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. This charming city boasts a delightful blend of suburban tranquility and vibrant coastal living, making it an ideal destination for families, retirees, and anyone seeking a serene lifestyle under the sun. With a rich history and a welcoming community, Holiday offers a unique atmosphere where neighbors become friends and outdoor adventures await around every corner.

One of the standout features of homes in Holiday is the abundance of properties with private pools. Imagine stepping into your own backyard oasis, where you can unwind, entertain, or simply soak up the Florida sunshine. These homes provide the perfect retreat after a day of exploring the nearby beaches or enjoying the local parks. With a variety of styles and sizes available, from cozy single-family homes to spacious estates, you’re sure to find the perfect match for your lifestyle.

Living in Holiday means you’re just a stone’s throw away from beautiful Gulf Coast beaches, world-class fishing, and a plethora of recreational activities. Whether you prefer lounging by your private pool or embarking on an adventure to discover the stunning natural beauty of the area, Holiday has it all.

Explore the vibrant local culture, with charming shops, delicious dining options, and community events that bring everyone together. Dive into the dream of owning a home with a private pool in Holiday, where every day feels like a vacation. Your perfect slice of paradise awaits!

Newest Holiday Homes with Private Pool type

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
$330,000
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
$379,900
3 Beds ⋅ 3 Baths ⋅ Holiday Lake Estates SubDv. ⋅ 34691 Zip Code
Virtually Staged. INVESTOR OPPORTUNITY! 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
$525,000
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
1117 Rushmore Drive, Holiday
$399,000
3 Beds ⋅ 2 Baths ⋅ Forest Hills SubDv. ⋅ 34690 Zip Code
Welcome to this Amazing Waterfront 3-bedroom, 2-bathroom residence, complete with a versatile bonus room! This home features a two-car garage and a wealth of exceptional upgrades. Step inside to find new tile flooring throughout the entryway, kitchen, bonus room, and recent remodeled guest bath. Enjoy the elegance of crown molding and ample closet space, including his and her walk-in closets in the Primary suite. The remodeled baths boast luxurious finishes, with a heated whirlpool tub in the master bath for your relaxation. Safety and convenience are paramount, with hurricane-proof replacement windows and a new garage door. Outdoor living is at its finest with a boat lift, floating dock, and davits, perfect for boating enthusiasts. Dive into your large in-ground pool while enjoying breathtaking views of the Anclote River and the vibrant local wildlife, all set against the backdrop of a wide canal and a high seawall. This home is a true gem for anyone seeking a waterfront lifestyle. Don't miss your chance to make it yours! CALL TODAY FOR YOUR PRIVATE TOUR...

1117 Rushmore Drive, 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
3748 Redwood 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
1324 Chancellor Drive, Holiday
$448,900
3 Beds ⋅ 3 Baths ⋅ Forest Hills SubDv. ⋅ 34690 Zip Code
Welcome to your own tropical oasis and the waterfront lifestyle you’ve been dreaming of! This beautifully renovated 3-bedroom, 3-bathroom waterfront pool home with a spacious bonus room is situated on a large lot along the Anclote River, offering approximately 70 feet of seawall and direct access to the Gulf. The sellers will have the solar panels removed and the roof replaced prior to closing, providing added peace of mind for the new owners. Inside, a desirable split-bedroom floor plan and new wood-plank tile flooring create a stylish and functional living space. The spacious living room flows seamlessly into the dining area, while sliding glass doors open to an expansive screened-in patio, bringing the best of Florida’s indoor-outdoor lifestyle home. A hallway off the main living area leads to two generously sized guest bedrooms. One features a private bathroom with convenient access to the pool area, while the second offers a large walk-in closet and easy access to the additional guest bathroom. The beautifully appointed kitchen features stainless-steel appliances, wood cabinetry, granite countertops, and a cozy breakfast nook—perfect for casual meals or morning coffee. The spacious primary suite offers a walk-in closet and an updated bathroom with a convenient step-in shower. Just beyond the primary suite, a large bonus room provides versatile space for a home office, den, nursery, gym, or additional living area. Step outside and discover your private Florida retreat. The expansive screened-in patio overlooks a sparkling swimming pool surrounded by stamped-concrete decking, while the large, fenced backyard provides plenty of space to relax, entertain, and enjoy the outdoors. A composite deck with pergola creates an inviting setting for outdoor dining, lounging, and soaking up the Florida sunshine year-round. And for boating enthusiasts, this property truly stands apart. Just steps from the deck, a composite boat dock with a 10,000-pound boat lift provides convenient access to the Anclote River and the Gulf. Spend the day boating, exploring nearby tropical islands, or enjoying the area’s beautiful sandy beaches—all from your own waterfront backyard. Bring your boat, your family, and your love of the water. This is Gulf Coast living at its best!

1324 Chancellor Drive, Holiday
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