Holiday Homes For Sale & Real Estate - 294 homes

Remarks: Under contract-accepting backup offers. Short Sale. *Short Sale Opportunity!** Seize this remarkable chance to own your dream home. This stunning 2-bedroom, 2½-bathroom residence, featuring a one-car garage and constructed in 2023, is situated in a serene and well-maintained neighborhood. The upper level includes two bedrooms, each with its own private bathroom, while the downstairs boasts a spacious living area that offers picturesque views of the pond, all under a covered patio. Additionally, there is an outdoor storage room for added convenience. This home seamlessly combines comfort, style, and value.

Listing is courtesy of: MARTINEZ 2 & ASSOCIATES OF FLO (813-431-8785)

Listing Agent: Stephanie Bonefont (813-504-5758)

Remarks: NEW ROOF 2025. NEW DUCTWORK 2022. NEW ELECTRIC PANEL 2022. Do I have your attention? This home is for someone who wants life to feel simple and comfortable. Not flashy, not overdone, just a place that feels easy to live in from day one. It’s the kind of home where you can work during the day, shut the laptop at five, and actually enjoy being at home. The big stuff is already handled, which matters if this is your first home. The roof is about a year old, the ductwork and electric panel was replaced around four years ago, and the home was fully updated floor to ceiling in 2022, including the kitchen and the bathrooms. New flooring, fresh paint… You’re not walking into projects or surprise expenses. Inside, the layout just works. There’s enough space to set up a dedicated work-from-home area without giving up your living space. The kitchen and bath feel fresh and current, and the home flows naturally for everyday life, whether you’re on video calls, cooking dinner, or hosting a couple friends. This is a great option if you’re done with renting and want something move-in ready without the stress. It’s manageable, comfortable, and updated in a way that fits how people actually live and work now. The location makes day-to-day life easier. Holiday gives you quick access to shopping, dining, parks, and main roads, plus an easy drive to the beaches. You’re close to everything but still in a neighborhood that feels settled and quiet. This is the kind of first home that just makes sense. Solid updates, practical space, and a location that supports your lifestyle without stretching you thin.

Listing is courtesy of: REALTY EXPERTS (727-888-1000)

Listing Agent: Donna Hildebrand, Llc (607-435-3404)

Remarks: Waterfront Living at its Finest – Nestled in a luxury, family-friendly neighborhood in Holiday, Florida. This stunning 3-bedroom, 2-bath waterfront home with nearly 1,900 sq ft. It offers the perfect blend of comfort, style, and a ultimate Florida boating lifestyle. This property is a true fisherman’s paradise with direct access to the Anclote River and just a short boat ride to the famous Tarpon Springs Sponge Docks then out to the Gulf of Mexico. A Home Designed for Comfort & Style. Step inside to an open-concept floor plan with seamless tile flooring throughout. This creates a clean and modern flow perfect for entertaining with everyday living. The custom kitchen is a true centerpiece, featuring: Striking waterfall marble countertops, black stainless steel appliances, generous prep including entertaining space and clear sightlines to the living and outdoor areas. The spacious primary suite is your private retreat, highlighted by a luxury wet steam room (5' x 9.5') large enough to accommodate multiple people-bringing spa-level relaxation right into your home. Additional upgrades include: Instant hot water heater – never run out of hot water, solar panels for energy savings, freshly painted, custom entry doors, newer roof, HVAC system, and windows. Outdoor Living Built for the Florida Lifestyle. This home truly shines outdoors. Relax or entertain from the screened-in patio overlooking the water, or take advantage of the huge covered patio with plenty of space for outdoor toys and gear. The beautifully maintained property also includes: New St. Augustine grass installed last year with irrigation system with its own well and on it's completely fenced side yard and backyard. Doggie door for convenient pet access, stamped cobblestone concrete driveway, super gutters installed around the entire home, two-car garage with professional epoxy flooring and warranty. Boater & Angler’s Dream! Situated at the end of the Anclote River, the property offers brackish waterfront known for abundant redfish and snook—often caught right off the dock. Your private waterfront setup includes: 10,000-lb boat lift, large oversized dock for entertaining, floating docks for kayaks, paddleboards, and water toys. double floating wave-runner dock available and recapped and stamped seawall. From your dock, enjoy a short scenic boat ride to the sponge docks, waterfront restaurants, and open Gulf waters. FYI this property has never flooded. Location Perks: You’re just minutes from: Gulf beaches, waterfront dining, boating and fishing hotspots, parks and local amenities. All while enjoying the tranquility of a quiet waterfront neighborhood perfect for families or those seeking the ultimate coastal lifestyle. Whether you’re a boater, fisherman, entertainer, or simply looking for the perfect waterfront retreat, this property delivers the Florida lifestyle at its absolute best.

