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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 review) 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 review) 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
Summertree
$200ks - $300ks
Summertree, New Port Richey, FL
Resale Only | 55+ age-restricted | Built 1974 - 2015 | 800 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
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Heather Lake Condominiums
$100ks
Heather Lake Condominiums, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1972 - 1978 | 200 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
5 rating (1 review) Village on the Green
$100ks - $200ks
Village on the Green, Clearwater, FL
Resale Only | 55+ age-restricted | Built 1978 - 1981 | 448 homes
2 rating (1 review) Beacon Lakes
$100ks
Beacon Lakes, New Port Richey, FL
Resale Only | 55+ age-restricted | Built 1975 - 1982 | 210 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
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
Esplanade at Starkey Ranc...
$300ks - $700ks
Esplanade at Starkey Ranc..., Odessa, FL
Resale Only | Age-targeted | Built 2016 - 2022 | 517 homes
Victoria Lakes
$800ks - $1Ms
Victoria Lakes, Odessa, FL
New Construction | Age-targeted | Built 2025 - present | 166 homes
Edgewater Arms
$400ks - $600ks
Edgewater Arms, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1970 - 1974 | 209 homes
Green Dolphin
$100ks
Green Dolphin, Tarpon Springs, FL
Resale Only | 55+ age-restricted | Built 1974 - 1990 | 315 homes
Pinehurst Village
$100ks
Pinehurst Village, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1973 - 1976 | 240 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
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
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.
Anchorage
$200ks - $300ks
Anchorage, Palm Harbor, FL
Resale Only | 55+ age-restricted | Built 1972 - 1979 | 279 homes
Key Vista Villas
$300ks
Key Vista Villas, Holiday, FL
Resale Only | 55+ age-restricted | Built 2001 - 2005 | 170 homes
Briar Patch
$100ks
Briar Patch, New Port Richey, FL
Resale Only | 55+ age-restricted | Built 1986 - 1993 | 198 homes
Imperial Pines Condominiu...
$100ks - $200ks
Imperial Pines Condominiu..., Clearwater, FL
Resale Only | 55+ age-restricted | Built 1985 - 1985 | 181 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
Soleta at Starkey Ranch
$500ks - $600ks
Soleta at Starkey Ranch, Odessa, FL
New Construction | Age-targeted | Built 2023 - present | 139 homes
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
New Port Corners
$200ks - $500ks
New Port Corners, New Port Richey, FL
New Construction | 55+ age-restricted | Built 2025 - present
Village on the Green 2543 ROYAL PINES CIR 17K, CLEARWATER, FL..., Clearwater, FL 33763
$235,000

2 beds

|

2 baths

|

1,030 sq ft

|

Condo

2543 ROYAL PINES CIR 17K, CLEARWATER, FL...
New Highland Lakes on Lake Tarpon 1146 RUSTLEWOOD CT, PALM HARBOR, FL, 346..., Palm Harbor, FL 34684
$439,900

2 beds

|

2 baths

|

1,532 sq ft

|

Villa

1146 RUSTLEWOOD CT, PALM HARBOR, FL, 346...
New Heather Lake Condominiums 960 VIRGINIA ST 206, DUNEDIN, FL, 34698, Dunedin, FL 34698
$109,000

1 beds

|

1 baths

|

800 sq ft

|

Condo

960 VIRGINIA ST 206, DUNEDIN, FL, 34698
New Pine Ridge at Palm Harbor 2600 PINE RIDGE WAY B2, PALM HARBOR, FL,..., Palm Harbor, FL 34684
$180,000

2 beds

|

1 baths

|

904 sq ft

|

Condo

2600 PINE RIDGE WAY B2, PALM HARBOR, FL,...
New Heritage Lake 9015 WARWICK LN, NEW PORT RICHEY, FL, 34..., New Port Richey, FL 34655
$225,000

2 beds

|

2 baths

|

1,728 sq ft

|

Condo

9015 WARWICK LN, NEW PORT RICHEY, FL, 34...
Community: Heritage Lake
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
New Heritage Lake 9730 CAVENDISH CT, NEW PORT RICHEY, FL, ..., New Port Richey, FL 34655
$245,000

2 beds

|

2 baths

|

1,350 sq ft

|

House

9730 CAVENDISH CT, NEW PORT RICHEY, FL, ...
Community: Heritage Lake
New Timber Greens 6623 GARDEN PALM CT, NEW PORT RICHEY, FL..., New Port Richey, FL 34655
$439,000

3 beds

|

3 baths

|

2,284 sq ft

|

House

6623 GARDEN PALM CT, NEW PORT RICHEY, FL...
Community: Timber Greens
New Heather Ridge 2187 NIMITZ DR 2187, DUNEDIN, FL, 34698, Dunedin, FL 34698
$310,000

2 beds

|

2 baths

|

1,370 sq ft

|

Condo

2187 NIMITZ DR 2187, DUNEDIN, FL, 34698
Community: Heather Ridge
New Green Dolphin 1250 S PINELLAS AVE 1007, TARPON SPRINGS..., Tarpon Springs, FL 34689
$189,900

2 beds

|

2 baths

|

871 sq ft

|

Condo

1250 S PINELLAS AVE 1007, TARPON SPRINGS...
Community: Green Dolphin
New Heritage Springs 1929 WESTERHAM LOOP, TRINITY, FL, 34655, Trinity, FL 34655
$445,000

