Quick Holiday FL MLS Search

Browse All Holiday FL Properties with Pool for Sale

$229,900
3 Beds 2 Baths Holiday Lake Estates 21 SubDv. 34691 Zip Code
Under contract-accepting backup offers. Auction Property. Short Sale. * * FANTASTIC OPPORTUNITY * * Welcome to this 3-bedroom, 2-bath POOL HOME located in the heart of Holiday, FL. This home offers the perfect blend of comfort, style, and indoor-outdoor living. Step inside to find a bright, open floor plan with abundant natural light, spacious living and dining areas, and a thoughtfully designed layout ideal for both everyday living and entertaining. The kitchen features ample cabinetry, generous counter space, and a convenient breakfast bar overlooking the main living area. The primary suite provides a relaxing retreat with large sliding doors that open to the screened patio. Two additional bedrooms offer flexibility for family, guests, or a home office. The fully fenced backyard offers privacy and space to unwind, entertain, or simply soak up the sunshine. Enjoy the warm Florida sun in the sparkling pool! Whether you're looking for a vacation home or a year-round residence, this home provides the perfect balance of comfort, convenience, and tranquility. * * PREMIUM LOCATION * * Easy access to multiple stores and restaurants. Just 4 miles away from Holiday's pride and joy for recreation; The J. Ben Harrill Recreation Complex. This Large Park offers tennis courts, basketball courts, hockey roller rink, soccer fields and is the home of the Greater Holiday Little League. Just minutes away from Key Vista Nature Park. A 101-acre park with nature trails, boardwalk and observation tower. Head 4 miles south and you can enjoy the World-Famous Sponge Docks of Tarpon Springs. Known for its fishing, food and entertainment. * * PLEASE NOTE * * It is buyer’s responsibility to verify all information. Information posted in MLS or any marketing is not guaranteed.

3105 Pinon Drive, Holiday

$1,859,900
4 Beds 4 Baths Baileys Bluff Estates SubDv. 34691 Zip Code
Stunning Ocean views from this waterfront paradise. The opportunity has arisen to acquire the former home of the renowned local artist Elaine Hahn and AIA emeritus architect Byron G McIntyre. Located in the sought-after Bailey’s Bluff community, this stunning 4-bedroom, 4-bath elevated home offers 3,412 square feet of coastal living with panoramic water views throughout and 160 feet of private water frontage with direct access to the Gulf. Located at the very end of a Cul-de-sac the private driveway leads to a spacious 4 plus vehicle garage. Take the inside elevator to the open plan 2nd floor, with feature light maple hardwood flooring accentuating the amazing natural light that flows into the living room. This floor also contains an open-plan kitchen, dining area, master bedroom suite and artist studio which has the most amazing views you will find for any home office. There is a covered front balcony and wrap around back balcony where you can enjoy the wonderful Gulf breezes. The third floor has three further bedrooms and addition Den/office. Also, you will find a secluded third-floor balcony that looks out at more spectacular views across to Anclote Key. In addition to the ground level garage, there is a covered parking area. Inside the garage is workshop space with French doors onto the pool deck. The backyard has a tranquil, tropical and beach feel with floating dock and boat lift. Take a 15-minute stroll to Key Vista Nature Park with its many trails and observation tower overlooking the Gulf. Enjoy boating, fishing, scalloping and island hopping. A short drive to a recreational complex, parks, beaches and the charming community of Tarpon Springs, complete with shopping and dining options. This home is solidly built to withstand hurricanes, being elevated, and with concertina or roll down shutters to all windows. During 2024 storms only suffered minor damage, not even losing power. There is no HOA, but an optional Baileys Bluff Civic Assoc. membership is just $100 a year, providing a private beach, boat ramp, & clubhouse. Don't miss the opportunity to make this slice of paradise your own!

