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

Total vacation rentals
Explore 40 vacation rentals in Castiglion Fiorentino

Nightly prices starting at
Castiglion Fiorentino vacation rentals start at G$16,736 GYD per night before taxes and fees

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Over 670 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
40 of Castiglion Fiorentino vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, 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.

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.

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

House Rigomagno Siena
Apartment with beamed ceilings and terracotta floors, this apartment is set in a 19th-century farmhouse located in the hills of Siena in Rigomagno Toscana. From the solarium next to the swimming pool in the middle of the olive trees, you can admire the panorama of the Sienese hills and the medieval village of Rigomagno ... all this characterizes the ideal holiday for couples or families who want to relax. Solarium, garden, terrace, swimming pool are exclusively for guests of the apartment.

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.

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

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.

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.

Old hayloft on the Chianti hills
Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.

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.

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

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.
Popular amenities for Castiglion Fiorentino rentals with a pool
House rentals with a pool

Hidden gem in Tuscany

Casa Lucy

Villa with Private Pool in the Tuscan Countryside

Il Vecchio Mulino

Country House in the Crete Senesi

Luxury Villa with a fantastic view

Romantic cosy flat - Toscana Italy

Private House for 4P – La Capanna Di Azzurra
Condo rentals with a pool

Loggiato 3 apartment in Tuscany near Siena

Charming Castle

Agriturismo Poggio Bonelli, 2 people apartment

Casa Granaio | Ground floor 1-bedroom apartment (2

House between Firenze, Arezzo, chianti e Siena

Apartment LA LOGGIA 2+2

Relaxation and peace in the countryside Cortona G

Charming Residence Castello di Orgiale near Siena
Home rentals with a private pool

Podere Molinaccio - Luxury Tuscan-style Eco Villa

Villa il Palagio in the Tuscan countryside

Bliss out in Historic Farmhouse on Organic Wine Estate with Tennis and Pool

Villa Pergo is an ancient charming country villa

Agriturismo Henni panoramic pool sauna and jacuzzi
Destinations to explore
- Villa rentals Castiglion Fiorentino
- Family-friendly rentals Castiglion Fiorentino
- Apartment rentals Castiglion Fiorentino
- Pet-friendly rentals Castiglion Fiorentino
- House rentals Castiglion Fiorentino
- Rentals with a fireplace Castiglion Fiorentino
- Smoking-friendly rentals Castiglion Fiorentino
- Rentals with a patio Castiglion Fiorentino
- Rentals with outdoor seating Castiglion Fiorentino
- Rentals with a washer and dryer Castiglion Fiorentino
- Rentals with pools Arezzo
- Rentals with pools Tuscany
- Rentals with pools Italy
- Cathedral of Santa Maria del Fiore
- Lake Trasimeno
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Mercato Centrale
- Stazione Santa Maria Novella
- Uffizi Gallery
- Fortezza da Basso
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Piazza della Repubblica
- Parco delle Cascine
- Piazzale Michelangelo
- Del Chianti
- Basilica of St Francis
- Pitti Palace
- Boboli's Garden
- Palazzo Vecchio
- Piazza della Signoria
- Centro Storico Orvieto
- Medici Chapel
- Basilica of Santa Croce
- Stadio Artemio Franchi





