Holiday Single Family Homes For Sale - 209 homes

Remarks: One or more photo(s) has been virtually staged. Welcome home to this beautiful 3-bedroom, 2-bathroom home with a two-car garage situated on the serene shores of Lake Conley. As you step inside, you will immediately appreciate the bright, open feel of the home, enhanced by a neutral color palette that creates a warm and inviting atmosphere. The spacious living room provides plenty of room for relaxing or entertaining guests, while the adjacent dining area, conveniently located between the living room and kitchen, offers the perfect setting for everyday meals or gatherings. The well-appointed kitchen features stainless steel appliances, granite countertops, and a convenient breakfast bar, making it both functional and stylish. In addition to the living room, the home offers a large family room, providing even more space for entertaining, relaxing, or creating a flexible living area to suit your needs. Just off the family room, you will find an enclosed back porch, the perfect place to unwind while enjoying peaceful views of the lake. Step outside to the open dock, where you can park your boat and enjoy easy access to the water, making lakefront living a reality. The primary bedroom is generously sized and features an en-suite bathroom complete with a large vanity offering plenty of storage and a walk-in shower. Conveniently located near US 19, this home provides easy access to shopping, dining, entertainment, and medical facilities, offering both comfort and convenience. Don’t miss this opportunity to enjoy lakefront living—schedule your private showing today!

Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)

Listing Agent: Dawn Walls

Remarks: Under contract-accepting backup offers. Welcome to this beautifully maintained and spacious 2-bedroom, 3-bathroom home offering exceptional curb appeal with lush landscaping and a charming front porch that creates a warm first impression. Step inside to an inviting open floor plan featuring a front living area that seamlessly flows into the dining space, kitchen, and an expansive family room, perfect for both everyday living and entertaining. The well-appointed kitchen boasts an abundance of wood cabinetry, granite countertops, stainless steel appliances, and a convenient breakfast bar overlooking the main living areas. The impressive family room is truly the heart of the home, showcasing soaring ceilings and a stunning fireplace that adds both character and comfort. Step outside to a spacious backyard designed for outdoor living, complete with a covered patio, ideal for relaxing, hosting gatherings, or enjoying Florida’s beautiful weather year-round. Thoughtfully updated, this home features hurricane-impact windows, UV filtration on the AC (2019), a brand-new roof installed in 2024, emergency generator interlock for power outages and fully paid-off solar panels for energy efficiency and long-term savings. Ideally located in Holiday, you’ll enjoy easy access to shopping, dining, top-rated Gulf beaches, and vibrant nearby downtown areas. This home offers the perfect blend of comfort, style, and location!

Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)

Listing Agent: Amie Lenhart (727-515-1626)

Remarks: Spacious single-family home in the Beacon Square Subdivision in the heart of Holiday. Home features 3 large bedrooms, 2 Full bathrooms with ceramic tile floors throughout home. The open floor plan creates a bright and spacious living area connecting the living room, dining room, kitchen, and enclosed Florida Room. And there's a 1 car garage and fenced backyard. Beacon Square is minutes away from the Gulf of Mexico with lots of activities such as shopping, dining out and beach activities.

Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)

Listing Agent: Michael Eddings (813-480-6026)

Remarks: Under contract-accepting backup offers. Beautiful property in Holiday

Listing is courtesy of: APPLE HOMES CORP (813-733-1540)

Listing Agent: Miguel Salinas (813-733-1540)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Back Up Offers Only !!Step into easy coastal living in this bright and beautifully updated block home in Tahitian Homes. Fresh tile flooring flows throughout the 2 bedrooms and 2 baths, complementing an upgraded kitchen with a subway-tile backsplash, stainless steel appliances, and a refreshed primary suite. The enclosed screened patio expands your living space and creates the perfect indoor-outdoor vibe for morning coffee, weekend lounging, or evening gatherings. A 1-car garage, central AC, newer roof, newer windows, and a fully vinyl-fenced yard add comfort, privacy, and plenty of room for the outdoor gardener—delivering both convenience and peace of mind. With no HOA or CDD fees and a location just minutes from beaches, parks, marinas, and daily essentials, this home offers the ideal blend of value, lifestyle, and low-maintenance living. Move right in and start enjoying the Florida lifestyle. Why rent when owning feels this good!Motivated sellers !

