Vacation rentals with a pool in Holiday
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Holiday
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Holiday rentals with a pool
House rentals with a pool
Home in Dunedin
4.93 out of 5 average rating, 120 reviewsEverything you'll need, plus! Park Model RV
Aug 23 – 30
Home in Crystal Beach
4.94 out of 5 average rating, 185 reviewsBeach Side Beauty-heated Pool
Oct 1 – 8
Home in Holiday
4.95 out of 5 average rating, 39 reviewsThe Richboro house
Apr 25 – May 2
Home in Holiday
5.0 out of 5 average rating, 13 reviews*NEW* Riverside Retreat w/Pool
Nov 24 – Dec 1
Home in Holiday
4.93 out of 5 average rating, 27 reviewsParadise!Renovated waterfront pool home.Sunsets!
Oct 27 – Nov 3
Home in Holiday
4.97 out of 5 average rating, 58 reviewsPrivate 3 Bedroom Saltwater Pool House!
Sep 2 – 9
Home in Port Richey
5.0 out of 5 average rating, 17 reviewsBahama Behms HeAtEd pool house by the marina
Jun 6 – 13
Home in Port Richey
4.96 out of 5 average rating, 45 reviewsBeachy 3 Bedroom Hot Tub and Saltwater Pool
Apr 21 – 28
Condo rentals with a pool
Condo in Redington Beach
4.97 out of 5 average rating, 459 reviewsAmazingBeachCondo/NoCleaningFee/AwesomeAmenities
Nov 9 – 16
Condo in Largo
4.89 out of 5 average rating, 180 reviewsModern and Cozy Condo 6 Minutes from the Beach !
Oct 26 – Nov 2
Condo in Redington Beach
4.84 out of 5 average rating, 174 reviewsRoyal Orleans and Redington Beach
Sep 29 – Oct 6
Condo in St. Pete Beach
4.91 out of 5 average rating, 213 reviewsSunset Beach Condo in Treasure Island
Nov 12 – 19
Condo in St. Petersburg
4.97 out of 5 average rating, 145 reviewsSea La Vie- Studio by the bay!
Aug 11 – 18
Condo in Indian Shores
4.96 out of 5 average rating, 143 reviews1 BR direct beachfront! Now avail. 8/29-9/11.
Dec 10 – 17
Condo in Redington Beach
4.85 out of 5 average rating, 570 reviewsCondo II:Beach 2 min walk:Heated Pool:2Bikes:Grill
Nov 15 – 22
Condo in Redington Beach
4.9 out of 5 average rating, 150 reviews2min walk to the beach/pool, BBQ/great area, RO110
Aug 31 – Sep 7
Quick stats about vacation rentals with a pool in Holiday
Total rentals
40 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
950 reviews
Nightly prices starting at
$30 before taxes and fees
Destinations to explore
- Tampa Vacation rentals
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