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Holiday rentals with a pool in Castiglione del Lago

Find and book unique homes with a pool on Airbnb

Quick stats about holiday rentals with a pool in Castiglione del Lago

  • Total holiday rentals

    Explore 10 holiday rentals in Castiglione del Lago

  • Nightly prices starting at

    Castiglione del Lago holiday rentals start at $153 AUD per night before taxes and fees

  • Verified guest reviews

    Over 200 verified reviews to help you choose

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Wi-Fi availability

    10 of Castiglione del Lago holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Castiglione del Lago rentals

  • 4.7 Average rating

    Castiglione del Lago stays receive an average rating of 4.7 out of 5 from guests

Top-rated rentals with a pool in Castiglione del Lago

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

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Guest favourite
A stone tower stands resiliently, featuring a rustic red-brick trim around the entrance. The wooden door leads to an inviting interior, while the surrounding grassy area is bordered by lush greenery and trees. The clear sky provides a bright, welcoming atmosphere.
Tower in Tuoro sul Trasimeno
4.94 out of 5 average rating, 460 reviews

Historic Tower with Views of the Lake and Countryside

Take in the stunning view over Lake Trasimeno. Nestled in the Umbrian and Tuscan countryside, in a protected area known for its natural scenic beauty, this tower built using reclaimed materials features a private garden, barbecue, and pergola. The swimming pool is open from 15 May to 30 September and it is shared with other our guests. The tower is created out of the restoration of an old abandoned stable situated in the centre of a small countryside hamlet called Sanguineto. This place takes its name from the famous bloody battle of 217 BC fought between the Roman army and the Carthaginian army (led by Hannibal). Today this area is classified as one of outstanding natural beauty, where traditional farming methods are still very much in evidence, the major crops being olives and wine grapes. The property have been luxuriously finished using traditional building methods and materials combined with the latest technology. It has its own independent liquid propane gas (LPG) central-heating system, with the boiler located outside the building, as well as its own electricity. A pergola, and a private garden giving out onto the surrounding landscape, offering a magnificent view over Lake Trasimeno, complete the building. The tower has two floors, one bedroom, a living room with kitchenette, one bathroom, private garden, and pergola. Swimming-pool. The tower and the private garden with sun loungers, barbecue, pergola with table and chairs, reserved parking space. The pool is shared with the other guests of Borgo Sanguineto. The area of Lake Trasimeno offers the opportunity to visit many medieval villages. It is also close to several historical cities, such as Siena, Perugia, Arezzo, Assisi, Cortona, Rome, and Florence. The tower has a private parking. is advisable to have a means of transport available to move.

Guest favourite
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
4.9 out of 5 average rating, 240 reviews

Tuscan charm of villa - countryside - Villa Senaia

In the charming Tuscan countryside, among olive trees and vineyards, a stone villa, in a strategic position to grasp the secrets of Tuscany and Umbria air conditioning and swimming pool with wellness area for your relaxation and comfort Villa Senaia is a large house with wooden beams, in a beautiful hillside location with idyllic views overlooking one of the favorite places in the Tuscan countryside, an attractive setting for outdoor dining, drinking Tuscan wine and listening to crickets and cicadas

Top Guest favourite
A charming cottage is shown with a terracotta facade and a tiled roof. A small table with two chairs is set on a patio, surrounded by potted plants. Lush greenery and trees can be seen in the background under a clear blue sky.
Guesthouse in Macciano
4.97 out of 5 average rating, 244 reviews

Tuscan cottage with an heavenly view

Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

Guest favourite
A serene outdoor pool area is surrounded by lush greenery and rustic stone pathways. Lounge chairs are positioned beside the pool, creating a space for relaxation. The picturesque villa can be seen in the background, framed by trees and gentle hillside.
Villa in Castiglione d'Orcia
4.94 out of 5 average rating, 145 reviews

Wp Relais Borgo Vignalunga

Discover Borgo Vignalunga by WP Relais, an charming hamlet set in a 46-hectare estate in the heart of the Val D'Orcia, a UNESCO World Heritage Site. Surrounded by woodland, pastures, a lush vegetable garden, cultivated fields and three olive groves with 1,500 olive trees, Borgo Vignalunga is the ideal place to experience the true essence of Tuscany. The property is close to historical villages, evocative architecture, unspoilt natural landscapes and renowned restaurants, bars and wineries.

Top Guest favourite
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
4.99 out of 5 average rating, 113 reviews

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.

