18,345

Holiday, FL Homes

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  • /52

    $415,000

    • 3 Beds
    • 2 Baths
    • 1,683 Sq Ft

    2817 Plantain Dr, Holiday, FL 34691

    Welcome home to 2817 Plantain Dr! This beautifully maintained home, located inside the gated 55+ Key Vista Villas community, is perfectly situated between two preservation areas teeming with awe-inspiring Florida wildlife. Inside, the home shows like a model with soaring ceilings, crown molding, wide-plank luxury vinyl flooring, and an abundance of natural light throughout. The open layout

    Agent Photo

    Christina Probeyahn

    COASTAL PROPERTIES GROUP INTERNATIONAL

    (727) 607-6761

    2817 Plantain Dr, Holiday, FL 34691
  • /13

    $1,640 Per Month

    • 2 Beds
    • 2 Baths
    • 1,226 Sq Ft
    • House for Rent

    3104 Primrose Dr, Holiday, FL 34691

    Property Id: 1861136This rental is located in Holiday Lake Estates and features two bedrooms, two bathrooms, screned-in lanai, separate den with fireplace, spacious yard, and single car attached garage. First month's rent and security deposit of one month required for move-in. Pets allowed contingent upon number, size, and breed. We are seeking applicants who can verify employment and

    (562) 217-6489

    3104 Primrose Dr, Holiday, FL 34691
  • 4699 Continental Dr Unit 144, Holiday, FL 34690

    $14,900 Sold Sep 08, 2025

    4699 Continental Dr Unit 144, Holiday, FL 34690

    • 1 Bed
    • 1 Bath
    • Built 1981

    Last Sold Summary

    • 17% Below List Price
    • 109 Days On Market

    Last Listing Agent Lane Parks Gulf Breeze Mobile Home Sales, LLC

    4699 Continental Dr Unit 144, Holiday, FL 34690
    • /3

      Not Listed For Sale

      4750 Betsy Dr, Holiday, FL 34690

      • 2 Beds
      • 2 Baths
      • 1,276 Sq Ft
      • Built 1980
      4750 Betsy Dr, Holiday, FL 34690

      Last Sold Summary

      • $121/SF
      • Last Sold Price $155,000
      • May 12, 2023

      Last Listing Agent Stellar Non-Member Agent FL_MFRMLS

  • /41

    $195,000 Pending

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

    3850 Sablewood Dr, Holiday, FL 34691

    Under contract-accepting backup offers. NEW LOW PRICE! NOT IN A FLOOD ZONE. Great starter home! This is a versatile, mid-size home with strong structural features and energy upgrades. Spacious 2 bedroom, 2 bath, boasts nearly 1400 sq ft.. This home is priced to reflect age of systems and possible cosmetic updates. EXPLORE THE POSSIBILITIES WITH THE 2 FLEXIBLE SPACES-CONVERT TO A 3RD BEDROOM OR

    Agent Photo

    Gail Urban

    CENTURY 21 COASTAL ALLIANCE

    (727) 337-7049

    3850 Sablewood Dr, Holiday, FL 34691
  • /5

    $1,999 Per Month

    • 3 Beds
    • 2 Baths
    • 1,625 Sq Ft
    • House for Rent

    5809 Elena Dr, Holiday, FL 34690

    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 $2143.90. That covers your base rent, $1999.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    (727) 513-2392

    5809 Elena Dr, Holiday, FL 34690
  • /2

    $320,000 Sold Oct 17, 2025

    2648 Grand Blvd, Holiday, FL 34690

    • Land
    • 5.13 Acres
    • $62,378 per Acre

    Last Sold Summary

    • 47% Below List Price
    • 96 Days On Market

    Current Estimated Value $470,143

    Last Listing Agent Robert Moore INTERNATIONAL TOP AGENTS REALTY

    2648 Grand Blvd, Holiday, FL 34690
    • /2

      Not Listed For Sale

      2443 Santiago Dr, Holiday, FL 34690

      • 2 Beds
      • 1 Bath
      • 672 Sq Ft
      • Built 1971
      2443 Santiago Dr, Holiday, FL 34690

      Last Sold Summary

      • $112/SF
      • 110 Days On Market
      • Last Sold Price $75,000
      • Mar 20, 2025

