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 vibrant community and picturesque landscapes, Holiday offers a unique blend of suburban charm and coastal allure. With its proximity to the stunning Gulf of Mexico, residents enjoy easy access to beautiful beaches, outdoor recreational activities, and a laid-back lifestyle that perfectly captures the essence of Florida living.

One of the standout features of homes in Holiday is the abundance of properties with private pools. Imagine stepping out into your own backyard oasis, where you can soak up the sun, host gatherings with friends and family, or simply unwind in your tranquil retreat. These homes with private pools offer the perfect setting for both relaxation and entertainment. Whether you’re enjoying a refreshing swim on a hot summer day or hosting a weekend barbecue by the pool, the possibilities are endless.

In addition to the allure of private pools, Holiday boasts a variety of amenities, including parks, shopping centers, and dining options that cater to all tastes. The community is also known for its friendly atmosphere and strong sense of belonging, making it an ideal place for families, retirees, and everyone in between.

If you’re seeking a residence that combines comfort, convenience, and a touch of luxury, look no further than the homes with private pools in Holiday, FL. Dive into the vibrant lifestyle this charming city has to offer, and discover your perfect home today!

Newest Holiday Homes with Private Pool type

2437 Fieldcrest Court, Holiday
$350,000
2 Beds ⋅ 2 Baths ⋅ Holiday Lakes West SubDv. ⋅ 34691 Zip Code
Lovely pool home with a large backyard and outdoor space! Don't be deceived by the front exterior of the home. This home is bigger on the interior and exterior than what you would think!! The home features 2 bedrooms, 2 full bathrooms, an office, a sunroom which can be used as a dining room, a kitchen with eat-in space, a living room with a wood burning fireplace, an interior laundry room and a 1-car garage. The home has a nice layout with split bedrooms (see attached floorplan). The kitchen is large, has double ovens, stainless-steel appliances and an eat-up bar! This home is clean and move-in ready. Roof 2018. New 200-amp panel with whole house surge protector 2026. A/C 2020. Hot water heater 2021. The outdoor area features an inground pool with solar heat, an outdoor cooking/bar area with a brick oven, dining area, lounge area, a firepit, a potting shed & garden space, a well for irrigation, and outdoor shower! The back yard has plenty of room for the kids and/or pets to play and even more room to park your boat and kayaks! This home is centrally located to the Anclote River, the Gulf of Mexico, Key Vista Nature Park, the Anclote Coastal Trail (which is right behind the house and offers over four miles of scenic paths that connect to the Pinellas Trail in Tarpon Springs), the Anclote River Park & boat launch, Fred Howard Park/Beach, schools, marinas, boating, fishing, waterfront dining, shopping, medical facilities and the Historic Tarpon Springs Sponge Docks. Welcome to the Florida lifestyle! This home is a must see and a pleasure to show!

2437 Fieldcrest Court, Holiday
2123 Bayou Drive, Holiday
$579,900
3 Beds ⋅ 2 Baths ⋅ Baileys Bluff Estates SubDv. ⋅ 34691 Zip Code
Waterfront living with Gulf access in Holiday. This 3-bedroom, 2-bathroom pool home at 2123 Bayou Dr sits on a saltwater canal with a private dock and seawall. It has 1,962 square feet of living space and a backyard made for the Florida boating lifestyle. Inside, the comfortable layout gives you room to spread out, with bright living areas for everyday living and hosting friends and family. The primary suite has its own private bath, and the two other bedrooms work well for guests, a home office, or hobbies. Step outside to your private pool overlooking the canal, the perfect spot to unwind and catch the breeze off the water. Tie up at your own dock, protected by a seawall, and cruise straight out to the Gulf of Mexico for fishing, sandbar days, and sunset rides. Boaters, kayakers, and anglers will love having the water right at their back door. You're minutes from Key Vista Nature Park, Anclote River Park, Gulf beaches, the historic Tarpon Springs Sponge Docks, and the shopping and dining along US-19. Clearwater, Tampa, and Tampa International Airport are an easy drive. Saltwater canal homes with a pool, dock, and Gulf access are hard to find. Schedule your private showing today.

