Some info is shown in its original language. Translate

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

  • Verified guest reviews

    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.

1 of 1 pages1 / 1
Top Guest favourite
Villa in Montepulciano

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.

ValueLocationParking

4.97 out of 5 average rating, 126 reviews
Top Guest favourite
A charming cottage is shown with a terracotta facade and a tiled roof. A small table with two chairs is set on a patio, surrounded by potted plants. Lush greenery and trees can be seen in the background under a clear blue sky.
Guesthouse in Macciano

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.

FamilyValueQuiet

4.97 out of 5 average rating, 251 reviews
Guest favourite
A stone villa surrounded by greenery is featured under a clear blue sky. A large swimming pool reflects the sunlight, complemented by sun loungers and colorful potted flowers along the edges. The outdoor area is perfect for relaxation with scenic views of the Tuscan hills.
Villa in Castiglion Fiorentino

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

LocationValueComfort

4.9 out of 5 average rating, 241 reviews
Guest favourite
A serene outdoor pool area is surrounded by lush greenery and rustic stone pathways. Lounge chairs are positioned beside the pool, creating a space for relaxation. The picturesque villa can be seen in the background, framed by trees and gentle hillside.
Villa in Castiglione d'Orcia

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.

ValueFamilyOutdoor spaces

4.95 out of 5 average rating, 146 reviews
Top Guest favourite
A serene pool area is showcased with two sun loungers positioned beside a tranquil salt-water pool. The expansive view of the valley and distant cityscape adds to the peaceful ambiance, while greenery surrounds the space, enhancing the sense of privacy and relaxation.
Farm stay in Monte San Savino

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.

LocationValueKitchen

4.99 out of 5 average rating, 116 reviews
Guest favourite
Villa in 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

LocationFamilyGetting around

4.8 out of 5 average rating, 110 reviews
Guest favourite
Aerial view of a scenic agriturismo surrounded by vineyards and rolling hills. The property features a pool and is framed by tall cypress trees, enhancing the natural landscape of lush green and golden fields under a partly cloudy sky.
Farm stay in Montepulciano

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.

LocationFamilyCheckout

4.96 out of 5 average rating, 116 reviews
Top Guest favourite
The farmhouse entrance is framed by two potted plants and orange pumpkins. A stone facade features a wooden door with gray shutters, complemented by a tiled roof. Natural surroundings are visible in the background, emphasizing the peaceful rural setting.
Home in Prato

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.

FamilyValueNearby

4.98 out of 5 average rating, 145 reviews
Top Guest favourite
The image depicts a serene pool area surrounded by lush Mediterranean greenery. A bright orange umbrella provides shade, while a well-maintained stone pathway leads to the entrance of a charming stone farmhouse in the background.
Home in Casalini

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.

ValueFamilyQuiet

4.99 out of 5 average rating, 111 reviews
Top Guest favourite
A spacious outdoor area features a swimming pool surrounded by lush green lawns and dotted with comfortable sun loungers. Umbrellas provide shade, and the serene landscape is framed by tall trees and gentle hills in the background.
Farm stay in Greve in Chianti

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.

LocationFamilyIndoor spaces

4.99 out of 5 average rating, 432 reviews
Top Guest favourite
Villa in Arezzo

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.

FamilyLocationParking

4.99 out of 5 average rating, 123 reviews
Guest favourite
A charming stone house with a terracotta roof features a welcoming entryway, shaded by umbrellas and surrounded by colorful flowers. In the background, a serene saltwater infinity pool is framed by landscaped greenery, complementing the tranquil rural setting.
Home in Foiano della Chiana

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

LocationValueComfort

4.92 out of 5 average rating, 173 reviews

Popular amenities for Castiglion Fiorentino rentals with a pool

Condo rentals with a pool

Guest favourite
A serene outdoor area features a swimming pool with clear blue water, bordered by wooden decking. Four lounge chairs face a vibrant garden of yellow flowers, offering expansive views of the surrounding hills and sky filled with fluffy clouds.
Condo in Castelfranco di Sopra

House between Firenze, Arezzo, chianti e Siena

FamilyLocationBathroom

4.84 out of 5 average rating, 302 reviews
Guest favourite
An aerial view captures the rural estate, showcasing a well-maintained lawn surrounded by lush vineyards. A private pool is visible, complemented by red umbrellas and lounge chairs. The rustic buildings reflect traditional architecture, while trees provide natural shade across the property.
Condo in Monte San Savino

Casa Granaio | Ground floor 1-bedroom apartment (2

FamilyValueNearby

4.96 out of 5 average rating, 82 reviews
Top Guest favourite
An outdoor dining area is presented on a wooden terrace, surrounded by trees and greenery. A table is elegantly set with plates and glassware, illuminated by soft light. Scenic views of rolling hills and vineyards are visible in the background, creating a serene atmosphere.
Condo in Montepulciano

Farm holidays in the countryside of Montepulciano

ValueFamilySleep quality

4.97 out of 5 average rating, 88 reviews
Guest favourite
A covered pergola provides shade over a seating area with a small table and chairs, surrounded by a lush green lawn. Stone walls of a nearby building blend with the natural landscape, while flower pots add color. A cat is seen on the lawn, contributing to the serene environment.
Condo in Castiglion Fiorentino

Appartamento IRIS - Agriturismo Mulino del Cilone

LocationFamilyIndoor spaces

4.89 out of 5 average rating, 27 reviews
Guest favourite
An aerial view captures a rustic stone building surrounded by lush greenery and tall cypress trees. A sparkling swimming pool is visible in the yard, complemented by sun loungers. Rolling vineyards stretch into the background, enhancing the serene landscape.
Condo in Castelnuovo Berardenga

Charming Residence Castello di Orgiale near Siena

LocationValueView

4.97 out of 5 average rating, 88 reviews
Guest favourite
Condo in Passignano sul Trasimeno

​Oasi La Perla, natura e relax al lago Trasimeno

ValueFamilyHospitality

4.88 out of 5 average rating, 69 reviews
Guest favourite
A warm living space showcases exposed wooden beams and light-colored walls. A staircase leads to an upper level, while a cozy seating area features a light gray sofa. A dining table is positioned near windowed doors that offer views of the surrounding countryside.
Condo in Montefollonico

Tuscan Dream Apt with Pool, View & Tennis Court

FamilyValueWi-Fi

4.91 out of 5 average rating, 97 reviews
Guest favourite
Condo in San Gimignanello

Il Loggiato, 2 bedrooms with a view

LocationFamilyAir conditioning

4.9 out of 5 average rating, 20 reviews