      Last Listing Agent Magdalena Czech HORAN REALTY GROUP LLC

  • /21

    $294,000

    • 3 Beds
    • 2 Baths
    • 1,308 Sq Ft

    5701 Canosa Dr, Holiday, FL 34690

    Welcome to this beautifully renovated 3-bedroom, 2-bath single-family home in Holiday! This move-in-ready property features a bright open floor plan with stylish vinyl laminate flooring throughout, creating a modern and inviting living space. The fully updated kitchen is a true highlight, showcasing elegant quartz countertops, brand-new appliances, and plenty of space for cooking and

    Agent Photo

    Miguel Davila, PA

    PEOPLE'S CHOICE REALTY SVC LLC

    (727) 746-5095

    5701 Canosa Dr, Holiday, FL 34690
  • /16

    $1,585 Per Month

    • 3 Beds
    • 1 Bath
    • 1,104 Sq Ft
    • House for Rent

    3916 Darlington Rd, Holiday, FL 34691

    Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with functionality in mind. Enjoy the storage space found in the kitchen and closets as well as the spacious living areas and natural light throughout. Enjoy outdoor living in your yard, perfect for gathering, relaxing, or gardening!Take advantage of the incredible location,

    (727) 607-2837

    3916 Darlington Rd, Holiday, FL 34691
  • /2

    $450,000 Sold Jul 03, 2025

    2924 Windridge Dr, Holiday, FL 34691

    • 3 Beds
    • 2 Baths
    • 2,069 Sq Ft
    • Built 1986

    Last Sold Summary

    • 2% Below List Price
    • $217/SF
    • 32 Days On Market

    Current Estimated Value $445,701

    Last Listing Agent Cortney Bain CHARLES RUTENBERG REALTY INC

    2924 Windridge Dr, Holiday, FL 34691
    • /45

      Est $536,348 Not Listed For Sale

      3196 Gina Ct, Holiday, FL 34691

      • 4 Beds
      • 4 Baths
      • 3,169 Sq Ft
      • Built 2018
      3196 Gina Ct, Holiday, FL 34691

      Last Sold Summary

      • 6% Below List Price
      • $180/SF
      • 71 Days On Market
      • Last Sold Price $570,000
      • Sep 15, 2023

      Last Listing Agent Susan Reynolds ARCHER REALTY

  • /46

    $125,000

    • 2 Beds
    • 2 Baths
    • 1,344 Sq Ft

    3229 Tiki Dr, Holiday, FL 34691

    Tiki Village. NON-FLOOD ZONE. Only $400 a year. Gated. 55 and Older. You OWN THE LAND. Massive front porch 9 feet by 19 feet. This spacious home stands out as one of the community’s largest units at 1344 Sq Feet. Home has an oversized living room, expansive dining area and generously sized kitchen, also features a screened-in side porch and a carport. The hall bathroom features a high-end walk-in

    Agent Photo

    Randal Jenkins

    FLORIDA REAL ESTATE PARTNERS

    (727) 334-2609

    3229 Tiki Dr, Holiday, FL 34691
  • /20

    $1,895 Per Month

    • 3 Beds
    • 2 Baths
    • 1,160 Sq Ft
    • House for Rent

    3423 Garfield 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 $2039.90. That covers your base rent, $1895.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    (727) 617-3254

    3423 Garfield Dr, Holiday, FL 34691
  • /2

    $239,000 Sold May 30, 2025

    2532 Fentress Place, Holiday, FL 34691

    • 2 Beds
    • 2 Baths
    • 1,231 Sq Ft
    • Built 1971

    Last Sold Summary

    • $194/SF
    • 2 Days On Market

    Current Estimated Value $239,371

    Last Listing Agent Julie Barnhardt BHHS FLORIDA PROPERTIES GROUP

    2532 Fentress Place, Holiday, FL 34691
    • /2

      Not Listed For Sale

      3420 Hampshire Dr, Holiday, FL 34690

      • 2 Beds
      • 2 Baths
      • 983 Sq Ft
      • Built 1972
      3420 Hampshire Dr, Holiday, FL 34690

      Last Sold Summary

      • $132/SF
      • 32 Days On Market
      • Last Sold Price $129,500
      • Apr 03, 2025

