Holiday, FL Homes

• 

  

  

  /16

  $437,000

  • 3 Beds
  • 3 Baths
  • 2,694 Sq Ft

  3040 Sheppards Crook Ct, Holiday, FL 34691

  Lowest Listing in neighborhood!! Don't let this opportunity pass you by**Quiet gated community with fewer than ten homes. This property offers a peaceful retreat on an expansive lot. The home features an open floor plan with split bedrooms for privacy and a lovely in-ground pool, ideal for relaxation and outdoor fun. While it could use some updating, it is competitively priced, providing an

  

  Nancy Yialouris

  Y GROUP REALTY

  (727) 617-3888

  3040 Sheppards Crook Ct, Holiday, FL 34691
• 

  

  

  /16

  $1,225 - $1,575 per month

  The Sunbay Apartments

  1-2 Beds

  4348 Plaza Dr, Holiday, FL 34691

  Come home to the quiet relaxation of The Sunbay Apartments. Private and luxurious, this is a haven with numerous amenities. Sunbay Apartments is perfectly located near major Highways with access to downtown, shopping, medical facilities, and recreation. Available for your convenience are 3 swimming pools, clubhouse, and New Playground as well as a dog park! Experience the ease of deluxe

  4348 Plaza Dr, Holiday, FL 34691
• 

  

  

  /40

  $22,500 Sold May 02, 2025

  • 28 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1990

  4699 Continental Dr Unit 575, Holiday, FL 34690

  This Adorable 1 Bedroom, 1 Bath Partially Furnished Home is in Holiday Travel Park, an All-Ages Community with LOW $659 Lot Rent. MOVING-MUST SELL. The Home has 792 Sq Ft with Maintenance Free Vinyl Siding, a Shingle Roof, Thermo-pane Windows, a Central Ac and Heating System, a New 30 Gallon Hot Water Heater, a Double Carport and a Decorative Stamped Driveway. The Add-on is 12'x33' and could be

  Lane Parks Gulf Breeze Mobile Home Sales, LLC

  4699 Continental Dr Unit 575, Holiday, FL 34690
• 

  

  

  /33

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft

  2045 Manoa Dr, Holiday, FL 34691

  2045 Manoa Dr, Holiday, FL 34691
• 

  

  

  /35

  $254,000

  • 2 Beds
  • 1 Bath
  • 966 Sq Ft

  2166 Dixie Garden Loop, Holiday, FL 34690

  Step inside this beautifully remodeled 2-bedroom, 1-bathroom gem that blends modern upgrades with timeless charm. Recently renovated from top to bottom, this home features a newer roof, AC, and energy-efficient windows for peace of mind. Inside, you’ll find waterproof vinyl flooring that flows seamlessly throughout the space, adding both style and durability. The kitchen is a true highlight,

  

  Drew Moser

  MAVREALTY

  (727) 591-4917

  2166 Dixie Garden Loop, Holiday, FL 34690
• 

  

  /29

  $2,350 per month

  • 3 Beds
  • 2.5 Baths
  • 1,444 Sq Ft
  • Townhouse for Rent

  3084 Inlet Breeze Way, Holiday, FL 34691

  Beautiful 3 bedroom-Townhome, Near Parks, Beaches & More!Available May 15, 2025. This spacious and modern 3 bedroom, 2.5 bathroom townhome offers comfortable two story living in the newer build community. Featuring an open floor plan, a 1 car garage, and included washer & dryer, this home has everything you need for convenient living. Enjoy maintenance free living at the DESIRABLE PRESERVE AT

  Maria Demellis FLORIDA LUXURY REALTY INC

  3084 Inlet Breeze Way, Holiday, FL 34691
• 

  /2

  $239,000 Sold May 02, 2025

  • 1,096 Sq Ft
  • $218/SF
  • 2 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1968

  5346 Riddle Rd, Holiday, FL 34690

  Get ready to fall in love with this beautifully renovated home in the heart of one of Holiday's most desirable neighborhoods. With a brand new 2025 roof, this stunning 3 bedroom, 1.1 bathrooms, this property offers an exceptional lifestyle in one of the city's fastest growing areas. This home was designed with family comfort in mind, featuring nice rooms and a smart layout that maximizes every

  Irina Dare STAR BAY REALTY CORP.

