
Vacation rentals with a pool in Casole d'Elsa
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Quick stats about vacation rentals with a pool in Casole d'Elsa

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Explore 10 vacation rentals in Casole d'Elsa

Nightly prices starting at
Casole d'Elsa vacation rentals start at G$14,634 GYD per night before taxes and fees

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Over 270 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!
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.

La Casetta
“La Casetta”, is a new restored enchanting apartment immersed in the splendid Tuscan countryside, only 2 kms from the medieval village of Casole d'Elsa in Siena province. Situated in a old farm complex with private entrance, large private garden, and access to the communal swimming pool. Furnished with utmost care down to the finest detail. Ideal for a relaxing, regenerative week with family or friends, emerged in an uncontaminated natural landscape. Possibility of excursions on foot and by bicycle in an evocative natural setting of lush forests and gentle hills of rare beauty. One can enjoy local dishes of the wonderful Tuscan tradition in many of the nearby restaurants or organize splendid home-cooked meals with the barbecue in the garden. Ideally situated for visits the many nearby towns and cities rich in art and beauty: 30 mins to Siena, 1 hour to Florence ,30 mins to San Gimignano and Volterra, 45 mins to the Chianti area. La Casetta is the ideal place to regenerate your body and mind. (We are the same owners of “La Senesina" apartment near Siena check out our rating on the web! Our 5 stars ratings are your warranty for a great stunning vacation)
4.93 out of 5 average rating, 197 reviews
Infinity pool in Chianti 1
Our house is a part of a stone farmhouse completely independent from the rest of the adjacent property. Arranged on three floors, on the ground floor there is a large entrance hall, a large living room with fireplace, a bedroom with 1 double bed and a bathroom with window. On the first floor there are two bedrooms (2 +2 beds) with a bathroom with window. In the basement, at garden level, there is the kitchen and the dining room. From the kitchen you access the outside where you will find an area for outdoor dining with a large dining table under a pergola. You then go down towards the garden with barbecue area.
5.0 out of 5 average rating, 143 reviews
Podere Vergianoni immerso nelChianti con piscina
Podere Vergianoni è un antica proprietà del 1600 a gestione familiare situato nelle splendide colline del Chianti in Toscana con la possibilità di organizzare navetta privata e esperienze locali direttamente con la nostra famiglia . L'appartamento è disponibile per 2 adulti con possibilità aggiunta divano letto per 2 bambini sotto i 12 anni . Nel grande cortile esterno troverete una piscina a sale con area relax su terrazza panoramica con vista su castello e vigneti con tramonti unici.
5.0 out of 5 average rating, 352 reviews
Palazzo Monaci - Piscina nelle crete Senesi
Benvenuti a Palazzo Monaci ! Un' oasi di natura e bellezza unica, nel cuore delle Crete Senesi, in Toscana. Un residence con piscina e vista mozzafiato sulle crete senesi. Perfetta per coppie o famiglie in cerca di una vacanza rilassante. La posizione è perfetta per esplorare le zone limitrofe. Potrete fare escursioni nella campagna toscana, visitare i borghi medievali caratteristici, assaggiare i vini locali prelibati e immergervi nella cultura e nella storia di questa affascinante regione.
4.96 out of 5 average rating, 142 reviews
Manuela appartamento con piscina in agriturismo
Sarete ospitati in un appartamento situato al primo piano ,con ingresso indipendente e vi si accede salendo 17 scalini .E' composto da una cucina , due camere, una matrimoniale e una con 2 letti singoli , un bagno con doccia zanzariere alle finestre. Piccolo balcone condiviso con l'appartamento GIRASOLI. È OBBLIGATORIO PAGARE LA TASSA DI SOGGIORNO AL CHECK IN 1€ a persona per i primi 5 giorni . Riscaldamento consentito dal 1^ novembre al 15 aprile (Legge regionale)€ 20,00 al giorno
4.97 out of 5 average rating, 119 reviews
Podere La Castellina - N°1 COTTAGE
Cottage indipendente in pietre e mattoni all'interno del "Podere la Castellina" (ex convento 13° secolo), nel magnifico parco naturale della Montagnola Senese. Il cottage può ospitare comodamente 5 persone e comprende: - ampio soggiorno con tv e camino - cucina abitabile con forno - camera matrimoniale - camera con tre letti singoli - bagno con doccia A disposizione degli ospiti piscina panoramica, solarium e terrazza con vista mozzafiato, dotata di forno a legna e barbecue.
4.97 out of 5 average rating, 162 reviews
Agriturismo La Villa - L'Olivo, Pool & Hot Tub
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.
4.98 out of 5 average rating, 241 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.
4.99 out of 5 average rating, 227 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.
4.98 out of 5 average rating, 107 reviews
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.
4.99 out of 5 average rating, 481 reviews
Cercis - La Palmierina
E' un appartamento facente parte di una tenuta completamente recintata di 60 ettari di natura incontaminata: più di 1000 ulivi, innumerevoli cipressi e foreste profumate creano un ambiente idilliaco per coloro che ricercano tranquillità e silenzi. La tenuta Palmierina è in prossimità di Castelfalfi (un vero gioiello di architettura medievale) e nelle vicinanze di Firenze (50 Km), Siena (50 Km), Pisa (50 Km). Nelle vicinanze ci sono due campi da golf.
4.96 out of 5 average rating, 147 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.
4.95 out of 5 average rating, 222 reviewsPopular amenities for Casole d'Elsa rentals with a pool
House rentals with a pool

