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

2 Beds ⋅ 2 Baths ⋅ Tahitian Homes SubDv. ⋅ 34691 Zip Code

Welcome to your private slice of Florida paradise! This beautifully updated 2-bedroom, 1 -1/2 bath ranch sits high and dry with no flood history and offers breathtaking sunset views over the water. Step inside to discover a stunning modern kitchen featuring solid cherry wood cabinets, stainless steel appliances, and granite countertops. The open layout flows effortlessly over stone travertine flooring throughout the kitchen, dining area, and bedrooms, combining elegance with easy coastal living. Unwind in the inviting Florida room, where large windows open to the serene outdoors filled with birds and natural wildlife. Outside, enjoy your heated pool with a newer saltwater system and skimmer, or cast a line from your newer huge Trex dock perfect for fishing, relaxing, or soaking in the view. Oversized one car garage with attached separate Landry room. The vinyl seawall with concrete cap (installed in 2014) and new roof (2020) ensure peace of mind and lasting value. Whether you’re looking for a full-time home, seasonal escape, or profitable investment, this property checks every box it’s been a successful income property since 2017 and comes fully furnished and ready to enjoy or rent from day one.

2203 Riomar Drive, Holiday

3 Beds ⋅ 3 Baths ⋅ Forest Hills SubDv. ⋅ 34690 Zip Code

Welcome to your tropical oasis and the waterfront lifestyle most people only dream about! This beautifully renovated 3-bedroom, 3-bathroom waterfront pool home with a bonus room is situated on a large lot along the Anclote River, featuring approximately 70 feet of seawall with direct Gulf access. Powered by solar, this stunning home offers a desirable split-bedroom floor plan and new wood-plank tile flooring throughout. As you enter, you'll immediately appreciate the spacious living area, which flows seamlessly into the dining room. Sliding glass doors open to an expansive screened-in patio, creating the perfect indoor-outdoor living experience. To the left, a hallway leads to two generously sized guest bedrooms. One features its own private bathroom with access to the pool area, while the second guest bedroom offers a large walk-in closet and is conveniently serviced by the additional guest bath. The beautifully appointed kitchen features stainless-steel appliances, wood cabinetry, granite countertops, and a cozy breakfast nook. The spacious primary suite offers a walk-in closet and an updated bathroom with a convenient step-in shower. Just off the primary suite, a large bonus room provides flexible space for a home office, den, nursery, or additional living area. Step outside and discover your own private Florida retreat. The expansive screened-in patio overlooks a beautiful swimming pool surrounded by stamped concrete, while the large, fenced backyard provides plenty of room to relax and entertain. A composite deck with pergola creates an inviting space for outdoor dining, lounging, and enjoying the Florida sunshine year-round. For the boating enthusiast, this property truly shines. Just steps from the deck is a composite boat dock with a 10,000-lb boat lift, offering direct access to the Gulf. Whether you're heading out for a day on the water, exploring nearby tropical islands, or enjoying the area's beautiful sandy beaches, this waterfront home makes it easy to embrace the Florida lifestyle. Bring your boat, your family, and your love of the water—this is Gulf Coast living at its best!

1324 Chancellor Drive, Holiday

3 Beds ⋅ 2 Baths ⋅ Oak Hill SubDv. ⋅ 34690 Zip Code

This 3-bedroom, 2-bathroom home is located in the Oak Hill Unit neighbourhood. This home features a welcoming open floor plan that creates a seamless flow throughout the main living spaces, perfect for both everyday life and entertaining. The updated kitchen is beautifully appointed with granite countertops and stainless-steel appliances. For your privacy, the primary bedroom includes a dedicated attached bathroom. Step outside to discover your own private swimming pool, offering a great space to relax and unwind. Conveniently located near public schools and just a short drive to Gulf beaches, shopping, dining, and other amenities. Schedule your private showing today!

2641 Flintwood Drive, Holiday

5 Beds ⋅ 6 Baths ⋅ Forest Hills Un #22 SubDv. ⋅ 34690 Zip Code

GREAT PRICE REDUCTION * HURRY BEFORE IT'S GONE * WHERE CAN YOU GET A 1.2 ACRE PIECE OF WATERFRONT PROPERTY WITH 5 BEDROOMS, 4 .5 BATHS AND UNOBSTRUCTED WATER VIEWS * 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, WITH 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 OF 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 * PRIVATE FINANCING WITH VERY GOOD TERMS AVAILABLE * Characters Remaining: 1731 *

1238 Flotilla Drive, Holiday

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 • Double-Pane, Impact-Rated Windows Installed, providing enhanced protection, energy efficiency, comfort, and peace of mind while also 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

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

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

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

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 pump 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 ⋅ 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

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