1906 Gulfview Drive, Holiday

$84,900
2 Beds 2 Baths Lake Conley Mhp SubDv. 34691 Zip Code
Big Price Reduction!! Great deal waiting for you in the gated, 55+ community of Lake Conley, in Holiday, Florida. You own the land here and have low +/- $70 a month HOA dues, no land lease. This is a 1,152 square foot 2-bedroom, 2 bath home. This pet-friendly park will allow with one dog, or one cat, no more than 25lbs. Service animals and Emotional Support animals require current documentation. No aggressive breeds. The home has a 2 carport, screened porch, storm shutters, shed with laundry and sink, a newer water heater, ceiling fans and comes furnished. The dining room has a built-in hutch, with a mostly original kitchen, but has a newer stainless-steel dishwasher and tiled backsplash. There is a family room and a somewhat updated hall bath, with tiled tub/shower surround and new hardware. It also has a newer sink and toilet, with the main bath having a walk-in shower. The homes floors do have significant soft spots in several areas and will likely need some sub-floor replacement. CASH only please. There’s a boat ramp and fishing pier here for residents to use, as well as a rentable additional boat/RV parking lot/storage area. The community pool and clubhouse are all here to be enjoyed by the residents. Golf carts and motorcycles welcome. Very private and peacefully tucked in off US 19 but yet so close to everything. It’s an easy drive to some of Florida most beautiful beaches, parks, restaurants and shopping. Also, with easy commute to Tarpon Springs. Community offers a heated pool all year round, active clubhouse with year around events, shuffleboard, boat ramp, fishing pier and much more. Call for a showing today.

2127 Oahu Drive, Holiday

$319,000
3 Beds 2 Baths Gulfwinds SubDv. 34691 Zip Code
Experience the best of the Florida lifestyle in this spacious, low-maintenance villa just minutes from charming downtown Tarpon Springs. Offering 1,740 square feet of thoughtfully designed living space, this 3-bedroom, 2-bath residence with a versatile den/office delivers the comfort and functionality of a single-family home without the upkeep. The open-concept floor plan seamlessly connects the kitchen, dining, and living areas—creating the perfect setting for entertaining guests or enjoying relaxed evenings at home. The kitchen shines with 42-inch maple cabinetry, granite countertops, and generous prep space, providing both style and practicality. Retreat to the expansive primary suite featuring a spa-inspired ensuite bath with dual vanities, a soaking tub, walk-in shower, and a large walk-in closet. Additional highlights include a full-size laundry room with utility sink and built-in shelving, as well as a spacious two-car garage with plenty of room for vehicles, beach gear, or recreational equipment. Located within a beautifully maintained community, the HOA covers lawn care, exterior painting, internet, cable, and trash service—allowing you to fully enjoy the amenities, including a resort-style pool and recreation area. Situated in a no-flood zone and just 10 minutes from the iconic Sponge Docks, marinas, parks, and top-rated schools, bike trail connected to the Pinellas Trail. Whether you're searching for a full-time residence, seasonal retreat, or investment opportunity, this villa offers exceptional value and convenience. Schedule your private showing today and discover everything this vibrant community has to offer.

