Simpson Bay Pickleball-Perfect Villa Rentals & Cottages

Find villas near Simpson Bay - We found 116 exact matches

About Simpson Bay Villa on PickleTrip

PickleTrip™ offers a wide range of luxury villas in the Simpson Bay area. These rentals are equipped with top-notch amenities such as pickleball courts or nearby facilities, private swimming pools, WiFi, hot tubs and more, to ensure a comfortable and enjoyable stay.

Whether you're traveling with a group of friends, family or planning a romantic getaway, PickleTrip™ has a variety of villa options to choose from in the Simpson Bay area. Each rental boasts its own unique style and features to suit your needs.

PickleTrip™'s villas are located in some of the most sought-after destinations around the world, including Simpson Bay. Whether you're looking for a beachfront, mountain, or seaside retreat, PickleTrip™ has a wide range of options to choose from, many of which feature pickleball courts or nearby facilities, private pools, luxurious bedrooms, and additional amenities such as tennis courts and fitness clubs.

With PickleTrip™, you can easily find and book last-minute villa rentals in Simpson Bay. Browse through our selection of villas and take advantage of special offers and deals on PickleTrip™ and other popular vacation rental platforms such as Airbnb and VRBO. Stay and play pickleball when you travel!

Show more
Show less

Frequently Asked Questions About Simpson Bay Rental Villas

There are a lot of options in Simpson Bay. If you plan on staying in the Simpson Bay area, consider making a reservation for a few nights at one of these properties as these have been rated the top Villa Rentals in Simpson Bay:

At PickleTrip, the average rental fee for standard villas in Simpson Bay is $1,141 per night. PickleTrip has a large database of quality villas near Simpson Bay that are suitable for families, a romantic getaway, or a solo trip with single or multiple bedrooms.
Yes, here are the top villas rentals in Simpson Bay that are pet friendly:See all pet-friendly vacation rentals in Simpson Bay on PickleTrip
Most of our listed villas are suitable for families. The number of rooms varies, and you can check out the complete list of villas in Simpson Bay to find what works for you.
Based on the 2025 data from our PickleTrip site, there are more than 116 private swimming pools or villas with indoor pools in or near Simpson Bay.
There are 116 villas in or near Simpson Bay that have hot tubs. The most popular places to stay with hot tubs include:See all holiday vacation rentals in Simpson Bay on PickleTrip
Most definitely! There are many luxury villas in Simpson Bay. Use our search filter to discover all of our luxury villas, and choose the one that matches your taste. Sorting by price is another way to find the most expensive villas in Simpson Bay.