Holiday Homes with Boatable Water Water Frontage

Holiday Homes with Boatable Water Water Frontage

Welcome to Holiday, a charming city located in Pasco County, Florida. Known for its picturesque waterfront views and vibrant community, Holiday offers a perfect blend of relaxation and recreation for residents and visitors alike.

One of the standout features of Holiday is its homes with boatable water frontage. Imagine waking up to the soothing sounds of the water lapping against the shore, stepping outside to your own private dock, and setting off on a leisurely boat ride along the scenic waterways. Whether you enjoy fishing, kayaking, or simply cruising along the coast, living in a home with boatable water frontage in Holiday allows you to embrace the waterfront lifestyle to the fullest.

In addition to the stunning waterfront properties, Holiday boasts a variety of amenities and attractions for residents to enjoy. From local shops and restaurants to parks and recreational activities, there is always something exciting to explore in this vibrant city. With its convenient location near the Gulf of Mexico, residents can also easily access beautiful beaches and outdoor adventures.

If you're looking for a place where you can relax, unwind, and indulge in waterfront living, Holiday is the perfect destination. Discover the beauty and charm of this waterfront city and find your dream home with boatable water frontage in Holiday, Florida.

Newest Holiday Homes with Boatable Water Water Frontage

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 ⋅ Lake Conley Mhp SubDv. ⋅ 34691 Zip Code

You'll love coming home to this beautifully remodeled 2-bedroom, 2-bathroom double-wide mobile home in the highly sought-after 55+ gated community of Lake Conley MHP, where you own the land! Enjoy peaceful water views from the spacious, fully enclosed front porch—the perfect spot to sip your morning coffee or unwind at the end of the day. From the moment you enter the meticulously maintained gates of Lake Conley MHP, you'll appreciate the pride of ownership, beautifully landscaped grounds, and welcoming atmosphere that define this exceptional community. Step inside this move-in-ready home—just bring your toothbrush! The light-filled, open floor plan has been thoughtfully updated with quality improvements throughout. The remodeled kitchen (2019) features new cabinetry and offers plenty of storage and workspace, while a new dishwasher was installed in 2025. Additional updates include new windows and blinds (2018), laminate flooring and subfloors (2018), remodeled bathrooms (2020), a new A/C system (2021), a decorative driveway (2022), a new electrical panel (2023), new porch screens (2023), new skirting (2024), and a roof resealed with a new vent installed (2025). Lake Conley MHP offers affordable living with low monthly HOA fees of just $63.82. This pet-friendly, golf cart community features an active social calendar, a heated swimming pool, shuffleboard courts, and a clubhouse. Residents also enjoy access to a private fishing dock and community boat ramp. RV and boat storage is available on-site for an additional annual fee, subject to availability (small spaces: $240/year; large spaces: $480/year). Conveniently located in Holiday, you'll be just minutes from shopping, restaurants, entertainment, beautiful Gulf beaches, Honeymoon Island, and the famous Tarpon Springs Sponge Docks. Tampa International Airport is approximately 35 minutes away, and Orlando's world-renowned theme parks are about a 90-minute drive. Don't miss this incredible opportunity to own a beautifully updated home in one of the area's most desirable 55+ communities. Pack your bags—you've just found your new home! Bonus Opportunity!!!!! Golf cart available for purchase! The golf cart may be included with the sale of the home with a full-price offer.

