Holiday Homes with Water View

Holiday Homes with Water View

Welcome to Holiday, Florida—a hidden gem nestled in the heart of Pasco County, where sun-kissed shores meet tranquil waters. Known for its charming neighborhoods and friendly atmosphere, Holiday offers an inviting blend of natural beauty and modern convenience. With its close proximity to the Gulf of Mexico, residents enjoy a laid-back lifestyle surrounded by picturesque landscapes and a vibrant community spirit.

One of the most alluring features of Holiday is its stunning homes with water views. Imagine waking up each morning to the gentle lapping of waves and breathtaking sunsets that paint the sky in hues of orange and pink. These homes, ranging from cozy bungalows to spacious waterfront estates, provide a serene retreat for those seeking peace and relaxation. Many properties boast private docks, allowing residents to indulge in boating, fishing, or simply soaking in the serene ambiance.

In addition to its scenic beauty, Holiday is conveniently located near shopping, dining, and recreational activities. With numerous parks and nature preserves, outdoor enthusiasts can explore hiking trails, picnic spots, and wildlife watching opportunities. The nearby beaches offer endless fun in the sun, while local eateries serve up delicious fresh seafood and other culinary delights.

Whether you're looking to raise a family, enjoy retirement, or simply escape the hustle and bustle of city life, Holiday, Florida, with its enchanting water views, is the perfect place to call home. Discover your dream property in this idyllic community and embrace a lifestyle filled with sunshine, serenity, and the beauty of nature.

Newest Holiday Homes with Water View

3 Beds ⋅ 3 Baths ⋅ TB8547859 MLS

Welcome to your tropical oasis and the waterfront lifestyle most people only dream about! This beautifully renovated 3-bedroom, 3-bathroom waterfront pool home with a bonus room is situated on a large lot along the Anclote River, featuring approximately 70 feet of seawall with direct Gulf access. Powered by solar, this stunning home offers a desirable split-bedroom floor plan and new wood-plank tile flooring throughout. As you enter, you'll immediately appreciate the spacious living area, which flows seamlessly into the dining room. Sliding glass doors open to an expansive screened-in patio, creating the perfect indoor-outdoor living experience. To the left, a hallway leads to two generously sized guest bedrooms. One features its own private bathroom with access to the pool area, while the second guest bedroom offers a large walk-in closet and is conveniently serviced by the additional guest bath. The beautifully appointed kitchen features stainless-steel appliances, wood cabinetry, granite countertops, and a cozy breakfast nook. The spacious primary suite offers a walk-in closet and an updated bathroom with a convenient step-in shower. Just off the primary suite, a large bonus room provides flexible space for a home office, den, nursery, or additional living area. Step outside and discover your own private Florida retreat. The expansive screened-in patio overlooks a beautiful swimming pool surrounded by stamped concrete, while the large, fenced backyard provides plenty of room to relax and entertain. A composite deck with pergola creates an inviting space for outdoor dining, lounging, and enjoying the Florida sunshine year-round. For the boating enthusiast, this property truly shines. Just steps from the deck is a composite boat dock with a 10,000-lb boat lift, offering direct access to the Gulf. Whether you're heading out for a day on the water, exploring nearby tropical islands, or enjoying the area's beautiful sandy beaches, this waterfront home makes it easy to embrace the Florida lifestyle. Bring your boat, your family, and your love of the water—this is Gulf Coast living at its best!

1324 Chancellor Drive, Holiday

3 Beds ⋅ 2 Baths ⋅ TB8546229 MLS

Welcome to this beautifully updated 3-bedroom, 2-bath home in the Gulf Winds community of Holiday, Florida. Designed for comfortable, low-maintenance living, the home features porcelain tile flooring throughout, a freshly painted interior and a bright, open layout that makes everyday living and entertaining easy. The kitchen includes a new LG stove, oven and microwave, a new dishwasher and an included refrigerator. Additional upgrades include an air-conditioning system replaced approximately three years ago, custom cabinetry in the primary walk-in closet, overhead garage storage and custom Bahama shutters in the living room. Step outside and enjoy the spacious 20-by-15-foot paver patio—perfect for outdoor dining, grilling or relaxing in the Florida sunshine. The exterior was painted by the HOA in 2025, and the seller reports that the roof is scheduled for replacement by the HOA in 2027. Conveniently located near Anclote Boulevard, Alternate US-19 and US-19, the home provides easy access to shopping, dining, medical facilities, parks and the Gulf Coast. Enjoy being close to Tarpon Springs, the historic Sponge Docks, local beaches and waterfront recreation while still having a peaceful place to call home. Whether you are looking for a primary residence, seasonal Florida retreat or a home offering a simpler maintenance lifestyle, this property combines thoughtful upgrades, outdoor living and a convenient Gulf Coast location.

