18,380

Holiday, FL Homes

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  • /8

    $315,000

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft

    2406 Arcadia Rd, Holiday, FL 34690

    Virtually Staged. Under Construction. BACK ON MARKET. Previous buyer's financing fell through. No fault of the property and all inspections cleared. This is your second chance!Welcome to this brand new construction home in Holiday, FL, perfect for first time buyers or savvy investors looking to add a turnkey property to their portfolio. This thoughtfully designed 3 bedroom, 2 bathroom home

    Agent Photo

    Tonino Damiano

    EXP REALTY LLC

    2406 Arcadia Rd, Holiday, FL 34690
  • /25

    $2,195 Per Month

    • 3 Beds
    • 2 Baths
    • 1,900 Sq Ft
    • *Ask about move in Special* 3BR/2BA Home with 2-Car Carport & RV/Boat Parking

    5015 Darlington Rd, Holiday, FL 34690

    Limited-Time May Move-In SpecialDon’t miss this opportunity to settle into your new home while saving on your move-in costs. Availability is limited, so contact us today to secure your unit! Let us know if you want to schedule a TourWelcome to this 3 bedroom 2-bathroom single-family home located at 5015 Darlington Rd in Holiday, FL. This well-maintained property offers a

    5015 Darlington Rd, Holiday, FL 34690
  • /2

    $132,500

    Sold Nov 04, 2025

    3849 Sailmaker Ln, Holiday, FL 34691

    • 2 Beds
    • 2 Baths
    • 1,114 Sq Ft
    • Built 1991

    Last Sold Summary

    • 5% Below List Price
    • $119/SF
    • 87 Days On Market

    Current Estimated Value $133,491

    Last Listing Agent Dean Anderson DELTA REALTY INTERNATIONAL INC

    3849 Sailmaker Ln, Holiday, FL 34691
    • /6

      Not Listed For Sale

      5886 Pappillion Ln, Holiday, FL 34690

      • 3 Beds
      • 2 Baths
      • 1,194 Sq Ft
      • Built 1981
      5886 Pappillion Ln, Holiday, FL 34690

      Last Sold Summary

      • 2 Days On Market

  • /34

    $447,400

    $3K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,848 Sq Ft

    5311 Boardwalk St, Holiday, FL 34690

    Beautifully updated townhome situated on a quiet street just minutes from major freeways, offering the perfect blend of luxury, comfort, and coastal living. This spacious 1,848-square-foot residence features 3 bedrooms and 2.5 bathrooms, enhanced by elegant eucalyptus wood flooring throughout. The tastefully remodeled kitchen showcases high-end cabinetry, stainless steel appliances, and elegant

    Johnny Loewy ALIGN RIGHT REALTY LLC

    5311 Boardwalk St, Holiday, FL 34690
  • /28

    $2,350 Per Month

    • 3 Beds
    • 2 Baths
    • 1,842 Sq Ft
    • House for Rent

    4036 Sunray Dr, Holiday, FL 34691

    FOR LEASE – Enjoy peaceful lakefront living in this beautifully updated three-bedroom, two-bathroom home in Holiday. With a spacious driveway, one-car garage, and inviting large front porch, this home offers both curb appeal and everyday convenience. Inside, you’ll find stunning luxury plank flooring and a bright, functional layout. The dining room and kitchen combination is perfect for

    Jeffrey Borham EXP REALTY LLC

    4036 Sunray Dr, Holiday, FL 34691
  • /2

    $171,000

    Sold Nov 24, 2025

    1415 Russel Ln, Holiday, FL 34691

    • 3 Beds
    • 1 Bath
    • 988 Sq Ft
    • Built 1971

    Last Sold Summary

    • 12% Below List Price
    • $173/SF
    • 103 Days On Market

    Current Estimated Value $183,496

    Last Listing Agent Kevin Barrow UNITED REALTY GROUP INC

    1415 Russel Ln, Holiday, FL 34691
    • /2

      Not Listed For Sale

      3325 Lanark Dr, Holiday, FL 34690

      • 2 Beds
      • 2 Baths
      • 1,056 Sq Ft
      • Built 1974
      3325 Lanark Dr, Holiday, FL 34690

