Holiday Homes with Boatable Water Water Frontage

Holiday Homes with Boatable Water Water Frontage

Welcome to Holiday, Florida—a delightful gem nestled in the heart of Pasco County! This charming community is known for its warm weather, friendly atmosphere, and stunning waterfront properties that offer a unique lifestyle for those who love the great outdoors. With its close proximity to the Gulf of Mexico, Holiday is a paradise for boating enthusiasts and water lovers alike.

One of the standout features of Holiday is its abundance of homes with boatable water frontage. Imagine waking up to serene waterfront views, stepping out onto your private dock, and setting sail into the shimmering waters of the nearby canals and bays. Whether you're an avid fisherman, a leisurely cruiser, or simply enjoy the tranquility that comes with living by the water, Holiday has the perfect home for you.

The community is not only ideal for water activities; it also boasts a rich array of parks, recreational facilities, and vibrant local events that bring residents together. With easy access to shopping, dining, and entertainment options, you'll find everything you need just a stone's throw away.

In addition to its natural beauty and active lifestyle, Holiday is conveniently located near major highways, making it easy to explore neighboring cities and attractions. Whether you're looking for a seasonal getaway or a permanent residence, Holiday offers a welcoming environment and a vibrant community that makes it a fantastic place to call home. Discover the charm of waterfront living in Holiday, where adventure awaits just outside your doorstep!

Newest Holiday Homes with Boatable Water Water Frontage

2529 San Luis Road, Holiday
$324,900
3 Beds ⋅ 2 Baths ⋅ Aloha Gardens SubDv. ⋅ 34691 Zip Code
WATERFRONT LIVING w/ BOAT ACCESS || NO FLOOD INSURANCE REQUIRED || NO REAR NEIGHBORS || SOLAR PANELS **PAID FOR** Saves You Thousands || UPDATED HURRICANE WINDOWS || NEW ROOF 2025 & NEW HVAC 2026. Step inside to a home with plenty of windows and natural light coming in to brighten your every day! This FLEX FLOORPLAN offers many possibilities for a 3rd or 4th bedroom. The Home is presently a 2BR home, but there are 2-3 BONUS ROOMS that could be turned into a bedroom naturally and easily. A Large Multi-Purpose Room with Open Concept Space Overlooking the Waterfront Features Dinette, Sitting Area and Possible Home Office Space. The Primary Bedroom features a Walk in Closet, Ensuite with a Shower and Additional Space for a Den or Home Office. Split bedroom plan with inside laundry room. The private dock provides a great spot for kayaking, fishing, or simply enjoying the waterfront, with access to Lake Conley and the surrounding chain of lakes. NEW ROOF 2025, NEW HVAC 2026, Hot Water Tank 2024, NEWER 150MPH HURRICANE WINDOWS, and Newer Solar Panels, NEWER paver driveway, Garage with insulated garage door. Solar Panels are ** PAID FOR ** SAVE THOUSANDS YEARLY** on electric bills with average $30 monthly. This Home Offers a Seamless Blend of In-Door Out-Door Living. Step Outside through the Newer Sliding Door onto a Large 1000sqft Deck and Lighted Gazebo, Providing the Perfect Area for Entertaining on the Water. Leave Your Personal Dock for a Boat Ride, Explore a Chain of 3 Lakes Where Fishing and Bird Life is Plentiful. Seawall. Designed for Panoramic Views of Breathtaking Sunsets. Enjoy wildlife and Florida’s water birds, it’s like having a bird sanctuary in your back yard. Fish for bass and snook, while catching blue crabs for alfresco dining on your deck. Designed for Entertaining and Relaxation, the Residence Captures a Peaceful Ambiance Perfect for Lake Front Living. Featuring Meticulously Landscaped Grounds and an irrigation system drawing water from the lake. NO HOA, NO CDD. Walk 1 block to dog park. Walk or bike several blocks to the IMPRESSIVE J. BEN HARRILL SPORTS COMPLEX with pickleball/ tennis courts, soccer fields, baseball diamonds, basketball courts, outdoor hockey rink, playground, and Air Conditioned Gym with pickleball. Right around the corner from miles of bike trails and nature trails. Plus near Anclote River Park with a beach, fishing pier and boating.

