Every week in my newsletter I send 5 to 10 new addresses that I spotted. To give you a taste for it, I list those with pools below. The newsletter include a wider variety of accommodations: inns, nice B&B without pools, smaller houses to rent, tree houses, lodges etc.. and the occasional foray outside of Europe. They are a good source of inspiration for your next chic escape.
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7 dammusi you can rent on the Italian island of Pantelleria
https://thespaces.com/dammusi-you-can-rent-pantelleria-italy/

Domed homes are unique to ‘the black pearl of the Mediterranean’, Pantelleria an island sixty miles southwest of Sicily, and thirty miles east of Tunisia, on the brink between Europe and Africa. This article lists 7 villas that you can rent for either a small family or a whole group.
Le Mas de Chabran, Provence

A beautiful luxury old mas in the Alpilles, one of the most beautiful areas of Provence. Prices for the whole house are way too high but you can stay in the bedrooms out of season and enjoy the wonderful decor and setting. There’s a pool of course and a nice view of the Baux de Provence. From 300 Euros
Masseria Calderisi, Puglia
https://fromthepoolside.com/masseria-calderisi

On the edge of the coast , the 17th-century farm has been revived as a charming boutique hotel, surrounded by 24 acres of olive groves, citrus and almond trees, herb gardens and vegetable beds. The hotel has a private beach and their shuttle can also take you to many other nice beaches. From £350.
Casa 1876, Family Mediterranean Rental House Portugal, Algarve

Casa 1876, boutique vacation home in Algarve, South Portugal. Unique rental house in Sao Bras de Alportel. Boho lifestyle, bare foot luxury & mediterranean vibes in a rural olive groves area with serene sea views.
Borgo Eibn – Mountain Lodge

A boutique hotel, spa & restaurant with chalet style accommodation. 15 rooms in Sauris, the “carnic alps” in Italy. There is also a wellness center with an indoor pool and a finish sauna.
Mezzatorre Hotel & Thermal SPA, Ischia
https://fromthepoolside.com/mezzatorre-booking
Just one hour by boat 18 from Naples, and a ferry ride from glamorous Capri, Ischia is an island that saw the favours of Luciano Visconti. Proudly surveying the seaside vistas from a rocky headland, the hotel rests on the ruins of a 16th-century watchtower, surrounded by 17 acres of pine wood forest. The island’s thermal hot springs, with healing properties, flow into three water therapy pools, while volcanic mud is used in spa treatments. From 440 Euros.
Saint Victor la Grand Maison
https://saintvictorlagrandmaison.com/en/

A French castle like in your dreams! The estate offers several cottages to rent and bedrooms in the chateau. There is also a pool in the vast park. The estate has been restored with care… deeply comfortable rooms in warm reds, blues and pastels with antiques, soft fabrics, gilt portraits, book-lined walls. Dinners are served either in the “petite salle à manger bu” or in the guard’s room for large tables… or else you can saunter down past the pool and picnic on homemade pâté under the 400 year old oak by the river.
Loire Valley Lodges
https://fromthepoolside.com/loire-valley-lodges-booking

18 lodges, hidden deep in the forest in Esvres-sur-Indre, near Tours. Alongside the tasteful decoration, the lodges boast a clear view, with large bay windows looking out on the trees and the nature all around. Each lodge features a work by an artist. A 20m long swimming pool is available from April to September, from 9am to 8pm.