
Vacation rentals with a pool in Cavriglia
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Cavriglia
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Podere Vergianoni immerso nelChianti con piscina
Podere Vergianoni is an ancient and authentic farmhouse dating back to the 17th century located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional local style of old Tuscany: ancient wooden beams, terracotta floors, and unique furniture. In the large outdoor courtyard, you'll find a large swimming pool on a panoramic terrace at your disposal, overlooking the valley with breathtaking views of vineyards and olive groves, where you can enjoy spectacular sunsets.

Palazzo Monaci - Pool in the Crete Senesi
Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

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

Private Chianti Cottage, Garden & Vineyard Views
Set in a picturesque hamlet, overlooking the Chianti hills, this charming country house is just 10 minutes from Siena and Castellina in Chianti. Recently renovated, it blends authentic Tuscan charm with modern comforts. The house features two bedrooms, two bathrooms, a cozy living area and a fully equipped kitchen with a dishwasher, two fridges, and a washing machine. Outside, enjoy a beautiful garden and relax in the outdoor marble hot tub, soaking in the breathtaking views.

Villa La Doccia, Greve in Chianti
Villa La Doccia is located about an 8-minute drive from the center of Greve in Chianti, in the area of Casole, in the heart of the beautiful Chianti countryside. The villa is located in a quiet and peaceful area, on a small farm surrounded by vineyards and olive groves, where guests can enjoy nature and the typical Tuscan landscapes. The location is ideal for those who want to relax in the countryside but at the same time be close to the center of Greve in Chianti.

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.

Infinity pool in Chianti area
On the Chianti hills, portion of an old stone farmhouse from the 1800s, located in S. Filippo, a small hamlet of Barberino Tavarnelle, halfway between Florence and Siena, a 30-minute drive from Florence airport, 1 hour from Pisa airport. Three bedrooms, two bathrooms, large living room with fireplace, eat-in kitchen and dining room. Magnificent view of the hills from every window! Beautiful infinity pool with whirlpool area, unheated and open from April to October.

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.

Chianti La Pruneta, Caravaggio apartment
A Jewel of an apartment in the heart of Tuscany. Stunning views over cypress and olive trees. Beamed ceilings, marble floors, all recently refurbished. The apartment includes an antique wooden bed and Venetian lights. You can relax and eat 'Al Fresco' in your own private garden where sun loungers a BBQ and a shaded eating area are all provided, enjoying the beautiful views.

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.

Villa Poggio in Mandria in Chianti
Villa Poggio a Mandria is the gateway to the Chianti; it is a good base to reach the most beautiful art cities of Tuscany (Arezzo, Florence, Siena, San Gimignano, Volterra) in about one hour time. On the surrounding hills there are medieval villages, which offer visitors a charming atmosphere of the past and the opportunity to take walks in an unspoiled countryside.
Popular amenities for Cavriglia rentals with a pool
House rentals with a pool

Cercis - La Palmierina

Ancient Barn in Chianti with Pool

Private Cottage with Plunge Pool in Tuscan Estate

Private villa/swimming pool in Tuscany

Romantic Tuscan Retreat • Pool&Views

Explore Chianti from a Charming Stone House

Villa Eroica

Antico Borgo Ripostena – n. 8 Old House
Condo rentals with a pool

Loggiato 3 apartment in Tuscany near Siena

Romantic Residence with Pool in Chianti

Stone House in Chianti with pool and parking

Fattoria Lornano Winery- villa ''Trebbiano''

Scenic Stilish Country

Casa Rebecca with a small private pool

💜 "Gaia" at Podere Le Fontanelle

Poggiolieto Suite - on hills 10' from city center
Home rentals with a private pool

Stone House with Exclusive Pool Codilungo in Chianti

Esplora la natura al centro di Vigneti Chianti

Historic home with exclusive pool

Villa il Palagio in the Tuscan countryside

Casa Luigi Suite with exclusive pool
Wp Relais Villa Vignalunga

Bliss out in Historic Farmhouse on Organic Wine Estate with Tennis and Pool

TREEhouse / casaBARTHEL
Quick stats about vacation rentals with a pool in Cavriglia

Total vacation rentals
Explore 190 vacation rentals in Cavriglia

Nightly prices starting at
Cavriglia vacation rentals start at G$8,367 GYD per night before taxes and fees

Verified guest reviews
Over 3,180 verified reviews to help you choose

Family-friendly vacation rentals
120 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 110 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
180 of Cavriglia vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Cavriglia rentals

4.7 Average rating
Cavriglia stays receive an average rating of 4.7 out of 5 from guests
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- Santa Maria Novella
- Cathedral of Santa Maria del Fiore
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- Lake Trasimeno
- Ponte Vecchio
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- Del Chianti
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- Strozzi Palace
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- Uffizi Gallery
- Piazza della Repubblica
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- Pitti Palace
- Parco delle Cascine
- Mugello Circuit
- Palazzo Vecchio
- Boboli's Garden
- Basilica Di San Miniato A Monte
- Avignonesi Winery Fattoria Le Capezzine
- Eremo Di Camaldoli
- Medici Chapel
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