      Last Listing Agent Sophia Arcese MCCULLOUGH & ASSOC REALTY INC

  • /31

    $99,900

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft

    4349 Tahitian Gardens Cir Unit G, Holiday, FL 34691

    FRESHLY PAINTED! NOT IN A FLOOD ZONE! Discover this bright and cheerful 1-bedroom condo in Tahitian Gardens, a well-kept GATED 55+ community. The expansive floor-to-ceiling windows in the living room create a luminous and open ambiance. This unit boasts modern flooring, an updated electrical panel, a new 50-gallon water heater (2022), ample storage with a large utility closet, and ceiling fans in

    Agent Photo

    Michael McAuley

    COASTAL FLORIDA REAL ESTATE

    (727) 617-3215

    4349 Tahitian Gardens Cir Unit G, Holiday, FL 34691
  • /17

    $1,695 Per Month

    • 2 Beds
    • 2 Baths
    • 1,042 Sq Ft
    • House for Rent

    3535 Devonshire Dr, Holiday, FL 34691

    This home is exclusively offered by Brandywine Homes USA on a first-come, first-approved basis until the lease is signed and the security deposit is paid. Rental Qualifications: Rental Fees: Security Deposit: Varies based on credit, with a standard deposit equal to 1 month's rent. Security Deposit Alternatives available - $150 fee (subject to approval).

    (727) 628-1148

    3535 Devonshire Dr, Holiday, FL 34691
  • /2

    $271,000 Sold May 07, 2026

    2440 Pinetta Ct, Holiday, FL 34691

    • 3 Beds
    • 2 Baths
    • 1,360 Sq Ft
    • Built 1988

    Last Sold Summary

    • $199/SF
    • 4 Days On Market

    Current Estimated Value $278,592

    Last Listing Agent Blake Keathley EVERYSTATE INC.

    2440 Pinetta Ct, Holiday, FL 34691
    • /21

      Not Listed For Sale

      1902 Shady Cove Dr, Holiday, FL 34691

      • 2 Beds
      • 2 Baths
      • 798 Sq Ft
      • Built 1962
      1902 Shady Cove Dr, Holiday, FL 34691

      Last Sold Summary

      • $150/SF
      • 103 Days On Market
      • Last Sold Price $120,000
      • Apr 02, 2024

      Last Listing Agent Jackie Little KELLER WILLIAMS REALTY- PALM H

  • /23

    $225,000 Pending

    • 2 Beds
    • 1.5 Baths
    • 1,108 Sq Ft

    5412 Golden Nugget Dr, Holiday, FL 34690

    Under contract-accepting backup offers. Beautiful 2-bedroom, 1.5-bathroom home in the heart of Holiday, featuring new windows, a large fenced yard, a screened patio, and fresh remodeling throughout, all in a fantastic location close to beaches, restaurants, and shopping. You must see this one before it’s gone. The property has no flooding history and is not in a flood zone, offering peace of mind

    Agent Photo

    Anita McCracken P.A.

    F I GREY & SON RESIDENTIAL

    (727) 261-2398

    5412 Golden Nugget Dr, Holiday, FL 34690
  • /16

    $2,050 Per Month

    • 3 Beds
    • 2 Baths
    • 1,854 Sq Ft
    • House for Rent

    2026 Tumbleweed Dr, Holiday, FL 34690

    Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with functionality in mind. Enjoy the storage space found in the kitchen and closets as well as the spacious living areas and natural light throughout. Enjoy outdoor living in your yard, perfect for gathering, relaxing, or gardening!Take advantage of the incredible location,

    (727) 513-1656

    2026 Tumbleweed Dr, Holiday, FL 34690
  • /24

    $223,000 Sold May 14, 2025

    1446 Normandy Blvd, Holiday, FL 34691

    • 2 Beds
    • 1.5 Baths
    • 980 Sq Ft
    • Built 1970

    Last Sold Summary

    • 5% Below List Price
    • $228/SF
    • 1 Day On Market

    Current Estimated Value $213,147

    Last Listing Agent Zerah Cruz REAL BROKER, LLC

    1446 Normandy Blvd, Holiday, FL 34691
    • /20

      Not Listed For Sale

      2017 Kepner Dr, Holiday, FL 34691

      • 2 Beds
      • 1 Bath
      • 800 Sq Ft
      • Built 1962
      2017 Kepner Dr, Holiday, FL 34691

      Last Sold Summary

      • $119/SF
      • 52 Days On Market
      • Last Sold Price $95,000
      • Jun 07, 2023

