Homes for Sale with a Pool in Holiday, FL

3 Beds ⋅ 2 Baths ⋅ Baileys Bluff Estates SubDv.

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

4365 Tahitian Gardens Circle Unit E, Holiday

$115,000

2 Beds ⋅ 1 Baths ⋅ Tahitian Gardens Condo SubDv.

CORNER UNIT with a private location! 2-bedroom condo in Tahitian Gardens, a GATED 55+ community. This corner unit features oversized living room windows, private kitchen area that can be closed off from the rest of the unit, newer luxury vinyl wood floors, newer hot water tank (2023). Included is a washer/dryer for your convenience. This unit would make a great year-round home or winter retreat. Tahitian Gardens has many activities including shuffleboard, arts and crafts, a bicycling club, bingo, dominoes, cards and more. Take a walk around the beautiful lake or sit on one of the many benches and enjoy watching the wildlife. You can also spend time relaxing in the large, heated swimming pool or play pool in the club house. Easy access to shopping, dining, and public transportation. Walking distance to CVS, Walgreens and Aldi. Located off US 19 in Holiday, FL with quick access to the Gulf of Mexico beaches, Tampa, Clearwater and St. Pete are less than an hour drive. Low down payment financing available to qualified individuals. Leased through 1/14/2027.

4365 Tahitian Gardens Circle Unit E, Holiday

$295,000

3 Beds ⋅ 2 Baths ⋅ Gulfwinds SubDv.

Virtually Staged. Welcome home to this 3 bedroom, 2 bath villa tucked at the end of a quiet cul-de-sac. With no neighbors behind you and generous space on the side of the home, you get the kind of privacy that's hard to find in villa living. Step out to the screened lanai with beautiful pavers and enjoy your morning coffee in peace. Inside, tall ceilings give the 1,740 square feet an open, airy feel. The kitchen features granite countertops and maple cabinets, and a separate laundry room keeps things organized. The primary suite sits at the back of the home and fills with natural light. The primary bath offers dual sinks, a soaking tub, and a large walk-in shower. Two additional bedrooms give you room for guests, a home office, or hobbies. The home has a 2026 roof, along with a clean four-point and wind mitigation inspection, which can help lower your insurance premium. Hurricane shutters are included, and the home is wired for a security system. Location makes it even better. You're minutes from the Tarpon Springs Sponge Docks and downtown Tarpon Springs for Greek restaurants, shops, and waterfront strolls. Launch your boat at the Anclote River Park ramp, spend the afternoon on the Gulf or walk / bike the paved Coastal Anclote Trail to Key Vista Nature Park. The low HOA fee of $350 covers outdoor maintenance, the community pool and clubhouse, plus cable and internet. Lock up and leave for the season, or settle in and enjoy more free time. An affordable, low-maintenance option whether you're looking for a seasonal home, an investment, or a simpler lifestyle.

2334 Barracuda Court, Holiday

$485,000

3 Beds ⋅ 2 Baths ⋅ Sand Bay SubDv.

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

4324 Tahitian Gardens Circle Unit D, Holiday

$119,500

2 Beds ⋅ 2 Baths ⋅ Tahitian Gardens Condo SubDv.

Experience the tranquility of condominium living. This turnkey two-bedroom, bath and a half condo is located in Tahitian Gardens, a fully gated, active 55+ community. This turnkey unit is offered fully furnished and boasts an upgraded bath with beautiful walk-in shower, large floor to ceiling living room windows plus updated bedroom windows. Relax on the tiled patio and enjoy the convenience of your assigned parking space directly in front of the unit. This residence is only minutes from the clubhouse, recreation center and heated swimming pool. Tahitian Gardens offers numerous activities such as shuffleboard, arts and crafts, bicycling club, bingo, dominoes, card groups, and more. Located off US 19 in Holiday, FL, with easy access to shopping and public transportation. Tampa and Clearwater airports are less than an hour’s drive. Walking distance to CVS, Walgreens and Aldi. Minutes away from Tarpon Springs, the Sponge Docks and the beach at Howard Park. Very easy to see but shown by appointment only.

4324 Tahitian Gardens Circle Unit D, Holiday

$335,000

3 Beds ⋅ 2 Baths ⋅ Gulfwinds SubDv.

Discover effortless Florida Gulf Coast living in this beautifully updated three-bedroom, two-bath villa in Gulfwinds, a low-maintenance, no age restrictions community in Holiday, Florida, near Tarpon Springs and the Gulf Beaches. Thoughtfully designed for comfort and convenience, this residence offers an inviting open-concept floor plan, refined finishes and exceptional indoor-outdoor living. The spacious kitchen features 42-inch maple cabinetry with crown molding, Caledonia granite countertops, stainless-steel appliances and convenient pull-out shelving. The adjoining dining and living areas create a seamless setting for everyday living and entertaining. The primary suite offers a custom California Closets walk-in closet and an en-suite bath with dual vanities, granite countertops, a soaking tub and separate shower. Additional bedrooms provide flexibility for guests or a home office, with custom closet systems throughout. Sliding doors open to an extended 16-by-16-foot screened lanai featuring terracotta pavers, a solid roof and retractable shades. Beyond, a paved backyard enclosed by a six-foot privacy fence creates a secluded outdoor retreat. Additional improvements include newer flooring, fresh interior paint, double-pane insulated windows, enhanced attic insulation, a 2023 A/C unit and a water softener. Residents enjoy convenient access to the nearby community pool and an ideal location for exploring Florida's Gulf Coast. Just minutes from Anclote River Park, Anclote Gulf Park and the historic Tarpon Springs Sponge Docks, Gulfwinds offers proximity to beaches, marinas, fishing, golf, shopping, dining and recreational trails connecting to the Pinellas Trail. Whether seeking a primary residence or seasonal retreat, this villa offers an appealing combination of low-maintenance living, thoughtful upgrades and coastal convenience.

