
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.

Stone farmhouse, exclusive private pool
Podere Montebono is located in the hills of Reggello, just 30 km from Florence. Ideal for getting to cities of art and natural sites. The farmhouse is secluded on a hill, immersed in nature, surrounded by olive trees, a garden and woodland. The guest house is an independent wing of the large farmhouse on two floors: 3 bedrooms, kitchen, living room, bathroom. The private swimming pool is exclusively for those who rent the house (max 4 people). We do not rent single rooms. Barbecue area. Total privacy.

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.

Infinity view
Completamente ristrutturata posizione con vista mozzafiato sul Valdarno. Il piano terra è composto da soggiorno con due vetrate che danno sul patio, camino, divano letto, bagno con grande doccia e cucina moderna con isola in acciaio, con tre porte finestre per accedere alla zona pranzo esterna con bbq. Il primo piano è composto da due camere matrimoniali ognuna dotata del proprio bagno con doccia. Giardino è moto curato,ci sono vari angoli relax, prendisole è una piscina infinity ad idrolisi

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.

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.

Il Roseto: your Villa in Tuscan Countryside
In the heart of Tuscany between Arezzo, Florence and Siena but far away from the bustle of the cities, you will find a pristine landscape where to enjoy nature and relaxing, amazing views and much more for a perfect getaway with your friends or family. A villa of 190 mq with 600 mq garden,where you can enjoy lunch outdoors, have fun making pizza and baking it in the wood- oven, or savour a wonderful barbeque. A comfortable Villa for guests who love being together.

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.

[Authentic StoneHouse]Jacuzzi & Viewpool Apartment
Nestled in a medieval village in the heart of Chianti, this exclusive historical apartment blends Tuscan charm with refined contemporary design. Enjoy a panoramic pool overlooking the hills, multiple terraces, and a unique hot tub Jacuzzi suite and bathroom carved in travertine. Designed for two, it’s the perfect place to slow down, reconnect, and experience Tuscany in total peace.

Casa Rosmarino Eco-Wellness Country Home
Price includes: - Infrared Sauna - Wood for Fireplace - Fire starters - Heating/Air Conditioning - Laundry/Dryer - Shower Gel/Shampoo/Bathrobes - Welcome Appetizer w/Wine - Treats during your stay Pool & parking lot are shared areas. We have 6 units for rent Extra activities (not included) : - Massages, Cooking Classes, Tours & Tasting Please INQUIRE for price & availability.

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 Casentino rentals with a pool
House rentals with a pool

Hidden gem in Tuscany

Private Chianti Cottage, Garden & Vineyard Views

Villa with Private Pool in the Tuscan Countryside

Podere Bocci residence in Casentino - Entire Villa

Charming estate with views. A/C in the bedrooms

Casa Macchia /Florence charming villa private Pool

Il Vecchio Mulino

Casa San Ripa: Relax Oasis with Private Pool
Apartment rentals with a pool

Casa Nonno Duilio | First floor 3-bedroom apartmen

"Antica Aia" apartment

Agriturismo Poggio Bonelli, 2 people apartment

large apartment with loggia in old farm with pool

Ginestra: Private Pool Overlooking Florence

Belvedere

Garden & SPA -FlorArt Boutique Apartment

Farmhouse near Florence - Fienile
Other holiday rentals with a pool

Garden Duomo House

romignano wine farm

Cabin in the woods in Tuscany with exclusive bathtub

Luxury Hilltop Villa | Infinity Pool, Sauna, View

Apartment Comfort | Quiet Escape in Tuscany

Casentino Villa Antonella

Cipressini 2 - pool and amazing views

Villa Piandarca-"Sole"-Tuscany-Chianti-pool
Destinations to explore
- Pet-friendly rentals Casentino
- Cottage rentals Casentino
- Bed and breakfasts Casentino
- Family-friendly rentals Casentino
- Holiday home rentals Casentino
- Apartment rentals Casentino
- House rentals Casentino
- Rentals with a firepit Casentino
- Villa rentals Casentino
- Smoking-friendly rentals Casentino
- Rentals with a hot tub Casentino
- Rentals with an EV charger Casentino
- Rentals with a washing machine and dryer Casentino
- Farm stay rentals Casentino
- Flat rentals Casentino
- Rentals with a fireplace Casentino
- Fitness-friendly rentals Casentino
- Rentals with lake access Casentino
- Rentals with outdoor seating Casentino
- Rentals with a patio Casentino
- Rentals with a sauna Casentino
- Rentals with breakfast 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
- Mugello Circuit
- Fiera Di Rimini
- Misano World Circuit
- 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
- Autodromo Enzo e Dino Ferrari
- Del Chianti
- Pitti Palace
- Palacongressi Della Riviera Di Rimini
- Boboli's Garden





