Holiday Homes with Private Pool type

Holiday Homes with Private Pool type

Welcome to Holiday, a charming city located in Pasco County, Florida. Known for its tranquil atmosphere and beautiful surroundings, Holiday is a hidden gem for those seeking a peaceful and relaxing lifestyle.

Situated in the heart of the Sunshine State, Holiday offers a wide range of amenities and attractions for residents and visitors alike. With its close proximity to the stunning Gulf of Mexico, outdoor enthusiasts can enjoy a variety of water activities such as fishing, boating, and swimming. The city is also home to several parks and nature reserves, providing ample opportunities for hiking, picnicking, and wildlife spotting.

If you're in search of a home with a private pool, Holiday has plenty to offer. Whether you prefer a cozy bungalow or a spacious family home, you'll find a variety of properties that feature private pools. Imagine spending hot summer days lounging by the poolside, hosting pool parties, or simply enjoying a refreshing swim after a long day.

Having a private pool not only provides a luxurious and convenient way to beat the Florida heat but also adds value to your property. It creates a private oasis where you can relax and unwind, away from the hustle and bustle of everyday life.

So, if you're looking for a peaceful city with a true sense of community, Holiday in Pasco County, Florida, is the perfect place to call home. With its idyllic surroundings and homes with private pools, you'll find the perfect retreat to enjoy the Florida lifestyle to its fullest.

Newest Holiday Homes with Private Pool type

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. 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

2 Beds ⋅ 2 Baths ⋅ Tahitian Dev Sub SubDv. ⋅ 34691 Zip Code

WELCOME TO WATERFRONT FLORIDA LIVING! This 2-bedroom, 2-bath POOL HOME offers picturesque water views, a PRIVATE DOCK, screened-in pool and lanai, and NO HOA. Situated along a wide lagoon of Lake Conley, this property is ideal for boating, fishing, kayaking, or simply relaxing and enjoying the peaceful waterfront setting. Step inside to a bright and inviting floor plan filled with natural light. The spacious living and dining areas flow into the kitchen and out to the screened pool and lanai, creating an ideal layout for indoor-outdoor living and entertaining. Both bedrooms are generously sized, and both full bathrooms have been updated. The outdoor living space is the true highlight. Enjoy the screened-in pool overlooking Lake Conley, with plenty of room for lounging, dining, and entertaining year-round. Beyond the pool, the backyard leads to your private custom dock, giving you direct access to the water from your own property. Launch a kayak, head out on the water, fish from the dock, or enjoy your morning coffee while taking in the peaceful waterfront views. This home also features an oversized 412 sq. ft. 1-car garage, double-pane windows, NEW A/C in 2025, washer and dryer, water heater approximately 4 years old, dishwasher and disposal approximately 3 years old, and pool filter approximately 2 years old. The home did NOT FLOOD in the recent hurricanes and offers an excellent opportunity as a full-time residence, vacation retreat, or investment property. With NO HOA OR CDD, you can enjoy waterfront living without the added community fees. Conveniently located in Holiday near Tarpon Springs and the Sponge Docks, Gulf beaches, parks, shopping, dining, medical facilities, and Tampa International Airport. Schedule your private showing today!

1954 Coolidge Road, Holiday

4 Beds ⋅ 2 Baths ⋅ Holiday Lakes West SubDv. ⋅ 34691 Zip Code

MOVE IN READY! This four bedroom two bath pool home has been renovated, updated, and upgraded - All this home needs is YOU! Attention was paid to every part of this home. Renovations, updates and upgrades are simply too numerous to completely describe but include: new flooring and trim work, kitchen new refrigerator, new fixtures, a complete interior and exterior repaint, some new doors and all new door hardware, and a whole house water filtration and softening system. The home also features a renovated kitchen with custom wooden cabinets, cement board exterior, a spacious salt pool inside a large lanai with all sides re-screened with a great entertaining area, and a fully fenced private backyard with a shed. The wooden fence is less than a year old, the HVAC and roof are only four years old. The luxury vinyl planking is upgraded and waterproof and the carpet is forty-four ounce Traffic Master with the upgraded padding. Conveniently located near SR 19 off Anclote Boulevard makes for easy access to commuting, along with shopping and restaurants, as well as being within a mile of Anclote State Park on the Anclote River with beaches, pavilions and boat ramps and within two miles of downtown Tarpon Springs and the Sponge Docks!

