
Holiday rentals with a pool in Gaiole in Chianti
Find and book unique homes with a pool on Airbnb
Quick stats about holiday rentals with a pool in Gaiole in Chianti

Total holiday rentals
Explore 10 holiday rentals in Gaiole in Chianti

Nightly prices starting at
Gaiole in Chianti holiday rentals start at $140 SGD per night before taxes and fees

Verified guest reviews
Over 150 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Wifi availability
10 of Gaiole in Chianti holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Gaiole in Chianti rentals

4.7 Average rating
Gaiole in Chianti stays receive an average rating of 4.7 out of 5 from guests
Top-rated rentals with a pool in Gaiole in Chianti
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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
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
Villa Padronale - IlVillinoFarmhouse
Intero piano superiore della Villa Padronale appena ristrutturata in stile tradizionale toscano.Gli alti soffitti con le travi a vista rendono il posto accogliente e perfetto per famiglie o gruppi di amici.Nella casa si trovano due grandi camini(in salotto e cucina)funzionali.Alloggio privato, non condiviso. La casa ha una ampia terrazza coperta,giardino con divani,bbq,firepit,parking privato. La piscina tra gli ulivi e i vigneti e' ideale per il relax ha un accesso privato alla zona condivisa
4.93 out of 5 average rating, 256 reviews
Charming estate with views. A/C in the bedrooms
The estate finely restored in 2016 is accessorized with all the confort you need for an holiday dedicated to the relax or to excursions The Breathtaking view on the Chianti Classico's vineyards give to the estate a unique feature perfect for a romantic holiday, small group of friend or a little family. The estate is provided of external Jacuzzi, private garden and we can arrange for you bike or hike excursions. The Village of Gaiole in Chianti is just 5 minutes away by car.
4.86 out of 5 average rating, 296 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
Villa Capanna, Private Pool, Breathtaking Views
Ancient restored barn with up to 6 bedrooms and 6 bathrooms, immersed in a historic wine estate, just 6 km from Siena. One of the most beautiful views that the Tuscan panorama can offer, airconditioned bedrooms, exclusive swimming pool, large triple garden, BBQ, poolside table, terrace to enjoy the sunset over the medieval towers on the horizon while sipping the organic wines of the estate, fireplace, parking free, WI-FI internet.
4.89 out of 5 average rating, 309 reviews
La Loggia. House with pool and stunning view
LA LOGGIA House, renovated in 2015, is a large independent apartment, ideal to be rented by those who love nature, tranquility and peace of these uncontaminated places immersed in nature. The apartment is characterized by a huge window overlooking the valley where you can enjoy one of the most spectacular views in the region. The view that can be admired from LA LOGGIA spans more than 60 km on the Chianti and the Crete Senesi.
4.99 out of 5 average rating, 104 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, 221 reviews
PIERFANTINI private Chianti house ♿️ 🏊♂️ 🐶
Pierfantini is a rustic farmhouse. It is located on a hill in the middle of a natural park. Isolated from the vitta, the nearest town is the medieval village of San Gusmè. The house is renovated and the ground floor adapted for disabled people or wheelchair users There are three apartments but I never rent them separately. The house rent is for all the property
4.91 out of 5 average rating, 100 reviews
Comfort Apartment tra i vigneti del Chianti
Appartamento al piano superiore della struttura caratterizzato da una vista meravigliosa sulle colline del Chianti, uliveti o sul patio. Ristrutturato mantenendo il fascino delle loro antiche mura ma aggiungendo ogni comfort. Comprende soggiorno, angolo cottura, una camera da letto matrimoniale, un bagno privato con doccia, aria condizionata.
4.93 out of 5 average rating, 455 reviewsPopular amenities for Gaiole in Chianti rentals with a pool
House rentals with a pool

Villa Lolù with private heated swimming-pool
4.98 out of 5 average rating, 160 reviews
Relax e charme tra le colline del chianti
4.99 out of 5 average rating, 115 reviews
Private Chianti Cottage, Garden & Vineyard Views
4.99 out of 5 average rating, 138 reviews
Infinity pool in Chianti 1
5.0 out of 5 average rating, 143 reviews
Agriturismo Casa Giulia di Sopra
4.95 out of 5 average rating, 106 reviews
Infinity view
4.88 out of 5 average rating, 204 reviews
Borgo Ripostena – n. 9 Frantoio
4.94 out of 5 average rating, 118 reviews
House Rigomagno Siena
4.96 out of 5 average rating, 125 reviewsApartment rentals with a pool

Apt.Panzanello-Panzano in Chianti
4.96 out of 5 average rating, 282 reviews
La Casetta
4.93 out of 5 average rating, 197 reviews
Poggiolieto Studio - on hills 10' from city center
4.85 out of 5 average rating, 214 reviews
Adalberto Apartment inside the Manor of Fulignano
4.95 out of 5 average rating, 152 reviews
Residenza Vintage con Piscina nel Chianti
4.96 out of 5 average rating, 148 reviews
Villa La Loggia 1.0
4.97 out of 5 average rating, 101 reviews
Scenic Stilish Country
4.88 out of 5 average rating, 137 reviews
Ginestra: Private Pool Overlooking Florence
4.95 out of 5 average rating, 117 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
Esplora la natura al centro di Vigneti Chianti
4.97 out of 5 average rating, 265 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 reviewsDestinations to explore
- Lake Trasimeno
- 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
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mercato Centrale
- Fortezza da Basso
- Uffizi Gallery
- Piazza della Repubblica
- Parco delle Cascine
- Piazzale Michelangelo
- Palazzo Vecchio
- Del Chianti
- Piazza della Signoria
- Pitti Palace
- Boboli's Garden
- Mount Amiata
- Stadio Artemio Franchi
- Medici Chapel
- Basilica of Santa Croce





