Holiday Homes with Private Pool type

Holiday Homes with Private Pool type

Welcome to Holiday, Florida – a hidden gem nestled in the heart of Pasco County! Known for its warm, inviting atmosphere and stunning coastal charm, Holiday is a vibrant community that offers a perfect blend of relaxation and adventure. With its picturesque landscapes, proximity to beautiful beaches, and a plethora of recreational activities, it's no wonder that residents and visitors alike find themselves captivated by this delightful locale.

One of the standout features of homes in Holiday is the availability of properties with private pools. Imagine coming home after a long day and stepping into your own serene oasis, where you can unwind in the crystal-clear waters of your private pool. These homes are designed for those who appreciate the luxury of outdoor living, perfect for entertaining guests or simply enjoying a quiet evening under the stars.

Whether you're looking for a cozy bungalow or a spacious family home, Holiday offers a variety of real estate options to suit your needs. Many of these homes with private pools are situated in friendly neighborhoods, close to parks, shopping, and dining. The community’s laid-back vibe is complemented by its accessibility to the stunning Gulf Coast beaches, providing endless opportunities for sun-soaked days and sunset strolls.

Experience the magic of Holiday, where your dream home with a private pool awaits. Embrace a lifestyle of leisure and enjoyment in this charming Florida community, where every day feels like a vacation!

Newest Holiday Homes with Private Pool type

$599,990
5 Beds ⋅ 6 Baths ⋅ Forest Hills Un #22 SubDv. ⋅ 34690 Zip Code
PRICED TO SELL * HERE'S ANOTHER OPPORTUNITY TO PURCHASE THIS UNIQUE AND MAGNIFICENT WATERFRONT HOME, SURROUNDED ON THREE SIDES BY SPECTACULAR WATER VIEWS * THIS HOME WITH SPANISH AND MEDITTERANEAN ARCHITECTURE, FEATURES SUCH AS BEAMED CEILINGS AND ARCHED OPENINGS THROUGHOUT IS VERY SPACIOUS AND HAS AN ATTRACTIVE LAYOUT ON TWO FLOORS * TWO MASTER BEDROOMS, EACH ACCESSED BY TWO SEPARATE STAIRWAYS OPEN UP TO DECKS WITH UNOBSTRUCTED WATER VIEWS * BEAUTIFUL MARBLED DESIGN CERAMIC TILE THROUGHOUT HOME * THE GROUND FLOOR IS ACCESSED BY A WELCOMING FOYER WITH STEP DOWN TO A LARGE LIVING ROOM ON ONE SIDE AND OFFICE/TV ROOM ON THE OTHER * HALLWAY LEADS TO A LARGE LIBRARY, A HALF BATH AND A STAIRWAY TO THE SECOND FLOOR * FOUR BEDROOMS AND 3 FULL BATHS GREET YOU WITH SERENE AND PEACEFUL VIEWS OF THE ANCLOTE RIVER * UPGRADES BY THE PRESENT OWNERS INCLUDE THREE AC SYSTEMS REPLACED WITHIN THE LAST 4 YREARS * 1 YR OLD HOT WATER HEATER * NEW KITCHEN WITH AMPLE CABINETS, ISLAND WITH SITTING AREA AND A SPACIOUS DINING AREA LEADING OUT TO THE POOL * THE GROUND FLOOR ALSO PROVIDES A MASSIVE GAMES ROOM WITH A WOOD BURNING FIREPLACE * PERFECT FOR GATHERINGS AND ENTERTAINTMENT * A FULL BATH WITH A SAUNA ADDS TO THE COMFORT OF THIS HOME * WALK OUTSIDE TO THE COVERED DECK FOR YEAR ROUND USE, HUGE PAVED DECK, POOL GAZEBO AND WATER VIEWS ALL AROUND. WITH 630 FEET OF WATERFRONT WALL PROVIDES NEW OWNERS THE OPPORTUNITY TO BUILD A DOCK WITH A BOAT LIFT AND POSSIBLY A BOATHOUSE * THE LARGE PIECE OF PROPERTY IS PERFECT FOR LOTS OF OUTDOOR ACTIVITIES * LOTS PARKING SPACE FOR MULTIPLE BIG TOYS AND VEHICLES * 3 LARGE OPEN GARAGE SPACES * DON'T MISS THIS ONCE IN A LIFETIME OPPORTUNITY TO OWN A BEAUTIFUL PIECE OF PARADISE * Characters Remaining: 1731 *