2235 Parrot Fish Drive, Holiday

3 Beds ⋅ 3 Baths ⋅ TB8547115 MLS ⋅ 2919 BLDG.

Virtually Staged. Model perfect with sunset views! Beautifully maintained townhome in the Preserve Community of sought after GULF TRACE is move-in ready. No CDD, maintenance free and low HOA. Fabulous! The home features 3 bedrooms, 2.5 baths and 1 car garage and is situated on a premium homesite with picturesque views of a serene pond surrounded by manicured landscaping and natural wild-life, all just a short walk to the community park and recreation center! The downstairs has an open floorplan with the kitchen overlooking the dining and great room. The kitchen has 42"cabinets with crown molding, a pantry and breakfast nook and newer stainless appliances including a brand-new range. Downstairs also includes a convenient half-bath. The dining and great rooms combine for spacious entertaining and family living and the pond views are sweeping. Sliding doors lead to a screened lanai perfect for morning coffee or afternoon cocktails at sunset… private and tranquil, with no back neighbors. The second-floor staircase leads to the bedrooms and a perfectly situated laundry closet. The owner's suite is a large retreat space with gorgeous pond views. It features a walk in closet and lovely ensuite bath with a dual sink vanity and walk-in shower. The two secondary bedrooms and a full bath complete with shower/tub combo are across the hall. The 1 car garage has an oversized driveway. The well-maintained community offers plenty of guest parking, a playground and dog park. HOA includes cable, internet and all exterior building maintenance. Location, location! Just minutes to local beaches, trails, restaurants, hospitals and shopping centers. MOVE IN READY!

2919 Jacob Crossing Lane, Holiday

3 Beds ⋅ 2 Baths ⋅ TB8545171 MLS

Welcome to effortless Florida living in this meticulously maintained 3-bedroom, 2-bath, single-story villa, offering approximately 1,740 square feet of spacious, maintenance free living with the comfort and feel of a single-family home. Situated on a premium pond-view lot in the desirable Gulfwinds community, this inviting residence combines thoughtful upgrades, stylish finishes, and a carefree Florida lifestyle. From the moment you enter, the open-concept kitchen, dining, and family room create a warm and welcoming space designed for both everyday living and entertaining. The well-appointed kitchen features 42-inch nutmeg hardwood cabinetry, Caledonia granite countertops, an undermount double sink, modern appliances, glass-top range, microwave/exhaust hood, dishwasher, and a convenient closet pantry. Beautiful 18-inch ceramic tile extends through the wet areas and hallways, while crown molding, pendant lighting, and recessed lighting add a sophisticated finishing touch. The main living area features hand-scraped engineered hardwood flooring and a contemporary industrial-style ceiling fan. Sliding glass doors open to an extended screened lanai and oversized paver patio, creating an exceptional outdoor living space overlooking the peaceful pond—a perfect setting for morning coffee, evening gatherings, or simply enjoying the beautiful Florida surroundings. The spacious primary suite continues the engineered hardwood flooring and offers a generous walk-in closet and an ensuite bath with dual vanities, a relaxing garden tub, and a separate step-in shower. Two additional bedrooms provide excellent flexibility for family, guests, hobbies, or a home office. One bedroom is currently configured as a craft room, with cabinetry that can remain or be removed to suit the new owner's needs. Energy efficiency and peace of mind are also priorities here, with double-pane insulated windows, R-38 attic insulation, and advanced air-sealing techniques. The HVAC SYSTEM WAS REPLACED IN 2022, and the home carries an ENERGY STAR rating. Additional benefits include no CDD fees and a location that is not in a Special Flood Hazard Area. Gulfwinds offers the ultimate in low-maintenance living. Residents enjoy a heated community pool and beautifully maintained grounds, while the HOA takes care of many of the major exterior responsibilities, including lawn and shrub care, roof repair and replacement, exterior painting, high-speed internet, and cable service, including Hulu, Disney+, and ESPN. It's an ideal lock-and-leave lifestyle for seasonal residents, frequent travelers, or anyone who simply wants to spend less time on home maintenance and more time enjoying Florida. Conveniently located near marinas, parks, golf, shopping, and dining, this home is just minutes from the Gulf of Mexico and the world-famous Tarpon Springs Sponge Docks. Enjoy the tranquility of a beautifully maintained community while remaining close to the very best of the Florida lifestyle.

2219 Parrot Fish Dr, Holiday

5 Beds ⋅ 6 Baths ⋅ OM731368 MLS

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 * TWO MASTER BEDROOMS, EACH 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 * Characters Remaining: 1731 *

1238 Flotilla Drive, Holiday

3 Beds ⋅ 2 Baths ⋅ TB8543294 MLS

Virtually Staged. TROPICAL POOL & POND PARADISE HOME FEATURING A SPARKLING SWIMMING POOL, 3 BEDROOMS, 2 BATHROOMS AND A LARGE COVERED LANAI AND SCREEN-ENCLOSED POOL-DECK. NEW ROOF, NEW KITCHEN, NEW AC, NEW APPLIANCES, QUARTZ COUNTERSTOPS, NEW LUXURY WATERPROOF VINYL PLANK FLOORS, new electrical panel, new pool pump and new cartridge filter! All new interior paint and fixtures. Beautiful curb appeal with a spacious driveway and covered front porch. 22 Ft long garage with side entrance door. Private backyard with pond access and beautiful wildlife views. Perfectly located near great shopping, restaurants, parks and beaches! Enjoy the fun in the sun that a tropical paradise pool home offers!

