Madeira Beach vacation rentals with pools

We found 31 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 Madeira Beach vacation homes where you can dive in, cool off, and catch some sun.

Top-rated Madeira Beach rentals with pools

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

Arie Dam 401
2 Bed | 2 Bath | Sleeps 6

Arie Dam 401 - Madeira Beach, FL

From $344
(excludes fees and taxes)
4.69 (26)
Sugar Sands C
4 Bed | 3 Bath | Sleeps 12

Sugar Sands C - Madeira Beach, FL

From $863
(excludes fees and taxes)
4.19 (62)
Sugar Sands B
2 Bed | 1 Bath | Sleeps 6

Sugar Sands B - Madeira Beach, FL

From $344
(excludes fees and taxes)
4.37 (57)
Sugar Sands A
1 Bed | 1 Bath | Sleeps 4

Sugar Sands A - Madeira Beach, FL

From $260
(excludes fees and taxes)
4.31 (55)

Explore All Vacation Rentals With Pools

Recent guest reviews

All around amazing! Views were awesome and very easy walk to beach and all things needed were there in the garage locker. Great spot for vacation!
geoff m. | Jul 2025
Let’s just start with the view!!! Check in was a breeze. Condo was very clean. All comfortable furniture. Water pressure was beyond expectations!! Location is perfect. You are half way between John’s Pass and Caddy’s (literally a few minutes walk). Elevator went down 2x 1 day but was fixed quickly. We’ve stayed at several other complexes with 2+ bedrooms but this trip was just the 2 of us and we had PLENTY of room. “Smaller” kitchen but so open that it was BEAUTIFUL.
Karen S. | Jun 2025
The beach was wonderful!
Brooke C. | Jun 2025
Our family absolutely loves the Gulf Coast of FL and its beaches! It's our go to for beach vacationing. The place itself is beautifully decorated and has all that is needed. A handful of items need updates, appliance wise and maybe better storage for the beach items they provide, but you will definitely be pleased with the amazing view, quiet building and the nice beach house decor. The place was very clean and spacious for 3 adults and a 7 year old. You could have 4 adults and 2 kids and still be comfortable. Lots of storage for your luggage and personal items. *NOTE: Pool was not accessible at the moment, as they are still recuperating from the damage made from last year's hurricane - however, the proximity to the beach makes up for it! You really forget about the pool with the gulf ocean and lovely white sands being so close. The only other set back was the elevator not working at all for the 5 days we were there. Again - understandable that they are recuperating still and repairing, however, communication on when the repairs will be completed would have been helpful. We did receive emails that repairs were being done to both the pool and elevator - and that the day of our arrival the elevator would have "limited" usage, however, when we got there it was completely out of order... and being on the 4th floor was a bit of a hike - but we made the best of it. The building management definitely needs to improve communication with Vacasa about repairs so guests can plan accordingly. Thankfully we were compensated for the setback from Vacasa and they were great with responding and consistently checking in on us during our stay. Overall - the location is great and the condo is lovely, but I highly recommend guests calling ahead to make sure the elevator is functional before your visit (honestly, if staying anywhere in this area - be sure to call about their elevators or potential repairs, as it will be a common issue sadly for many properties in this area).
Lena B. | 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.
USA > Florida > Madeira Beach > Pool