  5346 Riddle Rd, Holiday, FL 34690
• 

  

  /13

  Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 960 Sq Ft

  1919 Rally Ln, Holiday, FL 34690

  1919 Rally Ln, Holiday, FL 34690
• 

  

  /42

  $139,900

  • 2 Beds
  • 2 Baths
  • 1,141 Sq Ft

  3352 Kauna Point Dr, Holiday, FL 34691

  Tiki Village is a vibrant 55+ gated community located in the heart of Holiday, Florida, where you own the land (no lot rent) with an incredibly low HOA fee of just $40 a month! This spacious and well-maintained double-wide mobile home is ideal for year-round living or as a cozy winter retreat. Key features include a new A/C unit installed in July 2024, newer windows, a large Florida room, and a

  

  Andre Smallwood

  IMPACT REALTY TAMPA BAY

  (727) 955-2448

  3352 Kauna Point Dr, Holiday, FL 34691
• 

  

  /20

  $1,780 per month

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • House for Rent

  1919 Dartmouth Dr, Holiday, FL 34691

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $1924.90. That covers your base rent, $1780.00 + our required services designed to make your life easier: Air filter delivery ($9.95), Internet

  1919 Dartmouth Dr, Holiday, FL 34691
• 

  /2

  $249,999 Sold May 02, 2025

  • 1,002 Sq Ft
  • $250/SF
  • 233 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1963

  2120 Hess Dr, Holiday, FL 34691

  Charming moving-in-ready home in Ridgewood Gardens, Holiday FL. Located near US Highway 19. This great started home offers 3 bedrooms and 2 fully remodeled bathrooms, a living room, a brand-new kitchen with stainless steel appliances, refrigerator, dishwasher, stove and microwave are included, eat in kitchen, newly painted walls, terrazzo floors, 2 brand new bathrooms, one with a shower, and one

  Lilibeth Garcia LA ROSA REALTY LLC

  2120 Hess Dr, Holiday, FL 34691
• 

  

  /3

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,276 Sq Ft

  4750 Betsy Dr, Holiday, FL 34690

  4750 Betsy Dr, Holiday, FL 34690
• 

  /2

  $959,900

  • Land
  • 1.28 Acres
  • $749,922 per Acre

  0 Flotilla Dr Unit MFRU8228712, Holiday, FL 34690

  Beautiful 1.28 Acre Vacant Land on the Anclote River : On a dead end Peaceful Street with no through traffic : Land can be divided into 3 Lots, each approx .43 acre Waterfront lots or sold as one piece to a Developer : Could be ideal for A Townhome Developement : Or build a Gorgeous Large Family Home with tons of Privacy : Many Possibilities : Land is cleared and already has a concrete seawall

  Theresa Legatti

  CHARLES RUTENBERG REALTY INC

  (727) 607-6729

  0 Flotilla Dr Unit MFRU8228712, Holiday, FL 34690
• 

  

  /20

  $1,550 per month

  • 2 Beds
  • 1 Bath
  • 704 Sq Ft
  • House for Rent

  2625 Narcissus Dr, Holiday, FL 34691

  Welcome to this inviting two-bedroom, one-bathroom home with a one-car garage, ideally located in the serene community of Holiday, Florida. Perfect for small families or individuals seeking comfort and tranquility, this cozy residence offers a thoughtful layout and a touch of privacy. Step inside to discover a spacious open floor plan with tile flooring throughout, providing a clean,

  Chelsie Jacobs WRIGHT DAVIS REAL ESTATE

  2625 Narcissus Dr, Holiday, FL 34691
• 

  /2

  $180,000 Sold May 01, 2025

  • 1,584 Sq Ft
  • $114/SF
  • 4 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1985

  1339 Jambalana Dr, Holiday, FL 34691

  REHAB OPPORTUNITY FOR INVESTOR. CASH ONLY. CANNOT ASSIGN CONTRACT. NO SIGHT UNSEEN OFFERS. MUST USE TITLE COMPANY DESIGNATED BY SELLER'S ATTORNEY. NOT IN A FLOOD ZONE. Great potential in this 2/2/2 home with 1584 sq. ft. With the exception of the water heater which is new, it requires a full renovation.. Home is located on dead end with no street traffic. Holiday Lakes West subdivision is

  Shelbia Roberts, LLC RE/MAX ALLIANCE GROUP

  1339 Jambalana Dr, Holiday, FL 34691
• 

  