Guest favourite
Aerial view of a scenic agriturismo surrounded by vineyards and rolling hills. The property features a pool and is framed by tall cypress trees, enhancing the natural landscape of lush green and golden fields under a partly cloudy sky.
Farm stay in Montepulciano
4.96 out of 5 average rating, 115 reviews

Rural Tuscany | Family farmstay with restaurant

Via della Stella is a charming agriturismo with a housing surface of 530m², divided over nine separate apartments. Each apartment has its own living room, kitchen and one or more bath & bedrooms. The farmhouse has a wonderful panoramic swimming pool. Its great position with view over the hills heading up to Montepulciano create a serene atmosphere. The farmhouse has been carefully decorated in rural Tuscan style. Activities such as wine tastings and cooking classes are available onsite.

Guest favourite
A large dining area features a long table surrounded by white chairs, positioned before expansive glass windows. The view reveals a scenic landscape with a swimming pool and rolling hills extending into the distance, framed by wooden beams overhead.
Farm stay in San Fatucchio
4.9 out of 5 average rating, 258 reviews

2 room apartments in farmhouse whit pool

We have 4 apartments of this type on first floor and on two levels with two bedrooms (one double and a single bedroom. The single bedroom is in the attic and has no door it overlooks the living room), living room with kitchenette, bathroom with shower. The farmhouse enjoys a 360° view of the Umbrian and Tuscan hills and has a garden and shared swimming pool in summer, lounge and playground. This typology can NOT be booked with CHILDREN UNDER 12 or babies and is for max 3 people.

Guest favourite
A shaded gazebo features a wooden seating area with white cushions, positioned on a stone patio. The scene captures a serene sunset over the property, with distant views of a saltwater pool and rolling hills, creating a tranquil outdoor setting.
Home in Castiglione del Lago
5.0 out of 5 average rating, 6 reviews

Spectacular Poolside Sunsets of Tuscan Hill Towns

Enchanting villa with spectacular poolside views of Lago di Chiusi and nearby Tuscan hill towns (Chiusi, Montepulciano). Fall in love with rustic Italy, explore nearby medieval towns, interact with locals, relax by the saltwater pool, enjoy a glass of wine under the gazebo, and listen as the sound of birds and church bells punctuate the peaceful quiet. Experience a “picnicco” at nearby Madrevite winery, offering a fun family-friendly evening of food, wine, & music with locals.

Guest favourite
The pool area features a rectangular swimming pool surrounded by meticulously landscaped gardens. Olive trees, rosemary, and rose bushes complement the scenic views of rolling hills and distant mountains under a clear blue sky.
Villa in Pozzuolo
4.91 out of 5 average rating, 58 reviews

Fabulous Farmhouse with Pool & 360 Panoramic View

In the very centre of Italy, straddling the border of Umbria and Tuscany, this carefully restored farmhouse makes a great base for a memorable Italian holiday. Situated in an idyllic hillside position overlooking Montepulciano, ‘La Colomba’ is blessed with 360-degree views of iconic Italian landscape and fully equipped with all child amenities. Within easy reach of many of the world’s most important historical and cultural attractions, this house really is The Italian Dream.

Top Guest favourite
A serene outdoor area showcases a swimming pool surrounded by well-maintained gardens. Sun loungers are positioned near the pool, with shaded areas provided by umbrellas. The background features a historic building and lush greenery, enhancing the tranquil setting.
Apartment in Castiglione del Lago
4.94 out of 5 average rating, 155 reviews

Farmhouse close to Montepulciano

Farmhouse Santa Margherita is a splendidly restored 18th century house that sits on a hilltop on the Tuscan-Umbrian border in sight of Montepulciano.The farmhouse has been recently renovated in order to offer to its guests four vacation apartments. The rooms are very spacious and comfortable. The furnishings are luxurious and include wooden furniture, wrought iron beds and elegant lamps. The kitchens are well equipped so that all your culinary skills can be exercised.

Top Guest favourite
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
4.99 out of 5 average rating, 110 reviews

Cottage surrounded by nature

"IL PODERACCIO" is a typical stone farmhouse located on the hills surrounding Lake Trasimeno, immersed in beautiful Mediterranean vegetation. The building is spread across two floors. The pool and garden frame the whole. The swimming pool is open from May 1st to October 15th. Please note that following the COVID 19 emergency, all the directives required by the legislation have been adopted for cleaning and sanitizing the house.

Guest favourite
A rustic brick house is surrounded by greenery, with additional trees and shrubs in the background. A dining table set for several, with chairs in blue, is positioned on the grass, suggesting a welcoming outdoor space for gatherings.
Cottage in Frattavecchia
4.9 out of 5 average rating, 62 reviews

Casale Poggiolo Basso - The place of silence

Surrounded 360 degrees by fields and hills, with a large cypress and olive trees garden, Poggiolo Basso is an old brick house, built in the early '900 and remained intact over time. The ideal place to spend holidays or short breaks and experience nature, ”slowness", and especially silence; a place where you can cultivate love for art and culture, sport, cooking, and psycho-physical well-being.

Popular amenities for Castiglione del Lago rentals with a pool