1238 Flotilla Drive, Holiday
$459,500
3 Beds ⋅ 2 Baths ⋅ Glenwood Gulf Trace SubDv. ⋅ 34691 Zip Code
Beautifully Updated 3-Bedroom Home on an Oversized Cul-de-Sac Lot Welcome home! This beautifully maintained 3-bedroom, 2-bath home sits on an oversized corner lot in a desirable cul-de-sac, offering extra space, privacy, and flexibility. With an impressive list of updates already completed, this home is truly move-in ready! 2019 — Exceptional Kitchen, Pool & Window Upgrades • Windows replaced, enhancing curb appeal and comfort. • Pool refinished and filtration system replaced. • Granite countertops add beauty, durability, and elegance. • Stainless steel appliances create a modern kitchen. • Soft-close kitchen cabinet drawers provide a premium finishing touch. 2020 — Added Protection • Gutters installed, helping direct rainwater away from the home. Well-fed irrigation system helps keep the lawn and landscaping looking green, healthy, and beautiful while providing an economical irrigation source. 2023 — Major System Improvements • Roof replaced, providing valuable peace of mind. • HVAC system replaced, keeping the home comfortable year-round. 2024 — Fresh Exterior • Exterior painted, delivering a fresh, attractive appearance and enhanced curb appeal. 2025 — Garage Upgrade • Garage door replaced, adding functionality, security, and curb appeal. NEW — Beautiful Flooring Luxury Vinyl Plank flooring has been newly installed throughout the main living spaces, creating a stylish, durable, and easy-to-maintain foundation. The Secondary bedrooms feature comfortable carpeting, creating cozy private spaces. Flexible Space to Make Your Own The home's 3-bedroom, 2-bath layout also offers additional space that can be transformed into an office, craft room, hobby space, or potentially a 4th bedroom, depending on your needs and applicable requirements. THE BIG STORY This home offers the rare opportunity to enjoy the benefits of years of thoughtful improvements without taking on the projects yourself. Major updates include the roof, HVAC, windows, pool, filtration system, gutters, exterior paint, garage door, kitchen features, irrigation system, and NEW flooring. Add the oversized cul-de-sac lot, private pool, flexible living space, and move-in-ready condition, and this home delivers an incredible combination of comfort, style, functionality, and value! Come see it, and make it yours!

3225 Hearthstone Court, Holiday
$274,900
3 Beds ⋅ 2 Baths ⋅ Beacon Square SubDv. ⋅ 34691 Zip Code
Virtually Staged. TROPICAL POOL & POND PARADISE HOME FEATURING A SPARKLING SWIMMING POOL, 3 BEDROOMS, 2 BATHROOMS AND A LARGE COVERED LANAI AND SCREEN-ENCLOSED POOL-DECK. NEW ROOF, NEW KITCHEN, NEW AC, NEW APPLIANCES, QUARTZ COUNTERSTOPS, NEW LUXURY WATERPROOF VINYL PLANK FLOORS, new electrical panel, new pool pump and new cartridge filter! All new interior paint and fixtures. Beautiful curb appeal with a spacious driveway and covered front porch. 22 Ft long garage with side entrance door. Private backyard with pond access and beautiful wildlife views. Perfectly located near great shopping, restaurants, parks and beaches! Enjoy the fun in the sun that a tropical paradise pool home offers!

3349 Overland Drive, Holiday
$299,000
2 Beds ⋅ 2 Baths ⋅ Forest Hills SubDv. ⋅ 34690 Zip Code
Welcome to your slice of the Florida waterfront lifestyle. This 2-bedroom, 2-bathroom home sits directly on the Anclote River with deeded Gulf of Mexico access, a rare opportunity to own true boating water at an approachable price point, on a nice block of well-kept homes. Step into your own private oasis with a screened, in-ground pool overlooking the river, a private dock with new wood decking ready for your boat, a seawall in good condition, and a spacious backyard made for sunset views and morning coffee on the water, while new windows across the back of the home flood the living space with natural light and frame those river views beautifully. This home has been well cared for where it counts most, with a new roof (2025), HVAC (approx. 2 years), fencing (1 year old), and pool pump (1.5 years old) already updated, making this a true opportunity for an investor or a buyer ready to add cosmetic value through new flooring, kitchen, and bath finishes and build significant equity, whether renovating to sell, to rent, or to make it your own. Tucked in the Flotilla Dr riverfront enclave of Holiday, the home is minutes from Anclote River Park, with its boat ramp, kayak launch, and Gulf-access swimming, and just a short drive from the world-famous Tarpon Springs Sponge Docks, known for its historic Greek waterfront district, dolphin cruises, and waterfront dining, with boaters able to head straight out the Anclote River to Anclote Key Preserve State Park or nearby Fred Howard Park and Sunset Beach. Families will also appreciate the school zoning for Sunray Elementary, Paul R. Smith Middle School, and Anclote High School. Homes with true river frontage and Gulf access rarely come to market at this price point, so bring your contractor and your vision, and turn this riverfront gem into something spectacular!