  /24

  Est $139,473 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 825 Sq Ft

  4373 Tahitian Gardens Cir Unit G, Holiday, FL 34691

  4373 Tahitian Gardens Cir Unit G, Holiday, FL 34691
• 

  

  /25

  $214,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,190 Sq Ft

  4037 Chesswood Dr, Holiday, FL 34691

  You'll love this home less than 6 miles to the beach and less than one mile to shops and restaurants on US-19! This home features tile flooring throughout, granite countertops, a fenced in yard, and much more! As you walk in you will notice the nice open living/dining area with a great sized kitchen for all of your cooking needs. On the right when you walk in are two large bedrooms and a full

  

  Deanna Barr

  REAL BROKER, LLC

  (727) 594-7135

  4037 Chesswood Dr, Holiday, FL 34691
• 

  /2

  $1,595 per month

  • 2 Beds
  • 1 Bath
  • 956 Sq Ft
  • House for Rent

  2553 Chancery Dr, Holiday, FL 34690

  Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.This home features Progress Smart Home - Progress Residential's smart home app, which allows you to control the home securely from any of your devices. Learn more at This home is priced to rent

  2553 Chancery Dr, Holiday, FL 34690
• 

  /2

  $120,000 Sold May 01, 2025

  • 736 Sq Ft
  • $163/SF
  • 52 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1984

  2108 Hoyle Dr, Holiday, FL 34691

  Welcome to this charming two bedroom, two bathroom mobile home nestled on a cozy .08-acre lot in Buena Vista 3rd Addition Community! The affordable HOA fees include trash collection, street lighting, and access to the community clubhouse. The open floor plan creates a warm and inviting living space, complimented by a lovely Lanai off of the dining room. Located near shopping, restaurants, and

  Sara Henk LA ROSA REALTY CENTRAL FLORIDA

  2108 Hoyle Dr, Holiday, FL 34691
• 

  

  /31

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,250 Sq Ft

  3724 Bywater Dr, Holiday, FL 34691

  3724 Bywater Dr, Holiday, FL 34691
• 

  

  /16

  $199,900 Pending

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft

  3701 Oakhurst Dr, Holiday, FL 34691

  Under contract-accepting backup offers. This immaculate 2-bedroom, 1-bath home is move-in ready and packed with upgrades! Featuring a brand-new Central A/C system, septic tank, drain field, and repiping, this property ensures worry-free living. The updated kitchen boasts new granite countertops and modern appliances, perfect for home chefs. The roof was replaced in 2017, adding to the home's

  

  Frederic Samson

  NAMASTE REALTY LLC

  (727) 761-8064

  3701 Oakhurst Dr, Holiday, FL 34691
• 

  

  /25

  $2,000 per month

  • 2 Beds
  • 2 Baths
  • 1,257 Sq Ft
  • Condo for Rent

  4209 Castlewood Dr, Holiday, FL 34691

  Available now! Welcome to totally remodelled villa located at Edgewood of Gulf Trace in Holiday. This is one of the larger villas overlooking a huge back yard making it a perfect place to relax and call it home. The beautiful villa features an open split floor plan, vaulted ceilings and lots of windows for natural lighting. Tastefully remodelled 2 bedrooms, 2 baths with a huge living room/dining

  Tatyana Vasilkova REMAX Affinity Mercato

  4209 Castlewood Dr, Holiday, FL 34691
• 

  /2

  $205,000 Sold May 01, 2025

  • 1,096 Sq Ft
  • $187/SF
  • 56 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1972

  3519 Eisenhower Dr, Holiday, FL 34691

  MOVE IN READY 2/2 with a brand NEW ROOF! AC newer (2023). This open floor plan has the Kitchen, Dining, and Livingroom open to each other for easy entertaining. The additional room can be used for as your needs change....family room, office, playroom....the possibilities are endless. Entire interior just freshly repainted with quality paint. Professionally cleaned. NO CARPET!!! Great back yard

  Penny Perry RE/MAX CHAMPIONS

  3519 Eisenhower Dr, Holiday, FL 34691
• 

  

  /26

  Est $375,514 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,876 Sq Ft

  2154 Parrot Fish Dr, Holiday, FL 34691

  2154 Parrot Fish Dr, Holiday, FL 34691
• 

  

