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

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

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

1 Beds ⋅ 1 Baths ⋅ Holiday Lake Villas Condo SubDv. ⋅ 34691 Zip Code

Welcome home to total ease and true maintenance-free Florida living at 3806 Staysail Ln, a beautifully updated, spacious single-story block construction villa in a peaceful 55+ community with no stairs to entry and no unit or neighbors above! Located in a non-flood zone, this home offers added peace of mind before you even step inside. This move-in ready villa has been thoughtfully updated with fresh interior paint, new waterproof LVP flooring throughout, 2019 AC and newer water heater, while the HOA takes care of the exterior maintenance so you can spend more time enjoying life. A reserved covered carport (#3806) is conveniently located directly in front of the villa, with plenty of guest parking available nearby. Large windows fill the home with natural light, creating an inviting atmosphere throughout. The thoughtfully designed floor plan offers room for a full living room set, an eat-in kitchen with newer cabinetry, clean appliances, and bar stool seating at the counter, plus a separate walk-in utility room and an additional outdoor storage room so you'll never run out of space. The washer and dryer are already installed and convey with the home. Unwind in your enclosed Florida room or lanai, open the windows to enjoy the gentle breeze, and take in tranquil pond and fountain views while watching duck families, blue herons, and other birds gather near the water. The oversized primary bedroom features a large walk-in closet, while the spacious bathroom offers a step-in tile shower and plenty of room to navigate comfortably. The low $412/month HOA fee covers water, sewer, trash, cable, internet, roof, exterior building maintenance, exterior painting, lawn and grounds care, and pest control. Outside your door, you can walk to the active clubhouse for card games, bingo, community BBQs, reserve the space for hosting large family gatherings, enjoy the community pool year-round, play shuffleboard, or take a peaceful stroll around the beautifully maintained neighborhood. Conveniently located just minutes from the world-famous Tarpon Springs Sponge Docks, beautiful Gulf beaches, shopping, dining, medical facilities, and everyday conveniences, you'll enjoy the perfect balance of peaceful living and an unbeatable Florida lifestyle. Opportunities to own a beautifully updated, single-story pond view villa in this community don't come along often. Two small pets are welcome, making this the perfect place to enjoy easy, maintenance-free Florida living.

3806 Staysail Lane, Holiday

3 Beds ⋅ 3 Baths ⋅ Aloha Gardens SubDv. ⋅ 34691 Zip Code

Waterfront Fixer-Upper with Incredible Potential! Calling all investors, flippers, and renovation enthusiasts! This 3-bedroom, 3-bath waterfront property sits on a large lot and is packed with opportunity. Whether you're looking to renovate, rebuild, or create your dream waterfront retreat, the possibilities are endless. With a desirable waterfront location and plenty of space to work with, this is a rare chance to unlock significant value. Cash offers only. Don't miss this investment opportunity with outstanding potential!

4138 Star Island Drive, 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

Tahitian Dev SubDv. ⋅ 34691 Zip Code

Discover the perfect setting for your custom waterfront dream home on this expansive .39-acre canal-front lot located on a quiet cul-de-sac in Holiday. Offering ample space for a variety of home designs, outdoor living areas, and landscaping possibilities, this oversized property provides a rare opportunity to create your ideal Florida retreat. An added bonus - the adjacent lot is also available for purchase, allowing for an even larger homesite or future investment potential. Enjoy peaceful canal views and a tranquil setting in an up-and-coming neighborhood with numerous newly constructed homes. According to the owner, the property has never flooded during past storms, providing additional confidence as you plan your future build. With the property line extending into the water, there is potential to add a private dock, creating the perfect spot for fishing, launching kayaks or paddleboards, enjoying nature, or simply relaxing by the water. Whether you're seeking a waterfront lifestyle or a unique homesite with room to grow, this property offers exceptional possibilities. Conveniently located near shopping centers, restaurants, parks, and zoned schools, the property is also just minutes from the J. Ben Harrill Recreation Complex. Historic Tarpon Springs, known for its waterfront dining, unique shops, festivals, and year-round activities, is only about 15 minutes away. Gulf beaches and endless outdoor recreation opportunities are also within easy reach. Don't miss this rare chance to secure a spacious waterfront lot in a growing area and build the home you've always envisioned.

1504 Jackson Drive, Holiday

Tahitian Dev SubDv. ⋅ 34691 Zip Code

Rare opportunity to build your dream waterfront home on this expansive .27-acre canal-front lot located on a quiet cul-de-sac in Holiday. Offering beautiful canal views and a refreshing breeze, this property provides the ideal canvas for creating your custom Florida retreat. An added bonus - the adjacent lot is also available for purchase, creating the potential for an even larger homesite or investment opportunity. The property line extends into the water, presenting the possibility of adding a private dock and enjoying direct access to the canal. According to the owner, the lot has never flooded during past storms, offering additional peace of mind. Situated on an up-and-coming street, you'll find numerous newly constructed homes nearby, further enhancing the area's appeal. Conveniently located near shopping centers, restaurants, parks, and zoned schools, the property is also just minutes from the J. Ben Harrill Recreation Complex. Historic Tarpon Springs, known for its waterfront dining, sponge docks, local shops, festivals, and year-round activities, is approximately 15 minutes away. Gulf beaches, boating opportunities, and outdoor recreation are all within easy reach. Whether you're looking to build a primary residence, vacation getaway, or investment property, this waterfront lot offers location, potential, and a unique opportunity to enjoy the Florida lifestyle.

