Vacation rentals with a pool in Castiglione del Lago

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Top-rated rentals with a pool in Castiglione del Lago

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Top guest favorite

A spacious outdoor pool is framed by well-maintained greenery, with lounge chairs positioned alongside. The surrounding area includes mature trees and flowering plants, contributing to a serene environment. A shade umbrella is set near the pool, enhancing the inviting atmosphere.

Vacation home in Chianciano Terme

5 out of 5 average rating, 100 reviews

The Eagle and the Olive Tree

At Aquila e l'Ulivo, an ancient renovated farmhouse from the 1200s, you will not only find all the necessary comforts for a wonderful stay, but you will also experience the thrill of feeling free and immersed in the unspoiled nature of Val D'Orcia. Here you'll have the opportunity to walk with the two falcons Ayga and Sayen and interact with the eagles, and why not sip an excellent aperitif by the pool. We are waiting for you in our world, made up of animals, relaxation, nature and even a touch of Magic.

Guest favorite

A rustic stone farmhouse is surrounded by rolling hills and lush trees, featuring a swimming pool with sun loungers nearby. The expansive landscape showcases golden fields under a clear blue sky, highlighting the tranquil setting in the countryside.

Apartment in Castiglione del Lago

4.91 out of 5 average rating, 149 reviews

Ulivo - Charming apartment in the countryside

The independent, bright and welcoming apartment located on the ground floor of a renovated farmhouse from 1856, surrounded by green hills, consists of a large eat-in kitchen, a double bedroom with comfortable futon chair, independent bathroom. Triple exposure The apartment is equipped with: - centralized warming - fitted kitchen - bathroom with bathtub and shower - guest sheets and towels - stylish furnishings - veranda exclusive use with dining table overlooking the surrounding countryside.

Top guest favorite

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, 178 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 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

4.91 out of 5 average rating, 216 reviews

Tuscan charm of villa - countryside

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

Guest favorite

The pool area is surrounded by meticulously maintained grass and features comfortable lounge chairs placed along the edge. A rustic wooden structure with open sides provides shade, and lush greenery is visible in the background, enhancing the serene setting.

Villa in Castiglione d'Orcia

4.97 out of 5 average rating, 121 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 favorite

Aerial view of a serene agriturismo surrounded by lush vineyards and golden fields. The property features a pool set amidst well-kept gardens and tall cypress trees. Rolling hills in the background extend towards the horizon, contributing to the peaceful landscape.

Farm stay in Montepulciano

4.94 out of 5 average rating, 82 reviews

Via della Stella Farmhouse | Casa le Rose

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.

Top guest favorite

A serene outdoor area features a private swimming pool surrounded by olive trees, with a grassy lawn leading to a shaded seating area. Rolling hills and vineyards can be seen in the background, creating a tranquil countryside setting.

Villa in Montepulciano

4.97 out of 5 average rating, 112 reviews

Wine Experience Villa in Montepulciano

Villa Talosa è una residenza immersa tra i vigneti di "Fattoria della Talosa",Azienda vitivinicola di Montepulciano ove produciamo il Vino Nobile di Montepulciano d.o.c.g . Un luogo per godere di relax con una fantastica vista da ogni finestra della Villa. Distiamo 1.5 km dal centro storico,dove sarà possibile visitare la ns Cantina Storica risalente al 1500 A.D. e collocata sotto piazza Grande . Nota: Riscaldamento ed l’Aria condizionata sono dei costi aggiuntivi, in base al consumo.

Top guest favorite

A large swimming pool is set in a well-maintained garden, surrounded by tall trees and lush greenery. The villa, featuring a rustic brick façade with multiple windows, stands in the background against a clear blue sky.

Villa in Montepulciano

4.95 out of 5 average rating, 146 reviews

A paradise in Montepulciano...

Villa Il Cubo is a full centralized air conditioned private house with large private swimming pool placed in the best garden spot for incredible views on the countryside around. Decoration has been updated with charming details that will make you enjoy the best Tuscany has to offer. We have electric vehicle charging point. Supermarkets, restaurants, grocery stores, wineries are just a few minutes away. IN JULY AND AUGUST WE LET FOR A MINIMUM OF 7 DAYS FROM SATURDAY TO SATURDAY!!!!!!

Top guest favorite

A private swimming pool is framed by landscaped greenery, with steps leading into the clear water. The expansive water surface reflects the distant view of Lake Trasimeno and the surrounding landscape under a partly cloudy sky.

Home in San Feliciano

4.91 out of 5 average rating, 150 reviews

Casa dei 5 Sensi - Trasimeno view

Bio-ecological building in double class A, energy and environmental, consisting of two apartments, one on the ground floor and the other on the first floor. The one on the first floor is rented, consisting of a private entrance, kitchen/dining/living room, terrace, double bedroom and bathroom. 180-degree lake view, with swimming pool and outdoor green space. The pool is private and is shared with the property. IF THE PERIOD YOU CHOSE IS OCCUPIED, CONTACT ME, WE WILL FIND A SOLUTION

Guest favorite

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, 47 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 favorite

The historic farmhouse, surrounded by lush greenery, overlooks rolling hills and expansive fields. A serene swimming pool is framed by comfortable loungers and umbrellas, providing a relaxing outdoor space. The property features manicured gardens and inviting outdoor areas for guests to enjoy.

Apartment in Castiglione del Lago

4.92 out of 5 average rating, 128 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 favorite

A stone exterior is showcased, with a staircase leading up to the entrance. A shaded area features outdoor seating, including a table and chairs. Potted plants line the pathway, and greenery provides a serene backdrop, enhancing the outdoor living space.

Home in Prato

4.99 out of 5 average rating, 125 reviews

Tofanello Turquoise Luxury with Outdoor Pool

Escape to the rolling hills of Umbria in this updated farmhouse (90 m2 over 2 floors) that retains its original charm. The home features classic beamed vaulted ceilings, original stone finishes, an indoor wood-burning fireplace, private entrance and a private garden terrace. The shared pool has a large sun lounge area. If your favourite dates aren't available anymore take a look at our orange apartment. Orange: https://www.airbnb.com/rooms/plus/9429730