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

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

Remarks: Located in a quiet residential area of Holiday, this charming home offers comfort, functionality, and great potential for its next owner. The property features a well-designed layout with bright living spaces and an updated kitchen that blends beautifully with the main living area, creating a warm and inviting atmosphere for everyday living and entertaining. The home also includes a versatile bonus space that can be used as a home office or easily converted into a third bedroom, providing flexibility to fit your lifestyle. Natural light fills the interior, enhancing the welcoming feel throughout the home. Step outside and enjoy the outdoor space, perfect for relaxing, hosting gatherings, or simply enjoying the Florida sunshine. Conveniently located near shopping, dining, parks, and just a short drive from the beautiful Gulf Coast beaches. A wonderful opportunity for buyers looking for comfort, flexibility, and a great location.

Listing is courtesy of: AVENUE HOMES LLC (833-499-2980)

Listing Agent: Arlety Mollineda Fernandez (813-321-9395)

Remarks: One or more photo(s) has been virtually staged. This charming 1 story home offers 3 bedrooms, 1 bathroom with stylish living with stainless steel appliances, crisp white cabinets, and granite countertops that make the kitchen both elegant and functional. Step outside to enjoy a spacious yard enclosed by a wood fence, perfect for outdoor activities, pets, or relaxing in privacy. The screened back porch provides a serene space to unwind and enjoy the outdoors year-round. Schedule a showing today!

Listing is courtesy of: MAINSTAY BROKERAGE LLC (800-583-2914)

Listing Agent: Raquel Littlejohn (470-279-6333)

Remarks: Welcome to this beautifully updated one-story villa located at 3849 Staysail in Holiday. This 2-bedroom, 2-bath residence has been completely remodeled and features elegant Italian-inspired accents throughout. The modern, spacious kitchen is thoughtfully designed with granite countertops, pull-out drawers and cabinetry, and stainless-steel appliances that create both style and functionality. Both bathrooms have been fully renovated and showcase custom tile work with sleek glass-enclosed showers. High-quality, easy-care flooring flows seamlessly throughout the home, enhancing the clean, contemporary feel. The enclosed rear patio provides additional living space that can be enjoyed most of the year, perfect for relaxing or entertaining. A newer washer and dryer convey with the home, along with a well-maintained A/C system that is only a few years old and a water heater installed in 2023. The unit includes a convenient carport space directly in front, with ample guest parking available nearby. Ideally situated just steps from the clubhouse and pool, this move-in-ready villa is ready for immediate enjoyment. Located only minutes from beaches, parks, boat launches, shopping, dining, and the world-famous Sponge Docks of Tarpon Springs, this property offers the perfect blend of comfort, convenience, and Florida lifestyle living.

Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (727-799-2227)

Listing Agent: Melissa Jolis (727-455-8595)

Remarks: One or more photo(s) has been virtually staged. This well-maintained two-bedroom, one-and-a-half-bath mobile home is located in a community where you own the land and enjoy low HOA fees, offering a practical option for homeowners or investors. Recent updates include a new roof and an updated electrical panel, providing added peace of mind. Inside, the home features a functional layout with comfortable living space and the opportunity to personalize over time. The property is conveniently situated near the Anclote Boat Ramp, everyday shopping and dining, and the Gulf beaches in neighboring Pinellas County. This is a solid opportunity for a primary residence, seasonal use, or investment.

Listing is courtesy of: LIPPLY REAL ESTATE (727-314-1000)

Listing Agent: Megan Pargov (727-459-8997)

Remarks: Stop and check out this well-maintained home in a very active 55+ community. Home is furnished with 2 bedrooms, 2 bathrooms, finished Florida room with separate a/c. Central heat and air-conditioning NEW in 2022, NEW Refrigerator, NEW dryer, enclosed and screen lanai. Windows have been replaced; seller is not sure of year of replacement. Low monthly maintenance fee of $143.00 includes lawn service, garbage removal, maintenance of year-around-heated pool, Clubhouse, Shuffleboard and the common areas. You OWN YOUR LAND. Measurements are approx. Buyer to verify all information that is deemed to be accurate.