2123 Bayou Drive, Holiday
3024 Pineview Drive, Holiday
$485,000
3 Beds ⋅ 2 Baths ⋅ Sand Bay SubDv. ⋅ 34691 Zip Code
Beautifully maintained 3-bedroom, 2-bath, 2-car garage, pool home on an oversized lot! This home features an open floor plan with kitchen/family room and a living room/dining room areas. The kitchen features wood cabinets, granite countertops, stainless-steel appliances and a separate eat-in space area. The cozy family room features a fireplace and has sliding doors to the beautiful outdoor area. Split bedrooms. Roof 2017. A|C 2020. Hot water heater 2016. The screened lanai has covered space that overlooks the pool. The large yard and outdoor space is perfect for entertaining and features a gazebo, a firepit, picnic table & swing, outdoor kitchen & bar, and there is a playhouse that is finished with an a/c and loft! The outdoor area has plenty of room for the kids and/or pets to play. There is also an area for a garden. The side yard/driveway has space to park a boat and/or RV. This home is centrally located to the Anclote River, the Gulf of Mexico, Key Vista Nature Park, the Anclote Coastal Trail (which offers over four miles of scenic paths that connect to the Pinellas Trail in Tarpon Springs), the Anclote River Park & boat launch, Gulf beaches, marinas, boating, fishing, waterfront dining, shopping, medical facilities and the Historic Tarpon Springs Sponge Docks. Welcome to the Florida lifestyle! This home is a must see and a pleasure to show!

3024 Pineview Drive, Holiday
1539 Dartmouth Drive, Holiday
$320,000
3 Beds ⋅ 2 Baths ⋅ Holiday Lake Estates SubDv. ⋅ 34691 Zip Code
Welcome to 1539 Dartmouth Drive! This beautifully updated 3-bedroom, 2-bath home in the heart of Holiday Lake combines modern style with inviting spaces. Enjoy a modern Florida room and a private office that provides a dedicated space for work or study. The newly renovated kitchen features granite countertops and wood cabinetry, while both bathrooms have been updated with a fresh, contemporary look. New closets with modern lighting add a stylish finishing touch. Beautiful above-ground pool with an open deck to enjoy the beautiful nature. Enjoy Florida living with convenient access to nearby beaches, Anclote River Park, and the famous Greek community of Tarpon Springs. With thoughtful updates and versatile spaces, this home offers a beautiful setting for your next chapter. Schedule your showing today!

1539 Dartmouth Drive, Holiday
3708 Holiday Lake Drive, Holiday
$369,900
3 Beds ⋅ 3 Baths ⋅ Holiday Lake Estates SubDv. ⋅ 34691 Zip Code
Virtually Staged. INVESTOR OPPORTUNITY! NEW ROOF OCT 2026/ NO HOA / PAID-OFF SOLAR PANELS. This renovated 3-bedroom, 3-bath pool home offers approximately 1,726 SF and an adjacent area with its own private entrance that potentially may be used as an in-law suite, with separate driveway, bedroom, full bath and kitchenette, ideal for multigenerational living, extended family, guests, or potential rental income. The updated main residence features a kitchen quartz countertop, modern cabinetry, updated appliances, renovated bathrooms, Luxury vinyl and tile flooring, new baseboards, contemporary fixtures, and fresh interior/exterior paint. Enjoy a large screened pool with a new pump, filter, timer and lighting, plus the flexibility of a spacious corner lot. Major value-added features include FULLY PAID, SELLER-OWNED SOLAR PANELS, EV CHARGER, NO HOA, and a 2024 WHOLE-HOUSE REPIPE INCLUDING NEW MAIN WATER LINE. A rare combination of energy savings and major improvements at an attractive price point. Some photos have been virtually staged for visualization purposes only.

3708 Holiday Lake Drive, Holiday
1419 Blue Marlin Boulevard, Holiday
$500,000
4 Beds ⋅ 3 Baths ⋅ Gulfwinds SubDv. ⋅ 34691 Zip Code
SALTWATER POOL. NO REAR NEIGHBORS. 4 BEDROOMS + DEN. This Gulfwinds home brings together the space, privacy, and Florida lifestyle you are looking for. With 2,480 square feet and 3 FULL baths, the SINGLE-STORY split bedroom layout gives you plenty of room to spread out. The spacious kitchen opens to the family room, while separate living and dining areas add flexibility for entertaining, working from home, or simply having a little extra breathing room. Step outside to your own tropical retreat. The screened SALTWATER POOL offers plenty of space to relax, dine, and entertain, while NO REAR NEIGHBORS adds to the sense of privacy. And your furry friends will be happy with pet safe turf running under foot! Several of the big-ticket items are already done, including a NEW ROOF IN 2026, NEW WATER HEATER IN 2026, BRAND-NEW WATER SOFTENER, and A/C replaced in 2018. Gulfwinds offers a COMMUNITY POOL, SIDEWALKS winding throughout the neighborhood, and COMMUNITY PONDS for an evening stroll. And the location? You’re approximately 3 MINUTES FROM WATERFRONT DINING and just 5 MINUTES FROM THE TARPON SPRINGS SPONGE DOCKS, putting restaurants, shops, and one of the area’s most recognizable waterfront destinations practically in your backyard. Come see how much this home — and this location — has to offer.