Listing is courtesy of: RE/MAX REALTY UNLIMITED (813-684-0016)

Listing Agent: Marilyn Gioffre (347-802-5489)

Remarks: Charming, 2-bedroom, 1.5-bathroom single-family home available for sale in Holiday. This property boasts a renovated kitchen featuring wooden cabinets paired with granite countertops, offering a classic and modern look. Key updates include ceramic tile throughout, a new HVAC system (2025), a new electric water heater (2025), and a roof from 2015. The fully enclosed rear yard features low-maintenance vinyl fencing,  ensures a safe haven for pets and play while providing a serene retreat or quiet reflection. Whether you're seeking a permanent residence or an investment opportunity, this property provides excellent flexibility. It is centrally located in Holiday, just 0.7 miles from US 19 and less than 1.5 miles from supermarkets, dining, and entertainment. The home was not impacted by rising water during the last two storms. It has been meticulously maintained and is in move-in ready condition.

Listing is courtesy of: LONDON FOSTER REALTY (305-514-0100)

Listing Agent: Hector Mendez Garcia, Pa (786-683-9407)

Remarks: One or more photo(s) has been virtually staged. Welcome to 5313 Boardwalk Street — a beautifully updated 3 bedroom, 2.5 bath waterfront home offering incredible value in one of Holiday’s most desirable boating communities. This property experienced no flood damage from past hurricanes, providing peace of mind while enjoying true Florida waterfront living. Major systems have also been updated, including a 2021 HVAC system, adding comfort and efficiency for years to come. Out back, you’ll find a covered 10,000 lb boat lift plus a wet slip accommodating up to a 30’ vessel, making this home ideal for serious boaters. From your dock, enjoy easy navigation to the Gulf of Mexico, with multiple waterfront restaurants, marinas, and live music spots along the way. With world-class fishing and diving off Anclote, this truly is a boater’s paradise at an incredible price point. Inside, the home showcases tasteful updates and modern finishes throughout. The open layout features vaulted ceilings creating a bright, airy feel, stainless steel appliances, granite countertops, upgraded backsplash, modern fixtures and finishes, and an inside laundry room. The screened balcony overlooking the canal is a standout feature — the perfect place to enjoy sunrise coffee or unwind at sunset with a waterfront view. Downstairs, you’ll appreciate the huge garage with nearly 400 sq ft of additional storage space under the home, providing ample room for water toys, fishing gear, and all your boating essentials. If you’ve been searching for Gulf access, a private boat lift, updated interior finishes, and strong system updates — this home checks all the boxes. Schedule your private showing and start living the waterfront lifestyle. Flood Insurance only $826/year!!

Listing is courtesy of: COLDWELL BANKER REALTY (813-253-2444)

Listing Agent: Jonathan Hernandez (727-417-1122)

Remarks: Beautiful 2-bedroom, 1.5-bathroom home in the heart of Holiday, featuring new windows, a large fenced yard, a screened patio, and fresh remodeling throughout, all in a fantastic location close to beaches, restaurants, and shopping. You must see this one before it’s gone. The property has no flooding history and is not in a flood zone, offering peace of mind and easy Florida living.

Listing is courtesy of: F I GREY & SON RESIDENTIAL (727-495-2424)

Listing Agent: Anita Mccracken (727-776-4638)

Remarks: Welcome to this brand new listing in Holiday!!! Large and spacious home offers big rooms with an open feeling kitchen, living room and den. Full Garage, fully fenced oversized lot located on cul de sac providing safer low traffic for young children and pets to play! Enjoy morning coffee on front porch and relaxing evenings on your back porch. The back and side yard is equipped with a swing set and a jungle gym for the little ones making it wonderful space for family fun! All hurricane shutters are included for added peace of mind. Conveniently located close to beaches, restaurants, shopping and hospitals. Priced very attractively and full potential - this is a fantastic home for years to come!!