2334 Barracuda Court, Holiday

$825,000
3 Beds 3 Baths Baileys Bluff Estates SubDv. 34691 Zip Code
Virtually Staged. Open access to the Gulf!! Experience elevated waterfront living in this elegant 3 bed/2 bath residence with a versatile bonus room, thoughtfully designed to blend architectural charm, refined finishes, and seamless indoor–outdoor flow, all in the sought after Baileys Bluff Estates! The generously sized secondary bedrooms offer ample closet space and share a beautifully appointed full bath with a tub/shower combination. A hallway linen closet with built-in shelving provides additional storage. The primary suite is a true retreat, featuring sliding-door access to the lanai and a spa-inspired bath complete with a step-in shower with sliding glass doors—also opening to the exterior—dual-sink vanity, private water closet, and a dedicated dressing hallway with abundant closet space. A separate pool-access bath with sink and toilet can be closed off from the primary suite for added privacy. A nearby washer and dryer closet enhances everyday convenience. The main living areas impress with soaring volume ceilings, recessed lighting, and a striking corner stone fireplace anchoring the space. The chef’s kitchen is as functional as it is beautiful, showcasing wood soft-close cabinetry, granite countertops, stainless steel appliances, a breakfast bar, pantry closets with extensive shelving, a built-in corner desk, and a sun-filled breakfast nook. Architectural details add warmth and character, including a barn-style sliding door allowing the kitchen to be closed off when desired, and a decorative wicker-accent opening that enhances the home’s charm. A flexible dining area offers the option of formal dining and opens through sliding doors to a charming brick patio. The bonus room provides exceptional flexibility—ideal as a home office, media room, or optional fourth bedroom—complete with a utility sink closet, additional storage, and direct garage access. Outdoors, the expansive screened-in lanai and pool create a private oasis perfect for entertaining, complemented by an outdoor shower. The generous fenced backyard leads to your waterfront dock area, where tranquil water views can be enjoyed from the living room, breakfast nook, dining area, and kitchen. Additional highlights include light wood luxury vinyl flooring throughout; tile flooring in all bathrooms, oversized windows providing abundant natural light, ample storage throughout, and an oversized two-car garage. Located just two blocks from the Coastal Anclote Trail, which offers over four miles of scenic paths that connect to the Pinellas Trail in Tarpon Springs. Enjoy easy water access via the bayou and creek with just a five-minute boat ride to the Gulf. The area is also ideal for kayaking. Pickleball courts with weekly league play are located within one mile. This exceptional waterfront property offers the perfect blend of lifestyle, comfort, and convenience. Schedule your private showing today.

2138 Bayou Drive, Holiday

$329,980
3 Beds 2 Baths Gulfwinds SubDv. 34691 Zip Code
BEST VALUE IN GULFWINDS – A TURNKEY OPPORTUNITY WITH BUYER FLEXIBILITY! Major updates are already handled with a 2022 HVAC system and 2018 WATER HEATER, plus a WATER SOFTENER giving buyers peace of mind from day one. If you’ve been waiting for the right opportunity in Gulfwinds, this is it. This 3-bedroom, 2-bath home with 1,740 sq ft delivers space, updates, a private backyard, and a true maintenance-free lifestyle—positioned to stand out in today’s market. Inside, you’ll find vaulted ceilings with crown molding and an open layout that flows seamlessly between the living, dining, and kitchen areas—creating a bright, inviting space that lives larger than expected. The split floor plan offers privacy, with a spacious primary suite featuring a walk-in closet, dual vanities, soaking tub, and frameless glass shower. Secondary bedrooms are perfect for guests or a home office. The kitchen is both functional and spacious, featuring 42-inch cherry wood cabinetry, ample counter space, GE appliances, and Moen fixtures. Step outside to a screened lanai overlooking one of the larger fenced backyards in the community, ideal for relaxing or entertaining. The oversized two-car garage is highlighted by a newly installed premium decorative epoxy floor coating with an attractive flake finish, creating a clean, showroom-quality appearance while providing exceptional durability, stain resistance, and easy maintenance. Built with durability in mind, this home includes concrete block construction, hurricane shutters, low-E double-pane windows, R-30 insulation, and a 200-amp service. Gulfwinds offers a true maintenance-free lifestyle, with HOA covering roof maintenance, lawn care, exterior painting, cable, internet, community grounds, and a resort-style pool. Located just minutes from beaches, marinas, parks, shopping, dining, and the Tarpon Springs Sponge Docks, this home combines convenience with value. Homes in this price range are moving—don’t miss your chance. SELLER OFFERING $5,000 CREDIT TO BUYER AT CLOSING WITH ACCEPTABLE OFFER. Schedule your showing today!

