
Vacation rentals with a pool in Madeira Beach
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Madeira Beach
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Madeira Beach rentals with a pool
House rentals with a pool

Tootsie’s Beachside Retreat

Pretty-n-Pink Mid Century Mod Pool/Beach Home

Insta Worthy Retreat - Heated pool-putt putt | Bar

*POOL* Bar, Hottub, Central location

Heated Pool & Hot Tub 0.7 mile from Beach

Coastal Escape: heated saltwater pool & beaches

UTOPIA!Heated Pool &Hot Tub 2 master suites w KING

Stunning Lakefront-King bed - 10 min to beaches
Condo rentals with a pool

John's Pass/ Madeira Beach -2Bed / 2Bath

Beach Front Gulf View at John’s Pass Medeira Beach

Beachfront Ocean View! Large Family Friendly Condo

Toes in the Sand Beachfront penthouse condo

Chambre 102- Pool, Hot Tub, Walk to John's Pass!

Beachfront Bliss | King Bed | Heated Pool + Views!

Luxury coastal condo steps from the beach

2/2 Newly remodeled Beach Front - Sunset Vistas
Other vacation rentals with a pool

BRAND NEW Condo-Heated POOL&SPA-Walk to BEACH/SHOP

The Harbor Condo Beach Escape!

Tampa Luxe Waterfront Private Pool, Hot Tub & More

Oceanfront 3/2 with 180 degree view BOOK NOW!

Beachfront Condo Corner Unit2BR/2BA Prime Location

Waterfront Luxury | Sunset Views

40ft Floating Bungalow with Resort Perks

Tranquil "Ocean Breeze Retreat"
Quick stats about vacation rentals with a pool in Madeira Beach
Total rentals
1K properties
Nightly prices starting at
$41 CAD before taxes and fees
Total number of reviews
23K reviews
Family-friendly rentals
780 properties are a good fit for families
Pet-friendly rentals
70 properties allow pets
Rentals with dedicated workspaces
740 properties have a dedicated workspace
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- Rentals with a hot tub Madeira Beach
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- Rentals with pools Pinellas County
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- Anna Maria Island
- Siesta Beach
- Crescent Beach
- Dunedin Beach
- John's Pass
- Turtle Beach
- Raymond James Stadium
- Busch Gardens Tampa Bay
- Bean Point Beach
- Anna Maria Public Beach
- Amalie Arena
- Coquina Beach
- Cortez Beach
- Lido Key Beach
- Gulfport Beach Recreation Area
- Vinoy Park
- Jannus Live
- North Beach
- ZooTampa at Lowry Park
- Adventure Island
- Splash Harbour Water Park
- Tampa Palms Golf & Country Club
- River Strand Golf and Country Club
- Honeymoon Island Beach