
Holiday rentals with a pool in Castiglione del Lago
Find and book unique homes with a pool on Airbnb
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.

Wine Experience Villa in Montepulciano
🏡 Villa Talosa è immersa nei vigneti della Fattoria della Talosa, storica azienda vitivinicola di Montepulciano produttrice di Vino Nobile. Un luogo autentico, ideale per rilassarsi con la magia della campagna toscana e una vista incantevole da ogni finestra. A soli 1,5 km dal centro storico, raggiungibile anche a piedi, potrete visitare la nostra Cantina Storica del 1500 sotto Piazza Grande: un’esperienza unica tra storia, passione per il vino. Riscaldamento e aria condizionata sono inclusi.

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.

Villa Patrizia: Tuscany farmhouse apt 2
Villa Patrizia is the perfect place for a relaxing holiday with your family and for his unique position for someone who wants to enjoy art and historical cities like Cortona, Firenze, Perugia, is a typical Tuscan olive groves, with an amazing view of Trasimeno lake. The apartment offers you every kind of comfort you need. It has a portico, a great outdoors garden and even a big swimming pool where you and your children can spend time relaxing and having fun.The staff is always helpful.

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!!!!!!

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 with swimming pool and wonderful view
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 eight 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.

Tofanello Orange Luxury and Modern Comfort 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 turquoise apartment. Turquoise: https://www.airbnb.com/rooms/plus/9430389.

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.
Popular amenities for Castiglione del Lago rentals with a pool
House rentals with a pool

Italian Interior

Family Forest - Pool in the Crete Senesi

I Fuochi Farmhouse | Casa Susino

PoggioVaccaio -Casa Panoramic terrace with pool

Apt. Elena - Villa Augusto Estate

Traditional stone house in Tuscany

Country House in the Crete Senesi

Luxury Villa with a fantastic view
Condo rentals with a pool

Cortona – Pool & Relaxation among Olive Trees | Adults Only

Charming Castle

Fattoria Borgonuovo - L'Ortensia

La Foresteria | Granary House

Il Portico, 1 bedroom stylish apartment

Apartment in Cardaneto Castle

Casa Biancospino Crete Senesi | Fossaccio Farm

La Mangiatoia, farmhouse apartment
Home rentals with a private pool

Olindia by Interhome

La Felcaia by Interhome

Il Farinaio, by Interhome

Villa Pergo is an ancient charming country villa

Pianelli by Interhome

Casa Frati by Interhome

Podere Molinaccio - Luxury Tuscan-style Eco Villa

Val d'Orcia 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 $174 NZD per night before taxes and fees

Verified guest reviews
Over 180 verified reviews to help you choose

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

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

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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 Italy
- Lake Trasimeno
- Del Chianti
- Siena Cathedral
- Lake Bolsena
- Eremo Di Camaldoli
- Terme Dei Papi
- Avignonesi Winery Fattoria Le Capezzine
- Basilica of St Francis
- Villa Lante
- Mount Subasio
- Palazzo Pubblico
- Furlo Gorge Nature Reserve
- Santa Maria della Scala
- Abbey of Monte Oliveto Maggiore
- Cascate del Mulino
- Mount Amiata
- Castello di Volpaia
- Val di Chiana
- Piazza del Campo
- Saturnia Thermal Park
- Abbazia di San Galgano
- Cattedrale di San Rufino
- Cappella di San Galgano a Montesiepi
- Basilica Cateriniana San Domenico




