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Holiday, FL 55+ active adult communities & homes for sale

Living in Holiday

Holiday is a community located along the Gulf coast of Florida, in the Tampa metropolitan area. Surrounded by beaches and boardwalks, Holiday has a tropical atmosphere.…

Holiday is a community located along the Gulf coast of Florida, in the Tampa metropolitan area. Surrounded by beaches and boardwalks, Holiday has a tropical atmosphere. Additionally, the cost of living in Holiday is affordable and the weather throughout the year is pleasant. The weather, cost of living and beautiful scenery all combine to make Holiday 55+ communities popular with homebuyers.

Climate & Geography

The climate in Florida is generally characterized as humid subtropical. Summer temperatures in Holiday may reach temperatures in the high 80s and low 90s while winter temperatures may fall to the low 50s. Holiday gets heavy rains accumulating 51 inches of rain on average, per year.

Recreation, Culture & Entertainment

Some of the top attractions in Holiday include Anclote River Park, Key Vista Nature Park, Anclote Gulf Park, Absolute Florida Flats Fishing, Bottoms Up Fishing Excursions, Seal in the Sun Charters, Captain Dustin Fishing Charters, and Anclote Village Marina.

Residents enjoy miles of tropical beaches along the coast, and can drive to the city of Tampa in less than an hour to enjoy all of the big city amenities on offer there.

Cost of Living & Taxes

The cost of living in Holiday is notably lower than the state and national averages. Housing costs are very low and other factors like health care, grocery, utilities, and transportation are similar to the national averages.

Florida does not have a state income tax, therefore retirement income does not get additional state tax. Furthermore, qualifying residents over the age of 65 may request a homestead exemption to offset the cost of property taxes. The tax friendly regulations and lower cost of living are helpful to Holiday 55+ community residents on a budget.

Health Care

Although there are no hospitals in Holiday, there are a number of health care providers in the surrounding area that are rated high performing by U.S. News. The Medical Center of Trinity in Trinity and AdventHealth North Pinellas in Lake Tarpon are both less than 10 miles away. Other high performing hospitals close to Holiday include Mease Countryside Hospital, Regional Medical Center Bayonet Point, Morton Plant hospital, and Largo Medical Center.

Frequently Asked Questions


28 communities near Holiday

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5 rating (1 reviews) Highland Lakes on Lake Ta...
$100ks - $400ks
Highland Lakes on Lake Ta..., Palm Harbor, FL
Resale Only | 55+ age-restricted | Built 1977 - 1989 | 2,454 homes
5 rating (1 reviews) Timber Oaks
<$100k - $200ks
Timber Oaks, Port Richey, FL
Resale Only | 55+ age-restricted | Built 1973 - 1997 | 1,000 homes
Heritage Lake
$100ks - $200ks
Heritage Lake, New Port Richey, FL
Resale Only | 55+ age-restricted | Built 1981 - 1994 | 932 homes
4.7 rating (13 reviews) Heritage Springs
$200ks - $500ks
Heritage Springs, Trinity, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,337 homes
3.5 rating (2 reviews) Timber Greens
$200ks - $300ks
Timber Greens, New Port Richey, FL
Resale Only | 55+ age-restricted | Built 1994 - 2004 | 783 homes
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Summertree
$200ks - $300ks
Summertree, New Port Richey, FL
Resale Only | 55+ age-restricted | Built 1974 - 2015 | 800 homes
Heather Lake Condominiums
$100ks
Heather Lake Condominiums, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1972 - 1978 | 200 homes
2 rating (1 reviews) Beacon Lakes
$100ks
Beacon Lakes, New Port Richey, FL
Resale Only | 55+ age-restricted | Built 1975 - 1982 | 210 homes
5 rating (1 reviews) Village on the Green
$100ks - $200ks
Village on the Green, Clearwater, FL
Resale Only | 55+ age-restricted | Built 1978 - 1981 | 448 homes
Edgewater Arms
$400ks - $600ks
Edgewater Arms, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1970 - 1974 | 209 homes
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
3.3 rating (3 reviews) Royal Stewart Arms
$100ks - $300ks
Royal Stewart Arms, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1968 - 1975 | 449 homes
Victoria Lakes
$800ks - $1Ms
Victoria Lakes, Odessa, FL
New Construction | Age-targeted | Built 2025 - present | 166 homes
5 rating (2 reviews) Pine Ridge at Palm Harbor
$100ks - $200ks
Pine Ridge at Palm Harbor, Palm Harbor, FL
Resale Only | 55+ age-restricted | Built 1983 - 1983 | 264 homes
Esplanade at Starkey Ranc...
$300ks - $700ks
Esplanade at Starkey Ranc..., Odessa, FL
Resale Only | Age-targeted | Built 2016 - 2022 | 517 homes
Green Dolphin
$100ks
Green Dolphin, Tarpon Springs, FL
Resale Only | 55+ age-restricted | Built 1974 - 1990 | 315 homes
Imperial Pines Condominiu...
$100ks - $200ks
Imperial Pines Condominiu..., Clearwater, FL
Resale Only | 55+ age-restricted | Built 1985 - 1985 | 181 homes
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Patrician Oaks
$100ks
Patrician Oaks, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1975 - 1982 | 120 homes
Briar Patch
$100ks
Briar Patch, New Port Richey, FL
Resale Only | 55+ age-restricted | Built 1986 - 1993 | 198 homes
Pinehurst Village
$100ks
Pinehurst Village, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1973 - 1976 | 240 homes
Anchorage
$200ks - $300ks
Anchorage, Palm Harbor, FL
Resale Only | 55+ age-restricted | Built 1972 - 1979 | 279 homes
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Key Vista Villas
$300ks
Key Vista Villas, Holiday, FL
Resale Only | 55+ age-restricted | Built 2001 - 2005 | 170 homes
Scotsdale Cluster Condomi...
$200ks
Scotsdale Cluster Condomi..., Dunedin, FL
Resale Only | 55+ age-restricted | Built 1980 - 1983 | 148 homes
Heather Ridge
$100ks - $200ks
Heather Ridge, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1978 - 1987 | 273 homes
Linkside Village
$200ks
Linkside Village, Port Richey, FL
Resale Only | 55+ age-restricted | Built 1981 - 1985 | 100 homes
Heather Hills Villas
$100ks
Heather Hills Villas, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1971 - 1976 | 64 homes
Country Oaks
$100ks
Country Oaks, Hudson, FL
Resale Only | 55+ age-restricted | Built 1981 - 1986 | 42 homes
New Port Corners
$200ks - $500ks
New Port Corners, New Port Richey, FL
New Construction | 55+ age-restricted | Built 2025 - present
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Soleta at Starkey Ranch
$500ks - $600ks
Soleta at Starkey Ranch, Odessa, FL
New Construction | Age-targeted | Built 2023 - present | 139 homes
Village on the Green 2543 ROYAL PINES CIR 17K, CLEARWATER, FL..., Clearwater, FL 33763
$252,500