      Last Sold Summary

      • 82 Days On Market

  • /24

    $235,000

    • 3 Beds
    • 2 Baths
    • 992 Sq Ft

    4531 Aegean Ave, Holiday, FL 34690

    BRAND NEW ROOF installed in May. Welcome to this beautifully updated one-story home offering 3 bedrooms, 2 full bathrooms, and a 1-car garage, perfectly situated on a quiet dead-end street for added privacy and minimal traffic. This move-in ready property has been thoughtfully renovated throughout, making it an ideal option for both homeowners and investors alike. Step inside to discover a bright

    Linda Santa 27NORTH REALTY

    4531 Aegean Ave, Holiday, FL 34690
  • /25

    $1,090 Per Month

    • 1 Bed
    • 1 Bath
    • 700 Sq Ft
    • Townhouse for Rent

    1525 Swordbill Dr, Holiday, FL 34690

    Welcome to your next home in Holiday, FL – a charming 1-bedroom, 1-bath duplex unit offering 700 square feet of comfortable living in a peaceful neighborhood. Enjoy a spacious backyard perfect for outdoor relaxation, and benefit from quick access to local attractions, parks, shopping, and dining via nearby US-19. In addition to base-rent, there is a $125/month fee for water and sewer services

    1525 Swordbill Dr, Holiday, FL 34690
  • /2

    $225,600

    Sold Jun 05, 2026

    2547 Limewood Dr, Holiday, FL 34690

    • 2 Beds
    • 1 Bath
    • 956 Sq Ft
    • Built 1965

    Last Sold Summary

    • 3% Above List Price
    • $236/SF
    • 2 Days On Market

    Current Estimated Value $215,992

    Last Listing Agent John Birch BIRCH REAL ESTATE SERVICES LLC

    2547 Limewood Dr, Holiday, FL 34690
    • /2

      Not Listed For Sale

      3330 Chatford Dr, Holiday, FL 34690

      • 2 Beds
      • 2 Baths
      • 840 Sq Ft
      • Built 1980
      3330 Chatford Dr, Holiday, FL 34690

      Last Sold Summary

      • 68 Days On Market

  • /4

    $5,400,000

    • Land
    • 80 Acres
    • $67,500 per Acre

    3130 Shipwatch Dr, Holiday, FL 34691

    Discover the ultimate lifestyle property with tremendous investment potential. The property features multiple premium conservation lots, thoughtfully designed around a beautiful wetland system that wraps the development area to the east and north, creating a private and scenic natural buffer.Currently zoned for 60 single-family homes, the site offers the potential to rezone for additional

    Reed Fischbach Fischbach Land Company

    3130 Shipwatch Dr, Holiday, FL 34691
  • /14

    $1,450 Per Month

    • 2 Beds
    • 1 Bath
    • 1,568 Sq Ft
    • Townhouse for Rent

    5723 Silver Spur Dr, Holiday, FL 34690

    2 BED/1 BATH AVAILABLE NOW!Charming 2 bedroom, 1 bath duplex for rent in Holiday, Florida. This unit has an open floor plan with tile flooring throughout the living area and the kitchen with ample cabinet space. Includes Central AC. Conveniently located near US 19 for travelling throughout Pinellas County. Enjoy nearby restaurants, shopping and landmarks like Fred Howard Park.

    Kevin Byrne VALENCIA REALTY,LLC

    5723 Silver Spur Dr, Holiday, FL 34690
  • /2

    $285,000

    Sold Aug 11, 2025

    5132 Flora Ave, Holiday, FL 34690

    • 2 Beds
    • 2 Baths
    • 1,434 Sq Ft
    • Built 1969

    Last Sold Summary

    • 5% Below List Price
    • $199/SF
    • 46 Days On Market

    Current Estimated Value $287,052

    Last Listing Agent Jackie Johnson DALTON WADE INC

    5132 Flora Ave, Holiday, FL 34690
    • /2

      Not Listed For Sale

      3210 Birkdale Dr, Holiday, FL 34690

      • 2 Beds
      • 2 Baths
      • 864 Sq Ft
      • Built 1981
      3210 Birkdale Dr, Holiday, FL 34690

