
Holiday rentals with a pool in Castiglione del Lago
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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.

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.

Palazzo Monaci - Pool in the Crete Senesi
Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

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.

Nature Escape: Apartments & Pool
Casale in pietra immerso nella natura, con piscina e appartamenti indipendenti che garantiscono privacy e comfort. A 5 minuti da Castiglione del Lago, e dalla pista ciclopedonale sul Lago Trasimeno. A circa 30 minuti Montepulciano e la suggestiva Val d’Orcia, a breve distanza è possibile esplorare i tesori di Umbria e Toscana: Perugia, Assisi, Cortona, Pienza, Orvieto e molti altri borghi storici. Luogo perfetto per chi cerca relax in una posizione ideale per scoprire le eccellenze della zona.

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.

Separate room, between Cortona and Montepulciano
We are a small farm with a family-run farm on the border between Tuscany and Umbria. The old farmhouse in which we live with our children are surrounded by vineyards and olive groves with a splendid view of Montepulciano. We can sleep in 2 apartments and / or 1 independent room furnished with poor art and originality. In the large garden, available to all, there are two pools (one for children), games, organic vegetable garden. We have a restaurant Pierpaolo cooking the typical Tuscan dishes.

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.

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

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.

HISTORIC LUXORY APARTMENT - LAKE WIEW
This spacious and luxurious suite of 130 m2 has two double bedrooms, each with its own bathroom, offering its guests the utmost privacy. The larger bedroom has an additional single bed. A fully equipped kitchen with dining table, a room with a large living room in front of the fireplace and air conditioning in all rooms, make it a comfortable environment. The terrace with a magnificent view of the lake is ideal for organizing elegant aperitifs.

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.

Villa Feronia – Heated Pool & Rooftop Escape
Welcome to Villa Feronia, a contemporary 3-bedroom retreat nestled in a 2-hectare olive grove near Passignano sul Trasimeno. Enjoy refined indoor-outdoor living with 3.5 bathrooms, high-speed Wi-Fi, a smart home system, an infinity saltwater heated pool, and a rooftop terrace with a fire pit. Eco-friendly and elegantly designed, it’s the ideal escape to relax, recharge, and experience authentic Italian beauty.
Popular amenities for Castiglione del Lago rentals with a pool
House rentals with a pool

Hidden gem in Tuscany

I Fuochi Farmhouse | Casa Il Mandorlo

Italian Internal

Family Forest - Pool in the Crete Senesi

La Lisa: country house surrounded by fields

On vacation from Ines

Il nido del Rondone

Tofanello Orange Luxury and Modern Comfort with Outdoor Pool
Apartment rentals with a pool

Cortona – Pool & Relaxation among Olive Trees|Adults Only+16

La Loggia, farmhouse apartment

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Apartment in Cardaneto Castle

Il Portico, 1 bedroom stylish apartment

Casa Biancospino Crete Senesi | Podere Fossaccio

Poggio ai Gelsi, Pink Lodge

Castello di Orgiale Charme Residenz
Home rentals with a private pool

Olindia by Interhome

Il Farinaio, by Interhome

Villa Pergo is an ancient charming country villa

Agriturismo Henni panoramic pool sauna and jacuzzi

Casa Frati by Interhome

Podere Molinaccio - Luxury Tuscan-style Eco Villa

Val d'Orcia by Interhome

Borgo del Papa, by Interhome
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 $127 SGD per night before taxes and fees

Verified guest reviews
Over 180 verified reviews to help you choose

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
10 of Castiglione del Lago holiday rentals include wifi 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
Destinations to explore
- Family-friendly rentals Castiglione del Lago
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- Rentals with pools Perugia
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- Rentals with pools Italy
- Lake Trasimeno
- Lake Bolsena
- Del Chianti
- Eremo Di Camaldoli
- Cascate del Mulino
- Avignonesi Winery Fattoria Le Capezzine
- Basilica of St Francis
- Terme Dei Papi
- Villa Lante
- Furlo Gorge Nature Reserve
- Mount Subasio
- Santa Maria della Scala
- Palazzo Pubblico
- Siena Cathedral
- Rocca Maggiore
- Abbey of Monte Oliveto Maggiore
- Pozzo di San Patrizio
- Val di Chiana
- Girifalco Fortress
- Spoleto Cathedral
- Terme San Filippo
- Cathedral of San Lorenzo
- Giardini del Frontone
- Monte Cucco Regional Park