2122 Waterview Drive, Holiday

2 Beds ⋅ 2 Baths ⋅ Baileys Bluff Estates SubDv. ⋅ 34691 Zip Code

"Gulf Access Waterfront Home in Historic Baileys Bluff Estates" A rare opportunity to own a true waterfront gem with your own private boat ramp! Enjoy a quick 2-minute boat ride to the open Gulf and just 10 minutes more to Anclote Island—perfect for boating, fishing, and island adventures. This beautifully maintained 2-bedroom, 2-bath split floor plan home offers an open and inviting layout ideal for entertaining. The updated kitchen features granite countertops, solid maple wood cabinetry, and a spacious pantry. Rich dark wood flooring flows throughout the home, adding warmth and elegance. Wake up to Gulf views from the expansive primary suite, complete with a large walk-in closet and a luxurious en-suite bathroom featuring dual sinks and granite countertops. Relax in the Florida room overlooking a generous backyard and serene open water views of Anglers Cove, or unwind in the screened-in back porch while enjoying local wildlife. The ground level includes an oversized 2-car garage and an additional 1,360 sq ft of valuable storage space—perfect for all your recreational and boating needs. Recent updates provide added value and peace of mind, including a new roof (August 2022), new A/C system, and a brand-new paver driveway (July 2026). Baileys Bluff Estates is a vibrant, active community offering social gatherings at the Gulf-front clubhouse just across the street, where you can take in breathtaking sunsets. The Pinellas Trail is conveniently located at the community entrance, and Key Vista Nature Park is just a 15-minute walk away, offering scenic trails and shoreline exploration. The famous Tarpon Springs Sponge Docks, beaches, waterfront dining, shopping, are a short car drive away. Experience waterfront living at its best—schedule your private showing today!

2030 Gulfview Drive, Holiday

3 Beds ⋅ 2 Baths ⋅ Forest Hills SubDv. ⋅ 34690 Zip Code

MOTIVATED SELLER! No flood zone insurance is required. Some photos have been virtually staged. This waterfront home with direct access to the Gulf of America presents a rare opportunity to enjoy boating, kayaking, and breathtaking sunset views right from your own backyard. This move-in-ready residence offers the best of Florida waterfront living with three bedrooms, two updated bathrooms, and a spacious kitchen featuring plenty of cabinet storage. The roof was replaced in April 2026, and the water heater was replaced in February 2018. The backyard creates an ideal space for entertaining or relaxing while enjoying peaceful canal and sunset views. With no HOA, this property provides added flexibility and freedom of ownership. Conveniently located near shopping, dining, schools, medical facilities, Gulf Coast beaches, and Tampa International Airport, this waterfront home offers exceptional value for year-round living, a second home, or an investment opportunity. Schedule your private showing today and experience the Florida waterfront lifestyle for yourself!

1345 Basswood Drive, Holiday

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

Embrace Waterfront Florida living at its finest in this remodeled residence that carries no HOA restrictions. Designed for outdoor enthusiasts with frequent dolphin and manatee sightings, this home offers a scenic 20-minute boat cruise to the open Gulf, complete with ample docking space for your boat. Unwind and relax in the screened lanai to take in gorgeous evening sunsets. This home features 2 bedrooms, a spacious bonus room with water views that can be used as a 3rd bedroom, 3 full bathrooms and a built in office space that overlooks the gorgeous water views. Due to the home sitting on a higher foundation, it has been storm tested, and passed with no flooding, even from Hurricanes Helene, Milton, Ian and Irma. This home retreat is a proven short-term rental performer! Offers total versatility as a turn-key investment, personal vacation retreat, or full-time waterfront primary residence. With a newer roof and AC unit, this relaxing sanctuary is ready to call home.

1240 Trunkfish Drive, Holiday

2 Beds ⋅ 2 Baths ⋅ Aloha Gardens SubDv. ⋅ 34691 Zip Code

**Waterfront Living • Fully Furnished • Proven 5-Star Short-Term Rental** Whether you're searching for your own waterfront retreat or a turnkey investment opportunity, this beautifully maintained **2-bedroom, 2-bath** home offers the best of both worlds. Being offered **fully furnished (with the exception of artwork and some pieces, list attached) this waterfront gem has operated as a **successful 5-star short-term rental** with a proven rental history, making it an exceptional opportunity for investors while also serving as the perfect full-time residence, seasonal getaway, or vacation home. Buyer should verify local short-term rental regulations and future rental requirements. Inside, you'll find a bright, welcoming interior filled with vibrant coastal colors that perfectly complement the Florida lifestyle. The spacious **waterfront sunroom** provides panoramic canal views and is the perfect place to enjoy your morning coffee, curl up with a good book, or unwind while taking in the shimmering sunset reflections across the water. Step outside into your own tropical waterfront oasis where mature landscaping creates a peaceful, private setting ideal for entertaining family and friends or simply relaxing in the beauty of Florida's waterfront lifestyle. **Looking to maximize the waterfront lifestyle?** Nearby homeowners have enhanced their properties with private fishing docks, offering future owners the opportunity to explore adding their own private dock for fishing, kayaking, paddleboarding, or boating enjoyment (subject to buyer verification, permitting, and local regulations). Major improvements provide added value and peace of mind, including: New Roof(2019), Electrical Updated (2015), New Windows (2022), New A/C System (2023) Move right in or begin generating rental income from day one with this beautifully furnished waterfront property. Whether your dream is peaceful waterfront living or owning a proven income-producing investment, this exceptional home delivers comfort, charm, and endless possibilities. **Come experience the tranquility, beauty, and lifestyle that make waterfront living so special.

