Holiday Homes For Sale & Real Estate - 291 homes

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)