Listing is courtesy of: F I GREY & SON RESIDENTIAL (727-495-2424)

Listing Agent: Grace Pineyro (727-608-9600)

Remarks: Welcome to your new home! Located in Holiday FL with no Hoa, CDD, and Not in a Flood Zone. East of US Highway 19. 3 bedrooms and 2 bath 1 car garage and a pool. Large Kitchen with plenty of wood cabinets, Corian counter tops and open to the great room. This space is amazing for those who enjoy family and friends over to watch their favorite teams. Tile covers most of the entire house except for the Primary bedroom which is epoxy flooring. Primary bedroom has a walk-in closet with shelving throughout. Primary bathroom consists of dual sinks and a standup shower. Living room, dining room, and great room are all separate, with a split floor plan. Above ground pool helps keep you cool in the hot summer months of Florida. The front porch is entirely screened in. Shed in the back yard for extra storage.

Listing is courtesy of: F I GREY & SON RESIDENTIAL (727-495-2424)

Listing Agent: Michael Andrade (727-433-2748)

Remarks: Under contract-accepting backup offers. Opportunity awaits in Holiday! This two-bedroom, two-bathroom home offers a functional layout and great potential for buyers looking to add their personal touch. With a little TLC, this property can truly shine. Inside, you’ll find a nice open floor plan featuring a living room and dining room combination that flows seamlessly into the kitchen - perfect for everyday living and entertaining. The home includes two bathrooms, one conveniently located inside with a tub/shower combo, and another in the garage with a stand-up shower, offering added flexibility. Step out back to enjoy the enclosed porch, a great space for relaxing or additional entertaining, overlooking a fenced backyard ideal for pets, gatherings, or creating your own outdoor oasis. Conveniently located just minutes from US-19, you’ll have easy access to a wide variety of shopping, dining, and everyday conveniences. Whether you're an investor or a homeowner ready to customize, this is a great opportunity to make it your own! Schedule your showing today!

Listing is courtesy of: EXP REALTY LLC (866-308-7109)

Listing Agent: Jeffrey Borham, Pa (866-308-7109)

Remarks: This 2 Bedroom 2 Bath is a must see! Pride of ownership here for sure!! 1778 Sq feet of living space with 2 extra bonus rooms that could easily be turned into a 3- or 4-bedroom house!!Beautiful kitchen, New Hurricane Windows throughout home ($20,000)!! This property features smart devises for front door, thermostat, hot water heater, water shut off, irrigation and Blink security cameras. High ceilings throughout home (rare find!) Washer / Dryer & all appliances included!!This property could also come furnished!!This property has a huge spacious lot with room for storage all your boats and water toys (NO HOA!!)!! Could be a turnkey Air BnB!!This property has never Flooded!! Pet/smoke free for all known history !!Oversized garage has plenty of additional storage. This is the best neighborhood you will find in Holiday!! Wonderful neighbors!! You will not find a turnkey home for this low price anywhere ... (NO BLIND OFFERS!!) Owner will not respond to Blind Offers! Make your appointment today before it is gone.

Listing is courtesy of: PREMIER REALTY (727-687-2324)

Listing Agent: Shawn Miller (727-687-2324)

Remarks: One or more photo(s) has been virtually staged. Whether you're looking for a primary residence, vacation getaway, or rental opportunity, this home truly checks all the boxes! This well-maintained, adorable 2-bedroom, 2 full-bath home is all about easy Florida living. (both bathrooms are located inside the home)Start your mornings in the bright and breezy Florida Room, sipping coffee while enjoying peaceful water views right from your backyard—the perfect place to relax and unwind and listen to nature. The spacious great room offers flexibility as a second living area, home office, or potential 3rd bedroom. Step outside to a newer pergola, creating the perfect setting for cookouts and shaded outdoor lounging while enjoying your spacious yard overlooking the water. The backyard offers plenty of room to add a pool or play area. Inside, you’ll find new windows, tile and newer vinyl flooring throughout, and an updated kitchen with stone countertops and a beautiful backsplash, along with a newer hot water heater. This home is truly move-in ready. A shed provides extra storage for added convenience. Not feeling like maintaining your own pool? No problem! For a low annual fee, enjoy access to the Beacon Square heated pool and fitness center. Bonus: This home did NOT experience any water damage during the hurricanes. Don’t miss out—come enjoy the Florida lifestyle!

Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (727-847-4444)

Listing Agent: Venessa Finazzo (727-777-7506)

Remarks: Move-in ready home for you in a quiet neighborhood, but very close to shopping and easy to commute. Nicely updated and very little lived in by the owner, who was coming only for a couple of months in winter time. Roof, windows and entry door were replaced in 2015. All floors are tiled, kitchen has nice wooden cabinets, like new appliances, and washer and dryer in the garage. Furniture is negotiable. A good size enclosed back porch gives you place to relax and a very large back yard with chain link fence all around. Nice curb appeal and all rooms of good size. Owner recently installed additional insulation, for energy efficiency. This is a great opportunity for a first time buyer to enjoy homeownership.

Listing is courtesy of: OLYMPIC REALTY SERVICES LLC (727-937-0107)

Listing Agent: Maria Kastritsos (727-460-6383)

Remarks: 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.

Listing is courtesy of: RE/MAX CHAMPIONS (727-807-7887)

Listing Agent: Jennifer Tobey, Pa (727-871-1064)

Remarks: Under contract-accepting backup offers. Welcome home to the sought-after Key Vista community of Holiday! Perfectly positioned on a large corner lot, this beautifully maintained three-bedroom, two-bathroom residence offers the ideal blend of comfort and Florida outdoor living. Enjoy added peace of mind with major updates, including a 2018 Carrier AC system with a 2-stage air handler, a 2020 roof, and a GeoSpring hybrid water heater with heat pump technology - designed for exceptional energy efficiency. This home also offers upgraded New South impact-resistant windows, offering quiet, energy efficiency, and peace of mind. Step inside through the welcoming foyer, and you’ll immediately notice the wood-look porcelain tile flooring, high ceilings, and crown molding that flow throughout the home. The home opens up into a spacious open-concept layout featuring a dining area, family room, and kitchen - ideal for both everyday living and entertaining. The kitchen is a true centerpiece, boasting upgraded stainless steel appliances, a large island perfect for gathering, sleek granite countertops, and an abundance of cabinetry for storage. A separate pantry adds even more convenience, while the great room overlooks the pool area with sliding door access, creating a seamless indoor-outdoor connection. With a split floor plan, the primary suite is a private retreat, generously sized and featuring direct access to the large, heated saltwater pool through a set of doors. The en-suite bathroom is beautifully designed with a stone countertop dual-sink vanity, a luxurious standalone soaking tub, a frameless glass-enclosed shower with dual shower heads, and a large walk-in closet complete with custom organizers. The additional bedrooms are comfortably sized and share a recently updated bathroom with a walk-in shower. A dedicated laundry room with extra cabinetry provides added functionality and organization. Step outside and embrace true Florida living. The screened-in pool area is perfect for relaxing or entertaining, complete with an outdoor kitchen setup featuring a built-in grill, drawers, and a mini fridge. The vinyl-fenced backyard also offers a grassy area - perfect for pets or play. Residents of Key Vista enjoy fantastic community amenities, including a sparkling pool, tennis courts, playground, clubhouse, and biking and walking trails. Conveniently located near shopping, dining, and just a short drive to the beautiful Gulf beaches, this home truly has it all. Don’t miss your opportunity to own this exceptional Florida retreat!