      Last Listing Agent Jennifer Harper TROPIC SHORES REALTY LLC

  • /42

    $174,900

    • 2 Beds
    • 1.5 Baths
    • 842 Sq Ft

    4352 Tahitian Gardens Cir Unit M, Holiday, FL 34691

    OWNER FINANCING AVAILABLE! Come see this IMMACULATE, WATERFRONT, 2-bedroom, bath and a half townhouse in the GATED 55+ community of Tahitian Gardens. This updated townhouse has gorgeous WATER VIEWS and the largest floorplan in the community. Freshly painted with numerous updates! The spacious living and dining area feature an abundance of natural light from the oversized living room windows which

    Agent Photo

    Michael McAuley

    COASTAL FLORIDA REAL ESTATE

    (727) 310-2608

    4352 Tahitian Gardens Cir Unit M, Holiday, FL 34691
  • /14

    $1,749 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,541 Sq Ft
    • House for Rent

    5155 Forum Blvd, Holiday, FL 34690

    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 $1918.90. That covers your base rent, $1749.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    (727) 617-3194

    5155 Forum Blvd, Holiday, FL 34690
  • /2

    $280,000 Sold Sep 11, 2025

    Unlisted Address

    • 2 Beds
    • 2 Baths
    • 1,274 Sq Ft
    • Built 1970

    Last Sold Summary

    • $220/SF
    • 11 Days On Market

    Current Estimated Value $263,178

    Last Listing Agent Michael Constantine RE/MAX ALLIANCE GROUP

    Unlisted Address
    • /99

      Est $537,947 Not Listed For Sale

      3212 Gina Ct, Holiday, FL 34691

      • 4 Beds
      • 3.5 Baths
      • 2,880 Sq Ft
      • Built 2017
      3212 Gina Ct, Holiday, FL 34691

      Last Sold Summary

      • 4% Below List Price
      • $194/SF
      • 10 Days On Market
      • Last Sold Price $560,000
      • Jul 18, 2023

      Last Listing Agent Katrina Madewell REAL BROKER, LLC

  • /31

    $139,900 Pending

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft

    4312 Tahitian Gardens Cir Unit E, Holiday, FL 34691

    Experience the tranquility of condominium living with serene water views at your doorstep. This turnkey two-bedroom condo is located in Tahitian Gardens, a fully gated, active 55+ community. This corner unit is offered fully furnished and boasts significant upgrades including an open floor plan with tile flooring throughout. Large floor to ceiling living room windows. An updated bathroom which

    Agent Photo

    Michael McAuley

    COASTAL FLORIDA REAL ESTATE

    (727) 761-4257

    4312 Tahitian Gardens Cir Unit E, Holiday, FL 34691
  • /19

    $1,650 Per Month

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

    2509 Sweetwood Dr, Holiday, FL 34690

    Property Id: 2148271Welcome to your next home at 2509 Sweetwood Dr, Holiday, FL—a well-maintained 2-bedroom, 1-bathroom single-family residence offering comfort, functionality, and a flexible layout perfect for everyday living.Step inside to find spacious living and dining areas filled with natural light, creating an inviting space for both relaxing and entertaining. Both bedrooms

    (727) 607-4848

    2509 Sweetwood Dr, Holiday, FL 34690
  • /2

    $150,000 Sold Jul 14, 2025

    3214 Pinon Dr, Holiday, FL 34691

    • 2 Beds
    • 1 Bath
    • 792 Sq Ft
    • Built 1973

    Last Sold Summary

    • 25% Below List Price
    • $189/SF
    • 48 Days On Market

    Current Estimated Value $157,843

    Last Listing Agent Eric Jenkins, PA KELLER WILLIAMS REALTY- PALM H

    3214 Pinon Dr, Holiday, FL 34691
    • /27

      Est $352,585 Not Listed For Sale

      2200 Parrot Fish Dr, Holiday, FL 34691

      • 3 Beds
      • 2 Baths
      • 1,740 Sq Ft
      • Built 2013
      2200 Parrot Fish Dr, Holiday, FL 34691

      Last Sold Summary

      • 12% Below List Price
      • $230/SF
      • 123 Days On Market
      • Last Sold Price $400,000
      • Feb 16, 2024

      Last Listing Agent Michael Constantine RE/MAX

  • /30

    $124,900

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft

    4312 Tahitian Gardens Cir Unit A, Holiday, FL 34691

    TURN-KEY, CORNER UNIT now available! Discover Tahitian Gardens, an exclusive 55+ gated community featuring a heated pool, clubhouse, and recreation center. This two-bedroom unit boasts a bright, open floor plan with tile floors in the kitchen, living room, hall and bath. Enjoy the convenience of an in-unit washer and dryer. A private parking space is conveniently located just outside the unit.