2302 Barracuda Court, Holiday

$159,000
2 Beds 2 Baths Holiday Lake Villas Condo SubDv. 34691 Zip Code
Welcome to 1027 Bowsprit Lane, a well-maintained residence located in the heart of Holiday, Florida. This unit boasts of 1,534 SF and contains 2 bedrooms, 2 bathrooms, brand new kitchen (remodeled 2025), living room, laundry area, walk-in closet, walk-in pantry, and glass-covered lanai. This villa also has a small storage shed outside, parking for one car is assigned under a carport, and guest parking is available close to the entrance. The home features an updated kitchen with ample cabinetry and workspace, ideal for everyday living and entertaining. Spacious living and dining areas create a warm and welcoming atmosphere, while the thoughtfully designed layout maximizes functionality. The monthly maintenance fee of $613.00 covers building exterior, roof, water and sewer service, rubbish removal, basic cable TV, landscaping maintenance, escrow reserves, and insurance of the structure and common elements (a community owned clubhouse with heated pool). Conveniently located near shopping, dining, parks, and major roadways including US-19, offering easy access for commuting and daily errands. Whether you are downsizing, or looking for an excellent investment opportunity, this property presents great value in a growing area. Schedule your private showing today and experience all this home has to offer. Furniture negotiable. The community rules do not allow trucks, boats and motorcycles. Water heater 2022, AC 2023, don't miss this amazing opportunity, schedule your private showing today!

1027 Bowsprit Lane, Holiday

$175,000
2 Beds 2 Baths Tanglewood Mobile Village SubDv. 34690 Zip Code
NEW PRICING! This cozy, WATERFRONT home is nestled in Holiday, surrounded by Tarpon Springs, New Port Richey, and the glistening Gulf of Mexico. Overlooking Lake Tanglewood, the 2 bedroom/2 bath dwelling features water on two sides with just one neighbor on one side and a seawall around the water frontage. Here you’ll enjoy all the favorite local water sports; electric motorboats are permitted. Framed by palm trees and a lush lawn, the views are spectacular while the charming curb appeal extends all around to the stone patio in the backyard with ample room for loungers and a grill -- accompanied by steps that lead down to the water’s edge. The light and bright interior has been treated to plenty of UPGRADES including NEWER plywood sub flooring and NEWER tilt-out windows throughout; most of the walls are sheetrock. The sunroom is absolutely glorious with a huge serving port from the kitchen, a vaulted ceiling, panoramic water views from two walls of windows, and a door to the yard. NEWER neutral carpeting graces the spacious living room and bedrooms topped by crown molding. The formal dining room is adorned with versatile built-ins for stowing and showcasing precious mementos. As for the UPDATED kitchen, it shares color contrasting, easy care laminate flooring with the adjacent dining room. NEWER QUARTZ countertops are flanked by NEWER STAINLESS appliances. NEWER CABINETS are outfitted with soft close drawers and space-saving Lazy Susan pullouts to house everything from spices to saucepans. The master suite is wonderfully sunny courtesy of its multiple windows and has ample storage thanks to its walk-in closet decked with shelving. The ensuite bath is well appointed. A BRAND-NEW washer and dryer were just installed in the storage room. Tanglewood Mobile Village Condominium is a 55+ community that boasts a heated community pool along with a clubhouse, shuffleboard and horseshoe courts. While no leasing is allowed, the reasonable monthly HOA fee of $143 covers lawn care, trash removal, and use of all amenities. Waterfront and sun-filled: THIS is the Florida lifestyle!

4706 Burney Drive, Holiday

$294,000
3 Beds 2 Baths Beacon Square SubDv. 34691 Zip Code
***FEMA FLOOD INSURANCE PAID THROUGH NOVEMBER 2027***FULLY TRANSFERABLE TO THE NEW OWNER. INSTANT VALUE AND SAVINGS. DON’T MISS THIS PROTECTED HOME OPPORTUNITY. This beautifully updated 3-bedroom, 2-bath home features a spacious, open layout perfect for everyday living and entertaining. Enjoy ceramic tile floors throughout, remodeled bathrooms, and a modern kitchen with granite countertops and stainless steel appliances. The primary bathroom features dual sinks and granite finishes, adding a touch of elegance. Step outside to your private backyard retreat with an in-ground pool, screened enclosure, side jacuzzi, and a cozy patio with BBQ—ideal for outdoor gatherings. The home features a new roof (2026), resistant hurricane windows, hurricane shutters, a pavered driveway, fresh paint, lush landscaping, and major updates, including an updated electrical panel (2016), a water heater (2015), a brand-new AC unit inside (2025), an AC unit outside (2019) and a pool liner replacement in December 2025 for added peace of mind. Additionally, the home includes a finished bonus room located at the rear of the house, fully enclosed and with flooring, offering flexible use as a personal gym, meditation or relaxation room, home office, or creative studio—customizable to suit your lifestyle needs. Conveniently located near Anclote Beach, parks, and US-19, just 15 minutes from Tarpon Springs and 35 minutes from Honeymoon Island. Restaurants, shopping, and everyday essentials are only five minutes away. Updated, comfortable, and perfectly located—this home is ready to enjoy the Florida lifestyle.

