
Holiday rentals with a pool in Castiglion Fiorentino
Find and book unique homes with a pool on Airbnb
Quick stats about holiday rentals with a pool in Castiglion Fiorentino

Total holiday rentals
Explore 40 holiday rentals in Castiglion Fiorentino

Nightly prices starting at
Castiglion Fiorentino holiday rentals start at $140 NZD per night before taxes and fees

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Over 670 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
40 of Castiglion Fiorentino holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Castiglion Fiorentino rentals

4.7 Average rating
Castiglion Fiorentino stays receive an average rating of 4.7 out of 5 from guests
Top-rated rentals with a pool in Castiglion Fiorentino
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
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
Tuscan Villa Luigina with Pool & Panoramic View
If you want to live in a postcard .... Villa Luigina is the ideal place, all the rooms have a panoramic view, a dining room with a view ... a breakfast room with a view, or you can eat outside in the garden in front of the house and enjoy the spectacular view of the old town!! In the fascinating Tuscan hills, among olive trees and vineyards, a stone villa in perfect harmony with the environment in a strategic position to discover the secrets of Tuscany and Umbria. CIN:IT051012C2129WHTZX
4.8 out of 5 average rating, 110 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
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.
4.98 out of 5 average rating, 145 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 reviews
Typical Tuscan country house
Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence just 35 minutes by car This apartment is one level, totally independent with private garden. Restored and furnished with great care to make the guest's stay as comfortable and relaxing as possible, in the full respect of the Tuscan rural style.
4.99 out of 5 average rating, 432 reviews
Tuscany View - Villa Arianna
This beautiful villa, which can accommodate up to ten (10) people, will provide an unparalleled Tuscan experience. While positioned perfectly to allow easy access to the most beautiful towns and villages of southern/central Tuscany (such as Arezzo, Florence, Siena, Cortona, Montepulciano) and northern Umbria (such as Perugia, Orvieto, Assisi); you’ll find this villa offers complete privacy as well as a sense of peace and tranquility to all who visit.
4.99 out of 5 average rating, 123 reviews
Conca d'Oro villa with private pool, sleeps 4
Just 2 km from the village, cozy typical Tuscan farmhouse, tastefully furnished and equipped. The farmhouse is located in a panoramic position immersed in the peaceful Tuscan countryside. Guests have access to a beautiful infinity pool for their exclusive use, equipped with sun loungers, and a lovely garden with a patio furnished for outdoor dining and enjoying fantastic sunsets. A strategic location for tourists. Free high-speed satellite Wi-Fi
4.92 out of 5 average rating, 173 reviewsPopular amenities for Castiglion Fiorentino rentals with a pool
House rentals with a pool

Casa Lucy
4.95 out of 5 average rating, 110 reviews
Traditional stone house in Tuscany
4.97 out of 5 average rating, 102 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
Palazzo Monaci - Piscina nelle crete Senesi
4.96 out of 5 average rating, 142 reviews
Il Vecchio Mulino
4.91 out of 5 average rating, 114 reviews
Villa Lolù with private heated swimming-pool
4.98 out of 5 average rating, 160 reviews
Infinity view
4.88 out of 5 average rating, 204 reviewsCondo rentals with a pool

House between Firenze, Arezzo, chianti e Siena
4.84 out of 5 average rating, 302 reviews
Casa Granaio | Ground floor 1-bedroom apartment (2
4.96 out of 5 average rating, 82 reviews
Farm holidays in the countryside of Montepulciano
4.97 out of 5 average rating, 88 reviews
Appartamento IRIS - Agriturismo Mulino del Cilone
4.89 out of 5 average rating, 27 reviews
Charming Residence Castello di Orgiale near Siena
4.97 out of 5 average rating, 88 reviews
Oasi La Perla, natura e relax al lago Trasimeno
4.88 out of 5 average rating, 69 reviews
Tuscan Dream Apt with Pool, View & Tennis Court
4.91 out of 5 average rating, 97 reviews
Il Loggiato, 2 bedrooms with a view
4.9 out of 5 average rating, 20 reviewsHome rentals with a private pool

Esplora la natura al centro di Vigneti Chianti
4.97 out of 5 average rating, 265 reviews
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
- Lake Trasimeno
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Stazione Santa Maria Novella
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mercato Centrale
- Fortezza da Basso
- Uffizi Gallery
- Piazza della Repubblica
- Parco delle Cascine
- Piazzale Michelangelo
- Palazzo Vecchio
- Del Chianti
- Piazza della Signoria
- Basilica of St Francis
- Pitti Palace
- Boboli's Garden
- Mount Amiata
- Centro Storico Orvieto
- Stadio Artemio Franchi
- Medici Chapel





