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 sunshine and friendly community, Holiday offers a unique blend of suburban charm and natural beauty, making it an ideal place for families, retirees, and anyone seeking a tranquil lifestyle near the Gulf Coast.

One of the standout features of homes in Holiday is the abundance of properties boasting private pools. Imagine stepping into your backyard oasis, where you can relax and unwind in your own sparkling pool, surrounded by lush landscaping and the gentle sounds of nature. These homes provide the perfect setting for hosting summer barbecues, enjoying lazy afternoons under the sun, or simply taking a refreshing dip after a long day.

The real estate market in Holiday is diverse, with options ranging from cozy single-family homes to spacious estates, all designed to cater to your lifestyle needs. Many of these homes with private pools offer modern amenities, open floor plans, and easy access to the area's beautiful parks and recreational facilities. Whether you’re looking for a peaceful retreat or a vibrant community atmosphere, Holiday has something for everyone.

In addition to its beautiful homes, Holiday is conveniently located near stunning beaches, shopping centers, and excellent dining options. The nearby Anclote River and Gulf of Mexico provide endless opportunities for outdoor adventures, from fishing and boating to beachcombing and picnicking.

Discover the charm of Holiday, Florida, where your dream home with a private pool awaits! Embrace a lifestyle of relaxation and enjoyment in this delightful community.

Newest Holiday Homes with Private Pool type

$579,900
4 Beds ⋅ 4 Baths ⋅ Dodge City First Add SubDv. ⋅ 34690 Zip Code
Ok Let's try this again..... If space, comfort, and Florida living are at the top of your list, 5657 Oceanic Rd is a must-see! This beautifully maintained 4-bedroom, 3.5-bath home offers approximately 3,400 square feet of living space, giving you substantially more room than many of the surrounding homes. Two dedicated office spaces perfect for homeschooling or to set up arts and crafts. The spacious floor plan provides room to spread out, entertain, work from home, accommodate guests, and enjoy everyday Florida living without feeling cramped. The generous primary suite offers a private retreat, while the additional bedrooms provide flexibility for family. Step outside and enjoy your own private enclosed pool area, perfect for relaxing, entertaining, and taking advantage of Florida's year-round outdoor lifestyle. Assumable 2.37 VA loan for qualified buyers. Located in a quiet Holiday neighborhood with convenient access to beaches, the Sponge Docks, Honeymoon Island, Weeki Wachee Springs, shopping, restaurants, and Tampa Bay, this property offers both space and location. If you've been searching for a large Florida home without sacrificing location or lifestyle, this is the opportunity you've been waiting for.

5657 Oceanic Road, Holiday
$229,000
2 Beds ⋅ 2 Baths ⋅ Tahitian Dev SubDv. ⋅ 34691 Zip Code
Short Sale. **Short Sale:** This 3-bedroom, 2-bath home features an in-ground pool and is located in the desirable Tahitian Development neighborhood, conveniently close to shopping, schools, and beaches. The property boasts a spacious, tiered yard enclosed by vinyl fencing. The family room is adjacent to the kitchen, making it easy for busy families to spend time together. Additionally, the home has a split floor plan that separates the living room from the bedrooms, ensuring privacy and comfort.

2144 Harrison Drive, Holiday
$244,900
2 Beds ⋅ 2 Baths ⋅ Tahitian Homes SubDv. ⋅ 34691 Zip Code
Move-in ready and beautifully updated, this charming 2-bedroom, 2-bath home features an oversized one-car garage, a brand-new above-ground pool with ladder, and inviting indoor-outdoor living spaces. The bright, open floor plan is ideal for everyday living and entertaining, while the spacious, fully fenced backyard provides plenty of room to relax, gather, or enjoy time with pets. Recent improvements include a new A/C system, water heater, kitchen appliances, washer and dryer, lighting, screened front and rear patios, outdoor pool shower, and above-ground pool—all completed in 2026. The hallway bathroom was also refreshed in 2026 with new flooring, vanity, faucet, and lighting. Additional upgrades include fresh interior paint (2026), vinyl flooring (2025), new windows (2025), a privacy fence (2025), and a roof installed in 2019. With no HOA and no flood insurance currently required, this property offers added flexibility and value. Enjoy a convenient location approximately eight minutes from the famous Tarpon Springs Sponge Docks, 36 minutes from Clearwater Beach, and 37 minutes from Tampa International Airport, with shopping, dining, employment centers, and Tampa Bay destinations within easy reach. Everything has been thoughtfully prepared for its next owner—simply unpack, settle in, and start enjoying your new home.