2529 San Luis Road, Holiday
3138 Bluff Boulevard, Holiday
$649,000
2 Beds ⋅ 3 Baths ⋅ Baileys Bluff Estates SubDv. ⋅ 34691 Zip Code
GULF ACCESS AND AN OVERSIZED, ELEVATED WATERFRONT LOT IN BAILEYS BLUFF ESTATES! Discover waterfront living in Baileys Bluff Estates, a coastal community known for boating, fishing, and a relaxed Florida lifestyle. Set on an impressive 0.40-acre waterfront lot, this property features a residence positioned on the lot’s highest point, along with a seawall, existing dock, and space for a potential boat lift. The distinctive multi-level design takes advantage of the property’s natural elevation. The main living area offers comfortable living spaces, while the former lower-level garage has been converted into a flexible space with bathroom, spacious recreation room, and laundry area—ideal for guests, entertaining. This lower level got 4" of water during hurricane Helene. The expansive lot provides room to create a tropical retreat, outdoor entertaining area, or peaceful waterfront escape. Shopping, dining, beaches, a recreation center, and numerous parks are just a short drive away. THE REAL VALUE IS THE LOCATION! BRING YOUR BOAT AND MAKE YOUR WATERFRONT DREAMS A REALITY!

3138 Bluff Boulevard, Holiday
Bluff Boulevard, Holiday
$635,000
Bailey's Bluff Estates Unit 1 SubDv. ⋅ 34691 Zip Code
GULF-FRONT OPPORTUNITY IN BEAUTIFUL BAILEY'S BLUFF! Rare opportunity to build your dream waterfront estate directly on the Gulf in the desirable Bailey's Bluff subdivision of Holiday, Florida. This 85x293 Gulf-front lot offers breathtaking, long-range views of Anclote Island and the open waters of the Gulf. Featuring an impressive 80 feet of seawall, this exceptional homesite is surrounded by distinguished gulf front properties ranging from approximately $760,000 to $2.8 million. Imagine designing a custom coastal residence that captures spectacular sunsets, panoramic water views, and the beauty of Florida's Gulf Coast. An outstanding opportunity to secure a premier waterfront location and create a truly extraordinary home in an established luxury neighborhood. Bring your vision and make the Florida waterfront lifestyle yours!

Bluff Boulevard, Holiday
Bluff Boulevard, Holiday
$133,500
Baileys Bluff Estates SubDv. ⋅ 34691 Zip Code
Rare opportunity in Bailey’s Bluff! Build your dream Florida home on this vacant lot surrounded by mature trees and established homes. Enjoy the added benefit of private boat ramp access from the road behind the property, making it easy to take advantage of the beautiful waterways and coastal lifestyle. A peaceful setting with a great sense of privacy, yet close to everything Holiday and the Gulf Coast have to offer. Bring your plans and make this special property your own! **Located between 3028 and 3038 Bluff Blvd**

Bluff Boulevard, Holiday
5410 Flora Avenue, Holiday
$359,000
2 Beds ⋅ 2 Baths ⋅ Forest Hills SubDv. ⋅ 34690 Zip Code
Waterfront living with Gulf access in Holiday! This charming one-story concrete block home offers 2 bedrooms, 2 baths and 1,356 square feet of heated living space, ideally positioned on approximately 60 feet of frontage along the Anclote River. For boating and outdoor enthusiasts, the property features a new seawall, composite waterfront deck, dock with boat lift, and a separate floating dock perfect for jet skis, kayaks and paddle boards. The spacious screened-in lanai, finished with brick pavers, creates an inviting outdoor setting for relaxing, entertaining and taking in the ever-changing river views. Watch for dolphins, manatees and native birds, with beautiful sunsets providing an especially memorable backdrop. Inside, the home offers an updated kitchen with granite countertops, wood cabinetry and stainless-steel appliances, along with updated bathrooms and tile flooring throughout. A Florida room extends the living space, while a smaller screened lanai off the primary bedroom provides another peaceful spot to enjoy the outdoors. The roof was replaced in 2019. Conveniently located near Anclote River Park, Anclote Gulf Park, Key Vista Nature Park and Howard Park Beach, with easy access to Tarpon Springs, the historic Sponge Docks, shopping, restaurants and US-19. Whether you're looking for a full-time Florida residence, a second home or a waterfront retreat, this property offers an opportunity to enjoy the boating, fishing, nature and outdoor lifestyle that makes Florida waterfront living so appealing. Schedule your private showing today and experience the waterfront lifestyle for yourself.

