
Holiday 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.

Relaxation and charm in the Chianti hills
Beautiful stone farmhouse, detached, surrounded by olive trees and the Chianti hills, with private garden and panoramic swimming pool. Ground floor with large living rooms, antique fireplace and wood-burning oven, bright living room and fully equipped kitchen. On the first floor, three suites consisting of a bedroom, study and private bathroom. Access via gate and white road on private property just 500 meters from the village of Strada in Chianti. Ideal for peace and relaxation. Convenient location for visiting Tuscany.
FamilyLocationQuiet

Manor House - IlVillinoFarmhouse
Entire upper floor of the newly renovated Manor House in traditional Tuscan style. High ceilings with exposed beams make the place cozy and perfect for families or groups of friends. In the house, there are two large functional fireplaces (in the living room and kitchen). Private, non-shared accommodation. The house has a large covered terrace, garden with sofas, BBQ, fire pit, private parking. The swimming pool among the olive trees and vineyards is ideal for relaxation and has private access to the shared area
ValueFamilyCheck-in

Infinity view
Completely renovated location with breathtaking views of the Valdarno. The ground floor consists of a living room with two windows overlooking the patio, fireplace, sofa bed, bathroom with large shower and modern kitchen with steel island, with three French windows to access the outdoor dining area with BBQ. The second floor consists of two double bedrooms each with its own bathroom with shower. The garden is well-kept, there are various relaxation corners, a sundeck and an infinity pool with hydrolysis
LocationValueLong stay

Tuscan charm of villa - countryside - Villa Senaia
In the charming Tuscan countryside, among olive trees and vineyards, a stone villa, in a strategic position to grasp the secrets of Tuscany and Umbria air conditioning and swimming pool with wellness area for your relaxation and comfort Villa Senaia is a large house with wooden beams, in a beautiful hillside location with idyllic views overlooking one of the favorite places in the Tuscan countryside, an attractive setting for outdoor dining, drinking Tuscan wine and listening to crickets and cicadas
FamilyLocationLayout

TREEhouse / casaBARTHEL
casaBARTHEL is a perfect place for a vacation and an artist residency, immersed in the Tuscan landscape only 15' from the florentine Duomo. Come and live with us; enjoy the olive trees, the kitchen garden, our horse Astro and our family life style, away from the working rhythm. By providing wifi only in the communal courtyard we suggest to take a break from been connected with elsewhere and enjoy the 'here and now' . But if you need to work you can rent a portable private connection from us.
ValueFamilyIndoor spaces

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.
ValueLocationAmenities

Villa Tonacato - Charming Villa with private pool
Ancient rural farmhouse, located on the Tuscan hills with views of the surrounding countryside. Isolated and ideal for those who want to relax but close to the main Italian tourist cities. Each room is equipped with air conditioners with windfree technology, in the living room there is an 82" ULTRA HD TV with SKY and international channels. The pool is equipped with Philips Hue lighting to create the right atmosphere at all times and a Bose Soundtouch bluetooth sound system
ValueFamilyDecor

Country House w/ heated Pool near the City Centre
Nestled in a centuries-old park, this 16th-century house offers a serene retreat, just 15 minutes by tram from the city. The true gem is the underground heated pool at 31°C, complete with a jacuzzi and waterfall, providing moments of relaxation in total privacy. The 2 bright suites, 2 full bathrooms, kitchen, and living room welcome guests in an atmosphere of elegance. Upon request: Dinner with a private chef and free transfer to and from the airport and train station.
FamilyValueLong stay

The Castle of Ferrano - Castle in Tuscany
Try the experience of staying in a real Castle! Il Castello di Ferrano offers to its hosts the chance of living an unforgettable experience: you will be the only guests in the castle, and everything will be for you (private pool from June to September, gardens etc..). Historical building, surrounded by nature, finely decorated, frescoes/moulding on the ceiling, ample terrace w/ stone and terracotta floor, private outdoor pool.. Good position. Preferably come by car.
ValueFamilyWalkability

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.
FamilyLocationCleanliness

Tofanello Turquoise Luxury 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 orange apartment. Orange: https://www.airbnb.com/rooms/plus/9429730
LocationValueHospitality

A Big Dream in a Little Tower.
The Tower was created in the late 1800s by an illustrious Englishman, Sir John Temple Leader, in one of the oldest and most important stone quarries belonging to the Medici family. From the same quarry were extracted many important works such as the columns of the Medici chapels, the steps of the Laurenziana library .. all just 5 km from the historic center of Florence.
LocationValueOutdoor spaces
Popular amenities for Casentino rentals with a pool
House rentals with a pool

Private Chianti Cottage, Garden & Vineyard Views
LocationFamilyBathroom

Casa Giulia di Sopra Farmhouse
LocationFamilyView

PoggiodoroLoft, Tuscan dream e relax
FamilyValueOutdoor spaces

Villa Lolù with private heated swimming-pool
ValueFamilyCondition

Il Vecchio Mulino
FamilyValuePool

Ancient Tuscan Rural Residence
LocationFamilyLayout

Casetta Melograno – Cozy farmhouse in Chianti
ValueLocationOutdoor spaces

Explore Chianti from a Charming Stone House
ValueLocationOutdoor spaces
Condo rentals with a pool

Poggiolieto Suite - on hills 10' from city center
LocationValueLayout

Apt. Panzanello-Panzano in Chianti
FamilyLocationCheckout

Ginestra: Private Pool Overlooking Florence
FamilyLocationHot tub

Chianti, elegant barn among vineyards and pool
FamilyLocationKitchen

Garden & SPA -FlorArt Boutique Apartment
LocationFamilyComfort

New, bright, cozy Florence apartment with view
FamilyValueKitchen

Casa Rebecca with a small private pool
ValueFamilyAccuracy

Tuscany | Apartment in farm with restaurant & pool
ValueLocationPets
Other holiday rentals with a pool

Agriturismo I Gelsi
FamilyLocationHospitality

Stone farmhouse, exclusive private pool
FamilyLocationHospitality

la Balza
LocationValueHeating

[Authentic StoneHouse]Jacuzzi & Viewpool Apartment
FamilyLocationWi-Fi

Poggelleri the postcard on Poppi and Tuscan hills
ComfortViewHospitality

Morandi Mill - Morandi Mill
LocationBarbecueHospitality

Cipressini 1 - Swimming pool and stunning view
FamilyValueView

Podere Bocci residence in Casentino - Entire Villa
FamilyLocationCleanliness
Destinations to explore
- Pet-friendly rentals Casentino
- Cottage rentals Casentino
- Rentals with lake access Casentino
- Bed and breakfasts Casentino
- Family-friendly rentals Casentino
- Holiday home rentals Casentino
- Condo rentals Casentino
- House rentals Casentino
- Villa rentals Casentino
- Rentals with a hot tub Casentino
- Rentals with breakfast Casentino
- Rentals with a sauna Casentino
- Farmstay rentals Casentino
- Apartment rentals Casentino
- 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
- Pinarella Di Cervia
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Mirabilandia
- Fiera Di Rimini
- Misano World Circuit
- Stazione Santa Maria Novella
- Mugello Circuit
- Uffizi Gallery
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Fortezza da Basso
- Piazza della Repubblica
- Parco delle Cascine
- Del Chianti
- Autodromo Enzo e Dino Ferrari
- Piazzale Michelangelo
- Pitti Palace
- Palazzo Vecchio
- Piazza della Signoria
- Palacongressi Della Riviera Di Rimini