2232 Parrot Fish Drive, Holiday

$175,000

2 Beds ⋅ 2 Baths ⋅ Holiday Lake Villas Condo SubDv.

Great location with beautiful pond view from most windows, friendly surroundings, nature and tranquility. The open model perfect home with Vaulted ceilings is perfect for you, just move right in. Amazing updates include Quartz and Granite Countertops, recessed lighting, luxury vinyl floors along with newer ceramic tile and lace ceilings and newer Stainless Steel appliances. Sliders from both the Master Bedroom and Living room lead to Florida Room to relax and enjoy the views. The Master Bedroom has 2 large closets and Master Bath with dual sinks. Separate storage room and Reserved parking with plenty of guest spaces. Clubhouse with heated pool, shuffleboard and activities. The affordable HOA covers exterior maintenance, roof, lawn care, insurance, trash, cable TV, and internet, water/sewer and more, allowing you to truly enjoy worry-free living. Perfectly situated near some of the area’s best attractions, you’re just minutes from the white sandy beaches of the Gulf Coast, Anclote River Park, and the historic Tarpon Springs Sponge Docks, known for its Greek restaurants, local shops, and waterfront charm. Downtown Tarpon Springs offers year-round festivals, farmers markets, and cultural events, while nearby shopping centers, medical facilities, and golf courses ensure everythin you need is winin easy reach. No Flood Zone. Furniture negotiable. PRESENT ALL OFFERS!

1022 Bowsprit Lane Unit 1022, Holiday

$330,000

3 Beds ⋅ 2 Baths ⋅ Holiday Lake Estates SubDv.

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

$379,900

3 Beds ⋅ 3 Baths ⋅ Holiday Lake Estates SubDv.

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

$179,900

2 Beds ⋅ 2 Baths ⋅ Tanglewood Mobile Village SubDv.

Great Waterview as you relax in the Florida room and watch Florida’s wildlife. Home features Newer Windows, Newer Luxury Vinyl Floorings, Walk in closets, Newer HVAC system with UV light, Carport that fits 2 average size cars and Enclosed Porch to enjoy Florida’s nature without being bugged too much. This lovely home is located in a Active 55+ community with Clubhouse, Year round Heated Pool, play Shuffleboard with other home owners, friends or family and low maintenance/HOA fees which includes trash pick up, grounds maintenance, Private Roads and common area taxes. Measurements are approx and information is deemed to be accurate and for the buyer verify.

3211 Southport Drive, Holiday

$550,000

4 Beds ⋅ 3 Baths ⋅ Key Vista Prcl 18 SubDv.

Welcome to 1937 Blue River Road, located in the highly sought-after Key Vista community in Holiday. This spacious 4-bedroom, 3-bath home with a 3-car garage also features a bonus room and additional flex space, offering plenty of room for a home office, gym, playroom, media room, or guest space. The large kitchen features a generous eat-in area and several newer updates, including the stove, dishwasher, and sink, along with updated sinks and fixtures throughout the home. The interior has also been freshly painted, giving the home a bright, refreshed feel. Major improvements include a 2023 roof and updated front and rear windows with hurricane protection for added peace of mind. The outdoor living space is one of the home’s best features. Situated on an extra-large conservation lot in a non-flood zone, the backyard offers a peaceful and private setting with tranquil views of the surrounding natural landscape. A spacious screened lanai provides the perfect place for morning coffee, outdoor dining, or relaxing in the shade, while the separate pergola area with paver decking creates an additional outdoor entertaining space. Whether hosting friends, grilling on the weekends, or simply enjoying the quiet conservation views, the backyard offers multiple areas to enjoy Florida living year-round. The landscape lighting adds ambiance in the evenings and highlights the outdoor space beautifully. Additional features include an EV charger, garage shelving, and the convenience of a 3-car garage with plenty of room for vehicles, storage, and hobbies. With its flexible floor plan, newer roof, expansive conservation lot, inviting outdoor living areas, and desirable Key Vista location, this home offers an exceptional combination of space, privacy, and Florida lifestyle living.

1937 Blue River Road, Holiday

$500,000

4 Beds ⋅ 3 Baths ⋅ Gulfwinds SubDv.

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

Homes for Sale with a Pool in Holiday, FL

All Homes for Sale with a Pool in Holiday, FL

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