
Holiday rentals with a pool in Casole d'Elsa
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Casole d'Elsa
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Podere Vergianoni nestled in Chianti with a pool
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.

Podere La Castellina - No. 2 LECCETO
Stone and brick apartment inside the "Podere la Castellina" (former 13th century convent), in the magnificent natural park of Montagnola Senese. The apartment located on the ground floor can comfortably accommodate 2 people and includes: - living room with TV - kitchen with oven and electric stove - master bedroom - bathroom with large shower - private outdoor table Available to guests is a panoramic swimming pool, solarium and terrace with breathtaking views, equipped with a wood-burning oven and barbecue.

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.

Loggia 1 in farmhouse with shared pool
Apartment for 2 people in the Santa Lucia farmhouse (farmhouse DIVIDED IN 7 APARTMENTS) in the Crete Senesi, 10 km from Siena. Located on the second floor with a private table in front of the windows of the entrance loggia. It consists of a double bedroom (two single beds joined to form a double bed), a bathroom with shower and a living room with functional kitchen. Outdoor space with table and chairs available on the ground floor. AIR CONDITIONING in the room FOR A FEE according to consumption.

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.

Apartment in Chianti at Mulino dell'Argenna
The apartment of the Roses is located inside the Mulino dell'Argenna guest house. The property was completely restored in 2015. It is an ancient stone mill dating back to 1400, built along the course of the Borro dell'Argenna. The Mill is an enchanting place, surrounded by the greenery of the forest, with a beautiful one-hectare park and a large swimming pool. An ideal place to spend your days in Tuscany in maximum privacy, in full contact with nature.

Peaceful modern eco house in the Tuscan hills
A thoughtfully designed low impact house in a rural setting, away from the crowds between Florence and Siena. This is an annex building on a family run olive farm surrounded by unspoilt Tuscan countryside. Plenty of shaded outdoor space, barbecue, stunning views, fantastic sunsets and big night skies. We are an official agriturismo, there are two other independent apartments on the olive farm that share the pool and private parking.

Mini country house Podere Scorno with pool
Piccola e accogliente casa di campagna ideale per coppie, su una collina della campagna senese. Edificio in stile toscano in pietra, con una storia secolare. La proprietà è stata comprata e ristrutturata a fine anni '90. Con un ampio giardino con piscina, frutteto, oliveto, vigna e orto, per gli amanti del verde. La piscina è aperta da metà maggio a fine settembre. Non accettiamo animali domestici.

Girasoli apartment with pool in farmhouse
Going up 17 steps you will be hosted in an apartment located on the second floor with a separate entrance. Consisting of a kitchen, bathroom with shower and double bedroom with 2 windows overlooking the village of Casole d'Elsa and the swimming pool. Mosquito nets on the windows. Small terrace shared with the Manuela apartment TO BE PAID - ACCOMMODATION TAX €1 per person

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.

La Pieve - the house next to the church
To the right of the Argenina church, after which it is named, it has the persuasive look of its 2 small arches facing west. Perhaps it was once the parish priest's house, or the one where cooking was done in the large wood-burning oven, who knows?
Popular amenities for Casole d'Elsa rentals with a pool
House rentals with a pool

StageROOM03 - Idyllic Chianti cottage near Siena

Cercis - La Palmierina

Ancient Barn in Chianti with Pool

Villa Casabella near Siena

“il colle” nice house surrounded by vineyard

Charming estate with views. A/C in the bedrooms

Explore Chianti from a Charming Stone House

Leonardo - Chianti/Siena, Florence, San Gimignano.
Apartment rentals with a pool

Chianti La Pruneta, Michelangelo apartment.

Apartment in a villa with pool

Stone House in Chianti with pool and parking

Adalberto Apartment inside the Manor of Fulignano

Lornano Winery Farm - Villa ''Trebbiano''

💜 "Gaia" at Podere Le Fontanelle

House between Firenze, Arezzo, chianti e Siena

Vintage Residence with Pool in Chianti
Home rentals with a private pool

Sole by Interhome

Stone House with Exclusive Pool Codilungo in Chianti

Metallo by Interhome

Valle di Sotto Farmhouse by Interhome

Historic home with exclusive pool

Charming villa in the Chianti hills

Villa il Palagio in the Tuscan countryside

Casa Luigi Suite with exclusive pool
Destinations to explore
- Santa Maria Novella
- Cathedral of Santa Maria del Fiore
- Strozzi Palace
- Mercato Centrale
- Santa Maria Novella
- Ponte Vecchio
- Great Synagogue of Florence
- Basilica Di San Miniato A Monte
- Marina di Cecina
- Del Chianti
- Basilica of Santa Maria Novella
- Pisa Centrale Railway Station
- Cala Violina
- Spiagge Bianche
- Porta Elisa
- Piazza del Duomo (Pisa)
- Fortezza da Basso
- Uffizi Gallery
- Piazza della Repubblica
- Piazzale Michelangelo
- Pitti Palace
- Parco delle Cascine
- Piazza della Signoria
- Mugello Circuit




