
Vacation rentals with a pool in San Casciano dei Bagni
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Top-rated rentals with a pool in San Casciano dei Bagni
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.
5.0 out of 5 average rating, 129 reviews
Wine Experience Villa in Montepulciano
🏡 Villa Talosa is immersed in the vineyards of the Fattoria della Talosa, a historic winery in Montepulciano that produces Vino Nobile. An authentic place, ideal for relaxing with the magic of the Tuscan countryside and an enchanting view from every window. Just 1.5 km from the historic center, which can also be reached on foot, you can visit our Historic Winery from the 1500s under Piazza Grande: a unique experience between history and passion for wine. Heating and air conditioning are included.
4.97 out of 5 average rating, 126 reviews
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.
4.96 out of 5 average rating, 142 reviews
Exclusive 10 Acre Estate w/ Pool & Olive Grove!
Enchanting, exclusive 10acres estate on a hill, memorable sunsets; large pool framed by lavender&rosemary, open year-round. New air conditioning, Starlink internet. Very private&peaceful 2 floors, 4bedrooms, 4baths, jacuzzibathtub, 55inch smartTV, well-equipped kitchen, porch & pergola for alfresco dining, Weber barbecue, pizza oven, olive grove, fireplace; 20 min. to Orvieto,Todi,Amelia; 10 minutes drive to train station to Rome/Florence, 5min drive to shops in town. Grounds/pool caretaker
4.99 out of 5 average rating, 105 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
Vineyards Paradise
Amazing country house immersed in the vineyard of Cantina Lapone, viewing Orvieto. Recently restored, over 100 sm, organised on two floors. Ground floor is a single space with a big living room (with fireplace) and a spacious open kitchen. First floor with two bedrooms and two bathrooms: the main bedroom (looking at Orvieto) with a double bed and internal bathroom and a second one with a double bed and a bed sofa. Private garden and parking. Private pool (shared with another 4 guests house).
4.99 out of 5 average rating, 244 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
Tuscan farmhouse stay with restaurant and pool
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.
4.94 out of 5 average rating, 107 reviews
EcoLodge – modern design in a peaceful panoramic location
The modern, ecological and comfortable EcoLodge is quiet and secluded, surrounded by olive groves, chestnut and fruit trees, vines and meadows. In front of you are the hills of the Val d'Orcia; behind you is Monte Amiata. Three worlds meet here: Val d'Orcia, Monte Amiata, and Maremma. The Vielfältigkeit is an ideal base for culture, wine, hiking, mountain biking, hot springs and the sea – and at the same time a place to enjoy Tuscan country life away from the crowds of tourists.
4.94 out of 5 average rating, 111 reviews
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.
4.99 out of 5 average rating, 111 reviews
Cottage "L'Assolata" in Tuscany
A lovely cottage in the old farmhouse "Podere Maltaia" that overlooks the Unesco's Heritage protected area Orcia Valley, surrounded by large farmyards and 3 hectares of private land that includes an outdoor swimming pool (opened seasonally, based on outside temperature - please ask to know the dates for the upcoming or ongoing summer season), garden, outdoor dining area, BBQ and parking area (not-covered, free of charge).
4.91 out of 5 average rating, 157 reviews
Unique view 3 bdr villa with pool & A/C in Pienza
Nestled within the picturesque Val d'Orcia National Park and the enchanting Natural Reserve of Lucciola Bella, this apartment sits perched on a natural terrace, offering unparalleled views of Mount Amiata. Immerse yourself in the untouched beauty of this protected oasis, where the ever-changing play of sunlight and the rhythm of the seasons paint a constantly shifting panorama across the rolling hillsides.
4.95 out of 5 average rating, 104 reviewsPopular amenities for San Casciano dei Bagni rentals with a pool
House rentals with a pool

Il nido del Rondone
4.97 out of 5 average rating, 114 reviews
Conca d'Oro villa with private pool, sleeps 4
4.92 out of 5 average rating, 173 reviews
House Rigomagno Siena
4.96 out of 5 average rating, 125 reviews
Traditional stone house in Tuscany
4.97 out of 5 average rating, 102 reviews
La Vigna Farm - Orvieto Tourist Rental
4.99 out of 5 average rating, 113 reviews
"Palazzaccio Todi Estate" hideaway
4.84 out of 5 average rating, 171 reviews
A dreamy Tuscany: Vetrica,
4.83 out of 5 average rating, 23 reviews
THE HOUSE ON THE HILL
4.93 out of 5 average rating, 85 reviewsCondo rentals with a pool

Canonica, Camporsevoli
4.97 out of 5 average rating, 29 reviews
Charming Residence Castello di Orgiale near Siena
4.97 out of 5 average rating, 88 reviews
Tenuta Morcella - Olivo Suite
5.0 out of 5 average rating, 4 reviews
Tuscan Dream Apt with Pool, View & Tennis Court
4.91 out of 5 average rating, 97 reviews
Casa Granaio | Ground floor 1-bedroom apartment (2
4.96 out of 5 average rating, 82 reviews
Charming Castle
4.94 out of 5 average rating, 51 reviews
Farm holidays in the countryside of Montepulciano
4.97 out of 5 average rating, 88 reviews
Borgo 7 Tigli | King Suite & Tuscan Views
4.67 out of 5 average rating, 3 reviewsHome rentals with a private pool

Villa Pergo is an ancient charming country villa
5.0 out of 5 average rating, 65 reviews
Podere Molinaccio-Luxury Tuscan-style Eco Villa
4.93 out of 5 average rating, 27 reviews
Bliss out in Historic Farmhouse on Organic Wine Estate with Tennis and Pool
5.0 out of 5 average rating, 29 reviewsWp Relais Villa Vignalunga
4.93 out of 5 average rating, 117 reviewsDestinations to explore
- Lake Trasimeno
- Lake Bolsena
- Parco Regionale Della Maremma
- Feniglia
- Lake Vico
- Basilica of St Francis
- Mount Amiata
- Centro Storico Orvieto
- Cascate del Mulino
- Terme Dei Papi
- Villa Lante
- La Scarzuola
- Siena Cathedral
- Avignonesi Winery Fattoria Le Capezzine
- Vulci
- Val di Chiana
- Necropolis of Tarquinia
- Mount Subasio
- Palazzo Pubblico
- Valdichiana Outlet Village
- Saturnia Thermal Park
- Terme San Filippo
- Abbey of Sant'Antimo
- Abbey of Monte Oliveto Maggiore





