Top Weymouth rentals with pool or private pool - England

Explore Weymouth rentals with pools

Luxury mobile home with spectacular sea views.

Sleeps 6 · 2 bedrooms · 1 bathroom

Harbour's Edge - Beautiful cottage located directly on Weymouth's harbourside.

Sleeps 4 · 2 bedrooms

Top rated rentals with pools - Weymouth

Premier Host

What a glorious place!

Beautiful place, so well appointed and thoughtfully kitted out that it made our little holiday just perfect. Cracking views of the Fleet and Portland - great for bird watching and sunsets. I really hope I can stay again one day.

Eleanor R.

Stayed Apr 2025

Dorset Alpaca Shepherd's Hut was built to our specification, and is spacious!

Premier Host

ok for a short stay

Cute and a bit of a novelty, though lack of floor space means suitcases are a nuisance. There is plenty of drawer space under the bed if you want to unpack your stuff. The bathroom hut is lovely inside but the novelty of going from the living hut to the bathroom hut wears off fairly quickly. The charcoal fire/bbq was unusable. The owners were very friendly and it is a beautiful property.

neil and kaye j.

Stayed Apr 2025

Premier Host

Stunning Home.

A beautiful house, in a lovely location with an amazing view. Loved everything about this house, which truly felt like a home. Highly recommend!

Amanda B.

Stayed May 2024

Fantastic garden!

A great, well maintained cottage but the real highlight was the massive, private garden. Perfect for a picnic and prosecco in the evening. Would definitely stay here again, the welcome book was also incredibly comprehensive - much to do in the surrounding area!

Elyse J.

Stayed June 2023

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Frequently asked questions

Are there any holiday homes with a pool in Weymouth?

Take your pick of 16 holiday homes with a pool in Weymouth that offer all the privacy, amenities and space you need for a splashing good time. Consider houses in popular areas such as Overcombe, Preston and Winfrith Newburgh.

How much does it cost to stay in a holiday home with a pool in Weymouth?

If you'd love to grab a deal on your holiday home with a pool, our filters are here to help. After finishing your initial search, narrow down your results according to your preferences, including location, total price and features and amenities. We've got properties in Weymouth to suit any budget, so make the most of our filters to find your perfect stay.

When is the best time to book a holiday home with a pool in Weymouth?

If you want to experience Weymouth at a busy time, go in July. This is when average temperatures range from 15ºC (15ºC) to 18ºC (18ºC), and when most guests kick back in a holiday home with a pool here. Of course, there are other great times to travel to this part of Jurassic Coast, so do some homework into which month or season works best with your plans.

What holiday homes with a pool in Weymouth have nice views?

To make your trip to Weymouth even more special, book one of Stayz's holiday homes with a pool — and a beautiful view to top it off. Following your initial search, use our intuitive filters to tailor your results by area and the vistas you want to take in.