
Vacation rentals with a pool in Casole d'Elsa
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Top-rated rentals with a pool in Casole d'Elsa
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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.

Farmhouse with pool in Chianti
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 on the first floor of the main farmhouse, with independent access and garden with trees. The rustic furnishings in the classic Tuscan style, with wooden beam ceilings and terracotta floors give a characteristic touch to the environment.

Belforti Tower
Torre dei Belforti is the perfect place for people who love beauty, nature and art. Sleeping at the Tower is like traveling trough the time, between knights and princesses. The wonder of this place is enriched by a big garden, with its swimming pool, the cypresses alleys and the olive trees. The village is also a magic place well preserved and still alive. We are Emilia and Luca, we live here and our mission is to give the best to our guests, to fully enjoy this marvelous place.

Manuela apartment with pool in farmhouse
You will be staying in an apartment located on the second floor ,with an independent entrance and accessed by climbing 17 steps. It consists of a kitchen/ living room with fireplace, overlooking all the other rooms . It has two bedrooms, one double and one with 2 single beds, a bathroom with a shower, and mosquito nets on the windows. Before entering, there is a small balcony shared with the SUNFLOWERS apartment. Heating must be requested upon arrival for €20.00 per day

La Villa Farmhouse - Chestnut, Pool & Garden
Immersed in the green woods of the Senese hills, the beating heart of Tuscany, lies the La Villa estate. Characterized by a large park with swimming pool, gazebo, barbecue area and relaxation area, the farmhouse stands out for its strong link with the Tuscan tradition: a suggestive path will guide you to discover the woods surrounding the farm among olive trees and fields of lavender in bloom, among which you can forget the passage of time and enjoy the charms of nature.

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.

Wonderful Loft in Villa with Pool in Chianti
Located on the second and top floor of the "Suites le Valline" complex, the Piazzale Michelangelo loft offers a unique style in an ideal location for exploring Tuscany, a 15-minute drive from Florence and San Casciano! Treat yourself to a moment of relaxation on the beautiful panoramic terrace overlooking Florence, or cool off in the bio pool among the olive trees... and remember that all the vegetables from the Valline vegetable garden are at your disposal!

The Castle of Ferrano - Castle in Tuscany
Try the experience to stay in a real Castle! Il Castello di Ferrano offers to his hosts the chance of doing an unforgettable experiece:you will be the only guests in the castle and everythig will be for you (private pool from June to September, gardens ecc.)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.

Tenuta Chiudendone in Tuscany
Great place in the middle of Tuscan Hills, you will be sorrounded by nature but close to all the beautiful cities of Tuscany! We rent two apartments, one on the upper floor called Balla and one on the ground floor called Modigliani. Tell us which one you prefer. PLEASE NOTE YOU WILL NEED A CAR DURING YOUR STAY.

Countryside Dream farm in Tuscany
Great place in the middle of Tuscan Hills, you will be surrounded by nature but close to all the beautiful cities of Tuscany! We rent two apartments, one on the upper floor called Balla and one on the ground floor called Modigliani. Tell us which one you prefer. PLEASE NOTE YOU WILL NEED A CAR DURING YOUR STAY.

Podere Guidi
Apartment in a panoramic villa between Florence and Siena in the heart of Chianti in a charming village. The swimming pool is open from May 1st to September 30th, from 9 a.m. to 1 p.m. with exclusive use for guests during this time. For different needs, ask the host.
Popular amenities for Casole d'Elsa rentals with a pool
House rentals with a pool

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Explore Chianti from a Charming Stone House

Leonardo - Chianti/Siena, Firenze, San Gimignano.

Collina Power

Casa di Lyndall - Entire house with exclusive pool

Gaiole in Chianti Poggio Casabianca
Condo rentals with a pool

Chianti La Pruneta, Michelangelo apartment.

Loggiato 3 apartment in Tuscany near Siena

Lornano Winery Farm - ''Trebbiano'' villa

House between Firenze, Arezzo, chianti e Siena

Vintage apartment with swimming pool in Chianti

PODERE VAL DI GALLO CHIANTI SIENA

Garden & SPA -FlorArt Boutique Apartment

Tenuta di Pomine Certaldo (Fi) Edera Apartment
Home rentals with a private pool

Sole by Interhome

Podere Vignali by Interhome

Pino di Sopra, by Interhome

Historic home with exclusive pool

Villa Alba by Interhome

Podere San Lorenzo by Interhome

Villa il Palagio in the Tuscan countryside

Casa 360 by Interhome
Quick stats about vacation rentals with a pool in Casole d'Elsa

Total vacation rentals
Explore 10 vacation rentals in Casole d'Elsa

Nightly prices starting at
Casole d'Elsa vacation rentals start at G$14,656 GYD per night before taxes and fees

Verified guest reviews
Over 260 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Wi-Fi availability
10 of Casole d'Elsa vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Casole d'Elsa rentals

5 Average rating
Casole d'Elsa stays are highly rated by guests—averaging 5 out of 5!
Destinations to explore
- Santa Maria Novella
- Mercato Centrale
- Piazzale Michelangelo
- Cathedral of Santa Maria del Fiore
- Basilica of Santa Maria Novella
- Spiagge Bianche
- Ponte Vecchio
- Cala Violina
- Uffizi Gallery
- Piazza del Duomo (Pisa)
- Fortezza da Basso
- Gulf of Baratti
- Piazza della Repubblica
- Pitti Palace
- Parco delle Cascine
- The Boboli Gardens
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Spiaggia Libera
- Kite Beach Fiumara
- Avignonesi Winery Fattoria Le Capezzine
- Medici Chapel
- Palazzo Vecchio
- Stadio Artemio Franchi
- Spiaggia Marina di Cecina




