Holiday Homes with Waterfront

Holiday Homes with Waterfront

Welcome to Holiday, a charming city located in Pasco County, Florida. Known for its beautiful waterfront homes, Holiday is a paradise for those seeking a tranquil and picturesque living experience.

Situated in the heart of Florida, Holiday offers a unique blend of natural beauty and modern amenities. With its prime location on the Gulf of Mexico, residents can enjoy stunning waterfront views and easy access to a variety of water activities such as boating, fishing, and swimming.

If you've always dreamed of living by the water, Holiday is the perfect place for you. The city boasts an array of homes with waterfront views, allowing residents to wake up to the soothing sounds of the waves and enjoy breathtaking sunsets right from their own backyard. Whether you prefer a cozy cottage or a luxurious estate, there are plenty of options to choose from to suit your taste and budget.

Living in a waterfront home in Holiday offers more than just scenic views. It provides a lifestyle filled with relaxation, serenity, and endless recreational opportunities. Imagine spending your weekends lounging by the water, hosting barbecues, or simply taking a leisurely stroll along the shoreline.

Aside from its natural beauty, Holiday also offers a range of amenities and conveniences. From shopping centers and restaurants to parks and golf courses, there is always something to do in this vibrant city. Additionally, its proximity to major cities like Tampa and Clearwater ensures that you're never too far from urban attractions and entertainment.

If you're looking for a place where you can enjoy the best of both worlds - a peaceful waterfront retreat and easy access to modern amenities - then Holiday is the perfect place to call home. Explore the homes with waterfront views in this charming city and start living the life you've always dreamed of.

Newest Holiday Homes with Waterfront

3211 Southport Drive, Holiday
$179,900
2 Beds ⋅ 2 Baths ⋅ Tanglewood Mobile Village SubDv. ⋅ 34690 Zip Code
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
5410 Flora Avenue, Holiday
$359,900
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
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 an oversized 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
3532 Overland Drive, Holiday
$285,000
2 Beds ⋅ 2 Baths ⋅ Beacon Square SubDv. ⋅ 34691 Zip Code
Enjoy peaceful pond views and effortless Florida living in this beautifully updated, move-in-ready home in Holiday! From the stylish interior to the tranquil waterfront setting, this home offers an inviting place to relax, recharge, and feel right at home. The stunning kitchen features high-end cabinetry and elegant granite countertops, creating a beautiful space for everyday cooking and entertaining. Both bathrooms have been tastefully remodeled with contemporary vanities and stylish finishes. Thoughtful updates include a newer AC unit and ductwork, washer and dryer, gutters, garage door, and front entry door—adding comfort, convenience, and curb appeal. The true highlight awaits out back, where picturesque pond views provide a relaxing backdrop to your day. Enjoy your morning coffee by the water, cast a fishing line, or simply unwind while taking in the peaceful surroundings. This is the Florida lifestyle you’ve been looking for! Conveniently located just a short drive from Tarpon Springs, you can explore the historic Sponge Docks, enjoy delicious Greek dining, and discover charming local shops. Gulf Coast beaches and convenient airport access put recreation and travel within easy reach. Beautiful updates, a serene pondfront setting, and a convenient location—this home is ready for you to move in and start enjoying it all. Schedule your private showing today!

3532 Overland Drive, Holiday
2217 Harrison Drive, Holiday
$245,995
4 Beds ⋅ 2 Baths ⋅ Tahitian Development SubDv. ⋅ 34691 Zip Code
Virtually Staged. Waterfront living in the desirable Tahitian canal community of Holiday, FL! This beautifully updated 4-bedroom, 2-bath home offers 1,566 sq ft of living space on a spacious 12,000 sq ft (0.28-acre) lot with 60' of canal frontage and your own private dock — ready for boating, fishing, or just watching the sunset over the water. The split floor plan places a private primary suite — complete with en-suite bath and walk-in closet — on one side of the home, while three additional bedrooms and a second full bath sit on the other, including an oversized fourth bedroom well suited as a guest suite, home office, or in-law space. Rich wood-look flooring runs through the open living and dining area, creating an easy flow for entertaining, and a functional kitchen includes a walk-in pantry for extra storage. Step outside to a screened front porch and a side patio overlooking the canal, both perfect for enjoying the Florida weather. A fenced yard, attached one-car garage, and central AC complete the package. Tucked along the canal system just minutes from the Gulf of Mexico, this home puts you close to boat ramps, waterfront parks, and the historic Sponge Docks and shops of Tarpon Springs. Easy access to US-19 makes for a quick commute toward New Port Richey, Clearwater, or Tampa, while nearby beaches, dining, and everyday shopping are all within a short drive. A rare chance to own a move-in-ready waterfront retreat in one of Pasco County's favorite boating communities — this one won't last!

2217 Harrison Drive, Holiday
4036 Sunray Drive, Holiday
$300,000
3 Beds ⋅ 2 Baths ⋅ Aloha Gardens SubDv. ⋅ 34691 Zip Code
WATERFRONT LIVING AT ITS FINEST — PRICED TO SELL! Discover this beautifully updated 3-bedroom, 2-bathroom lakefront home offering modern finishes, peaceful waterfront living, and a convenient Florida location just minutes from Lake Tarpon and the Gulf of Mexico. Never flooded and untouched by the effects of Hurricanes, this move-in-ready home offers an exceptional opportunity for waterfront living. A one-car garage and extra-large driveway provide ample parking. Step inside to a light and bright interior featuring upgraded double-pane windows, new flooring throughout, high-end two-panel doors with stylish pine trim, modern LED lighting and ceiling fans, fresh interior and exterior paint, and updated switches and finishes. The open floor plan seamlessly connects the living, dining, and kitchen areas while large windows fill the space with natural light and offer beautiful waterfront views. The gorgeous updated kitchen features stainless steel appliances, including a glass-top range, American Walnut countertops, custom cabinetry, and elegant brushed-gold fixtures. The primary suite is a true retreat, offering serene waterfront views, a beautifully updated en-suite bathroom with a spa-like shower, custom shelving in the walk-in closet, and a full-length mirror. Outside, enjoy a large backyard and your own private waterfront setting with a personal dock — perfect for relaxing, fishing, entertaining, or simply enjoying the Florida lifestyle. Conveniently located near Lake Tarpon, the Gulf of Mexico, shopping, dining, entertainment, and major airports. Approximately 9.5 miles to St. Pete-Clearwater International Airport and 15 miles to Tampa International Airport, with Aldi, Publix, and Walgreens just minutes away. Nearby beaches include Sunset Beach, Howard Park, and Honeymoon Island. Beautifully updated, waterfront, never flooded, and priced to sell — schedule your private showing today!

4036 Sunray 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
3349 Overland Drive, Holiday
$249,999
3 Beds ⋅ 2 Baths ⋅ Beacon Square SubDv. ⋅ 34691 Zip Code
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
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
3852 Sunray Drive, Holiday
$239,900
2 Beds ⋅ 2 Baths ⋅ Aloha Gardens SubDv. ⋅ 34691 Zip Code
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
2578 Charlan Court, Holiday
$255,000
3 Beds ⋅ 3 Baths ⋅ Townes/Darlington SubDv. ⋅ 34690 Zip Code
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
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