2 beds

|

2 baths

|

1,030 sq ft

|

Condo

2543 ROYAL PINES CIR 17K, CLEARWATER, FL...
Heritage Lake 4903 LEYTE CT 67, NEW PORT RICHEY, FL, 3..., New Port Richey, FL 34655
$169,900

2 beds

|

2 baths

|

1,135 sq ft

|

Condo

4903 LEYTE CT 67, NEW PORT RICHEY, FL, 3...
Community: Heritage Lake
New Highland Lakes on Lake Tarpon 3444 CARMICHAEL ST, PALM HARBOR, FL, 346..., Palm Harbor, FL 34684
$429,000

2 beds

|

2 baths

|

1,460 sq ft

|

House

3444 CARMICHAEL ST, PALM HARBOR, FL, 346...
New Summertree 11829 IVYWOOD PL, NEW PORT RICHEY, FL, 3..., New Port Richey, FL 34654
$249,000

3 beds

|

2 baths

|

1,632 sq ft

|

House

11829 IVYWOOD PL, NEW PORT RICHEY, FL, 3...
Community: Summertree
New Heritage Lake 9336 CAPE CHARLES AVE, NEW PORT RICHEY, ..., New Port Richey, FL 34655
$285,000

2 beds

|

2 baths

|

1,342 sq ft

|

House

9336 CAPE CHARLES AVE, NEW PORT RICHEY, ...
Community: Heritage Lake
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
New Highland Lakes on Lake Tarpon 1109 TARTAN DR B, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$279,000

2 beds

|

2 baths

|

1,080 sq ft

|

Villa

1109 TARTAN DR B, PALM HARBOR, FL, 34684
New Highland Lakes on Lake Tarpon 1619 WHITHORN PL B, PALM HARBOR, FL, 346..., Palm Harbor, FL 34684
$249,000

2 beds

|

2 baths

|

1,000 sq ft

|

Villa

1619 WHITHORN PL B, PALM HARBOR, FL, 346...
New Heritage Lake 4620 TIBURON DR, NEW PORT RICHEY, FL, 34..., New Port Richey, FL 34655
$282,000

2 beds

|

2 baths

|

1,268 sq ft

|

House

4620 TIBURON DR, NEW PORT RICHEY, FL, 34...
Community: Heritage Lake
New Timber Oaks 8220 SEVEN OAKS CT 5, PORT RICHEY, FL, 3..., Port Richey, FL 34668
$121,000