5410 Flora Avenue, 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
4349 Tahitian Gardens Circle Unit C, Holiday
$94,900
1 Beds ⋅ 1 Baths ⋅ Tahitian Gardens Condo SubDv. ⋅ 34691 Zip Code
NEWER AC SYSTEM! Welcome to this bright, well-maintained one-bedroom condominium in Tahitian Gardens, a gated 55+ community. Expansive floor-to-ceiling living room windows fill the residence with natural light and create an open, inviting atmosphere. The home features tile flooring throughout, a walk-in shower, and a kitchen equipped with brand-new stainless-steel appliances, including a range, range hood, and refrigerator. Ceiling fans are located in the living room, kitchen and bedroom. The patio offers a partial lake view, and a private parking space is conveniently situated directly in front of the unit. Residents can enjoy the large, heated swimming pool, scenic community pathways, and lakeside setting. Tahitian Gardens also offers a variety of activities, including shuffleboard, arts and crafts, a cycling club, bingo, dominoes, and card groups. The community is conveniently located near dining and shopping, with CVS, Walgreens, Publix, and Aldi just minutes away. A short drive to Tarpon Springs provides access to the Sponge Docks, Sunset Beach, and Fred Howard Park. Tampa International Airport and St. Pete–Clearwater International Airport are both less than an hour away. The property is easy to show, and all reasonable offers will be considered. This residence is an excellent option for a primary home or seasonal retreat.

4349 Tahitian Gardens Circle Unit C, 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
1238 Flotilla Drive, Holiday
$549,900
5 Beds ⋅ 6 Baths ⋅ Forest Hills Un #22 SubDv. ⋅ 34690 Zip Code
GREAT PRICE REDUCTION * HURRY BEFORE IT'S GONE * WHERE CAN YOU GET A 1.2 ACRE PIECE OF WATERFRONT PROPERTY WITH 5 BEDROOMS, 4 .5 BATHS AND UNOBSTRUCTED WATER VIEWS * HERE'S ANOTHER OPPORTUNITY TO PURCHASE THIS UNIQUE AND MAGNIFICENT WATERFRONT HOME, SURROUNDED ON THREE SIDES BY SPECTACULAR WATER VIEWS * THIS HOME WITH SPANISH AND MEDITTERANEAN ARCHITECTURE, WITH FEATURES SUCH AS BEAMED CEILINGS AND ARCHED OPENINGS THROUGHOUT IS VERY SPACIOUS AND HAS AN ATTRACTIVE LAYOUT ON TWO FLOORS * TOTAL OF 4 MASTER BEDROOMS SUITES, ACCESSED BY TWO SEPARATE STAIRWAYS * OPEN UP TO DECKS WITH UNOBSTRUCTED WATER VIEWS * BEAUTIFUL MARBLED DESIGN CERAMIC TILE THROUGHOUT HOME * THE GROUND FLOOR IS ACCESSED BY A WELCOMING FOYER WITH STEP DOWN TO A LARGE LIVING ROOM ON ONE SIDE AND OFFICE/TV ROOM ON THE OTHER * HALLWAY LEADS TO A LARGE LIBRARY, A HALF BATH AND A STAIRWAY TO THE SECOND FLOOR * FOUR BEDROOMS AND 3 FULL BATHS GREET YOU WITH SERENE AND PEACEFUL VIEWS OF THE ANCLOTE RIVER * UPGRADES BY THE PRESENT OWNERS INCLUDE THREE AC SYSTEMS REPLACED WITHIN THE LAST 4 YREARS * 1 YR OLD HOT WATER HEATER * NEW KITCHEN WITH AMPLE CABINETS, ISLAND WITH SITTING AREA AND A SPACIOUS DINING AREA LEADING OUT TO THE POOL * THE GROUND FLOOR ALSO PROVIDES A MASSIVE GAMES ROOM WITH A WOOD BURNING FIREPLACE * PERFECT FOR GATHERINGS AND ENTERTAINTMENT * A FULL BATH WITH A SAUNA ADDS TO THE COMFORT OF THIS HOME * WALK OUTSIDE TO THE COVERED DECK FOR YEAR ROUND USE, HUGE PAVED DECK, POOL GAZEBO AND WATER VIEWS ALL AROUND. WITH 630 FEET OF WATERFRONT WALL PROVIDES NEW OWNERS THE OPPORTUNITY TO BUILD A DOCK WITH A BOAT LIFT AND POSSIBLY A BOATHOUSE * THE LARGE PIECE OF PROPERTY IS PERFECT FOR LOTS OF OUTDOOR ACTIVITIES * LOTS OF PARKING SPACE FOR MULTIPLE BIG TOYS AND VEHICLES * 3 LARGE OPEN GARAGE SPACES * DON'T MISS THIS ONCE IN A LIFETIME OPPORTUNITY TO OWN A BEAUTIFUL PIECE OF PARADISE * PRIVATE FINANCING WITH VERY GOOD TERMS AVAILABLE * REPAIRS NEEDED BUT AT THIS PRICE THE NEW OWNER WILL STILL HAVE HIGH BUILT IN EQUITY IN THE HOME Characters Remaining: 1731 *

1238 Flotilla Drive, Holiday
1332 Flotilla Drive, Holiday
$289,000
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
2122 Waterview Drive, Holiday
$139,900
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
2030 Gulfview Drive, Holiday
$774,900
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
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