
Vacation rentals with a pool in Castiglione del Lago
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Castiglione del Lago

Total vacation rentals
Explore 20 vacation rentals in Castiglione del Lago

Nightly prices starting at
Castiglione del Lago vacation rentals start at ﺩ.ﺇ 367 per night before taxes and fees

Verified guest reviews
Over 180 verified reviews to help you choose

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Castiglione del Lago vacation 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.

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.

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.

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

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.

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.

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.

Villa Bellora | Pool & Panoramic Views | Cortona
Villa Bellora: Your Tuscan Summer Escape Perched among Tuscany's rolling hills and vineyards, Villa Bellora sits 20 minutes from both Cortona and Montepulciano. Spend your days by the private pool, with a sun deck overlooking the views. Three bedrooms, two bathrooms — ideal for families, couples, or friends. Tuscany's best wine estates, hilltowns, and thermal spas are all within reach. We're happy to share our favorite local spots.

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.

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.

Explore nature in the center of Vigneti Chianti
Feel close to the land in a rustic building on a Tuscan farm. Old stone walls, ceilings with exposed beams and terracotta floors are the backdrop to a characteristic apartment with fireplace. Plunge into an infinity pool for a unique view of the surrounding landscape. Dine outdoors, with the fresh air caressing you, sit and relax admiring the sunset under the ancient cypresses.
Popular amenities for Castiglione del Lago rentals with a pool
House rentals with a pool

Hidden gem in Tuscany

Italian Internal

Il nido del Rondone

House Rigomagno Siena

Casa dei 5 Sensi – SPA – Trasimeno View

The Lost Stone paradise with pool, views and AC

Tofanello Turquoise Luxury with Outdoor Pool

Poggiodoro, your charming villa in Tuscany
Condo rentals with a pool

Loggiato 3 apartment in Tuscany near Siena

Charming Castle

[Capolinea Holidays] "Terra" | Lake Trasimeno

Casa Biancospino Crete Senesi | Podere Fossaccio

Rural Tuscany | Farmstay with pool & restaurant

Tuscany accommodation with panoramic view terrace

La Mangiatoia, farmhouse apartment

Relaxation and peace in the countryside Cortona G
Other vacation rentals with a pool

Villa La Pieve

Il Noce – Peaceful Tuscan Haven with Pool & Views

Lake View Private Villa w Pool

Elegant historic Palazzo, views of Tuscan valley

Tuscan Suite Amiata in Villa Q Dimorae Adults Only

La vite - spacious beautiful and comfortable apartment

Villa in Tuscany with private pool, relaxing nature

Country Charm & Jacuzzi
Destinations to explore
- Rentals with outdoor seating Castiglione del Lago
- Apartment rentals Castiglione del Lago
- House rentals Castiglione del Lago
- Family-friendly rentals Castiglione del Lago
- Rentals with a washer and dryer Castiglione del Lago
- Villa rentals Castiglione del Lago
- Pet-friendly rentals Castiglione del Lago
- Rentals with a patio Castiglione del Lago
- Bed and breakfasts Castiglione del Lago
- Rentals with pools Perugia
- Rentals with pools Umbria
- Rentals with pools Italy
- Lake Trasimeno
- Lake Bolsena
- Centro Storico Orvieto
- Basilica of St Francis
- Terme Dei Papi
- Villa Lante
- Del Chianti
- Avignonesi Winery Fattoria Le Capezzine
- Furlo Gorge Nature Reserve
- La Scarzuola
- Cascate del Mulino
- Mount Subasio
- Palazzo Pubblico
- Siena Cathedral
- Valdichiana Outlet Village
- Eremo Di Camaldoli
- Abbey of Sant'Antimo
- Santa Maria della Scala
- Val di Chiana
- Mount Amiata
- Terme San Filippo
- Abbey of Monte Oliveto Maggiore
- Casa Vasari
- Saturnia Thermal Park





