Vacation rentals with a pool in Casentino

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Casentino

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

The outdoor area features a large swimming pool surrounded by lush greenery, including trees and shrubs. Sun loungers are positioned nearby for relaxation. The rustic farmhouse is visible in the background, showcasing traditional Tuscan architecture with terracotta accents.

Guesthouse in Antria

4.92 out of 5 average rating, 126 reviews

A charming Tuscan retreat

Villa Pianelli is a traditional farmhouse dating from the 1500's and consists of 2 structures. The main house where I live, always available to ensure your stay runs smoothly and the Garden apartment. Both are completely independant with separate entrances. The Garden apartment is composed of 5 rooms on ground level, the interiors have retained the Tuscan characteristics with brick ceilings and chestnut beams and terracotta floors. There are 2 double bedrooms, 1 bathroom with shower, 1 lounge with a wood burning stove and open plan kitchen - dining area. The kitchen is equipped with fridge,oven and ceramic hob. From the lounge you access the spa room with sauna and from there onto a terraced garden complete with b.b.q. The swimming pool is 8mx16m and is open May through September, furnished with sun loungers,a b.b.q area and a large covered pergola with dining tables and chairs. Villa Pianelli is secluded in a quiet corner of the Tuscan countryside, nestled in the hills of Arezzo, surrounded by vineyards, olive groves and oak forests.We can offer our guests a dimension of peace and quiet whilst ensuring various possibilities of entertainment in wineries, restaurants,shopping etc just a few kilometres away in Arezzo. Please note that the house has two bedrooms but if the booking is for two people only one bedroom will be provided.If required there is an additional cost of 50 euro per night for the second bedroom.

Guest favorite

A historic stone building rises against a clear blue sky, surrounded by olive trees. The inviting pool stretches alongside the structure, enhanced by a smooth stone edge, creating a serene outdoor space for relaxation.

Apartment in Montone

4.96 out of 5 average rating, 28 reviews

Annex in the Cardaneto Castle

Studio apartment in the Cardaneto Castle (8th century) with swimming pool, private parking and 4,000 sqm of garden. 2 km from one of the most beautiful villages in Italy, Montone, famous for the tourist attractions and events that make it a unique place. The studio of about 50 sqm has a separate entrance overlooking the garden, a living room entrance, a double bedroom and a bathroom. ADSI historic residence. Panoramic swimming pool overlooking Montone. Also available apartment with kitchens and private balcony.

Superhost

A large outdoor swimming pool is visible under a clear blue sky, surrounded by lush greenery. The tranquil water reflects the sunlight, creating a calming atmosphere. Vegetation frames the scene, enhancing the privacy of the pool area.

Home in Montespertoli

4.83 out of 5 average rating, 70 reviews

Vacation immersed in the Tuscan countryside 'Canaiolo'

"💖Treat yourself to a vacation immersed in the Tuscan countryside, with a large equipped pool 🌞💐The scents of nature, the breathtaking landscapes and the swimming pool will be the setting for the relaxation you are looking for. 🚴🏻‍♂️🏃‍♀️Then if you feel the need to move around you can swim, walk, or run through the trails around your country home. 🏛The strategic location of the apartment allows you to hike in Florence, Siena and Pisa. ✨The apartments are recently renovated in Tuscan style.”

Guest favorite

A clear swimming pool is visible, reflecting the blue sky above. Surrounding the pool are stone walkways and lush greenery with olive trees. Lounge chairs are positioned nearby, offering a place to relax and enjoy the tranquil outdoor environment.

Condo in Cortona

4.96 out of 5 average rating, 24 reviews

Relaxation and peace in the countryside Cortona G

"Le Oche Grigie" was the first Charming Home in Cortona totally dedicated to people in love. Unlike other lodgin we only accept couples without children. This means for our guests memorable romantic experiences, emotions and complicity in a country house, away from the distractions of daily life. Strategically positioned in the center of an area of extraordinary beauty, only 3 exclusive and independent apartments, renovated with fine finishing and natural materials. Garden and swimming pool.

Guest favorite

A spacious living room features exposed wooden beams above, with a cozy seating arrangement of soft sofas. A rustic wooden coffee table sits in the center, surrounded by warm, terracotta-tiled floors. A classic fireplace provides a focal point, complemented by thoughtful decorative accents.

Home in San Casciano In Val di Pesa

4.84 out of 5 average rating, 92 reviews

Tuscan Villa Featured Conde Nast Best Villas Italy

Step under archways into a home where the original wood ceilings and tiled floors showcase Tuscan style. Enjoy delicious meals on the terrace with sweeping views of Tuscany, winters curled up in front of a huge fire place or relaxing on warm summer days by the pool. Savour the best of Tuscan food and wine with cooking classes with a Michelin chef, master classes in wine and visits to local artisan cheese and wine makers. Listed by Condé Nast as one of the most beautiful villas in Italy.