Relax e charme tra le colline del chianti
4.99 out of 5 average rating, 115 reviews
Podere Collina
4.93 out of 5 average rating, 204 reviews
Open space immerso nella natura
4.96 out of 5 average rating, 137 reviews
Explore Chianti from a Charming Stone House
4.98 out of 5 average rating, 123 reviews
Private Chianti Cottage, Garden & Vineyard Views
4.99 out of 5 average rating, 138 reviews
SuiteLouise.pool, Hot Tub,homeGym & private Garden
4.91 out of 5 average rating, 128 reviews
Agriturismo Casa Giulia di Sopra
4.95 out of 5 average rating, 106 reviews
Ancient Barn in Chianti with Pool
4.89 out of 5 average rating, 125 reviewsCondo rentals with a pool

House between Firenze, Arezzo, chianti e Siena
4.84 out of 5 average rating, 302 reviews
Apt.Panzanello-Panzano in Chianti
4.96 out of 5 average rating, 282 reviews
Scenic Stilish Country
4.88 out of 5 average rating, 137 reviews
Adalberto Apartment inside the Manor of Fulignano
4.95 out of 5 average rating, 152 reviews
Casa Luna-Splendida vista piscina e natura toscana
4.97 out of 5 average rating, 151 reviews
Relax Tra Le Vigne Del Chianti-IlVillinoFarmhouse
4.81 out of 5 average rating, 366 reviews
Poggiolieto Studio - on hills 10' from city center
4.85 out of 5 average rating, 214 reviews
[Ninfea] Ancient House in Tuscany
4.92 out of 5 average rating, 121 reviewsHome rentals with a private pool

Stone House with Exclusive Pool Codilungo in Chianti
4.98 out of 5 average rating, 218 reviews
TREEhouse/casaBARTHEL
4.88 out of 5 average rating, 821 reviews
Suite Casa Luigi con piscina esclusiva
4.95 out of 5 average rating, 122 reviews
Luxe Estate nr Florence. Vineyard, Pool, Privacy
4.97 out of 5 average rating, 73 reviewsHistoric villa x8 with exclusive pool
4.87 out of 5 average rating, 46 reviews
Villa Fonteintanata Ground floor
4.8 out of 5 average rating, 76 reviewsDestinations to explore
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Piazza del Duomo (Pisa)
- Basilica of Santa Maria Novella
- Stazione Santa Maria Novella
- Cala Violina
- Parco Regionale Della Maremma
- Mercato Centrale
- Mugello Circuit
- Spiagge Bianche
- Pisa Centrale Railway Station
- Fortezza da Basso
- Uffizi Gallery
- Gulf of Baratti
- Piazza della Repubblica
- Piazzale Michelangelo
- Palazzo Vecchio
- Del Chianti
- Parco delle Cascine
- Piazza della Signoria
- Pitti Palace
- Boboli's Garden





