Windward Cay rentals with pool

We found 1,217 rentals with pool — enter your dates for availability

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  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

Are there any holiday rentals with a pool in Windward Cay?
Windward Cay has 1,217 holiday rentals with a pool, so be sure to pack your swimsuit. Eager to do some sightseeing? Old Town, Fun Spot America and Medieval Times are some major attractions within close reach.
How much does it cost to stay in a holiday rental with a pool in Windward Cay?
If you'd love to grab a deal on your holiday rental with a pool, our filters are there to help. After finishing your initial search, narrow down your results according to your preferences, including location, price and features and amenities. We've got properties in Windward Cay to suit any budget, so make the most of our filters to find the perfect stay.
When is the best time to book a holiday rental with a pool in Windward Cay?
You'll have a splashing great time no matter when you visit Windward Cay. If you want to experience this destination at its most energetic, March is when the majority of Stayz guests book a holiday rental with a pool here.
What holiday rentals with a pool in Windward Cay have nice views?
Stayz makes it simple to find a stay with impressive views and access to poolside relaxation. Just use our "Location" filter to narrow down the type of area you prefer to be in, and the scenery you like to gaze out at, while browsing for holiday rentals with a pool in Windward Cay.
Are there holiday rentals with a private pool in Windward Cay?
From poolside gatherings to late-night swims under the stars, a holiday rental with a private pool offers plenty of possibilities for relaxation and fun. If you're headed for Windward Cay, use our "Private pool" filter to find holiday homes that come with this luxurious extra.
What are the top things to do in Windward Cay?
With a terrific holiday home rental with a pool to wind down in and must-see attractions like Old Town close by, your Windward Cay trip is going to be awesome. Stay in this neighbourhood and you'll also enjoy easy access to other family-friendly sights like Fun Spot America and Medieval Times.
Why should I book my holiday rental with a pool with Stayz?
When you opt for a Stayz holiday rental with a pool, the only people you have to share your space with are whoever you bring with you. It's only you and your closest companions with the whole property to yourselves having a splashing good time. Our flexible cancellation policies also mean you can book your rental house with confidence should your plans change.