Holiday, FL Homes

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  /58

  $180,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,320 Sq Ft

  2101 Hilo Dr, Holiday, FL 34691

  Under contract-accepting backup offers. Wow! What a well-maintained 2-bedroom, 2-bath home with carport and screened porch, located in the gated 55+ community of Lake Conley. All furniture and furnishings are optional. This inviting double-wide manufactured home offers strong curb appeal with neutral siding, a bank of bright double-pane windows, mature landscaping, paved driveway (2021), and a

  

  Jodi Avery

  KELLER WILLIAMS SOUTH TAMPA

  (727) 380-6830

  2101 Hilo Dr, Holiday, FL 34691
• Explore Holiday

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  /26

  $2,150 per month

  • 3 Beds
  • 2 Baths
  • 1,740 Sq Ft
  • House for Rent

  Unlisted Address

  Welcome to this beautifully maintained 3-bedroom, 2-bath home located in the desirable Gulfwinds Community in Holiday, Florida. Offering approximately 1,740 sq ft of living space, this spacious residence features an open and inviting floor plan with abundant natural light, high ceilings, and comfortable living areas perfect for everyday living and entertaining. The kitchen offers ample cabinetry,

  

  Gabriela Lopez

  HOME PRIME REALTY LLC

  (727) 382-3079

  Unlisted Address
• 

  

  /2

  $170,000 Sold Sep 23, 2025

  3136 Birkdale Dr, Holiday, FL 34690

  • 2 Beds
  • 2 Baths
  • 1,156 Sq Ft
  • Built 1982

  Last Sold Summary

  • 3% Below List Price
  • $147/SF
  • 33 Days On Market

  Last Listing Agent Stella Wooster CITY BREEZE ACTION REALTY

  3136 Birkdale Dr, Holiday, FL 34690
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  /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

  Last Listing Agent Magdalena Czech HORAN REALTY GROUP LLC
• 

  

  

  /87

  $575,000

  • 5 Beds
  • 3.5 Baths
  • 3,198 Sq Ft

  3238 Mela Ct, Holiday, FL 34691

  5 Bedroom, 3.5 Bath, 2 Story home located in the Gated Community of Vista Lakes, perfectly situated on an extra large pool size premium corner lot with fenced back yard and lighted gazebo overlooking a serene pond plus NO FLOOD INSURANCE. This gorgeous 2 story home boasts a wonderful floor plan with soaring ceilings and generous windows providing lots of natural light. On the first floor, you’ll

  

  Mary Kay Likly

  REALTY ONE GROUP ADVANTAGE

  (727) 606-8575

  3238 Mela Ct, Holiday, FL 34691
• 

  

  /13

  $1,100 per month

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

  5441 Oceanic Rd, Holiday, FL 34690

  UPDATED one bedroom one bath villa unit with 416 square foot carport in a triplex community just past the Pinellas/Pasco County line into Holiday. All tiled floors, wood kitchen and bath cabinets. Back door with access to the backyard area. Small covered area outside front door for a lawn chair or two across from the side yard. Directly off US 19 and travel to Grand Blvd, then north to Oceanic

  Colleen Tuttle

  RE/MAX REALTEC GROUP INC

  (727) 387-2545

  5441 Oceanic Rd, Holiday, FL 34690
• 

  /2

  $235,000 Sold Jun 20, 2025

  3445 Pinehurst Dr, Holiday, FL 34691

  • 3 Beds
  • 1 Bath
  • 1,014 Sq Ft
  • Built 1965

  Last Sold Summary

  • $232/SF
  • 4 Days On Market

  Current Estimated Value $223,851

  Last Listing Agent Josh Jacobs FUTURE HOME REALTY INC

  3445 Pinehurst Dr, Holiday, FL 34691
• 

  

  /43

  Not Listed For Sale

  3307 Chatford Dr, Holiday, FL 34690

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft
  • Built 1979

  3307 Chatford Dr, Holiday, FL 34690

  Last Sold Summary

  • $146/SF
  • 6 Days On Market

  Last Sold Price $122,960

  Last Listing Agent Diane Costello CHARLES RUTENBERG REALTY INC
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  /28