  /27

  $200,000 Open Sun 11AM - 1PM

  • 2 Beds
  • 1.5 Baths
  • 1,052 Sq Ft

  4017 Moog Rd, Holiday, FL 34691

  Welcome to this charming home nestled on a desirable corner lot in sunny Florida. This residence blends classic Florida style with thoughtful updates, including original Old Florida terrazzo floors that exude timeless character. The updated kitchen features pristine cabinets, perfect for both everyday cooking and entertaining. Enjoy year-round relaxation in the fully enclosed lanai, ideal for

  

  Jackie Little

  KELLER WILLIAMS REALTY- PALM H

  (727) 607-5347

  4017 Moog Rd, Holiday, FL 34691
• 

  

  /10

  $1,870 per month

  • 3 Beds
  • 2 Baths
  • 1,380 Sq Ft
  • House for Rent

  1117 Jambalana Dr, Holiday, FL 34691

  We are currently making final preparations for this home to be available. We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be

  1117 Jambalana Dr, Holiday, FL 34691
• 

  /2

  $237,000 Sold May 01, 2025

  • 1,048 Sq Ft
  • $226/SF
  • 107 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1969

  3332 Brookfield Dr, Holiday, FL 34691

  ASK me about special financing with ZERO down payment. No water or flood damage from hurricane season! This well-maintained 3 bedroom home features a spacious living room with bamboo flooring, updated porcelain tile flooring, newer cabinetry, and appliances. The split-bedroom floor plan offers both privacy and a spacious feel. Both bathrooms have been remodeled within the last couple of years,

  Dario Vitagliano REALTY ONE GROUP SUNSHINE

  3332 Brookfield Dr, Holiday, FL 34691
• 

  

  /38

  Est $139,094 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 825 Sq Ft

  4375 Tahitian Gardens Cir Unit G, Holiday, FL 34691

  4375 Tahitian Gardens Cir Unit G, Holiday, FL 34691
• 

  

  /33

  $184,900

  • 2 Beds
  • 2 Baths
  • 1,296 Sq Ft

  2133 Oahu Dr, Holiday, FL 34691

  Welcome to this beautifully updated 2-bedroom, 2-bathroom manufactured home on owned land in the gated 55+ community of Lake Conley Mobile Home Park. From the moment you arrive, you’ll feel the coastal charm with a custom tiki bar that greets you upon entry into the spacious family room. This versatile space, featuring French doors, can be used as a guest room, office, or casual hangout area.

  

  Becky Billeci

  IMPACT REALTY TAMPA BAY

  (727) 291-1727

  2133 Oahu Dr, Holiday, FL 34691
• 

  

  /15

  $1,850 per month

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • House for Rent

  3221 Fairmount Dr, Holiday, FL 34691

  House for rent, Holiday Lakes Estates, private owner, not an absentee corporate owned property, updated 2 bedroom, one bath home, all impact Storm windows, no storm shutters required, large one car garage and utility area, new privacy gated fence, new air conditioning system, kitchen updated, all tile floors, new bathroom, back street no traffic, washer dryer, all appliances, large outdoor

  Charlie Primm CHARLES PRIMM

  3221 Fairmount Dr, Holiday, FL 34691
• 

  /2

  $128,250 Sold Apr 30, 2025

  • 825 Sq Ft
  • $155/SF
  • 34 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1979

  4319 Tahitian Gardens Cir Unit E, Holiday, FL 34691

  Welcome to this charming, well-maintained 2-bedroom, 1.5-bathroom end-unit condo located in the highly sought-after 55+ gated community of Tahitian Gardens in Holiday. Nestled in a quiet and private location on the non-traffic side of the building, this beautiful condo offers a peaceful retreat with the convenience of being just minutes from the historic town of Tarpon Springs Sponge Docks, local

  Jolene Schotter EXP REALTY LLC

  4319 Tahitian Gardens Cir Unit E, Holiday, FL 34691
• 

  

  /65

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,180 Sq Ft

  3131 Bixler Ct, Holiday, FL 34690

  3131 Bixler Ct, Holiday, FL 34690
• 

  