      Last Sold Summary

      • 167 Days On Market

  • /57

    $399,900

    Pending
    • 4 Beds
    • 3 Baths
    • 2,418 Sq Ft

    2330 Society Dr, Holiday, FL 34691

    Under contract-accepting backup offers. Welcome to this waterfront pool home in the desirable Aloha Gardens community of Holiday! This property features a functional layout with approximately 2400+ square feet of living space, including a main living room, two additional bonus living areas, and a separate dining room, offering flexibility for entertaining, relaxing, or accommodating guests. Step

    Candice Johnson COLDWELL BANKER REALTY

    2330 Society Dr, Holiday, FL 34691
  • /20

    $1,800 Per Month

    • 3 Beds
    • 2 Baths
    • 1,620 Sq Ft
    • House for Rent

    3600 Darlington Rd, Holiday, FL 34691

    This spacious 3-bedroom, 2-bathroom home offers an inviting open floor plan, perfect for both relaxation and entertaining. The generously sized bedrooms provide ample personal space, with two featuring large walk-in closets that cater to all your storage needs. With over 1,600 square feet of meticulously maintained living space, the home includes a large formal living room designed for gatherings

    3600 Darlington Rd, Holiday, FL 34691
  • /2

    $46,250

    Sold Feb 09, 2026

    1919 Dixie Ln, Holiday, FL 34690

    • 2 Beds
    • 1 Bath
    • 390 Sq Ft
    • Built 1959

    Last Sold Summary

    • 16% Below List Price
    • $119/SF
    • 3 Days On Market

    Last Listing Agent Jennifer Franke NJS REALTY PLLC

    1919 Dixie Ln, Holiday, FL 34690
    • /2

      Not Listed For Sale

      4755 Burney Dr, Holiday, FL 34690

      • 2 Beds
      • 2 Baths
      • 1,248 Sq Ft
      • Built 1981
      4755 Burney Dr, Holiday, FL 34690

      Last Sold Summary

      • 1 Day On Market

  • /45

    $149,900

    $3K PRICE DROP Pending
    • 2 Beds
    • 2 Baths
    • 1,056 Sq Ft

    2029 Wailua Dr, Holiday, FL 34691

    Under contract-accepting backup offers. Lake Conley Mobile Home Park welcomes you into this gated home in Desirable 55+ community. This tastefully meticulously well kept home is ready for you with all furnishings provided. You enter through a coded secure gate while enjoying the private lake view, wild bird life and tranquil community. There is so much to enjoy!! You have fishing, boating, golf

    Linda Saunders PARADISE WEST REALTY, INC

    2029 Wailua Dr, Holiday, FL 34691
  • /9

    $1,700 Per Month

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

    1301 Greenlea Dr, Holiday, FL 34691

    CUTE AS A BUTTON...2 bedroom, 1 bath, 1 car garage. Inside Laundry! Freshly painted entire outside of home and new stockade fenced yard for your little ones or your Pet or both. Great location and close to many restaurants and stores. Don't wait, this one won't last!!!

    Randall Smith INVESTMENT FLORIDA REALTY LLC

    1301 Greenlea Dr, Holiday, FL 34691
  • /2

    $224,000

    Sold Apr 28, 2026

    3335 Allandale Dr, Holiday, FL 34691

    • 2 Beds
    • 2 Baths
    • 1,088 Sq Ft
    • Built 1975

    Last Sold Summary

    • 3% Below List Price
    • $206/SF
    • 223 Days On Market

    Current Estimated Value $222,345

    Last Listing Agent Jennifer McDonnell REALTY EXPERTS ASSOCIATES

    3335 Allandale Dr, Holiday, FL 34691
    • /46

      Not Listed For Sale

      3413 Tiki Dr, Holiday, FL 34691

      • 2 Beds
      • 1.5 Baths
      • 768 Sq Ft
      • Built 1985
      3413 Tiki Dr, Holiday, FL 34691