1332 Flotilla Drive, Holiday
$379,000
3 Beds ⋅ 2 Baths ⋅ Forest Hills SubDv. ⋅ 34690 Zip Code
Welcome to 1346 Chancellor Dr, a charming house that invites you to explore its unique character and potential.Direct canal access to the gulf, New Roof .Nestled in a desirable location, this property accords a wonderful opportunity for those seeking a place to call home. With its classic architectural design, the exterior exudes curb appeal, while the interior awaits your personal touch. Whether you're looking to relax in a cozy living space or entertain guests, this house provides a versatile layout to suit your needs. The surrounding area accords a peaceful atmosphere, appropriate for enjoying outdoor activities and leisurely strolls. Don't miss the chance to make this house your own and create lasting memories in a welcoming community.

1346 Chancellor Drive, Holiday
$550,000
4 Beds ⋅ 3 Baths ⋅ Gulfwinds SubDv. ⋅ 34691 Zip Code
Welcome to 2309 Swordfish Ave, a beautifully maintained 4-bedroom, 3-bathroom, 2,462-square-foot single-story home situated on a spacious 10,320-square-foot lot in the desirable Gulfwinds community of Holiday, Florida. Offering an ideal combination of comfortable living space, thoughtful updates, privacy, and exceptional outdoor amenities, this home is designed for both everyday living and entertaining. The freshly painted interior features a spacious and versatile floor plan with tile flooring throughout the kitchen, breakfast nook, family room, living room, and dining room. The primary bedroom features attractive wood-look tile flooring, while the three additional bedrooms are carpeted. A dedicated office provides an ideal work-from-home space and features brand-new epoxy-resin flooring. Plantation shutters enhance the windows and sliding glass doors throughout the home. The kitchen offers granite countertops, a backsplash installed approximately two years ago, under-cabinet lighting, and a double-door refrigerator. The washer and dryer are included. The primary suite features an updated bathroom with new granite countertops, new tile, new faucets, a walk-in shower, and a walk-in tub. Additional improvements include a roof approximately three years old, a four-year-old HVAC system that has been recently serviced, and a tankless water heater. Outside, the private backyard is enclosed by a vinyl privacy fence and features a screened outdoor living area with a heated saltwater pool and heated hot tub, each equipped with its own separate pump. A newer double-wide side entrance can provide convenient access for a boat, recreational vehicle, or additional vehicle, subject to applicable HOA and county regulations. The property also features an irrigation system and a 3-car garage with newly installed aluminum attic steps for convenient access to additional storage. For added preparedness, the home features a dedicated generator connection with its own junction box and dedicated electrical circuits, providing a convenient setup for connecting a generator when needed. Residents of Gulfwinds enjoy community amenities including a nearby community pool, with HOA services covering community pool access, community grounds maintenance, cable TV, and internet. Gulfside Elementary in Holiday, Florida, closed in mid-2026 and has merged with Paul R. Smith Middle School K1-8. The two nearby, under-capacity campuses combined to form a single unified K-8 school operating at the Paul R. Smith site on Sweetbriar Drive. Conveniently located near the historic Tarpon Springs Sponge Docks, Belle Harbour and Port Tarpon Marinas, Fred Howard Park Beach, boating, dining, shopping, riding and walking trails, the Anclote River and Gulf parks, nearby islands, and spectacular Gulf Coast sunsets. With four bedrooms, three full bathrooms, a dedicated office, multiple living and dining areas, a 3-car garage, private fenced yard, heated saltwater pool and hot tub, tankless water heater, plantation shutters, and numerous recent improvements, 2309 Swordfish Ave offers an exceptional combination of comfort, functionality, and Florida outdoor living. Experience effortless Florida living in Gulfwinds—schedule your showing today!