  $225,000 Pending

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft

  3625 Windham Dr, Holiday, FL 34691

  Under contract-accepting backup offers. NEW ROOF INSTALLED MARCH 2026, MOVE-IN READY | NO HOA | NO FLOOD INSURANCE REQUIRED. STOP SEARCHING! This impeccably updated 3-bedroom, 1-bathroom home in the heart of Holiday is the unicorn you’ve been waiting for. Enjoy the ultimate freedom of NO HOA and NO CDD fees, plus the massive savings of NO flood insurance required!Step inside to a bright, open

  

  Lilibeth Garcia

  LA ROSA REALTY, LLC

  (727) 617-3069

  3625 Windham Dr, Holiday, FL 34691
• 

  

  /16

  $1,150 per month

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

  4358 Tahitian Gardens Cir Unit H, Holiday, FL 34691

  JUST IN TIME FOR WINTER! This beautiful 1-bedroom lake view condo can be yours. Located in Tahitian Gardens, a beautifully maintained 55+ gated community. This open floor plan corner unit features tile and luxury vinyl flooring, granite counters in the kitchen and bath, stainless-steel range and microwave. Tahitian Gardens has many activities including shuffleboard, arts and crafts, a bicycling

  

  Michael McAuley

  COASTAL FLORIDA REAL ESTATE

  (727) 624-1776

  4358 Tahitian Gardens Cir Unit H, Holiday, FL 34691
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  /2

  $380,000 Sold Jun 26, 2025

  2749 Plantain Dr, Holiday, FL 34691

  • 4 Beds
  • 2 Baths
  • 1,819 Sq Ft
  • Built 2004

  Last Sold Summary

  • 8% Below List Price
  • $209/SF
  • 129 Days On Market

  Current Estimated Value $376,913

  Last Listing Agent Barbara Ann Grady, PA CHARLES RUTENBERG REALTY INC

  2749 Plantain Dr, Holiday, FL 34691
• 

  /2

  Not Listed For Sale

  3201 Nantucket Dr, Holiday, FL 34690

  • 2 Beds
  • 2 Baths
  • 768 Sq Ft
  • Built 1978

  3201 Nantucket Dr, Holiday, FL 34690

  Last Sold Summary

  • $166/SF
  • 31 Days On Market

  Last Sold Price $127,500

  Last Listing Agent Ashley Gillum Smith REAVES REAL ESTATE PROFESSIONALS LLC
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  /52

  $418,000

  • 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

  

  Christina Probeyahn

  COASTAL PROPERTIES GROUP INTERNATIONAL

  (727) 607-6761

  2817 Plantain Dr, Holiday, FL 34691
• 

  

  /20

  $1,550 per month

  • 2 Beds
  • 2 Baths
  • 1,018 Sq Ft
  • House for Rent

  3741 Kingsbury Dr, Holiday, FL 34691

  Welcome to this charming single-family home nestled in the desirable Beacon Square community. This delightful property features 2 bedrooms, 2 bathrooms, and a 1-car garage, offering comfortable living spaces for you and your family. As you step inside, you're greeted by a cozy family room adorned with a lovely fireplace, perfect for relaxing evenings with loved ones. The spacious bedrooms provide

  

  Antje Anderson

  COASTAL PROPERTIES GROUP INTERNATIONAL

  (727) 606-8030

  3741 Kingsbury Dr, Holiday, FL 34691
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  /2

  $257,500 Sold Apr 02, 2025

  5331 Skyland Dr, Holiday, FL 34690

  • 3 Beds
  • 2 Baths
  • 1,272 Sq Ft
  • Built 1971

  Last Sold Summary

  • 6% Below List Price
  • $202/SF
  • 148 Days On Market

  Current Estimated Value $261,876

  Last Listing Agent Cindy Greco EXP REALTY LLC

  5331 Skyland Dr, Holiday, FL 34690
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  /2

  Not Listed For Sale

  3214 Hampshire Dr, Holiday, FL 34690

  • 2 Beds
  • 2 Baths
  • 943 Sq Ft
  • Built 1974

  3214 Hampshire Dr, Holiday, FL 34690

  Last Sold Summary

  • $93/SF
  • 36 Days On Market

  Last Sold Price $87,500

  Last Listing Agent Stella Wooster CITY BREEZE ACTION REALTY
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  /53