1503 Jackson Drive, Holiday

2 Beds ⋅ 2 Baths ⋅ Country Estates SubDv. ⋅ 34690 Zip Code

Come check out this gorgeous updated waterfront pool home featuring an open, inviting floor plan and serene views of a natural water setting. Designed for both everyday living and entertaining, the spacious layout seamlessly connects the main living areas while showcasing beautiful waterfront vistas throughout the home. Recent updates include: New fencing for added privacy New flat roof Custom island and pantry upgrades New gutters Step outside to your private backyard oasis, where the sparkling pool and tranquil water views create the perfect setting for relaxing or hosting family and friends. Don't miss this opportunity to own a beautifully updated waterfront retreat that combines comfort, style, and exceptional outdoor living.

4704 Koala Drive, Holiday

Tampa Tarpon Spgs Land Co SubDv. ⋅ 34690 Zip Code

ISLAND READY FOR DEVELOPMENT - 6.4 Acres- Approved for 87 units, multi- family, ENTITLEMENTS GRANTED, PASCO COUNTY. LOCATED ON BERRY HILL ROAD, HOLIDAY, FL, East of Grand Blvd. Parcel ID 29-26-16-0000-00500-0050 FOREST HILL EAST DEVELOPMENT designated and approved for 87 multiple-family apartment units, waterfront, adjacent to the Anclote River with Gulf access. A rare multifamily development opportunity on a private 6.45-acre island surrounded by water, proposed 87-unit luxury apartment community... Designed as a three-story mid-rise development totaling approximately 96,842 SF, the project features modern construction, water-view patios and balconies, covered entrances, assigned parking and storage, elevators, and a resort-inspired amenity package.... Planned community features include a clubhouse with exercise room, kitchenette, conference room, and office, pool, tiki bar, pavilion, and BBQ area.... Including fishing, kayaking, canoeing, and direct access to the Anclote River with routes to the open Gulf waters and Tarpon Springs.... The property blends privacy, recreation, and upscale design into a truly unique rental concept surrounded by natural beauty. Floor plans, renderings, and site plans available.... Its proximity to Pinellas County, one of Florida's most densely populated counties, enhances its appeal for residential, mixed-use, or investment potential. A rare chance to capitalize on the continued growth and demand along Florida's Gulf Coast.

Berry Hill Road, 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

3 Beds ⋅ 2 Baths ⋅ La Villa Gardens SubDv. ⋅ 34690 Zip Code

Virtually Staged. This 3-bed, 2-bath, 1-car garage home offers a brand-new roof, AC, windows, garage door, and fencing. The entire interior is fully renovated from top to bottom including a sparkling kitchen with quartz countertops, stainless steel appliances, tile backsplash, and recessed lighting. Modern, bright, with a private large yard overlooking a creek.

3042 Bahia Avenue, Holiday

2 Beds ⋅ 2 Baths ⋅ Holiday Lake Villas Condo SubDv. ⋅ 34691 Zip Code

Welcome to this well-maintained 2 bedroom, 2 bath condominium in the coastal community of Holiday, offering comfort, convenience, and peaceful living along Florida’s Gulf Coast. Flood insurance is not required because located in zone X500. This single-level home features a functional kitchen with appliances and ample counter space, flowing into comfortable living areas designed for easy everyday living. Major updates include a 2020 HVAC system, 2021 hot water heater, and hurricane-impact windows for added peace of mind and efficiency. Two standout features of this unit is its prime setting overlooking a tranquil lake, offering relaxing water views and added privacy. Unlike other units in the community that back to a busy road or have upstairs neighbors, this single-story layout provides a quieter, more desirable living experience with no one above you. Second, there are guest spots easily accessible along with a carport for the owner to park just outside the front door! This Condo is 1,318 SqFT, but if you add in the Florida Room’s SqFT you have 1,542 SqFT of Entertainment Space making the price point of this unit a RARITY! The purchase of the home includes all furnishings and household items, making it truly move-in ready and ideal as a primary residence, seasonal retreat, or investment property. Residents enjoy nearby access to beautiful outdoor destinations such as Anclote River Park and the stunning beaches of Anclote Key Preserve State Park, as well as the charming waterfront dining and cultural experiences in Tarpon Springs. With its combination of updates, furnishings, lake views, and desirable layout, this condo offers an exceptional opportunity to enjoy relaxed Florida living at its best.

3801 Sailmaker Lane, Holiday

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