2309 Swordfish Avenue, Holiday
$252,000
2 Beds ⋅ 2 Baths ⋅ Holiday Lake Estates SubDv. ⋅ 34691 Zip Code
Summer may almost be over, but it’s still not too late to own a pool home and enjoy the Florida lifestyle for years to come! Located in beautiful Holiday Lake Estates, this two-bedroom, two-bath home with a one-car garage offers plenty of potential for the buyer ready to make it their own. The home features a living and dining room combination, Florida room, spacious bedrooms, and a primary suite with direct access to the pool area from the primary bathroom. Step outside to enjoy the in-ground pool, covered porch, fenced yard, and the added privacy of having no neighbor on one side. Conveniently located near the world-famous Tarpon Springs Sponge Docks, Fred Howard Park, and Sunset Beach, with an easy commute to Honeymoon Island, downtown Dunedin, and gorgeous Clearwater Beach. The home is in need of updating, so bring your vision and your tools, roll up your sleeves, and take advantage of the opportunity to build some sweat equity and make this one your own! Case #: 093-973243 Finance Escrow may apply. Finance Code: IE.

3221 Roxbury Drive, Holiday
$225,000
2 Beds ⋅ 2 Baths ⋅ Beacon Square SubDv. ⋅ 34691 Zip Code
Welcome to this move-in-ready 2-bedroom, 2-bath pool home with garage, offering a great combination of comfort, energy efficiency, valuable updates, and easy access to Florida’s Gulf Coast lifestyle. Enjoy your own private pool and the benefits of several major improvements already completed, including a new roof installed in June 2026, 2024 HVAC system, new water heater in 2026, and fully paid-off solar panels installed in 2022. The solar system provides excellent potential for long-term energy savings, with Duke Energy previously quoting an average electric bill of approximately $60.55 per month. Inside, the home offers a comfortable and functional layout with both full bathrooms located within the interior of the home, providing added privacy and convenience. The kitchen appliances are in good condition, and the property has been clean and well maintained. For additional peace of mind, the home did not flood during Hurricanes Milton or Helene. The location makes it easy to enjoy everything the area has to offer. Spend your days boating, fishing, visiting nearby beaches, or exploring the Gulf Coast. The home is conveniently located near Anclote River Park, offering beach access, boat ramps and fishing piers, as well as a nearby dog park, marinas, restaurants and nature trails. The historic Tarpon Springs Sponge Docks are approximately 10 minutes away, and popular waterfront destinations such as Miss Vicki's On The River are also nearby. Whether you're searching for a primary residence, seasonal Florida retreat, or investment property, this home delivers an appealing combination of affordability, energy efficiency, recent improvements, a private pool, and a location close to the water and outdoor recreation.

3153 Moog Road, Holiday
$299,900
2 Beds ⋅ 2 Baths ⋅ Beacon Square SubDv. ⋅ 34691 Zip Code
Welcome to this beautifully remodeled 2-bedroom, 2-bathroom pool home offering an open, light-filled layout, peaceful water views, and plenty of indoor-outdoor living space. An oversized driveway provides abundant parking in addition to the 2-car garage, while the unique front courtyard creates a welcoming entry and adds character from the moment you arrive. Inside, the home has undergone a full interior remodel with LVP flooring and an open floor plan designed to take advantage of the natural light and views. The sunken living room adds architectural interest, while designated living and dining areas provide plenty of room to gather. Multiple sets of sliding glass doors line the back of the home, filling the interior with light and keeping the pool and water views front and center. The fully renovated kitchen features quartz countertops, all-new appliances, soft-close cabinetry, and a clean, modern design that flows seamlessly into the surrounding living spaces. The spacious primary suite opens directly to the screened pool area and includes a walk-in closet and beautifully renovated en suite bathroom. The guest bathroom has also been completely updated. A new water heater was installed in 2026, adding another recent update to the home. Outside, enjoy true Florida living with a screened-in pool, covered patio, and tranquil water views. Sliding doors from both the living and dining spaces create effortless access to the pool area, making the backyard feel like a natural extension of the home. Located in Holiday, this home puts you close to the best of Florida's Gulf Coast lifestyle, with nearby waterfront parks, nature trails, boating and fishing opportunities, including Key Vista Nature Park, Anclote Gulf Park, and Anclote River Park. You're also just minutes from Tarpon Springs, local shopping, dining, and everyday conveniences, with easy access to US-19 for travel throughout the Tampa Bay area.