  $219,900

  • 3 Beds
  • 1 Bath
  • 884 Sq Ft

  3426 Pinon Dr, Holiday, FL 34691

  One or more photo(s) has been virtually staged. Move In Ready in Holiday Lake Estates. Freshly painted w updated Kitchen and Bathroom, this home lives large. Two spacious bedrooms with large closets PLUS Bonus Room as Possible 3rd bedroom. As you enter you'll note that the tile flows seamlessly through all the main rooms and bedrooms- NO CARPET for easy maintenance. The kitchen has just been

  

  Tina Serfozo

  RE/MAX PREMIER GROUP

  (727) 739-2634

  3426 Pinon Dr, Holiday, FL 34691
• 

  

  /22

  $1,250 per month

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

  4348 Tahitian Gardens Cir Unit B, Holiday, FL 34691

  This beautiful turnkey, fully furnished, 1-bedroom condo can now be yours to enjoy. Located in Tahitian Gardens, a beautifully maintained 55+ GATED community. Updated throughout, featuring beautiful wood kitchen cabinets and stainless-steel appliances. Large plantation shutters for all windows complement the open floor plan. The living room includes an entertainment center with fireplace and TV.

  

  Michael McAuley

  COASTAL FLORIDA REAL ESTATE

  (727) 607-4443

  4348 Tahitian Gardens Cir Unit B, Holiday, FL 34691
• 

  /2

  $229,900 Sold Apr 14, 2025

  3403 Garfield Dr, Holiday, FL 34691

  • 2 Beds
  • 1 Bath
  • 816 Sq Ft
  • Built 1978

  Last Sold Summary

  • $282/SF
  • 4 Days On Market

  Current Estimated Value $221,586

  Last Listing Agent Wayne Gabriel RE/MAX PREMIER GROUP

  3403 Garfield Dr, Holiday, FL 34691
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  /2

  Not Listed For Sale

  3620 Kauna Point Dr, Holiday, FL 34691

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft
  • Built 1972

  3620 Kauna Point Dr, Holiday, FL 34691

  Last Sold Summary

  • $119/SF
  • 284 Days On Market

  Last Sold Price $80,000

  Last Listing Agent Diana Schlafley CHARLES RUTENBERG REALTY INC
• 

  

  /50

  $88,000

  • 2 Beds
  • 1 Bath
  • 784 Sq Ft

  3707 Tiki Dr, Holiday, FL 34691

  Tiki Village, a gated 55+ community where you own the land and enjoy affordable Florida living. This well-maintained community features a low HOA fee of only $400 a year.This furnished 2-bedroom, 1-bath home offers comfortable living with inviting outdoor spaces, including a beautiful paver drive and carport. Plus, a cement picnic table in the backyard.Inside, the home reflects pride of

  

  Randal Jenkins

  FLORIDA REAL ESTATE PARTNERS

  (727) 628-0864

  3707 Tiki Dr, Holiday, FL 34691
• 

  

  /32

  $1,500 per month

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft
  • Condo for Rent

  4337 Tahitian Gardens Cir Unit F, Holiday, FL 34691

  TURNKEY! Come see this stylishly updated, fully furnished, 2-bedroom, condo in the gated 55+ community of Tahitian Gardens. This exceptionally clean unit features granite counters, plentiful kitchen cabinets, dishwasher and an open floor plan. The master bedroom and living room have flat screen televisions. Ceiling fans in all rooms with both bedrooms having thermal windows for energy efficiency.