3625 Richboro Drive, Holiday

$316,000
3 Beds 2 Baths Gulfwinds SubDv. 34691 Zip Code
2153 Barracuda Court is a 3-bedroom, 2-bath villa with 1,740 square feet of single-story living — and it shows beautifully in person. Three solar tube skylights and vaulted ceilings make the space feel open and bright in a way that photos honestly don't do justice. Engineered hardwood floors run throughout, and the split floor plan keeps the primary suite tucked away from the guest bedrooms — a layout that works equally well for full-time living, part-time seasonal use, or working from home. Out back is where this home really sets itself apart. The screened lanai opens to a fully fenced backyard with an extended brick-paver patio — private, low-maintenance, and the kind of outdoor space you'll actually use year-round in Florida. The major systems have been updated: HVAC 2019, water heater 2022, whole-house surge protector 2022, water softener included. The HOA covers lawn care, exterior painting, cable, internet, and roof maintenance — with a scheduled replacement in 2027 at no cost to you. Residents also enjoy access to the community's resort-style pool, perfect for those Florida afternoons when you just want to relax without leaving the neighborhood. Flood Zone X, so no flood insurance required. Two-car garage. The location here is genuinely hard to beat at this price point. You're minutes from the Tarpon Springs Sponge Docks, Anclote River Park with direct Gulf water access, area beaches, marinas, local restaurants, medical facilities, and everyday shopping. Clearwater and Tampa are both an easy drive — everything that makes this corner of Florida worth living in is right outside your door. A preferred lender rate buydown is available to qualified buyers, reducing your monthly payment in the first year of ownership — ask the listing agent for details. Schedule your private showing today. This one is worth seeing in person.

2153 Barracuda Court, Holiday

$275,000
2 Beds 2 Baths Key Vista Ph 02 SubDv. 34691 Zip Code
Welcome to one of Holiday’s most sought after 55+ gated communities, where privacy, comfort, and an active Florida lifestyle come together seamlessly. This beautifully maintained 2 bedroom, 2 bath home in Key Vista offers 1,555 square feet of well designed living space, along with a versatile office/flex room that can easily serve as a third bedroom, hobby room, or dedicated workspace. Situated on a rare homesite with no neighbor to the right or behind, this property provides exceptional privacy and tranquility. Inside, you’ll find an inviting open floor plan filled with natural light and thoughtfully designed for everyday living and effortless entertaining. The spacious kitchen is a highlight, featuring a large island, breakfast bar, pantry, and plenty of cabinetry ideal for meal prep, gatherings, and morning coffee. The oversized living and dining areas provide flexible layout options and a warm, welcoming feel. A screened-in lanai extends your living space outdoors, perfect for relaxing, dining al fresco, or unwinding while enjoying Florida’s calming breezes. The primary suite offers comfort and functionality with ample closet space and an ensuite bath. The guest bedroom and bath are equally inviting, offering privacy for visitors. Additional features include an attached two-car garage and dedicated laundry area. Residents enjoy low HOA fees, no CDD, and access to two clubhouses. One exclusively for 55+ residents with a private pool, plus a master clubhouse with a pool, spa, gym, tennis and pickleball courts, sand volleyball, playground, and more. On site RV and boat storage is also available for a small monthly fee. If you're looking to venture outside of the community there is nearby Key Vista Nature Park. Enjoy incredible sunsets or walk through one of the many nature trails to enjoy everything Gulf Coast living. This home is also close to parks, shopping, dining, and Gulf beaches. Everyday conveniences are also close at hand. This Holiday gem blends privacy, space, and resort-style amenities in an unbeatable location. Schedule your private tour today!