3611 Delta Place, Holiday
$575,000
4 Beds ⋅ 3 Baths ⋅ Glenwood Gulf Trace SubDv. ⋅ 34691 Zip Code
Welcome to this spacious 4-bedroom, 3-bath pool home offering approximately 2,857 square feet of comfortable living space in the desirable Gulf Trace community of Holiday. Designed with both everyday living and entertaining in mind, the home features a split-bedroom floor plan, an expansive family room with a cozy fireplace, a generous kitchen with abundant cabinetry, a bright breakfast nook, a formal dining room, separate living room, dedicated laundry room, and an oversized 2-car garage. The private primary suite includes a large walk-in closet and spacious en-suite bath, while three additional bedrooms and multiple bathrooms provide flexibility for family, guests, or a home office. Step outside to an impressive screen-enclosed pool and oversized lanai, creating the perfect setting for year-round Florida living. Ideally located just minutes from the Gulf of Mexico, you'll enjoy easy access to Key Vista Nature Park, Anclote River Park, Gulf beaches, boating, fishing, waterfront dining, and the historic Tarpon Springs Sponge Docks, with Clearwater Beach, Tampa, and Tampa International Airport all within an easy drive. Combining generous living space, a functional layout, and an exceptional location, this home offers the very best of Florida's Gulf Coast lifestyle.

3225 Glenwood Circle, Holiday
$459,900
4 Beds ⋅ 3 Baths ⋅ Forest Hills SubDv. ⋅ 34690 Zip Code
Welcome to true waterfront living in this beautifully remodeled 4-bedroom, 3-bath home with direct Gulf access, incredible privacy, and upgrades throughout. Located along a scenic bend of the river, the backyard overlooks a private island preserve, so there are no rear neighbors—just peaceful water views and frequent visits from dolphins, manatees, and local wildlife. The home has remained high and dry during recent storms, offering added peace of mind. Inside, the split floorplan includes two private en suites on opposite sides of the home, making it perfect for multigenerational living, guests, or anyone who wants extra privacy. The brand-new kitchen features updated appliances, a Moen motion-sensor faucet with WiFi controls, and a clean, modern design. Major improvements include a 2025 whole-home Halo water treatment system, Uponor PEX plumbing, propane tankless water heater, new doors and windows, added attic insulation, and a generator-ready electrical setup. Outside, enjoy the heated pool with new 2024 pump and heat pump, a gravity overflow drain, private dock, and 10,000-pound boat lift with new stainless-steel cables. Additional features include an EV charging outlet, commercial-grade garage door opener, rebuilt garage door, WiFi-controlled sprinkler system supplied by a private well, ADT security system, Ring doorbell, garage camera, 2018 roof, and 2018 HVAC system. This move-in-ready home combines modern updates, waterfront privacy, and the relaxed Florida lifestyle buyers are looking for. Schedule your private showing today!

1166 Chancellor Drive, Holiday
$399,990
4 Beds ⋅ 3 Baths ⋅ Holiday Lake Estates SubDv. ⋅ 34691 Zip Code
Beautifully remodeled corner-lot home with excellent investment potential! This spectacular property features 3 bedrooms, 2 full bathrooms, and a private efficiency with its own separate entrance, ideal for generating additional income, accommodating extended family, or creating a private guest space. The home has been recently remodeled, offering modern finishes, spacious living areas, and a functional layout. It also features a large private swimming pool, perfect for entertaining, relaxing, and enjoying Florida living year-round. Designed with energy efficiency and convenience in mind, the property includes solar panels and an installed electric vehicle charging station, adding comfort, savings, and valuable modern features for the new owners. Situated on a desirable corner lot, the property offers additional privacy, abundant natural light, and extra parking space. The location is another major advantage, with convenient access to schools, shopping, restaurants, major roadways, and the beautiful beaches along the Gulf of Mexico, where residents can enjoy crystal-clear waters, unforgettable sunsets, and a variety of outdoor activities. This unique property combines comfort, modern design, energy efficiency, and excellent income-producing potential through its private efficiency with a separate entrance, making it an ideal opportunity for both homeowners and investors. Do not miss this exceptional opportunity. Schedule your private showing today!

3708 Holiday Lake Drive, Holiday
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