      Last Sold Summary

      • 113 Days On Market

  • /100

    $610,000

    $90K PRICE DROP Pending
    • 6 Beds
    • 4 Baths
    • 3,384 Sq Ft

    1734 Rumar Ln, Holiday, FL 34691

    Under contract-accepting backup offers. Take advantage of a unique opportunity to own an expansive duplex that includes both units of the property. Each side features 3 bedrooms and 2 bathrooms with nearly 1,700 square feet of living space, totaling 3,384 heated square feet and 7,062 square feet overall, with one unit being sold furnished for added convenience. Both units offer oversized two-car

    Erin Floyd COLDWELL BANKER REALTY

    1734 Rumar Ln, Holiday, FL 34691
  • /12

    $1,425 Per Month

    • 3 Beds
    • 1 Bath
    • House for Rent

    4018 Darlington Rd, Holiday, FL 34691

    Welcome to 4018 Darlington Rd in Holiday, FL—a charming and well-maintained 3-bedroom 1 bath home offering comfort, convenience, and Florida living at its best. This inviting property features a bright and open layout, spacious living areas, and a functional kitchen perfect for everyday living and entertaining. Enjoy generously sized bedrooms, ample natural light, and a private outdoor space

    4018 Darlington Rd, Holiday, FL 34691
  • /2

    $552,500

    Sold Jun 02, 2026

    2638 Jays Nest Ln, Holiday, FL 34691

    • 5 Beds
    • 3 Baths
    • 3,072 Sq Ft
    • Built 2001

    Last Sold Summary

    • 2% Below List Price
    • $180/SF
    • 5 Days On Market

    Current Estimated Value $561,192

    Last Listing Agent Judi Pobst KELLER WILLIAMS REALTY- PALM HARBOR

    2638 Jays Nest Ln, Holiday, FL 34691
    • /2

      Est $507,742

      Not Listed For Sale

      3171 Marisa Place, Holiday, FL 34691

      • 4 Beds
      • 3 Baths
      • 2,498 Sq Ft
      • Built 2017
      3171 Marisa Place, Holiday, FL 34691

      Last Sold Summary

      • 11 Days On Market

  • /31

    $315,000

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,047 Sq Ft

    1415 Brixton Ln, Holiday, FL 34691

    Welcome Home. Charming home in a peaceful, low-maintenance neighborhood — no HOA and no CDD! This beautifully remodeled block home features 3 bedrooms and 2 baths with a smart split-floor plan that provides privacy and flow. The one-car garage and fully fenced backyard add convenience and security, while the tile floors throughout make upkeep easy. Interior highlights include a bright, open

    Sean Bowes FRANK ALBERT REALTY

    1415 Brixton Ln, Holiday, FL 34691
  • /17

    $1,175 Per Month

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft
    • Apartment for Rent

    5633 Golden Nugget Dr, Holiday, FL 34690

    Cozy 1BD 1BTH Retreat in Holiday - Discover your Ideal Space! Cozy retreat 1-bed, 1-bath unit at 5633 Golden Nugget Dr, Holiday, FL! (END UNIT) Annual/Unfurnished Rental. No Utilities Included. Discover your ideal space and be welcomed with an open layout with the living, dining, and kitchen areas all connected – perfect for cozy living. The backyard space allows for outdoor BBQ and the fresh

    JENNIFER VERBEL RENT SOLUTIONS

    5633 Golden Nugget Dr, Holiday, FL 34690
  • /2

    $250,000

    Sold Apr 20, 2026

    3525 Emory Dr, Holiday, FL 34691

    • 3 Beds
    • 2 Baths
    • 1,283 Sq Ft
    • Built 1969

    Last Sold Summary

    • 4% Above List Price
    • $195/SF
    • 9 Days On Market

    Current Estimated Value $249,448

    Last Listing Agent Robert Jones OFFERPAD BROKERAGE FL, LLC

    3525 Emory Dr, Holiday, FL 34691
    • /53

      Est $359,459

      Not Listed For Sale

      3341 Mela Ct, Holiday, FL 34691

      • 3 Beds
      • 2 Baths
      • 1,483 Sq Ft
      • Built 2017
      3341 Mela Ct, Holiday, FL 34691