    Agent Photo

    Michael McAuley

    COASTAL FLORIDA REAL ESTATE

    (727) 855-8709

    4312 Tahitian Gardens Cir Unit A, Holiday, FL 34691
  • /20

    $1,850 Per Month

    • 2 Beds
    • 1 Bath
    • 1,052 Sq Ft
    • House for Rent

    3624 Oakhurst Dr, Holiday, FL 34691

    Property Id: 2148295Welcome to this beautifully updated 2-bedroom, 2-bath home offering modern comfort, flexible living, and the ideal Florida lifestyle. Inside, you'll find updated flooring throughout, a refreshed kitchen with contemporary finishes, and renovated bathrooms that bring a clean, modern feel to the home.A versatile flex space provides the perfect bonus area ideal for

    (941) 206-7721

    3624 Oakhurst Dr, Holiday, FL 34691
  • /2

    $290,000 Sold Feb 02, 2026

    3103 Muir St, Holiday, FL 34691

    • 3 Beds
    • 2 Baths
    • 1,368 Sq Ft
    • Built 2003

    Last Sold Summary

    • 9% Below List Price
    • $212/SF
    • 38 Days On Market

    Current Estimated Value $291,926

    Last Listing Agent Jesus Quique Van Der Henst KELLER WILLIAMS REALTY- PALM H

    3103 Muir St, Holiday, FL 34691
    • /26

      Not Listed For Sale

      1936 Orange Dr, Holiday, FL 34691

      • 3 Beds
      • 2 Baths
      • 1,806 Sq Ft
      • Built 1956
      1936 Orange Dr, Holiday, FL 34691

      Last Sold Summary

      • $121/SF
      • 63 Days On Market
      • Last Sold Price $218,000
      • Sep 14, 2023

      Last Listing Agent Nicholas Vavoulis RE/MAX

  • /28

    $299,000 Pending

    • 2 Beds
    • 2 Baths
    • 1,334 Sq Ft

    3228 Rock Valley Dr, Holiday, FL 34691

    Welcome to this charming two bedroom, two bath home with a spacious Florida room that offers beautiful water views. The semi-open floor plan features updated kitchen counters, and fresh paint, along with new flooring installed after last year’s storms. Enjoy the serene water view complemented by a mature tree in the backyard, perfect for fishing and budget friendly lifestyle. The home has been

    Agent Photo

    Guillermina Rickey

    ENGEL & VOLKERS BELLEAIR

    (727) 761-7551

    3228 Rock Valley Dr, Holiday, FL 34691
  • /20

    $1,045 Per Month

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

    2133 Melody Dr, Holiday, FL 34691

    Step into this single-family home featuring wood plank floors. Equipped with modern amenities, this residence is ready to welcome you.- Electric range and refrigerator included- Off-street parking available- Heat pump and Ceiling fans- Relaxing patio spaceNestled in a convenient location, enjoy easy access to local shops and dining options.1 Gig internet

    (205) 325-3380

    2133 Melody Dr, Holiday, FL 34691
  • /2

    $330,000 Sold Jun 27, 2025

    6321 Staunton Dr, Holiday, FL 34690

    • 2 Beds
    • 2 Baths
    • 1,689 Sq Ft
    • Built 1985

    Last Sold Summary

    • 7% Below List Price
    • $195/SF
    • 159 Days On Market

    Current Estimated Value $329,368

    Last Listing Agent Melissa Hoglund COLDWELL BANKER REALTY

    6321 Staunton Dr, Holiday, FL 34690
    • /2

      Not Listed For Sale

      3303 Hampshire Dr, Holiday, FL 34690

      • 2 Beds
      • 1 Bath
      • 672 Sq Ft
      • Built 1973
      3303 Hampshire Dr, Holiday, FL 34690

      Last Sold Summary

      • $101/SF
      • 102 Days On Market
      • Last Sold Price $68,000
      • Feb 01, 2025

      Last Listing Agent Stella Wooster CITY BREEZE ACTION REALTY

Showing Results 41 - 80, Page 2 of 18

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