1419 Blue Marlin Boulevard, Holiday
2831 Blossom Lake, Holiday
$379,900
3 Beds ⋅ 2 Baths ⋅ Holiday Lakes West SubDv. ⋅ 34691 Zip Code
This 3-bedroom, 2-bath home features fresh interior and exterior paint, new LVP flooring, and stainless steel appliances. The kitchen offers plenty of cabinet and counter space, a large window overlooking the backyard, and a breakfast bar that opens to the living area. The open living space features vaulted ceilings, mirrored accent wall panels, and French doors leading to the screened-in pool area. The backyard offers a peaceful screened pool, creating a great space for relaxing or entertaining.

2831 Blossom Lake, Holiday
3143 Pineview Drive, Holiday
$1,299,999
4 Beds ⋅ 4 Baths ⋅ Baileys Bluff Estates SubDv. ⋅ 34691 Zip Code
Welcome to your dream waterfront estate in the sought-after Baileys Bluff community! This stunning custom mini mansion is perched high and dry with no HOA, offering unparalleled privacy and luxury. Enjoy direct Gulf access with a new dock equipped with electric and water, a seawall, and a serene backyard oasis featuring a lagoon-style saltwater pool, spa, waterfall, expansive Belgard paver deck, outdoor shower, travertine rear porch, and cedar trellis dining area—all with no rear neighbors. Step inside to soaring 10-14 foot ceilings, nine sets of French doors, and rare Santos Mahogany floors that exude timeless elegance. The chef’s kitchen is a masterpiece with granite counters, custom cabinetry, a large island, and a high counter perfect for entertaining. The first-floor primary suite is a true retreat with dual walk-in closets, private pool access, and an opulent spa bath with whirlpool tub and dual shower. Upstairs features a full secondary residence with three bedrooms, two baths, a massive living area, balcony with stunning sunset views, and a second laundry. The home also includes three spacious porches, a four-car garage with 14-foot ceilings, a six-inch slab, lift potential, and abundant workshop space. Luxury upgrades include impact windows, full hurricane strapping, exterior insulation, three new AC systems (2024), and a new tankless water heater. Baileys Bluff offers a community boat ramp, clubhouse, and parks, with nearby Anclote boat launch, marinas, waterfront dining, and the world-famous Tarpon Springs Sponge Docks accessible via quiet neighborhood roads. This estate blends sophistication, comfort, and waterfront living in one spectacular package.

3143 Pineview Drive, Holiday
5657 Oceanic Road, Holiday
$549,900
4 Beds ⋅ 4 Baths ⋅ Dodge City First Add SubDv. ⋅ 34690 Zip Code
Welcome to 5657 Oceanic Road, Holiday, Florida — a unique property offering an impressive 3,535 square feet of living space, a massive 1,900-square-foot garage, and a large pool, all situated on an oversized lot in a quiet, peaceful neighborhood. Designed for those who value space, flexibility, and comfort, this property offers room to live, work, entertain, and store vehicles, recreational equipment, or hobby essentials. The expansive garage provides exceptional versatility for car enthusiasts, workshop needs, storage, or additional workspace. Upstairs, the spacious primary suite features its own private living room or sitting area, creating a relaxing retreat separate from the rest of the home. Two dedicated office spaces offer excellent flexibility for remote work, a home-based business, creative pursuits, or additional workspace. Step outside and enjoy the large pool and oversized lot, offering plenty of room to relax, entertain guests, and enjoy the Florida lifestyle. Located in a quiet neighborhood, this property combines generous interior space with outdoor enjoyment and a sense of privacy. An exceptional financing opportunity adds even more appeal: a potential assumable VA loan at an outstanding 2.37% interest rate for qualified VA buyers, subject to lender approval and eligibility requirements.

5657 Oceanic Road, Holiday
2144 Harrison Drive, 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
2203 Riomar Drive, Holiday
$275,000
2 Beds ⋅ 2 Baths ⋅ Tahitian Homes SubDv. ⋅ 34691 Zip Code
Welcome to your private slice of Florida paradise! This fully furnished 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
2641 Flintwood 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! One or more photos in this listing have been virtually staged.

2641 Flintwood Drive, Holiday
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