      Last Sold Summary

      • 65 Days On Market

  • /40

    $142,900

    • 2 Beds
    • 2 Baths
    • 960 Sq Ft

    4809 Empress Ln, Holiday, FL 34690

    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

    Stella Wooster CITY BREEZE ACTION REALTY

    4809 Empress Ln, Holiday, FL 34690
  • /18

    $1,595 Per Month

    • 2 Beds
    • 2 Baths
    • 848 Sq Ft
    • House for Rent

    3516 Sheryl Hill Dr, Holiday, FL 34691

    Beautiful 2/2 with one car garage single family home for rent. Located in the desirable area of Beacon Square on a quiet road but close the main Moog Rd. which was recently re paved with side walk for your evening or morning walk. This home has fresh interior paint, granite counter tops, wood cabinet, newer AC with duct work and R38 insulation to keep your electric bill down while keep you cool.

    3516 Sheryl Hill Dr, Holiday, FL 34691
  • /2

    $129,000

    Sold Apr 10, 2026

    Unlisted Address

    • 4 Beds
    • 4 Baths
    • 1,140 Sq Ft
    • Built 1950

    Last Sold Summary

    • 5% Below List Price
    • $113/SF
    • 6 Days On Market

    Last Listing Agent Nicholas Colamarino CIRCUITOUS REALTY

    Unlisted Address
    • /53

      Not Listed For Sale

      3426 Tiki Dr, Holiday, FL 34691

      • 2 Beds
      • 1 Bath
      • 624 Sq Ft
      • Built 1974
      3426 Tiki Dr, Holiday, FL 34691

      Last Sold Summary

      • 203 Days On Market

  • /28

    $289,999

    • 3 Beds
    • 2.5 Baths
    • 1,440 Sq Ft

    3083 Victoria Inlet Dr, Holiday, FL 34691

    Skip the projects, skip the surprises, and step into a home that already feels dialed-in. Built in 2023, this 3-bedroom townhome delivers that crisp, like-new vibe—without the builder waitlist or the premium price tag. The main level has an easy, open flow from the living area into a kitchen designed for real everyday use. This one upgrades the standard package with stainless steel appliances, a

    Erica Antonakos QUICKSILVER REAL ESTATE GROUP

    3083 Victoria Inlet Dr, Holiday, FL 34691
  • /7

    $1,450 Per Month

    • 2 Beds
    • 1 Bath
    • 784 Sq Ft
    • Townhouse for Rent

    1551 Swordbill Dr, Holiday, FL 34690

    2BED/1BATH Duplex AVAILABLE NOW!This 2 bedroom, 1 bath duplex for rent in Holiday features tile flooring through out. The open concept and windows with plenty of natural lighting make it feel very spacious. The kitchen has ample cabinet space and an additional pantry for storage. Stackable washer and dryer connections

    Kevin Byrne VALENCIA REALTY,LLC

    1551 Swordbill Dr, Holiday, FL 34690
  • /2

    $394,995

    Sold Jul 01, 2025

    3873 Gainer Springs Ave, Holiday, FL 34690

    • 4 Beds
    • 2.5 Baths
    • 1,870 Sq Ft
    • Built 2020

    Last Sold Summary

    • 3% Above List Price
    • $211/SF
    • 162 Days On Market

    Last Listing Agent Michael Conlon DALTON WADE INC

    3873 Gainer Springs Ave, Holiday, FL 34690
    • /51

      Est $497,542

      Not Listed For Sale

      2450 Triggerfish Ct, Holiday, FL 34691

      • 4 Beds
      • 3 Baths
      • 2,658 Sq Ft
      • Built 2010
      2450 Triggerfish Ct, Holiday, FL 34691

      Last Sold Summary

      • 15 Days On Market

Showing Results 161 - 200, Page 5 of 18

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