3349 Overland Drive, Holiday

2 Beds ⋅ 2 Baths ⋅ TB8542308 MLS

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

2 Beds ⋅ 2 Baths ⋅ TB8541635 MLS

WELCOME TO WATERFRONT FLORIDA LIVING! This 2-bedroom, 2-bath POOL HOME offers picturesque water views, a PRIVATE DOCK, screened-in pool and lanai, and NO HOA. Situated along a wide lagoon of Lake Conley, this property is ideal for boating, fishing, kayaking, or simply relaxing and enjoying the peaceful waterfront setting. Step inside to a bright and inviting floor plan filled with natural light. The spacious living and dining areas flow into the kitchen and out to the screened pool and lanai, creating an ideal layout for indoor-outdoor living and entertaining. Both bedrooms are generously sized, and both full bathrooms have been updated. The outdoor living space is the true highlight. Enjoy the screened-in pool overlooking Lake Conley, with plenty of room for lounging, dining, and entertaining year-round. Beyond the pool, the backyard leads to your private custom dock, giving you direct access to the water from your own property. Launch a kayak, head out on the water, fish from the dock, or enjoy your morning coffee while taking in the peaceful waterfront views. This home also features an oversized 412 sq. ft. 1-car garage, double-pane windows, NEW A/C in 2025, washer and dryer, water heater approximately 4 years old, dishwasher and disposal approximately 3 years old, and pool pump approximately 2 years old. The home did NOT FLOOD in the recent hurricanes and offers an excellent opportunity as a full-time residence, vacation retreat, or investment property. With NO HOA OR CDD, you can enjoy waterfront living without the added community fees. Conveniently located in Holiday near Tarpon Springs and the Sponge Docks, Gulf beaches, parks, shopping, dining, medical facilities, and Tampa International Airport. Schedule your private showing today!

1954 Coolidge Road, Holiday

2 Beds ⋅ 2 Baths ⋅ TB8538680 MLS

Virtually Staged. INVESTMENT OPPORTUNITY OR FIRST-TIME HOMEOWNER OPPORTUNITY IN A OPORTUNE LOCATON! Minutes from Pinellas County and Tarpon Spring BEACHES! This charming 2-bedroom, 1.5-bathroom Lake Conley home offers an exciting opportunity to create the waterfront home you’ve been dreaming of or add a promising property to your investment portfolio. With a brand-new kitchen, updated windows, a 2019 A/C unit, roof replaced approximately four years ago, and a spacious 1.5-car garage, several of the major updates are already in place—leaving you the opportunity to add your own personal touches and build equity. Situated directly on beautiful Lake Conley, this property offers tranquil water views and a desirable waterfront lifestyle. The versatile layout features an A/C-cooled Florida room flowing into an additional uncooled sunroom overlooking the lake, creating flexible space for relaxing, entertaining, a home office, or simply enjoying the peaceful surroundings. Step outside to discover a back lanai and checkered-style paver patio overlooking the water—perfect for morning coffee, afternoon relaxation, or entertaining while taking in the lake views. Whether you're a first-time buyer looking for an affordable way to enter the market and customize a home to your taste, a buyer seeking a waterfront property with room to add value, or an investor searching for your next opportunity, this Lake Conley property offers LOCATION, WATERFRONT LIVING, AND POTENTIAL! Bring your vision and make this home your own!

3852 Sunray Drive, Holiday

3 Beds ⋅ 3 Baths ⋅ W7888795 MLS ⋅ 2578 BLDG.

Virtually Staged. INVESTMENT PROPERTY. SOLD WITH AMAZING TENANT IN PLACE. NEW PRICE- SELLER MOTIVATED! Beautiful, three bedroom townhome in well maintained community. Townes at Darlington is close to everything! Built in 2023 the community is practically new! Lower level with living room, dining area, kitchen with breakfast bar, pantry and sliding access to covered rear patio with waterfront view. Stairs to access bedrooms. Large primary suite with walk in closet and en suite bath. En suite bath with double sinks and walk in shower. All bedrooms have ceiling fans. Laundry room on upper level with bedrooms. Guest bath with tub/shower. One car garage and one car driveway. Max 2 cars. Lease will be assigned at closing. Escrow will be transferred at closing.

2578 Charlan Court, Holiday

2 Beds ⋅ 2 Baths ⋅ W7888180 MLS

"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

2 Beds ⋅ 2 Baths ⋅ TB8535861 MLS

Discover your own slice of paradise in this lakefront home in Tanglewood Mobile Village, this is a 55+ community with low monthly maintenance fee of $143.00 per month which includes lawn maintenance, garbage service, maintenance of year-around-heated pool, a very active clubhouse, shuffleboard courts, and much more. Home features load of storage shed, large, enclosed porch overlooking the lake, where you can watch all the wildlife, separate dining room, oh plus 2 walk-in closets, plus master bath in master bedroom. Home is furnished and ready for you to enjoy. Measurements are approx. Buyer to verify all information that is deemed to be accurate. Sold As Is.

3201 Brewster Drive, Holiday

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