Listing is courtesy of: EXP REALTY LLC (866-308-7109)

Listing Agent: Jeffrey Borham, Pa (866-308-7109)

Remarks: Completely Renovated!!! Welcome to 3317 Honeymoon Lane in Holiday, Florida—a charming and well-maintained home offering comfort, convenience, and Florida living at its best. This property features a spacious layout with abundant natural light, a functional floor plan, and inviting living areas perfect for both relaxing and entertaining. The kitchen offers ample cabinet and counter space, making meal preparation easy, while the adjoining dining area provides a cozy setting for everyday living. Bedrooms are generously sized, and the home provides flexible space to suit a variety of needs, whether for guests, a home office, or hobbies. Step outside to enjoy a private backyard with plenty of room for outdoor gatherings, gardening, or simply soaking up the Florida sunshine. Located in a quiet neighborhood, this home is just minutes from local parks, shopping, dining, and Gulf Coast beaches. Whether you’re a first-time buyer, seasonal resident, or looking to invest, this property is a fantastic opportunity in a convenient location. Schedule your private showing today and discover all that this home has to offer!

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Demetroula Katechis (845-633-3723)

Remarks: Welcome to your new home in the Holiday Lake Estates community that's only a couple of miles away from the Gulf of America to the west and Tarpon Springs to the south! No HOA, no CDD, and this property is eligible for a zero down payment mortgage (100% financing) without PMI! Amazing location with convenient access to US Hwy 19 and three beautiful parks nearby that are connected by the Coastal Anclote Trail: Anclote River Park, Anclote Gulf Park and Key Vista Nature Park. Several beautiful beaches are located less than 30 minutes away, including Howard Park Beach, Honeymoon Island Beach and Clearwater Beach, and the Tampa International Airport is only 25 miles away! The house features many recent upgrades: roof replaced in 2022, HVAC only 3 years old, tankless water heater, 200 Amp electrical panel, windows were replaced less than a year ago, tile floors throughout the entire house, new screen door, and it was freshly painted two weeks ago. This property has no backyard neighbors, has several mature fruit trees, an above ground pool, is located on a quiet street with minimal traffic and can serve as a great starter home or investment property (the furniture is negotiable!). Schedule your showing and submit your offer before it's gone!

Listing is courtesy of: DALTON WADE INC (888-668-8283)

Listing Agent: Serghei Diaconu (813-970-7800)

Remarks: Welcome to 3816 Beacon Square Drive—a charming 3-bedroom, 2-bath single-family home nestled on a generous lot with a peaceful conservation view in the heart of Holiday. Surrounded by abundant outdoor space and palm trees, this home offers a serene Florida retreat with classic style, that has been impeccably maintained. Inside, luxury vinyl flooring flows throughout, enhancing the home’s timeless appeal. Filled with natural light, the interior is bright, inviting, and truly move-in ready. Thoughtful upgrades blend vintage character with modern comfort. Enjoy the spacious, fully fenced backyard—perfect for pets, gardening, or outdoor gatherings—along with the convenience of a single-car garage for parking or additional storage. Rediscover the essence of a simpler lifestyle in this well-appointed home. In 2019, the home received a new roof, new ductwork and insulation, along with a complete main-house renovation that included a new kitchen, flooring, baseboards, ceiling fans, main bathroom, lighting, doors, and appliances. Since then, additional major updates include new windows and a new garage door in 2023, as well as a new dishwasher and a new AC unit and handler in 2025. The property has also been refreshed with updates to the in-law suite (including new flooring and vanity), main bathroom floor tile, patio improvements, fresh interior and exterior paint, and new toilets throughout. Conveniently located near Gulf beaches, dining, and shopping, and the Beacon Square Civic Association. This property also remained unaffected during the 2024 hurricanes. With solid block construction and a prime location, this home offers exceptional potential—schedule your private showing today!

Listing is courtesy of: COLDWELL BANKER REALTY (813-253-2444)

Listing Agent: Michael Owens (727-204-7204)

Remarks: Move-in ready pool home! 3BR/2BA, 2,648 SF heated with private pool. Excellent location. Minutes to beaches, shopping & dining. Don’t miss this opportunity Sellers may financing

Listing is courtesy of: GLOBAL FORTUNE REALTY LLC (813-876-8329)

Listing Agent: Francisco Rojas (813-345-7177)