 reviews
Top guest favorite
The image depicts a serene pool area surrounded by lush Mediterranean greenery. A bright orange umbrella provides shade, while a well-maintained stone pathway leads to the entrance of a charming stone farmhouse in the background.
Home in Casalini

Casolare immerso nella natura

ValueLocationAmenities

4.99 out of 5 average rating, 110 reviews
Top guest favorite
Home in Terranuova Bracciolini

Villa Lolù with private heated swimming-pool

ValueLocationComfort

4.97 out of 5 average rating, 159 reviews
Top guest favorite
A cozy bedroom is highlighted with a floral wallpaper featuring vibrant colors. A bedside table made of wood stands beside a spacious bed dressed in pink bedding. A modern lamp provides warm lighting, enhancing the inviting details of the room.
Home in Pievescola

Borgo Ripostena – n. 8 Casa Vecchia

FamilyValueSleep quality

4.95 out of 5 average rating, 200 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

FamilyLocationQuiet

4.99 out of 5 average rating, 136 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

ValueLocationComfort

4.98 out of 5 average rating, 122 reviews

Condo rentals with a pool

Top guest favorite
An aerial view captures the sprawling vineyards and olive groves surrounding Podere Vergianoni. The property features a salt-water pool positioned on a terrace, offering panoramic views of the lush Chianti landscape and medieval castle in the distance. Rustic buildings line the garden area.
Condo in Noce

Antico Podere del 1600 nel Chianti in Toscana

LocationValueBathroom

5.0 out of 5 average rating, 218 reviews
Guest favorite
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

La Casetta

FamilyLocationDecor

4.93 out of 5 average rating, 194 reviews
Top guest favorite
Condo in Panzano in Chianti

Apt.Panzanello-Panzano in Chianti

LocationFamilySleep quality

4.96 out of 5 average rating, 280 reviews
Superhost
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

FamilyValueComfort

4.84 out of 5 average rating, 300 reviews
Superhost
The swimming pool glimmers under a partially cloudy sky, surrounded by lush olive trees and vegetation. Sun loungers are positioned nearby, offering space for relaxation, while a stone wall provides a rustic backdrop, enhancing the serene atmosphere of the outdoor area.
Condo in Fiesole

Poggiolieto Suite - on hills 10' from city center

FamilyLocationDecor

4.83 out of 5 average rating, 227 reviews
Superhost
Condo in Asciano

Cozy home in countryside with tennis and pool

LocationFamilyComfort

4.54 out of 5 average rating, 90 reviews
Guest favorite
The building, with rustic stone exterior, is framed by green grass and features multiple windows that allow natural light to enter. A covered porch is accessed by a series of steps, while the surrounding landscape includes olive trees, enhancing the serene countryside setting.
Condo in Asciano

AGRITURISMO PODERE SCURCOLI

LocationFamilyHospitality

5.0 out of 5 average rating, 11 reviews
Guest favorite
A spacious living area features a striped sofa with soft cushions, complemented by a wooden coffee table and a vase of fresh flowers. The warm terracotta flooring and rustic beams enhance the inviting ambiance. Steps lead to additional rooms, visible in the background.
Condo in Montisi

Apartment in ancient house + pool and terrace

FamilyLocationGetting around

4.94 out of 5 average rating, 18 reviews

Home rentals with a private pool

Guest favorite
Villa in Castiglione d'Orcia

Wp Relais Villa Vignalunga

LocationValueAccess

4.93 out of 5 average rating, 116 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

FamilyLocationPool

4.98 out of 5 average rating, 216 reviews
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

LocationValueLaundry

4.88 out of 5 average rating, 820 reviews
Top guest favorite
Farm stay in Arezzo

Esplora la natura al centro di Vigneti Chianti

FamilyLocationCleanliness

4.97 out of 5 average rating, 264 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

FamilyLocationAmenities

4.95 out of 5 average rating, 121 reviews
Guest favorite
A serene infinity pool is framed by neatly trimmed cypress trees, overlooking expansive green hills. Sun loungers are positioned along the poolside, inviting relaxation amid the natural landscape under a clear blue sky.
Villa in San Casciano dei Bagni

Magnificent Tuscan Villa, amazing interiors & view

LocationFamilyCheck-in

5.0 out of 5 average rating, 16 reviews
Guest favorite
Villa in San Miniato

Historic villa x8 with exclusive pool

LocationFamilyQuiet

4.87 out of 5 average rating, 46 reviews
Top guest favorite
A charming stone farmhouse is situated amidst a vibrant field of sunflowers, with bright yellow blooms stretching across the landscape. The clear blue sky above contrasts with the lush green leaves, creating a serene rural atmosphere.
Home in Panicale

Podere Molinaccio-Luxury Tuscan-style Eco Villa

FamilyLocationParking

4.93 out of 5 average rating, 27 reviews

When is the best time to visit Asciano?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$42,678 GYDG$43,096 GYDG$40,795 GYDG$41,422 GYDG$43,096 GYDG$43,724 GYDG$51,464 GYDG$50,627 GYDG$44,351 GYDG$41,004 GYDG$39,958 GYDG$44,142 GYD
Avg. temp5°C6°C9°C12°C16°C21°C23°C24°C19°C14°C9°C5°C

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