2 beds

|

2 baths

|

954 sq ft

|

Condo

8220 SEVEN OAKS CT 5, PORT RICHEY, FL, 3...
Community: Timber Oaks
New Highland Lakes on Lake Tarpon 1681 MACDONNELL CT, PALM HARBOR, FL, 346..., Palm Harbor, FL 34684
$435,500

2 beds

|

2 baths

|

1,879 sq ft

|

House

1681 MACDONNELL CT, PALM HARBOR, FL, 346...
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
New
Cindy Certified
1520 SAN MATEO DR, DUNEDIN, FL, 34698, Dunedin, FL 34698
$999,900

4 beds

|

2 baths

|

2,328 sq ft

|

House

1520 SAN MATEO DR, DUNEDIN, FL, 34698
New Edgewater Arms 622 EDGEWATER DR 721, DUNEDIN, FL, 34698, Dunedin, FL 34698
$899,000

3 beds

|

2 baths

|

2,060 sq ft

|

Condo

622 EDGEWATER DR 721, DUNEDIN, FL, 34698
Community: Edgewater Arms
New Timber Oaks 11508 ORLEANS LN, PORT RICHEY, FL, 34668, Port Richey, FL 34668
$175,000

2 beds

|

2 baths

|

1,395 sq ft

|

Villa

11508 ORLEANS LN, PORT RICHEY, FL, 34668
Community: Timber Oaks
New Heritage Lake 9601 NOBLE CT, NEW PORT RICHEY, FL, 3465..., New Port Richey, FL 34655
$320,000

2 beds

|

2 baths

|

1,646 sq ft

|

House

9601 NOBLE CT, NEW PORT RICHEY, FL, 3465...
Community: Heritage Lake
New Royal Stewart Arms 7 DUNOON PL 104, DUNEDIN, FL, 34698, Dunedin, FL 34698
$299,900

2 beds

|

2 baths

|

1,141 sq ft

|

Condo

7 DUNOON PL 104, DUNEDIN, FL, 34698
Community: Royal Stewart Arms
New Key Vista Villas 2939 WOOD POINTE DR, HOLIDAY, FL, 34691, Holiday, FL 34691
$318,000

2 beds

|

2 baths

|

1,280 sq ft

|

House

2939 WOOD POINTE DR, HOLIDAY, FL, 34691
Community: Key Vista Villas
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
New Heather Lake Condominiums 936 VIRGINIA ST 306, DUNEDIN, FL, 34698, Dunedin, FL 34698
$169,000

2 beds

|

2 baths

|

927 sq ft

|

Condo

936 VIRGINIA ST 306, DUNEDIN, FL, 34698
Highland Lakes on Lake Tarpon 3280 SKENE TER, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$510,000

3 beds

|

2 baths

|

1,863 sq ft

|

House

3280 SKENE TER, PALM HARBOR, FL, 34684
Heritage Springs 1213 FLORA VISTA ST, TRINITY, FL, 34655, Trinity, FL 34655
$339,900

2 beds

|

2 baths

|

1,535 sq ft

|

Villa

1213 FLORA VISTA ST, TRINITY, FL, 34655
Community: Heritage Springs
Cindy Certified
200 MAIN ST 202, DUNEDIN, FL, 34698, Dunedin, FL 34698
$780,000

2 beds

|

2 baths

|

1,426 sq ft

|

Condo

200 MAIN ST 202, DUNEDIN, FL, 34698
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Highland Lakes on Lake Tarpon 1382 GLENGARRY DR, PALM HARBOR, FL, 3468..., Palm Harbor, FL 34684
$400,000

2 beds

|

2 baths

|

1,376 sq ft

|

House

1382 GLENGARRY DR, PALM HARBOR, FL, 3468...
Highland Lakes on Lake Tarpon 1309 GILLESPIE DR, PALM HARBOR, FL, 3468..., Palm Harbor, FL 34684
$525,000

2 beds

|

2 baths

|

1,674 sq ft

|

House

1309 GILLESPIE DR, PALM HARBOR, FL, 3468...
Edgewater Arms 620 EDGEWATER DR 103, DUNEDIN, FL, 34698, Dunedin, FL 34698
$249,900

1 beds

|

1 baths

|

840 sq ft

|

Condo

620 EDGEWATER DR 103, DUNEDIN, FL, 34698
Community: Edgewater Arms
Heritage Springs 1237 RAMBLING VINE CT, TRINITY, FL, 3465..., Trinity, FL 34655
$575,000

3 beds

|

2 baths

|

2,409 sq ft

|

House

1237 RAMBLING VINE CT, TRINITY, FL, 3465...
Community: Heritage Springs
Village on the Green 2525 ROYAL PINES CIR 26H, CLEARWATER, FL..., Clearwater, FL 33763
$179,000