2453 Pleasant Hill Lane, Holiday

$125,000
2 Beds 2 Baths Lake Conley Mhp SubDv. 34691 Zip Code
Welcome to on Lake Conley a large Mobile Home Park in the city of Holiday Florida of Pasco County! This is a Gated 55+ Community with MULTIPLE amenities and a very low community fee. **No lot Rent here so you own the land** The Amenities include: Community Boat Ramp, Fishing Pier, Clubhouse, heated Pool, Shuffleboard Court, Horseshoe Court, Lakefront Dock to sit and enjoy sunset, RV/Boat Parking and much more! This double wide mobile home is 1,056sqft and bright with a lot of natural light all throughout the home. From the exterior you have a large Carport, Large Shed with Shelves and the Washer & Dryer plus the Whole Home Water Softener System. The Inside is charming with a great layout complete with 2 Bedrooms, 2 Bathrooms, Kitchen, large Living room, Dining Space with Built In cabinets, and an enclosed patio. Some of the Updates include: NEW ROOF 2026, AC SYSTEM Replaced 2024, New Electrical Panel, New Carpet, New GFCI throughout, New Hot Water Neater added 2024, Plumbing Updated throughout with New toilets, New sub flooring 3/4 plywood in living and dining room areas, Skirting around home coming June 2026, and more, Priced to Sell! Add to your short list to see and buy before its gone. *Lake Conley is a Golf Cart Friendly updated Community with a very low HOA fee of only $60 a month* Reminder that this versatile space, featuring Updated Sliders, can be used as an office or casual hangout area. Also this home offers a relaxed Florida living lifestyle that is centrally located to all shopping, restaurants, less than 20 minutes to Florida's most beautiful beaches, Places of worship, nature trails, Parks and many outdoor entertainment. to sum it up: Lake Conley is highly sought after for its privacy, amenities, low HOA fees, location, Gated, Golf carts welcome, Storage, Boast ramp, own your lot, and peaceful surroundings! Call for additional information!

2127 Wailua Drive, Holiday

$120,000
2 Beds 2 Baths Holiday Lake Villas Condo SubDv. 34691 Zip Code
Auction Property. Welcome to Holiday Lake Condos and enjoy peaceful water views right from your own living room! This well-maintained GROUND FLOOR unit features an open floor plan with plenty of natural light. Galley kitchen with eat-in space. Inside utility closet. Living room. Separate dining room. Bonus Florida room with wonderful views of the pond. Split bedroom plan. Master suite is quite large with full master bathroom. Bedroom #2 is adjacent to bathroom #2 for privacy. The community offers a relaxing atmosphere complete with a pool, clubhouse, shuffleboard courts, and a recreational facility! Whether you're looking for a vacation home or a year-round residence, this condo provides the perfect balance of comfort, convenience, and tranquility. Premium location as it has easy access to multiple stores and restaurants. Just 4 miles away from Holidays pride and joy for recreation; The J. Ben Harrill Recreation Complex. This Large Park offers tennis courts, basketball courts, hockey roller rink, soccer fields and is the home of the Greater Holiday Little League. Just minutes away from Key Vista Nature Park. A 101-acre park with nature trails, boardwalk and observation tower. Head 4 miles south and you can enjoy the World-Famous Sponge Docks of Tarpon Springs. Known for its fishing, food and entertainment. * * PLEASE NOTE * * It is buyer’s responsibility to verify all information. Information posted in MLS or any marketing information is not guaranteed.

1034 Bowsprit Lane, Holiday

Start Your Search

Holiday Homes with Pool

Our website features the best real estate search for properties available in Holiday and surrounding areas with pool. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood! 

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Contact us today to find out how we can be of assistance to you!