Listing is courtesy of: CITY BREEZE ACTION REALTY (727-372-9000)

Listing Agent: Stella Wooster (727-247-2790)

Remarks: Charming 3-bedroom, 2-bath, 1-car garage home in Holiday offering approximately 1,600 sq ft of living space and a desirable Eldorado floorplan featuring a welcoming front courtyard—perfect for enjoying Florida’s beautiful weather. This well-maintained home is in great condition and move-in ready with a newer roof (4 yo) and numerous updates throughout. Interior features include all tile flooring, newer windows, a spacious living room filled with natural light, and a functional kitchen with solid wood cabinets and a convenient breakfast counter. The home offers a split comfort setup with a dedicated mini-split unit in the third bedroom. The primary suite features a walk-in closet and direct access to a Jack-and-Jill style bathroom with double sinks and a tub with shower. Step outside to a large fenced backyard with plenty of room to relax, garden, or entertain. Unique privacy surrounds this property with vacant lots on both sides of the home, creating extra space and openness. One of the neighboring lots is available for purchase from a separate owner, presenting a potential opportunity for expansion or added privacy. Located just minutes from a county waterfront park with public boat launches, this home offers easy access to boating, fishing, and outdoor recreation. Enjoy comfortable Florida living in a well-cared-for home that is ready for its next owner.

Listing is courtesy of: FUTURE HOME REALTY (800-921-1330)

Listing Agent: Vera Ziegler (800-921-1330)

Remarks: Price Improvement! Discover peaceful living in this charming 2-bedroom, 1.5-bath home nestled along the banks of Lake Conley. Perfect for nature lovers and weekend anglers, this property offers a rare blend of comfort, convenience, and outdoor beauty. Fire up the barbecue and enjoy the fresh landscaping. This home is perfect for those seeking a laid-back lifestyle with a touch of adventure at an affordable price. Whether you're casting a line off the dock or watching herons glide across the water, every day feels like a getaway. Book your showing today.

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

Listing Agent: Aaron Burke (813-789-8375)

Remarks: Under contract-accepting backup offers. Price Drop! No flood zone. No HOA. Leaseable. Major systems updated- NEW HVAC (2024), NEW water heater (2024), NEW septic tank (2021), and a new roof with a lifetime warranty. Double pane windows added and impact garage door only a couple years old.

Listing is courtesy of: HOMEFRONT REALTY (727-641-4444)

Listing Agent: Mary Debaggis (704-819-5568)

Remarks: Welcome to this beautiful 5 bedroom 3 bathroom two-story home located in the highly desirable community of Key Vista. Upon entry you immediately feel welcome and at home with the large formal dining area and front living area with electric fireplace. The large kitchen boasts tall cabinetry and plenty of counter space with amazing views of the tree line that reflects along the waters edge. One bedroom with private bathroom is conveniently located on the first floor and four bedrooms are located on the second story with the large master bedroom with private bathroom also has an adjoining bonus room. Enjoy the privacy of no rear neighbors with breathtaking views of nature in your own backyard!!! Only minutes away from some of the most beautiful beaches and parks in Florida. Schedule your private showing today!!!

Listing is courtesy of: INVESTMENT FLORIDA REALTY LLC (727-940-5909)

Listing Agent: Jason Scott (727-364-4749)

Remarks: Serene Pinewood Villas neighborhood is close to shopping and dining for convenience. This two bedroom two full bath home has tile flooring throughout. Extra living area makes this one of the larger units in the community with an extra large side lot for gathering with friends. Main living area has high ceilings with windows allowing for extra light. Community has sparkling pool, clubhouse and shuffleboard with picnic tables for grabbing lunch by the pool. Low HOA fee makes this a affordable place to live. Hot water heater replaced 2020. Newer kitchen faucet and garbage disposal. Washer just one month new. Thermostat fully programable and newer. Call to make an appointment today.

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

Listing Agent: Jennifer Hallett (727-686-6969)

Remarks: Under contract-accepting backup offers. Unaffected by recent storm activity and located in Flood Zone X (no mandatory flood insurance required), this Beacon Square home offers smart, cost-conscious ownership. With no HOA fees, a roof only 9 years old, and a 2017 A/C system, key mechanical updates help reduce future expense concerns. This move-in-ready 3-bedroom, 2-bath home features 1,534 heated sq ft plus an approximate 200 sq ft bonus room with a private entrance — ideal for a home office, guest space, or multi-generational living, potentially reducing the need for outside rental or workspace costs. Interior highlights include Saltillo tile floors, an updated kitchen with stainless steel appliances and breakfast bar, reverse osmosis system, whole-house water softener, open living/dining layout, and a walk-in closet in the primary bedroom. The fenced backyard with two storage sheds, extended driveway, and one-car garage complete this well-located property near US-19 and SR-54 with convenient access to beaches, parks, shopping, and dining.

Listing is courtesy of: RE/MAX ALLIANCE GROUP (813-259-0000)

Listing Agent: Maria Orozco (786-333-1803)