
Vacation rentals in Pian dell'Isola
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Top-rated vacation rentals in Pian dell'Isola
Guests agree: these stays 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.
LocationFamilyCondition
4.99 out of 5 average rating, 113 reviews
Tuscan Country house with panoramic pool
Old stone Country House located on the top of an uncontaminated hill in a secluded atmosphere, with stunning 360° panoramas over the hills and the Arno river. Surrounded by private olives grooves, the accommodation offers an ideal mix between peaceful relaxation and opportunities for outdoor activities. With easy access to Florence (18 km) and major arts sites of Tuscan region such as Siena, San Gimignano, Pisa, Lucca, the wine Chianti area and many others landscaping or trekking attractions.
LocationFamilyBiking
4.89 out of 5 average rating, 132 reviews
Stone farmhouse, exclusive private pool
Podere Montebono is located in the hills of Reggello, just 30 kilometers from Florence. Ideal for reaching art cities and natural sites. The farmhouse is isolated on a hill, immersed in nature, surrounded by olive trees, a garden, and woods. The guest house is an independent wing of the large farmhouse on two floors: 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.
FamilyLocationQuiet
4.96 out of 5 average rating, 193 reviews
Villa la Loggia 2.0
Villa La Loggia🌱 In the heart of Tuscany, just minutes away from major cities such as Florence, Arezzo and Siena, but immersed in the countryside, in a small and quiet village, Villa La Loggia offers a beautiful and spacious apartment. • 2 bedrooms 💕with 2 private bathrooms 🚿 • 1 double sofa bed 🛋️ • 2 deck chairs + 1 umbrella in the shared pool🏖️ and all the amenities for a perfect overnight stay. Florence: 30 km/25 min Arezzo: 50km/40min Siena: 60km/60min
FamilyLocationBeach
5.0 out of 5 average rating, 45 reviews
Il Castello di 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.
LocationValueParking
4.99 out of 5 average rating, 226 reviews
Podere Tignano, 4-bedroom villa in the Chianti!
Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.
FamilyLocationBackyard
4.98 out of 5 average rating, 105 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.
ValueFamilyHospitality
4.99 out of 5 average rating, 510 reviews
Felciolina Medieval Countryfarm close to Florence
FELCIOLINA is a historic farmhouse dating back to the year 1000, surrounded by nature and boasting a large terrace. The perfect way to experience the Tuscan countryside in complete freedom and relaxation, just 30 minutes from Florence and the Chianti region. Ideal for families and groups of friends. Enjoy the views and scents of nature: you'll be greeted with fresh fruit and a fine local wine for a welcome aperitif. Book now, we look forward to seeing you!
FamilyValueBathroom
5.0 out of 5 average rating, 86 reviews
Tower Penthouse in small castle near Florence
900 year old Tower-Penthouse apartment in Chianti Villa, spacious & super-scenic historical home that combines magical atmosphere with space, light, history, convenience. (AC throughout). Painting-like 360° views of Tuscan Hills all the way to Florence; sun-filled, private grounds. Perfect location for an unforgettable family stay. Ample private property (including forest). Walking distance from village shops. Convenient location, Florence in sight.
FamilyValueBreakfast
4.96 out of 5 average rating, 138 reviews
Cabin in the woods in Tuscany with exclusive bathtub
You'll stay in a fantastic and exclusive wooden cabin nestled in a forest in a fabulous natural park in the Florentine hills. Twenty minutes from Florence and at the gates of Chianti, you can fully connect with nature while enjoying every comfort: the cabin is equipped with a large exclusive outdoor bathtub (unheated), air conditioning, kitchen, bathroom with hydromassage shower, large covered outdoor patio to dine or enjoy an aperitif from our farm.
FamilyLocationHiking
5.0 out of 5 average rating, 56 reviews
VILLA with Pool - 3 Bedrooms (each with bathroom)
In the heart of the Florentine Chianti region, a few km from the Incisa-Reggello motorway exit and the big designer Outlet The Mall, stands Villa Luisa, a recently restored residence where past and present merge into a unique mix to guarantee guests maximum comfort. The property offers ideal accommodations for group stays or large families vacations. The outdoor swimming pool is a pleasant diversion on hot summer days.
LocationFamilyCleanliness
4.91 out of 5 average rating, 99 reviews
Villa Beatrice with Exclusive Garden
This independent residence in Rignano spans two levels and is surrounded by a 2,500-square-meter private fenced park. The outdoor space is designed for autonomy and privacy, featuring a large table for al fresco dining and a six-person jacuzzi for exclusive use. Convenience is guaranteed by private parking for up to three vehicles located directly alongside the house.
LocationFamilyPets
5.0 out of 5 average rating, 9 reviewsPopular amenities for Pian dell'Isola vacation rentals
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Exclusive Tuscan Villa with Private Pool
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Luxory house with private pool
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Il Palazzaccio
LocationFamilyView
5.0 out of 5 average rating, 11 reviews
11th Century Tuscan Villa - Beautifully Renovated
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5.0 out of 5 average rating, 9 reviews
Villa with pool, wi-fi, garden, air conditioning
FamilyLocationCondition
4.85 out of 5 average rating, 53 reviewsDestinations to explore
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Stazione Santa Maria Novella
- Mugello Circuit
- Mercato Centrale
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Uffizi Gallery
- Fortezza da Basso
- Piazza della Repubblica
- Parco delle Cascine
- Del Chianti
- Piazzale Michelangelo
- Palazzo Vecchio
- Piazza della Signoria
- Pitti Palace
- Boboli's Garden
- Autodromo Enzo e Dino Ferrari
- Porta Elisa
- Stadio Artemio Franchi
- Basilica of Santa Croce
- Medici Chapel