  /65

  $400,000

  • 2 Beds
  • 2 Baths
  • 1,555 Sq Ft

  2344 Pleasant Hill Ln, Holiday, FL 34691

  Enjoy peaceful 55+ maintenance free living in the gated Vista Point at Key Vista. This beautifully maintained 2BR + Den, 2BA home offers stunning pond and conservation views, no front yard neighbors, an open floor plan, high ceilings, and a spacious layout perfect for entertaining. The updated kitchen features Corian countertops, stainless steel appliances, LED recessed can lighting and a center

  

  Gail Urban

  CENTURY 21 COASTAL ALLIANCE

  (727) 607-2969

  2344 Pleasant Hill Ln, Holiday, FL 34691
• 

  

  /20

  $1,680 per month

  • 3 Beds
  • 1 Bath
  • 1,225 Sq Ft
  • House for Rent

  3555 Winder Dr, Holiday, FL 34691

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $1824.90. That covers your base rent, $1680.00 + our required services designed to make your life easier: Air filter delivery ($9.95), Internet

  3555 Winder Dr, Holiday, FL 34691
• 

  /2

  $150,000 Sold Apr 30, 2025

  • 1,014 Sq Ft
  • $148/SF
  • 92 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1965

  3445 Pinehurst Dr, Holiday, FL 34691

  Welcome home to this 2 bedroom 1 bath and 1 car garage all under 220k. Walking in you will see the large ceramic tile throughout the home and spacious living room. Kitchen features newer cabinets and granite countertops next to the dining/office space. The backyard is fully fenced in and offers plenty of space.

  Trevor Skeens RE/MAX REALTY UNLIMITED

  3445 Pinehurst Dr, Holiday, FL 34691
• 

  

  /35

  Est $138,811 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 825 Sq Ft

  4367 Tahitian Gardens Cir Unit B, Holiday, FL 34691

  4367 Tahitian Gardens Cir Unit B, Holiday, FL 34691
• 

  

  /33

  $250,000

  • 2 Beds
  • 2 Baths
  • 1,398 Sq Ft

  3850 Sablewood Dr, Holiday, FL 34691

  Great Location, Not in a Flood Zone, and no issues from the 2 hurricanes.  Spacious 2 bedroom, 2 bath, home boasts nearly 1400 sq ft and offers flexible space to potentially convert to a 3 bedroom.  This home features an open floor plan with a family room with double pane windows, a sunroom with access to the backyard where there is a covered patio with an insulated pan roof to take refuge from

  

  Gail Urban

  CENTURY 21 COASTAL ALLIANCE

  (727) 349-4875

  3850 Sablewood Dr, Holiday, FL 34691
• 

  

  /18

  $1,929 per month

  • 3 Beds
  • 2.5 Baths
  • 1,640 Sq Ft
  • House for Rent

  6214 Hopewell Dr, Holiday, FL 34690

  Take a look at this beautiful home, Clean and Move-In Ready, split plan featuring 3 bedrooms, 2.5 bathrooms, (NOTE PROPERTY AMENITIES LIKE IN-GROUND POOL, SS APPLIANCES, FENCED BACKYARD, SCREEN PORCH, FLOORING, ETC), 1 car garage and approximately 1,640 heated square feet. (NOTE HOA AMENITIES – LIKED GATED, POOL, PLAYGROUND AND BRIEF RESTRICTIONS - LIKE LEASE TERM, APPROVALS). Enjoy the freedom

  Mileyka McElla TAH FLORIDA LLC

  6214 Hopewell Dr, Holiday, FL 34690
• 

  /2

  $185,000 Sold Apr 30, 2025

  • 1,232 Sq Ft
  • $150/SF
  • 239 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1987

  2839 Featherstone Dr, Holiday, FL 34691

  PRICED TO SELL!!! COME SEE IT TODAY!!Very Motivated sellers, Newly Remodeled 2 Bedroom, 2 Bath newer home, with new AC unit installed 1/2025 new Hot Water Heater in 2024 new roof in 2022, fresh paint, new bathrooms and new kitchen with all new stainless appliances and granite countertops. plus HOA fees include all but electric. Beautiful community pool and spa. Close to Honeymoon Island and

  Donna Kroll HOMETRUST REALTY GROUP

  2839 Featherstone Dr, Holiday, FL 34691
• 

  

  /45

  Est $579,851 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,169 Sq Ft

  3196 Gina Ct, Holiday, FL 34691

  3196 Gina Ct, Holiday, FL 34691

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