Guest favorite

A serene pool with a smooth surface reflects the surrounding greenery. Tall cypress trees and lush garden areas border the pool, complemented by colorful plants and a well-maintained lawn. The sky is bright and clear, adding to the tranquil ambiance of the outdoor space.

Home in Cerbaia

4.9 out of 5 average rating, 21 reviews

Villanuova Power 2

Cute apartment in the tuscan countryside with a beautiful pool, set in Cerbaia, 20 km away from Florence. It is in a great position to visit many of the highlights of Tuscany and the wine region of Chianti. We rent a small apartment that has a living room with kitchen, a main bedroom, one bathroom. The house has a beautiful and spacious garden with a big pool overlooking the tuscan hills. In the property there is the villa of the owners and another apartment that we rent here on airbnb.

Guest favorite

A private pool is surrounded by sun loungers, set on a wooden deck. The pool area features natural stone paving and is enclosed by a child-proof fence. Lush greenery and olive trees outline the space, providing a serene environment for relaxation.

Home in Lecchi in Chianti

4.96 out of 5 average rating, 136 reviews

Casa di Lyndall - Entire house with exclusive pool

Welcome to “Casa di Lyndall” My home is located in the medieval village of Lecchi in Chianti, set in rolling hills, castles, vineyards & olive groves, & provides a view that extends nearly 50 kms. It’s a perfect choice for a family or group of four people. My home is built in typical Tuscan style with exposed chestnut beams, fireplace, and a well appointed kitchen. The 8 metre pool is private & located on the top terrace of the olive grove, has a child proof fence, and 4 sun lounges.

Guest favorite

A clear blue pool reflects the surrounding greenery, enhancing the outdoor area. Sun loungers and umbrellas are positioned around the pool, offering shaded seating. A terraced lawn rises gently behind the pool, featuring well-maintained plants and pathways that lead to the restored farmhouse.

Apartment in Umbertide

4.87 out of 5 average rating, 30 reviews

Charming farmhouse apartment with swimming pool

Set within a cluster of self catering apartments in this restored farmhouse with pool. Offering one bedroom with en-suite bathroom this is our smallest apartment but still perfectly formed. There's a custom kitchen with marble counter top with french doors leading to a private flag stoned terrace. Feature exposed stone walls and hand made terracotta floors complete the rustic feel. The comfy sofa in the lounge can convert to a double bed with deep springy mattress.

Top guest favorite

Loft in Scandicci

4.98 out of 5 average rating, 108 reviews

Wonderful Loft in Villa with Pool in Chianti

Located on the second and top floor of the "Suites le Valline" complex, the Piazzale Michelangelo loft offers a unique style in an ideal location for exploring Tuscany, a 15-minute drive from Florence and San Casciano! Treat yourself to a moment of relaxation on the beautiful panoramic terrace overlooking Florence, or cool off in the bio pool among the olive trees... and remember that all the vegetables from the Valline vegetable garden are at your disposal!

Guest favorite

Home in Magliano

5 out of 5 average rating, 11 reviews

Sunset in Chianti

Relax with the whole family in this quiet, panoramic accommodation immersed in the beauty of the Tuscan countryside. This apartment offers a view that will leave you breathless. Equipped with a large garden, above ground pool, 2 cozy bedrooms, 2 elegant bathrooms, a fully equipped kitchen, a comfortable living area and a panoramic terrace with a table, perfect for dining under the stars. This place is ideal for living a unique and unforgettable experience.

Top guest favorite

A clear blue pool is framed by lush greenery and terracotta paths, with several lounge chairs positioned nearby. The house sits atop a gentle hill, surrounded by tall trees and vibrant shrubs, offering a serene perspective of the Tuscan landscape.

Villa in Siena

4.85 out of 5 average rating, 86 reviews

Enchanting Rose Garden Pool Villa

Truthful Tuscan paradise just 12mins from Siena. Boasting two doubles and two twins, 3 bathrooms, a very large leaving room, a beautiful dining room with fire place, park, parking and pool are all private. It is the ideal old and authentic family retreat, nestled on top of the Montechiaro hill with 360 degrees views over Chianti. The host leaves in the adjacent house. In winter and early spring there is an extra charge of 50€ a day for heating.

Top guest favorite

Apartment in Mercatale Valdarno

4.98 out of 5 average rating, 80 reviews

Panoramic view from stone Apartment- Pool and A/C

Unique experience in a real, old Tuscan farmhouse. Podere Casa Muricce is the place for people who love nature, animals, woods, but also close to the main places of interest in Tuscany. Situated on the top of a hill high 400mt, carefully restructured according to the tradition, Casa Muricce is the typical ancient Tuscany house in stone: all the furnishings, even doors, are original from Tuscany houses of `700/'800.