
Pet-friendly holiday rentals in Castiglion Fiorentino
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Top-rated pet-friendly home rentals in Castiglion Fiorentino
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Under the sunset, Montepulciano
In 2023 my son Guglielmo and I decided to restore the old oratory of a church from the 1600s by creating a two floor apartment: upstairs we have 2 bedrooms equipped with AC and 2 en-suite bathrooms with shower; downstairs a spacious living room with stereo Available a table outside with great view and a nice garden 50 mt away where to have a private wine tasting for all the guests of our 4 apartments We can organize barbecue with paired wines after 7 pm. Large free parking area 100 mt away

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
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

Stuart White Tea Central Panoramic & Garden
Offering ample space, the apartment features two double bedrooms, two full bathrooms, and a living room with a kitchen. The bedroom balconies offer stunning views of the valley and natural light. Its proximity to all town amenities ensures convenience, while a delightful café downstairs provides a delectable gourmet breakfast. It has also access to a secluded, terraced backyard garden. It provides a comfortable retreat perfect for long term stays. A public parking is available nearby.

Piazza Grande Boutique Apartment
Affacciato sulla più bella piazza del centro storico di Arezzo, dove si svolge la rievocazione della Giostra del Saracino, il Piazza Grande Boutique Apartment è situato al secondo piano di un palazzo medievale, con vista sui bellissimi palazzi e le Logge Vasariane ed è una location unica nel suo genere. L'arredamento, opera della contessa Cesaroni Venanzi è stato realizzato con bellissimi mobili antichi reinterpretrati in chiave moderna ed arricchiti da contaminazioni contemporanee.

La Perla del Lago Holiday home on Lake Trasimeno
Forget all your worries in this oasis of serenity. Let yourself be soothed by our amazing views and the sunsets that the lake offers us every evening The Holiday Home La Perla del Lago overlooks Lake Trasimeno. 8 minutes away is the highway from which you can easily reach Florence, Perugia,Gubbio, Spoleto, Norcia and many others In the village, there are bars, food restaurants, a pharmacy, an ATM, a small playground, and a beautiful swimming pool for the hottest days, 2 km away.
La Piazzetta - Cozy open space in the historic center of Montepulciano
Pour yourself a glass of wine and sit next to the fireplace of this open space with a warm Tuscan atmosphere: wooden beams, terracotta floors, stone walls. Then go outside and admire the magnificent view of the Valdichiana. Pour yourself a glass of wine and sit next to the fireplace of this open space with a warm Tuscan atmosphere: wooden beams, terracotta floors, and stone walls. Enjoy yourself and relax! Then go out and admire the magnificent view of the Valdichiana Valley.

Green – The meadows in Tuscany
Apartment consisting of 1 double bedroom, equipped kitchen, large living room and bathroom TV, BBQ, (we provide the washing machine from 9 a.m. to 8 p.m. which is in our laundry room for those who request it). We recommend the car as we live in the countryside, both to be independent and to visit the magnificent Tuscany You'll like the outdoor environment because it's magical, day and night Free parking and wifi Strategic location for visiting Tuscany and Umbria.

Resort Panoramic view - Free parking
Appartamento nuovo , potente Wi-Fi, SMART TV, bagno privato , Aria Condizionata, cucina privata , lavanderia , parcheggio privato gratuito . Sala da tea ad uso gratuito . Vista panoramica mozzafiato . Tra le Crete Senesi e la Val D’Orcia , a 800metri dal centro del paese , con ristoranti , bar e supermercati . Posto strategico per visitare le principali località in Toscana : Montalcino , Pienza , Siena , Arezzo , Rapolano Terme , Montepulciano .

Casa Bonari - a paradise for the eyes
Casa Bonari is a single-level independent apartment inside a villa at the foot of Monticchiello. It consists of 3 bedrooms, 2 bathrooms, an equipped kitchen and a living room. The rooms are bright and furnished in Tuscan style, with old restored family furniture combined with contemporary elements. The kitchen is fully equipped and the apartment is surrounded on all sides by a large garden, so that all rooms boast a beautiful view of the countryside.