3748 Redwood Drive, Holiday
$182,150
2 Beds ⋅ 2 Baths ⋅ Orangewood Village SubDv. ⋅ 34690 Zip Code
Welcome to 4640 Tropical Lane in Holiday! This 2-bedroom, 1.5-bath single-family home offers 988 square feet of living space with a flexible floor plan and plenty of potential. Features include a spacious living area, Florida room, attached one-car garage, fenced backyard and private in-ground pool. The additional flex space provides options for a home office, guest space or hobby room. Conveniently located near shopping, dining and major roadways. This property is ready for a new owner to bring their personal touches and make it their own. Property is being sold as-is. Schedule your showing today!

4640 Tropical Lane, Holiday
$449,000
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
$284,900
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
$499,900
3 Beds ⋅ 2 Baths ⋅ Key Vista Ph 04 SubDv. ⋅ 34691 Zip Code
Welcome to this beautifully updated three-bedroom, two-bathroom pool home in the gated community of Key Vista in Holiday! Offering an impressive combination of thoughtful updates, smart-home technology, and resort-style amenities, this home is designed for comfortable and easy Florida living. Major improvements include a 2024 roof with a 25-year warranty, 2024 water heater, 2019 windows, 2021 Shaw Luxury Vinyl Plank flooring with 5¼-inch baseboards, and a 2020 AC compressor replacement featuring a 3-ton, 14 SEER heat pump with a 10-year warranty. The AC condenser is also from 2020. Additional updates include 2019 kitchen appliances, 2021 garage door opener and springs, 2017 washer and dryer, 2021 renovations to both bathrooms, and permanent exterior lighting installed in 2025. The open-concept interior offers a spacious and inviting layout with a large kitchen island perfect for meal preparation and casual dining, granite countertops, stainless steel appliances, abundant cabinetry, and a breakfast nook overlooking the pool. A separate dining room provides additional space for entertaining. The spacious primary bedroom features a vaulted ceiling, ceiling fan, and relaxing pool views. The beautifully renovated primary bathroom features a dual-sink granite-top vanity, glass-enclosed shower, and newly tiled finishes, while the second bathroom was also renovated in 2021. Step outside and enjoy your private pool and fenced backyard, designed for effortless outdoor living. The pool features Hayward OmniLogic automation that allows you to control the pump, spa, and heater remotely from your smartphone, making it easy to turn everything on before you even step outside. The pool and spa lights can also be operated remotely, eliminating the need to go outside the screened enclosure to adjust switches. A 2025 salt cell replacement provides added convenience, while 2026 LED pool and spa lights offer enhanced lighting and remote operation. The pool also features beautiful natural travertine decking, a built-in pool-wall vacuum system, and an included Hayward robotic pool cleaner. The extended screened lanai features an Elite roof, creating additional covered outdoor living space. Smart technology continues throughout the home with a Sensi smart thermostat that can be controlled through your smartphone and a smart garage door opener that can notify you if the garage is left open too long or when you leave home. The home includes a generator that provides backup power for lighting, ceiling fans, and other select areas of the home that is prewired with a transfer switch, which was installed around 2023. Additional exterior features include gutters, a professionally installed drainage system, hurricane shutters for the entire home, front-door and Palladian-window mesh hurricane protection, and a professionally painted exterior using Sherwin-Williams Emerald Shield paint in 2021. Ring Doorbell and Ring security cameras provide additional smart-home convenience and security around the front garage area and pool lanai. The Key Vista community offers an outstanding lifestyle with a community pool, clubhouse, sport courts, and additional amenities, while the master association includes cable. Conveniently located near the J. Ben Harrill Recreation Complex, numerous parks and trails, dining and shopping options, and zoned schools. Schedule your showing today!

2530 Arrowpointe Drive, Holiday
$459,500
3 Beds ⋅ 2 Baths ⋅ Glenwood Gulf Trace SubDv. ⋅ 34691 Zip Code
Per recent Appraisal square footage is living space of 2151! 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
$249,999
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
$545,000
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
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