Siesta Key rentals with pool

Book one of our 4,889 vacation rentals with a pool and start planning your trip to Siesta Key. Whether you’re going to stay in Siesta Key Village, Aloha Kai, Bay Isle or another in-demand area, you’ll find the ideal poolside escape on Vrbo.

Plunge pool or rooftop pool, sprawling or compact, peak season or low season — how much you’ll pay for your Siesta Key stay is influenced by all sorts of factors. But one thing that doesn’t change? Our vacation rentals with a pool are something special. To find a place that fits your budget, narrow your search results by your maximum price. You can also use our “Discounts” filter to find vacation rentals that offer discounts for longer stays.

First, consider if you prefer the buzz of high season or the quieter vibe of low season. Also think about things like the weather conditions and what you want to do in Siesta Key. Whenever you go, we’ll help you find a vacation rental with a pool where you can finish your day with a swim.

Houses with beach views are just one of the types of vacation rentals with a pool available in Siesta Key. If you’re searching for stays that promise a splashing good time on top of outlooks worth bragging about, you’ll find them on Vrbo.

Stay in a vacation rental with a private pool in Siesta Key and go for a morning swim or late-night soak — or whenever the mood strikes! You can keep your kids easily occupied, and you’ll never have to worry about sharing with other guests. Use our “Private pool” filter to find your ideal vacation rental.

Fun times in Siesta Key await for all ages when you stay at a vacation home rental with a pool. As well as discovering top attractions like Siesta Key Beach, Mote Marine Laboratory & Aquarium and Sarasota Jungle Gardens, you’ll be able to spend your downtime practicing cannonballs.

Booking your vacation rental with a pool with Vrbo means you get the entire place to yourselves — your own private oasis to have a splashing good time without any distractions from others. Plus, our easy payment and cancellation policies give you the freedom to change your plans if you need to. And if you join our free One Key™ rewards program, you’ll be able to earn OneKeyCash™* on eligible bookings on Vrbo, Expedia and Hotels.com. *OneKeyCash disclaimer - OneKeyCash is not redeemable for cash and can only be used on Hotels.com, Expedia and Vrbo.