Siesta Key vacation rentals with pools

We found 13 vacation rentals waiting for you.

Find your ultimate splash pad

From plunge pools for a quick dip to infinity pools with a view, here are the Siesta Key vacation homes where you can dive in, cool off, and catch some sun.

Top-rated Siesta Key rentals with pools

Our guests have spoken. Explore their favorite and top-rated homes in Siesta Key with refreshing pools, sun-splashed decks, and poolside seating.

Parrot Beach Cottages Suite #2
0 Bed | 1 Bath | Sleeps 2

Parrot Beach Cottages Suite #2 - Siesta Key, FL

From $228
(excludes fees and taxes)
4.62 (86)
Parrot Beach Cottages Suite #1
0 Bed | 1 Bath | Sleeps 2

Parrot Beach Cottages Suite #1 - Siesta Key, FL

From $205
(excludes fees and taxes)
4.49 (81)
Parrot Beach Cottages Suite #4
1 Bed | 1 Bath | Sleeps 4 (2 Adults Max)

Parrot Beach Cottages Suite #4 - Siesta Key, FL

From $270
(excludes fees and taxes)
4.35 (72)
Parrot Beach Cottages Suite #3
1 Bed | 1 Bath | Sleeps 4 (2 Adults Max)

Parrot Beach Cottages Suite #3 - Siesta Key, FL

From $233
(excludes fees and taxes)
4.17 (80)

Explore All Vacation Rentals With Pools

Recent guest reviews

We loved everything about this property. It was close to the ocean and the downtown village shops. Everything was in walking distance.
Heather C. | Jul 2025
This is the perfect location to the beach, restaurants, and shopping. All within short walking distance. It is also a very convenient location for venturing out and seeing everything Sarasota has to offer. We absolutely loved Cottage #1. We liked the convenience of the kitchen for breakfast and lunch. I will admit the walls are a bit thin and the WiFi was a bit spotty - but, we didn’t really need WiFi and with the AC fan running at night, we were not inconvenienced by either. We did bring our own beach chairs, umbrella, cooler, etc - not sure if any were available. As for cockroaches- we encountered ZERO! The cottage was clean, the bed was comfortable and space was the perfect size for two people. We look forward to staying here again. Just the location to the beach is priceless!
Michelle B. | Jun 2025
Our family of four stayed here for a week and loved it. The location is excellent, and the place has everything a family could need. The kitchen is well stocked, as well as the utility closet. We hope to stay here again in the future!
Tiffani R. | Jun 2025
Cottage and location were perfect.
Demmings H. | Jun 2025
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FAQ

Our vacation rentals offer both private and shared pools. Each property’s listing description will specify whether the pool offered is private or shared.

Every home is stocked with plenty of towels. However, the availability of pool towels varies by property.

Some pools are heated, and there may be an additional fee for this service. You can find more information about heating fees in the property description.

Yes, pool maintenance is included during your stay. We ensure that pools and hot tubs are regularly cleaned and maintained to provide an optimal experience. If you encounter any issues with the pool during your stay, contact our Guest Experience team immediately.

Many of our properties include lounge chairs, umbrellas, or shaded areas by the pool, but this can vary. Check the property details and listing photos for specific details.

Generally, food and drinks are allowed by—but not in—the pool. However, to be safe, it’s best not to use glass or china in the pool area.

Pool toys, floaties, or inflatables are typically not provided. You may want to bring your own, if needed.

Some properties include a poolside grill or outdoor kitchen area, but this is not standard across all rentals. Check the property listing for details.

We have a good neighbor policy that includes quiet hours from 10 p.m. to 8 a.m. In addition, certain communities have noise policies in place. Unauthorized parties are not allowed, and excessive noise can lead to intervention and removal from a property.

If you encounter any issues with the pool during your stay, contact our Guest Experience team immediately. Your local Vacasa team will work to resolve the problem as quickly as possible.

Not all pools are open all year round. Some pools—depending on the destination—are seasonal only. Read the listing description for specific operating times for the pool.

More ways to stay in Siesta Key

Dog-friendly
Hot tub
Internet
Electric vehicle charger
Lake view
Lakefront
Ocean view
Oceanfront

Nearby destinations

Gulf Coast
Florida Gulf Coast
Southwest Florida
Sarasota
Osprey
Nokomis
Longboat Key
Venice
USA > Florida > Siesta Key > Pool