4114 Sunray Drive, Holiday

3 Beds ⋅ 2 Baths ⋅ Forest Hills SubDv. ⋅ 34690 Zip Code

Welcome to this spectacular waterfront property in the Forest Hills subdivision, a true tropical paradise and boater's dream offering direct Gulf access from your private dock and 10,000-pound boat lift. From the grand circular driveway and beautifully updated landscaping to the expansive wrap-around screened lanai, this ranch-style home is designed for seamless indoor-outdoor living against the backdrop of stunning Anclote River sunrises and sunsets. Inside, a spacious great room features elegant tile flooring, fresh paint, and insulated windows that flood the home with natural light, leading into a beautiful kitchen equipped with premium Bosch, Frigidaire, and Whirlpool appliances. The primary suite serves as a relaxing sanctuary with dual sliding closet doors, a dedicated mini-split AC, and dramatic floor-to-ceiling windows overlooking the water, while the secondary bedrooms offer incredible versatility, including a bonus space with a dry bar and mini-fridge ideal for a home office or gym. Both bathrooms have been completely renovated, featuring modern fixtures, a laundry closet with a premium LG washer and dryer, and a walk-in shower with a stylish glass backsplash and supportive grab bars. Outside, elegant pavers guide you to the private pier where you can catch snook and redfish right from the backyard, while the fenced green space provides a wonderful area for pets to roam. Complete with a converted garage perfect for a workshop and three storage sheds for outdoor gear, this one-of-a-kind riverfront retreat is entirely move-in ready and waiting for your watercraft.

1133 Grand Boulevard, Holiday

2 Beds ⋅ 2 Baths ⋅ Baileys Bluff Estates SubDv. ⋅ 34691 Zip Code

NEVER FLOODED DURING HURRICANE HELENE! This is a rare opportunity to own a Gulf-access waterfront home that offers both an exceptional boating lifestyle and added peace of mind. According to the seller, the home has never experienced flooding or water intrusion, making it an outstanding choice for buyers seeking waterfront living with confidence. Nestled in the highly desirable Baileys Bluff Estates, this move-in-ready waterfront home sits on an oversized 0.31-acre lot with approximately 55 feet of saltwater canal frontage, offering direct Gulf access in about one minute. Bring your boat, kayaks, paddleboards, and fishing gear—your waterfront adventures begin right in your own backyard. Boaters will appreciate the private boat ramp, 10,000-pound boat lift, with, stationary dock, and concrete seawall, making launching and storing your boat effortless. Spend your days fishing, scalloping, island hopping to Anclote Key, or watching spectacular Gulf sunsets just minutes from home. Inside, you'll find an inviting floor plan featuring 2 bedrooms, 1.5 baths, an updated kitchen with solid wood cabinetry, updated bathrooms, comfortable living spaces, and a bright Florida room overlooking the tranquil canal. The home has been well maintained and is ready for its next owner. Major recent improvements provide outstanding value, including a brand-new roof (2025) and a brand-new air conditioning system, helping reduce future maintenance costs while increasing buyer confidence. The spacious backyard provides plenty of room to entertain, garden, or simply relax while enjoying peaceful waterfront views and abundant Florida wildlife. Located just minutes from Anclote River, the Gulf of Mexico, Key Vista Nature Park, the famous Tarpon Springs Sponge Docks, beaches, waterfront dining, shopping, and medical facilities, this home offers the perfect balance of recreation and convenience. Whether you're looking for a year-round residence, seasonal retreat, or waterfront investment, opportunities like this are becoming increasingly difficult to find. No HOA, Move-in ready. Schedule your private showing today and discover why this exceptional Gulf-access waterfront property is one of Holiday's best boating values.