  

  Michael McAuley

  COASTAL FLORIDA REAL ESTATE

  (727) 607-5122

  4337 Tahitian Gardens Cir Unit F, Holiday, FL 34691
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  $21,900 Sold Jan 02, 2026

  4699 Continental Dr Unit 309, Holiday, FL 34690

  • 2 Beds
  • 1 Bath
  • Built 1984

  Last Sold Summary

  • 17 Days On Market

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

  4699 Continental Dr Unit 309, Holiday, FL 34690
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  /55

  Not Listed For Sale

  3101 Southport Dr, Holiday, FL 34690

  • 2 Beds
  • 2 Baths
  • 1,392 Sq Ft
  • Built 1980

  3101 Southport Dr, Holiday, FL 34690

  Last Sold Summary

  • $116/SF
  • 65 Days On Market

  Last Sold Price $161,500

  Last Listing Agent Ashley Gillum Smith REAVES REAL ESTATE PROFESSIONALS LLC
• 

  

  /41

  $195,000

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

  3850 Sablewood Dr, Holiday, FL 34691

  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 HOME OFFICE, HOBBY ROOM. This home has

  

  Gail Urban

  CENTURY 21 COASTAL ALLIANCE

  (727) 349-4875

  3850 Sablewood Dr, Holiday, FL 34691
• 

  

  /18

  $1,849 per month

  • 3 Beds
  • 2.5 Baths
  • 1,634 Sq Ft
  • House for Rent

  5172 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 $2018.90. That covers your base rent, $1849.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  5172 Forum Blvd, Holiday, FL 34690
• 

  /2

  $225,000 Sold Nov 25, 2025

  4841 Aegean Ave, Holiday, FL 34690

  • 3 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • Built 1965

  Last Sold Summary

  • 6% Below List Price
  • $223/SF
  • 9 Days On Market

  Current Estimated Value $226,891

  Last Listing Agent Doug Addeo COMMUNITY REALTY ASSOCIATES

  4841 Aegean Ave, Holiday, FL 34690
• 

  /2

  Est $244,383 Not Listed For Sale

  5119 Mitzi Ln, Holiday, FL 34690

  • 3 Beds
  • 2 Baths
  • 816 Sq Ft
  • Built 1968

  5119 Mitzi Ln, Holiday, FL 34690

  Last Sold Summary

  • 2% Below List Price
  • $305/SF
  • 34 Days On Market

  Last Sold Price $249,000

  Last Listing Agent Rosely Testino EXP REALTY LLC
• 

  

  /46

  $134,000

  • 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

  

  Randal Jenkins

  FLORIDA REAL ESTATE PARTNERS

  (727) 334-2609

  3229 Tiki Dr, Holiday, FL 34691
• 

  

  /20

  $2,300 per month

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

  2814 Jacob Crossing Ln, Holiday, FL 34691

  Desirable Jacobs Crossing Rental | Wi-Fi & Cable Included Welcome to 2814 Jacobs Crossing Lane, a well-maintained home located in the sought-after Jacobs Crossing community in Gulf Trace, Holiday. This property offers a functional two-story floorplan with comfortable living spaces, perfect for everyday living and entertaining. Enjoy stainless steel appliances in the kitchen with granite counters

  Cherie Kelly BHHS FLORIDA PROPERTIES GROUP

  2814 Jacob Crossing Ln, Holiday, FL 34691
• 

  /2

  $415,000 Sold Jun 02, 2025

  2510 Big Pine Dr, Holiday, FL 34691

  • 4 Beds
  • 2 Baths
  • 2,022 Sq Ft
  • Built 2003

  Last Sold Summary

  • 8% Below List Price
  • $205/SF
  • 147 Days On Market

  Current Estimated Value $407,839

  Last Listing Agent Ron Mastrodonato SANDPEAK REALTY

  2510 Big Pine Dr, Holiday, FL 34691
• 

  /2

  Est $355,752 Not Listed For Sale

  5404 Flora Ave, Holiday, FL 34690

  • 3 Beds
  • 2 Baths
  • 1,678 Sq Ft
  • Built 1969

  5404 Flora Ave, Holiday, FL 34690

  Last Sold Summary

  • 2% Below List Price
  • $215/SF
  • 164 Days On Market

  Last Sold Price $361,500

  Last Listing Agent Jessica Kruse FUTURE HOME REALTY INC
• 

  

