
Holiday rentals with a pool in Castiglione del Lago
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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 $154 AUD per night before taxes and fees

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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, 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
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.

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.
4.97 out of 5 average rating, 126 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.
4.97 out of 5 average rating, 251 reviews
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.
4.95 out of 5 average rating, 229 reviews
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
4.9 out of 5 average rating, 241 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.
4.95 out of 5 average rating, 146 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.
4.99 out of 5 average rating, 116 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.
4.96 out of 5 average rating, 116 reviews
A paradise in Montepulciano...
Villa Il Cubo has a large private park and swimming pool and marvellous views on the Tuscan countryside. It is fully air-conditioned and the decoration has been updated with charming details that will make you enjoy the best Tuscany has to offer. We have electric vehicle charging point at a moderate extra contribution. IN JULY AND AUGUST WE LET FOR A MINIMUM OF 7 DAYS FROM SATURDAY TO SATURDAY. Exceptions are possible only if don't create unrentable gaps between one guest and the next.
4.96 out of 5 average rating, 168 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.
4.9 out of 5 average rating, 260 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.
4.92 out of 5 average rating, 61 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.
4.88 out of 5 average rating, 144 reviews
Casolare immerso nella natura
"IL PODERACCIO" è un tipico casolare in pietra posto sulle colline che circondano il Lago Trasimeno immerso in una stupenda macchia mediterranea. Il fabbricato si sviluppa su due piani. La piscina ed il giardino fanno da cornice al tutto. Apertura Piscina dal 1 Maggio al 1 5 Ottobre. Si fa presente che in seguito alla emergenza COVID 19 per la pulizia e la sanificazione della casa sono state adottate tutte le direttive previste dalla normativa in merito.
4.99 out of 5 average rating, 111 reviewsPopular amenities for Castiglione del Lago rentals with a pool
House rentals with a pool

Tofanello Orange Luxury and Modern Comfort with Outdoor Pool
4.98 out of 5 average rating, 145 reviews
Casa Lucy
4.95 out of 5 average rating, 110 reviews
House Rigomagno Siena
4.96 out of 5 average rating, 125 reviews
La Lisa: country house surrounded by fields
4.94 out of 5 average rating, 135 reviews
Casa dei 5 Sensi - SPA - Trasimeno view
4.91 out of 5 average rating, 164 reviews
Il nido del Rondone
4.97 out of 5 average rating, 114 reviews
Villa Bellora | Pool & Panoramic Views | Cortona
4.92 out of 5 average rating, 36 reviews
Casale Toppello sul Lago Trasimeno
4.99 out of 5 average rating, 69 reviewsCondo rentals with a pool

Oasi La Perla, natura e relax al lago Trasimeno
4.88 out of 5 average rating, 69 reviews
Casa Granaio | Ground floor 1-bedroom apartment (2
4.96 out of 5 average rating, 82 reviews
[Capolinea Holidays] "Terra" | Lago Trasimeno
5.0 out of 5 average rating, 36 reviews
Tuscan Dream Apt with Pool, View & Tennis Court
4.91 out of 5 average rating, 97 reviews
La Mangiatoia, appartamento in agriturismo
4.95 out of 5 average rating, 41 reviews
Charming Castle
4.94 out of 5 average rating, 51 reviews
Borgo 7 Tigli | King Suite & Tuscan Views
4.67 out of 5 average rating, 3 reviews
Tenuta Morcella - Olivo Suite
5.0 out of 5 average rating, 4 reviewsHome rentals with a private pool

Villa Pergo is an ancient charming country villa
5.0 out of 5 average rating, 65 reviews
Bliss out in Historic Farmhouse on Organic Wine Estate with Tennis and Pool
5.0 out of 5 average rating, 29 reviews
Podere Molinaccio-Luxury Tuscan-style Eco Villa
4.93 out of 5 average rating, 27 reviewsWp Relais Villa Vignalunga
4.93 out of 5 average rating, 117 reviewsDestinations to explore
- Family-friendly rentals Castiglione del Lago
- Villa rentals Castiglione del Lago
- Apartment rentals Castiglione del Lago
- House rentals Castiglione del Lago
- Bed and breakfasts Castiglione del Lago
- Pet-friendly rentals Castiglione del Lago
- Rentals with pools Perugia
- Rentals with pools Umbria
- Rentals with pools Italy
- Lake Trasimeno
- Lake Bolsena
- Del Chianti
- Basilica of St Francis
- Mount Amiata
- Centro Storico Orvieto
- Cascate del Mulino
- Terme Dei Papi
- Furlo Gorge Nature Reserve
- Eremo Di Camaldoli
- Villa Lante
- La Scarzuola
- Siena Cathedral
- Avignonesi Winery Fattoria Le Capezzine
- Val di Chiana
- Mount Subasio
- Palazzo Pubblico
- Valdichiana Outlet Village
- Saturnia Thermal Park
- Gola del Furlo
- Terme San Filippo
- Abbey of Sant'Antimo
- Abbey of Monte Oliveto Maggiore
- Piazza del Campo





