
Holiday rentals with a pool in Casentino
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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.
FamilyValueLong stay
4.99 out of 5 average rating, 114 reviews
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
4.88 out of 5 average rating, 203 reviews
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
ValueLocationBreakfast
4.9 out of 5 average rating, 241 reviews
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.
ValueFamilyBreakfast
4.99 out of 5 average rating, 116 reviews
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 woods. The guest house is a separate wing of the large two-storey farmhouse: 3 bedrooms, kitchen, living room, bathroom. The private pool is exclusively for those who rent the house (max 4 people). We do not rent single rooms. Barbecue area. Total privacy.
LocationFamilyPool
4.96 out of 5 average rating, 195 reviews
La Vignaccia (Farmhouse) - villa w/private pool
Nestled amidst the rolling hills of Tuscany, La Vignaccia beckons you to experience the true essence of Italian living. This enchanting villa, set within a sprawling estate, offers a haven of tranquility, where you can unwind and immerse yourself in the beauty of the Tuscan countryside. A secluded garden awaits, providing a serene setting for relaxation and alfresco dining. Take a refreshing dip in the sparkling pool, surrounded by breathtaking views of the Tuscan landscape.
ValueLocationOutdoor spaces
4.96 out of 5 average rating, 102 reviews
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.
FamilyLocationGetting around
4.99 out of 5 average rating, 227 reviews
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.
LocationValueAccuracy
4.99 out of 5 average rating, 124 reviews
Farmhouse in Chianti with Swimming Pool
Agriturismo Il Colle is located on one of the Chianti hills. The structure 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 The apartment is located on the ground floor of the main farmhouse, with independent access and private space. The care taken in the restoration and furnishing make the house particularly welcoming, respecting the rural style.
FamilyLocationOutdoor spaces
4.99 out of 5 average rating, 516 reviews
Villa Capanna, Private Pool, Breathtaking Views
Ancient restored barn with up to 6 bedrooms and 6 bathrooms, immersed in a historic wine estate, just 6 km from Siena. One of the most beautiful views that the Tuscan panorama can offer, airconditioned bedrooms, exclusive swimming pool, large triple garden, BBQ, poolside table, terrace to enjoy the sunset over the medieval towers on the horizon while sipping the organic wines of the estate, fireplace, parking free, WI-FI internet.
FamilyValuePool
4.89 out of 5 average rating, 309 reviews
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.
LocationFamilyWalkability
4.95 out of 5 average rating, 221 reviews
Casa Rosmarino Eco-Wellness Country Home
Price includes: - Infrared Sauna - Wood for Fireplace - 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.
FamilyValueHeating
4.99 out of 5 average rating, 273 reviewsPopular amenities for Casentino rentals with a pool
House rentals with a pool

Tofanello Orange Luxury and Modern Comfort with Outdoor Pool
LocationValueWalkability
4.98 out of 5 average rating, 145 reviews
Villa Lolù with private heated swimming-pool
ValueLocationBreakfast
4.98 out of 5 average rating, 160 reviews
Country Rentals - La Canonica
FamilyLocationWi-Fi
4.86 out of 5 average rating, 101 reviews
PoggiodoroLoft, Tuscan dream e relax
ValueFamilyOutdoor spaces
4.87 out of 5 average rating, 167 reviews
TREEhouse / casaBARTHEL
FamilyLocationBackyard
4.88 out of 5 average rating, 821 reviews
Casa Macchia /Florence charming villa private Pool
LocationFamilyAir conditioning
4.96 out of 5 average rating, 102 reviews
Il Vecchio Mulino
ValueLocationComfort
4.91 out of 5 average rating, 114 reviews
A Home in the Florentine Hills | La Nepitella
FamilyLocationAir conditioning
4.84 out of 5 average rating, 289 reviewsCondo rentals with a pool

Chianti, elegant barn among vineyards and pool
ValueFamilyView
4.95 out of 5 average rating, 181 reviews
Apt.Panzanello-Panzano in Chianti
FamilyLocationNearby
4.96 out of 5 average rating, 282 reviews
Poggiolieto Studio - on hills 10' from city center
LocationFamilyBiking
4.85 out of 5 average rating, 214 reviews
Villa La Loggia 1.0
FamilyValueLaundry
4.97 out of 5 average rating, 101 reviews
Ginestra: Private Pool Overlooking Florence
ValueFamilyParking
4.95 out of 5 average rating, 117 reviews
The House in Chianti - IlVillinoFarmhouse
FamilyValueAmenities
4.78 out of 5 average rating, 246 reviews
Casa Rebecca with a small private pool
ValueFamilyView
4.92 out of 5 average rating, 526 reviews
Belvedere
LocationFamilyAmenities
4.91 out of 5 average rating, 179 reviewsOther holiday rentals with a pool

PIERFANTINI private Chianti house ♿️ 🏊♂️ 🐶
LocationFamilyGetting around
4.91 out of 5 average rating, 100 reviews
La Balza
LocationFamilyAccuracy
4.93 out of 5 average rating, 128 reviews
Villa Podere Cerretino
FamilyLocationBathroom
5.0 out of 5 average rating, 67 reviews
Villa Montanina - exclusive relaxation in Tuscany
ValueFamilyView
4.99 out of 5 average rating, 85 reviews
Casentino Villa Antonella
LocationFamilyKitchen
4.95 out of 5 average rating, 20 reviews
romignano wine farm
ValueFamilyComfort
4.74 out of 5 average rating, 57 reviews
Podere Bocci residence in Casentino - Entire Villa
FamilyValueCondition
5.0 out of 5 average rating, 49 reviews
Villa Piandarca - Tuscany - WIFI - private pool
LocationValueIndoor spaces
4.98 out of 5 average rating, 60 reviewsDestinations to explore
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- Lake Trasimeno
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Pinarella Di Cervia
- Mirabilandia
- Basilica of Santa Maria Novella
- Stazione Santa Maria Novella
- Misano World Circuit
- Mugello Circuit
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mercato Centrale
- Fortezza da Basso
- Uffizi Gallery
- Piazza della Repubblica
- Parco delle Cascine
- Piazzale Michelangelo
- Palazzo Vecchio
- Del Chianti
- Piazza della Signoria
- Palacongressi Della Riviera Di Rimini
- Pitti Palace
- Boboli's Garden