3318 Pineview Drive, Holiday

Ibis Sub SubDv. ⋅ 34691 Zip Code

One of the last opportunities to build a custom coastal estate in the exclusive gated community of Ibis. With only 13 homesites originally offered and just 8 custom residences currently built, this private enclave delivers a rare combination of luxury, privacy, and oversized estate-style living. Situated on over half an acre at the end of a quiet cul-de-sac on a dead-end street, this homesite offers the ideal setting to design and build your dream retreat surrounded by nature and upscale custom homes. Community guidelines require a minimum 2,500 sq ft residence, preserving the architectural integrity and luxury character of the neighborhood. Enjoy the best of Florida living just minutes from Key Vista Nature Park, the Anclote Coastal Trail, waterfront parks, public boat ramps, Gulf beaches, and vibrant local dining. Conveniently located approximately 15 minutes from Downtown New Port Richey and the historic Tarpon Springs Sponge Docks, with Clearwater and Tampa International Airport within an easy commute. Whether you envision a modern coastal masterpiece, private pool retreat, or forever home tucked away in a peaceful gated setting, this is a rare chance to secure one of the few remaining homesites. AI-enhanced conceptual renderings shown for inspirational purposes only. No home currently exists on the property.

3046 Sheppards Crook Ct, Holiday

2 Beds ⋅ 2 Baths ⋅ Aloha Gardens SubDv. ⋅ 34691 Zip Code

Virtually Staged. OPPORTUNITY knocks!! Back on market due to buyers inability to perform. Tucked along the shores of Lake Conley, this turn key 2 bedroom, 2 bathroom home feels like the kind of place where mornings start slow with coffee on the porch and evenings end around the fire pit or swinging by the water under the stars. From the moment you arrive, the covered front porch with its welcoming bench invites you to sit down, relax, and stay awhile. Inside, natural light pours through the generous-sized rooms, creating a bright and cheerful feel throughout the home. The kitchen is both stylish and functional, featuring quartz countertops, abundant cabinetry, all stainless appliances included, and even a brand new microwave! The spacious primary suite offers its own private ensuite bath, while the inside laundry room adds everyday convenience. Step out back and discover the true heart of the property. The backyard is a little slice of Florida paradise with a mature mango and banana trees, a charming gazebo with swing, screened back porch, cozy fire pit area, and a brand new crushed concrete seawall overlooking the lake. Whether you're entertaining friends, gardening, fishing, or simply unwinding after a long day, this fenced backyard was made for making memories. Complete with a one-car garage and a 2025 roof, this move in ready home blends comfort, charm, and waterfront living into one special package! Also a great investment option for short or long term rental!

2146 Society Drive, Holiday

Total of 1.4675 acres, 2 parcels of land. Owner will not sell properties individually. Nestled on the shimmering Anclote River in prime territory in Holiday, Florida. Situated on a waterway that leads out to the Gulf. Located on a coveted cul-de-sac, 200 feet of water frontage is retained by an existing seawall and encircled by trees for privacy. The property has direct views of a conservation island. ALL utilities including city water, power, and sewer are present. A myriad of possibilities are available including subdividing the land into three individual lots (each .48 acres) or retaining the parcel to accommodate a large, single-family home. Zoning permits a SFH structure or a duplex on each lot; one per lot if so desired. For investors or individuals, this prospect offers true flexibility and the chance to acquire a rare stretch in a market hungry for property to support new construction in well-positioned Pasco County. Minutes from: the sparkling Gulf, the culinary delights found in Tarpon Springs, all the retail you need on US Highway 19, and the multi-faceted Anclote River Park offering kayak/fishing access, picnic area, playground, 24/7 boat ramps, recreational courts and more! This nuanced investment suits numerous objectives. Buyer to verify all dimensions, lot sizes, zoning, permitting, leasing restrictions etc.

Flotilla, Holiday

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