2526 Fieldcrest Court, Holiday

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

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

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

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

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

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

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

4 Beds ⋅ 2 Baths ⋅ Key Vista Ph 04 SubDv. ⋅ 34691 Zip Code

Virtually Staged. WOW! Take a look at this 4 BEDROOM, 2 BATHROOM, 3 CAR GARAGE POOL HOME LOADED WITH UPDATES AND UPGRADES IN THE STUNNING KEY VISTA COMMUNITY ON A QUIET CUL DE SAC. The open kitchen has been remodeled. THE CABINETS AND COUNTER TOPS HAVE BEEN REPLACED, NEW REFRIGERATOR, AND A NEW DISHWASHER. The QUARTZ KITCHEN ISLAND IS EXCELLENT FOR ENTERTAINING AND USING AS A CASUAL SPACE FOR BAR STOOLS. The big open family says bring your sectional and huge TV because there is plenty of room! THE SLIDERS TO THE POOL HAVE RECENTLY BEEN REPLACED AS WELL AS NEW WINDOWS IN THE BACK OF THE HOUSE. It sure feels like Florida here with the PLANTATION SHUTTERS and light bright colors and SPARKLING SWIMMING POOL. There are no rear neighbors, you can enjoy your pool and outdoor space in private. New interior paint in many of the rooms. THE PRIMARY BEDROOM HAS MORE THAN ENOUGH ROOM FOR A KING SIZE BED AND THE PRIMARY BATHROOM FEATURES A STAND UP SHOWER AND SOAKING TUB. There is enough room to stretch out with double sinks too! Some other noteworthy things about this very special home are HIGH CEILINGS, a NEW ROOF IN 2023, NEW AC IS 2017 AND A NEW HOT WATER HEATER. You don't have to go far to enjoy the community amenities! There is a huge heated pool, clubhouse, playground, tennis and pickleball courts, fitness center, and more. Key Vista Nature Park is about a mile away, Sunset Beach and Fred Howard Park in Tarpon Springs are just a short drive away!

2811 Ravendale Lane, Holiday

3 Beds ⋅ 4 Baths ⋅ Ibis Sub SubDv. ⋅ 34691 Zip Code

"Luxury Living in an Exclusive Gated Community" Experience coastal elegance in this custom-built executive residence, privately situated on a quiet cul-de-sac within an exclusive gated community. Offering 2,367 square feet of thoughtfully designed living space, this exceptional three-story home combines luxury, comfort, and functionality with partial Gulf views from multiple balconies. From the moment you arrive, the impressive stamped concrete driveway and striking architectural design create unforgettable curb appeal. Inside, you'll find soaring ceilings, custom 8-foot doors, elegant crown molding, engineered hardwood flooring, marble and travertine finishes, and an open-concept floor plan designed for both entertaining and everyday living. The gourmet kitchen is truly the heart of the home, featuring granite countertops, abundant custom cabinetry, a walk-in pantry, breakfast bar, and newer stainless-steel appliances—perfect for preparing meals while staying connected with family and guests. Escape to the luxurious owner's retreat occupying the entire upper level. This private sanctuary offers partial Gulf views, a spacious walk-in closet, and a spa-inspired ensuite featuring dual vanities, an oversized walk-in shower, and a relaxing whirlpool tub. Step outside and enjoy Florida living at its finest. Four travertine balconies provide multiple places to relax and enjoy the coastal breeze, while the beautiful in-ground pool and expansive paver patio create the perfect setting for entertaining family and friends. The oversized garage offers room for multiple vehicles, a workshop, abundant storage, and even includes a convenient full pool bath.Recent upgrades provide peace of mind and modern convenience, including: New roof (2021), Newer-zone HVAC system, Updated stainless-steel kitchen appliances Central vacuum system Premium flooring throughout. Ideally located enjoy indoor pickleball, weekly gymnasium schedule, summer camp, soccer fields, baseball, tennis and more at J. Ben Harrill Recreation Center is a short walk from your front gate. Just minutes from Anclote Gulf Park, public boat ramps, Gulf beaches, the Pinellas Trail, and the world-famous Tarpon Springs Sponge Docks, you'll also enjoy convenient access to shopping, dining, and endless waterfront recreation. Luxury, location, and lifestyle come together in one extraordinary home. Schedule your private showing today and discover why this exceptional property is one you won't want to miss.

3020 Sheppards Crook Court, Holiday

Start Your Search