Casa del Passerino
Apartment located inside a historic building in Cortona, dating back to the 1500s, overlooking the city's main square... Our property, while condemning the war, dissociates itself from all racist behavior towards the Russian and Belarusian population. At Casa del Passerino, people of these nationalities are welcome and will be treated the same as everyone else. We look forward to seeing you in Tuscany!

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 Castiglion Fiorentino pet-friendly home rentals
Pet-friendly house rentals

La Lisa: country house surrounded by fields

Luxury Villa with a fantastic view

Il Focolare - Superior Tuscany Apartment

Gaiole in Chianti Poggio Casabianca

Romantic cosy flat - Toscana Italy

Casa dei 5 Sensi - Trasimeno view

Montalcino Townhouse with Private Garden & Spa

il Fienile - (Typical Tuscan rural accommodation)
Pet-friendly home rentals with a pool

Tuscany Villa Mammi

The Eagle and the Olive Tree

Wp Relais Borgo Vignalunga

Ortaglia di Sotto Farm

San Giovanni in Poggio, villa Meriggio 95mq

Villa Patrizia: Tuscany farmhouse apt 2

Farmhouse with swimming pool with wonderful view

Romantic and with a view. Swimming pool open : )
Private, pet-friendly home rentals

Breathtaking view of the valley right in the center

The small tower

Via della Stella Farmhouse | Casa le Rose

Pendici 15, small apartment

Life is beautiful

casa Sonia

Casa Letizia apartment in the historic center

Wine Loft in the vineyards
When is the best time to visit Castiglion Fiorentino?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $164 NZD | $136 NZD | $159 NZD | $241 NZD | $223 NZD | $221 NZD | $256 NZD | $209 NZD | $237 NZD | $191 NZD | $198 NZD | $195 NZD |
| Avg. temp | 5°C | 6°C | 9°C | 12°C | 16°C | 21°C | 23°C | 24°C | 19°C | 14°C | 9°C | 5°C |
Quick stats about holiday rentals that are pet-friendly in Castiglion Fiorentino

Total holiday rentals
Explore 50 holiday rentals in Castiglion Fiorentino

Nightly prices starting at
Castiglion Fiorentino holiday rentals start at $53 NZD per night before taxes and fees

Verified guest reviews
Over 1,210 verified reviews to help you choose

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

Holiday rentals with a pool
30 properties feature pools

Rentals with dedicated workspaces
20 properties have a dedicated workspace

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

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

4.8 Average rating
Castiglion Fiorentino stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
- Villa rentals Castiglion Fiorentino
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- Apartment rentals Castiglion Fiorentino
- House rentals Castiglion Fiorentino
- Rentals with a washing machine and dryer Castiglion Fiorentino
- Family-friendly rentals Castiglion Fiorentino
- Rentals with a patio Castiglion Fiorentino
- Rentals with a fireplace Castiglion Fiorentino
- Rentals with pools Castiglion Fiorentino
- Pet-friendly rentals Tuscany
- Pet-friendly rentals Italy
- Santa Maria Novella
- Piazzale Michelangelo
- Lake Trasimeno
- Duomo di Firenze
- Basilica of Santa Maria Novella
- Ponte Vecchio
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mercato Centrale
- Uffizi Gallery
- Fortezza da Basso
- Piazza della Repubblica
- Pitti Palace
- Parco delle Cascine
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- The Boboli Gardens
- Avignonesi Winery Fattoria Le Capezzine
- Medici Chapels
- Tenuta Le Velette
- Palazzo Vecchio
- Stadio Artemio Franchi
- Basilica of St Francis
- Basilica di Santa Croce
- Castiglion del Bosco Winery
- Palazzo Medici Riccardi