2 beds

|

2 baths

|

1,030 sq ft

|

Condo

2525 ROYAL PINES CIR 26H, CLEARWATER, FL...
Heritage Lake 9022 RAMSGATE DR, NEW PORT RICHEY, FL, 3..., New Port Richey, FL 34655
$150,000

2 beds

|

2 baths

|

1,215 sq ft

|

Condo

9022 RAMSGATE DR, NEW PORT RICHEY, FL, 3...
Community: Heritage Lake
Village on the Green 2546 OAKLEAF LN 35C, CLEARWATER, FL, 337..., Clearwater, FL 33763
$215,000

2 beds

|

2 baths

|

960 sq ft

|

Condo

2546 OAKLEAF LN 35C, CLEARWATER, FL, 337...
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Timber Oaks 10531 MEADOW HILL DR, PORT RICHEY, FL, 3..., Port Richey, FL 34668
$329,000

3 beds

|

2 baths

|

1,700 sq ft

|

House

10531 MEADOW HILL DR, PORT RICHEY, FL, 3...
Community: Timber Oaks
Edgewater Arms 622 EDGEWATER DR 523, DUNEDIN, FL, 34698, Dunedin, FL 34698
$230,000

1 beds

|

1 baths

|

950 sq ft

|

Condo

622 EDGEWATER DR 523, DUNEDIN, FL, 34698
Community: Edgewater Arms
Heather Ridge 1370 HEATHER RIDGE BLVD 104, DUNEDIN, FL..., Dunedin, FL 34698
$129,900

2 beds

|

1 baths

|

990 sq ft

|

Condo

1370 HEATHER RIDGE BLVD 104, DUNEDIN, FL...
Community: Heather Ridge
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Highland Lakes on Lake Tarpon 1617 KILWINNING CT, PALM HARBOR, FL, 346..., Palm Harbor, FL 34684
$439,900

3 beds

|

2 baths

|

1,579 sq ft

|

House

1617 KILWINNING CT, PALM HARBOR, FL, 346...
Heritage Springs 1201 DUSTAN PL, TRINITY, FL, 34655, Trinity, FL 34655
$419,900

3 beds

|

2 baths

|

2,032 sq ft

|

House

1201 DUSTAN PL, TRINITY, FL, 34655
Community: Heritage Springs
Royal Stewart Arms 9 FORBES PL 412, DUNEDIN, FL, 34698, Dunedin, FL 34698
$315,000

2 beds

|

2 baths

|

1,181 sq ft

|

Condo

9 FORBES PL 412, DUNEDIN, FL, 34698
Community: Royal Stewart Arms
Timber Oaks 8330 HIGH POINT CIR 6, PORT RICHEY, FL, ..., Port Richey, FL 34668
$174,900

2 beds

|

2 baths

|

1,210 sq ft

|

Condo

8330 HIGH POINT CIR 6, PORT RICHEY, FL, ...
Community: Timber Oaks
Timber Oaks 10707 FALLEN LEAF LN, PORT RICHEY, FL, 3..., Port Richey, FL 34668
$275,000

2 beds

|

2 baths

|

1,670 sq ft

|

House

10707 FALLEN LEAF LN, PORT RICHEY, FL, 3...
Community: Timber Oaks
Heritage Lake 4922 GRIST MILL CIR, NEW PORT RICHEY, FL..., New Port Richey, FL 34655
$156,700

1 beds

|

1 baths

|

723 sq ft

|

Townhouse

4922 GRIST MILL CIR, NEW PORT RICHEY, FL...
Community: Heritage Lake
Heather Lake Condominiums 948 VIRGINIA ST 210, DUNEDIN, FL, 34698, Dunedin, FL 34698
$145,000

2 beds

|

2 baths

|

1,112 sq ft

|

Condo

948 VIRGINIA ST 210, DUNEDIN, FL, 34698
Village on the Green 2569 LAURELWOOD DR 11B, CLEARWATER, FL, ..., Clearwater, FL 33763
$210,000

2 beds

|

2 baths

|

1,030 sq ft

|

Condo

2569 LAURELWOOD DR 11B, CLEARWATER, FL, ...
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Imperial Pines Condominiums 3076 EASTLAND BLVD 203, CLEARWATER, FL, ..., Clearwater, FL 33761
$260,000

2 beds

|

2 baths

|

1,250 sq ft

|

Condo

3076 EASTLAND BLVD 203, CLEARWATER, FL, ...
Patrician Oaks 820 VIRGINIA ST 104, DUNEDIN, FL, 34698, Dunedin, FL 34698
$169,900

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

820 VIRGINIA ST 104, DUNEDIN, FL, 34698
Community: Patrician Oaks
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.

Frequently Asked Questions


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