Pool Homes for Sale in Holiday, FL
Buyers who want a pool search for the pool first. This page tracks every Holiday listing whose MLS record reports a private pool, by community, with live counts and asking prices, and what the pool adds to the cost of ownership.
39 homes with a private pool are for sale or pending in Holiday, FL today across 22 communities. The median asking price is $379,900, from $129,000 to $1,299,999. Listings in Holiday without that feature have a median of $225,000. Most listings right now: Forest Hills (5), Holiday Lake Estates (5), Beacon Square (4). Updated October 17, 2026 from the MLS.
Live pool homes in Holiday: the listings
29 active listings carry the flag today (10% of Holiday inventory), median asking $450,000, $236/sq ft, median 34 days on market. Photo cards link to the listing; refreshed nightly.
Newest pool homes in Holiday
The most expensive pool homes in Holiday
| Listing | Asking | Sq ft | Community |
|---|---|---|---|
| 1906 Gulfview Drive | $1,859,900 | 3,412 | pasco county |
| 3143 Pineview Drive | $1,369,990 | 4,204 | pasco county |
| 3143 Pineview Drive | $1,299,999 | 4,204 | Baileys Bluff Estates |
| 3114 Bluff Boulevard | $1,265,000 | 3,234 | pasco county |
| 3020 Sheppards Crook Court | $559,000 | 2,367 | Ibis Sub |
| 1238 Flotilla Drive | $549,900 | 5,360 | — |
| 2309 Swordfish Avenue | $545,000 | 2,462 | Gulfwinds |
| 3225 Glenwood Circle | $525,000 | 2,857 | Glenwood Gulf Trace |
| 1419 Blue Marlin Boulevard | $525,000 | 2,480 | Gulfwinds |
| 2210 Bayou Drive | $499,999 | 2,861 | Baileys Bluff Estates |
Pool Homes by price
| Band | For sale | Share |
|---|---|---|
| Under $300K | 6 | 21% |
| $300K–$500K | 14 | 48% |
| $500K–$750K | 5 | 17% |
| $1M+ | 4 | 14% |
Holiday pool homes by community
Click a community for its full guide: prices, HOA reality, insurance posture and the homes for sale.
| Community | Pool Homes | New build | Median list | From |
|---|---|---|---|---|
| Forest Hills | 5 | 0 | $399,000 | $289,000 |
| Holiday Lake Estates | 5 | 0 | $328,200 | $227,000 |
| Beacon Square | 4 | 0 | $269,949 | $199,000 |
| Baileys Bluff Estates | 3 | 0 | $775,000 | $499,999 |
| Gulfwinds | 2 | 0 | $535,000 | $525,000 |
| Glenwood Gulf Trace | 2 | 0 | $492,250 | $459,500 |
| Key Vista Ph 04 | 2 | 0 | $469,950 | $460,000 |
| Tahitian Dev | 2 | 0 | $339,500 | $229,000 |
| Key Vista Ph 1 | 1 | 0 | $609,900 | $609,900 |
| Ibis Sub | 1 | 0 | $559,000 | $559,000 |
| Dodge City First Add | 1 | 0 | $549,900 | $549,900 |
| Forest Hills Un #22 | 1 | 0 | $549,900 | $549,900 |
| Sand Bay | 1 | 0 | $485,000 | $485,000 |
| Shadow Oaks Sub | 1 | 0 | $380,000 | $380,000 |
| Holiday Lakes West | 1 | 0 | $379,900 | $379,900 |
| Forest Hills Unit 22 | 1 | 0 | $350,000 | $350,000 |
| Oak Hill | 1 | 0 | $284,900 | $284,900 |
| Tahitian Dev Sub | 1 | 0 | $255,000 | $255,000 |
| Tahitian Homes | 1 | 0 | $244,900 | $244,900 |
| Pinewood Villas Ph 02 | 1 | 0 | $199,900 | $199,900 |
| Orangewood Village | 1 | 0 | $182,150 | $182,150 |
| Tahitian Gardens Condo | 1 | 0 | $129,000 | $129,000 |
What a private pool actually costs to own
Budget three things beyond the price: the pool itself (chemicals, pump electricity and a service if you do not want to do it yourself typically run $150 to $300 a month), the screen enclosure where there is one (a full re-screen every 8 to 12 years; a replacement enclosure is a five-figure job after a storm), and insurance, where a pool adds liability exposure and many carriers require a fence, self-latching gate or approved alarm. Florida’s Residential Swimming Pool Safety Act requires at least one safety feature on a new pool, and lenders and insurers ask about it on older ones. Have the pool inspected separately from the house: the pump, heater, surface finish and deck are the expensive items. Our true cost of ownership calculator puts insurance, taxes and upkeep into one monthly number.
Questions to ask about any pool listing
How old are the pump, filter and heater, and is there a warranty? When was the surface last refinished? Is the enclosure permitted and when was it last re-screened? Is there a barrier or alarm that satisfies the insurer? What did the seller pay for homeowners insurance last year, and did the carrier require anything for the pool? A local agent who works the area will know which enclosures came through the last storm.
Common questions
How many homes with a private pool are for sale in Holiday?
What do pool homes cost in Holiday?
Which Holiday community has the most pool homes for sale?
Does a pool raise homeowners insurance in Florida?
Keep exploring Holiday
- All homes for sale in Holiday
- Holiday ZIP codes with prices
- Holiday waterfront homes
- Holiday gated community homes
- Holiday 4-bedroom homes
- Holiday homes under $300K
- Holiday homes $300K–$500K
- Pool Homes in every city
Pool Homes in nearby Pasco County cities
- New Port Richey pool homes (194 for sale)
- Wesley Chapel pool homes (107 for sale)
- Hudson pool homes (106 for sale)
- Land O Lakes pool homes (100 for sale)
- Port Richey pool homes (92 for sale)
- Odessa pool homes (91 for sale)
- Dade City pool homes (55 for sale)
- Trinity pool homes (34 for sale)
Live data: Stellar MLS, refreshed with every MLS pull; this page rebuilds on every ship. Community-level aggregates only: active and pending residential listings in Holiday, FL whose MLS record reports a private pool. Prices are asking prices, not values. Property features and prices only; nothing on this page describes residents. Equal Housing Opportunity.