  /31

  $104,900

  • 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

  

  Michael McAuley

  COASTAL FLORIDA REAL ESTATE

  (727) 295-0326

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

  

  /16

  $1,735 per month

  • 3 Beds
  • 2 Baths
  • 1,024 Sq Ft
  • House for Rent

  1103 Chelsea Ln, 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,

  1103 Chelsea Ln, Holiday, FL 34691
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  /2

  $104,000 Sold Jan 14, 2026

  3136 Buckner Ct, Holiday, FL 34690

  • 2 Beds
  • 2 Baths
  • 768 Sq Ft
  • Built 1978

  Last Sold Summary

  • 10% Below List Price
  • $135/SF
  • 254 Days On Market

  Last Listing Agent John Grey FI GREY & SON INC COMMERCIAL

  3136 Buckner Ct, Holiday, FL 34690
• 

  /2

  Est $263,767 Not Listed For Sale

  3214 Merita Dr, Holiday, FL 34691

  • 3 Beds
  • 2 Baths
  • 1,134 Sq Ft
  • Built 1970

  3214 Merita Dr, Holiday, FL 34691

  Last Sold Summary

  • 2% Below List Price
  • $237/SF
  • 7 Days On Market

  Last Sold Price $269,000

  Last Listing Agent Paul VonFeldt SUNSTAR REAL ESTATE LLC
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  /36

  $319,900

  • 3 Beds
  • 2 Baths
  • 1,102 Sq Ft

  1408 Jennings Dr, Holiday, FL 34690

  Beautifully RENOVATED 3-bedroom, 2-bath home located in Flood Zone X (no flood insurance required). Move-in ready with modern finishes and essential upgrades. Interior updates include new bathroom fixtures, granite countertops, kitchen appliances, new flooring throughout, fresh interior/exterior paint, new blinds, and dimmable lighting. Exterior enhancements include new front and back pagodas,

  

  Michael McAuley

  COASTAL FLORIDA REAL ESTATE

  (727) 361-9268

  1408 Jennings Dr, Holiday, FL 34690
• 

  

  /22

  $1,825 per month

  • 2 Beds
  • 1 Bath
  • 1,176 Sq Ft
  • House for Rent

  1050 Clairborne St, Holiday, FL 34690

  Beautifully updated 3 bedroom, 1 bath home with a 1 car garage, located in a convenient and desirable area near Pinellas. This home features elegant porcelain tile throughout, a modern kitchen with granite countertops and solid wood cabinets, and updated finishes in both the kitchen and bathroom. Enjoy a spacious living room and a separate dining area, perfect for entertaining. The fully fenced

  Maria Demellis FLORIDA LUXURY REALTY INC

  1050 Clairborne St, Holiday, FL 34690
• 

  /2

  $199,900 Sold Feb 06, 2026

  3326 Garfield Dr, Holiday, FL 34691

  • 3 Beds
  • 2 Baths
  • 1,308 Sq Ft
  • Built 1978

  Last Sold Summary

  • $153/SF
  • 55 Days On Market

  Current Estimated Value $199,582

  Last Listing Agent Jim Steele BHHS FLORIDA PROPERTIES GROUP

  3326 Garfield Dr, Holiday, FL 34691
• 

  /2

  Est $195,442 Not Listed For Sale

  5117 Cape Cod Dr, Holiday, FL 34690

  • 2 Beds
  • 1.5 Baths
  • 1,004 Sq Ft
  • Built 1970

  5117 Cape Cod Dr, Holiday, FL 34690

  Last Sold Summary

  • 3% Above List Price
  • $189/SF
  • 8 Days On Market

  Last Sold Price $190,000

  Last Listing Agent Christa Setzer SIGNATURE REALTY ASSOCIATES

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