3 beds

|

2 baths

|

1,850 sq ft

|

House

1929 WESTERHAM LOOP, TRINITY, FL, 34655
Community: Heritage Springs
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
270 DIOGENES ST, DUNEDIN, FL, 34698, Dunedin, FL 34698
$475,000

3 beds

|

2 baths

|

1,364 sq ft

|

House

270 DIOGENES ST, DUNEDIN, FL, 34698
New Heritage Springs 12116 BROADGREEN PL, TRINITY, FL, 34655, Trinity, FL 34655
$389,000

3 beds

|

2 baths

|

1,793 sq ft

|

House

12116 BROADGREEN PL, TRINITY, FL, 34655
Community: Heritage Springs
New Beacon Lakes 4036 DAVIT DR, NEW PORT RICHEY, FL, 3465..., New Port Richey, FL 34652
$159,900

2 beds

|

2 baths

|

1,144 sq ft

|

Condo

4036 DAVIT DR, NEW PORT RICHEY, FL, 3465...
Community: Beacon Lakes
New Summertree 11814 IVYWOOD PL, NEW PORT RICHEY, FL, 3..., New Port Richey, FL 34654
$285,000

3 beds

|

2 baths

|

1,572 sq ft

|

House

11814 IVYWOOD PL, NEW PORT RICHEY, FL, 3...
Community: Summertree
New Timber Oaks 10526 QUIMBY DR, OTHER, FL, 34668, Other, FL 34668
$5,000

2 beds

|

2 baths

|

1,802 sq ft

|

House

10526 QUIMBY DR, OTHER, FL, 34668
Community: Timber Oaks
New Summertree 11048 PARADISE POINT WAY, NEW PORT RICHE..., New Port Richey, FL 34654
$299,000

3 beds

|

2 baths

|

1,558 sq ft

|

House

11048 PARADISE POINT WAY, NEW PORT RICHE...
Community: Summertree
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
New Highland Lakes on Lake Tarpon 2297 LARK CIR D, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$235,000

2 beds

|

2 baths

|

1,230 sq ft

|

Villa

2297 LARK CIR D, PALM HARBOR, FL, 34684
Timber Oaks 11430 CARRIAGE HILL DR 2, PORT RICHEY, F..., Port Richey, FL 34668
$120,000

2 beds

|

2 baths

|

1,210 sq ft

|

Villa

11430 CARRIAGE HILL DR 2, PORT RICHEY, F...
Community: Timber Oaks
Patrician Oaks 831 MAPLE CT 103, DUNEDIN, FL, 34698, Dunedin, FL 34698
$120,000

2 beds

|

1 baths

|

1,004 sq ft

|

Condo

831 MAPLE CT 103, DUNEDIN, FL, 34698
Community: Patrician Oaks
Highland Lakes on Lake Tarpon 1743 MACDONNELL DR, PALM HARBOR, FL, 346..., Palm Harbor, FL 34684
$449,900

2 beds

|

2 baths

|

1,642 sq ft

|

House

1743 MACDONNELL DR, 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.
Linkside Village 11149 SANDTRAP DR, PORT RICHEY, FL, 3466..., Port Richey, FL 34668
$228,500

2 beds

|

2 baths

|

1,646 sq ft

|

Condo

11149 SANDTRAP DR, PORT RICHEY, FL, 3466...
Community: Linkside Village
Timber Oaks 11149 SANDTRAP DR, PORT RICHEY, FL, 3466..., Port Richey, FL 34668
$228,500

2 beds

|

2 baths

|

1,646 sq ft

|

Condo

11149 SANDTRAP DR, PORT RICHEY, FL, 3466...
Community: Timber Oaks
Highland Lakes on Lake Tarpon 3812 TARPON POINTE CIR, PALM HARBOR, FL,..., Palm Harbor, FL 34684
$475,000

3 beds

|

2 baths

|

2,086 sq ft

|

House

3812 TARPON POINTE CIR, PALM HARBOR, FL,...
Highland Lakes on Lake Tarpon 3554 OAK LAKE DR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$450,000

2 beds

|

2 baths

|

1,700 sq ft

|

House

3554 OAK LAKE DR, PALM HARBOR, FL, 34684
Cindy Certified
2713 SAN LUIS RD, HOLIDAY, FL, 34691, Holiday, FL 34691
$414,900

3 beds

|

2 baths

|

1,460 sq ft

|

House

2713 SAN LUIS RD, HOLIDAY, FL, 34691
Heritage Springs 1149 WOLFORD DR, NEW PORT RICHEY, FL, 34..., New Port Richey, FL 34655
$335,000

2 beds

|

2 baths

|

1,581 sq ft

|

Villa

1149 WOLFORD DR, NEW PORT RICHEY, FL, 34...
Community: Heritage Springs
Highland Lakes on Lake Tarpon 3109 MISSION GROVE DR D, PALM HARBOR, FL..., Palm Harbor, FL 34684
$109,900

2 beds

|

2 baths

|

806 sq ft

|

Condo

3109 MISSION GROVE DR D, PALM HARBOR, FL...
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Pinehurst Village 1701 PINEHURST RD 15H, DUNEDIN, FL, 3469..., Dunedin, FL 34698
$195,000

2 beds

|

2 baths

|

1,025 sq ft

|

Villa

1701 PINEHURST RD 15H, DUNEDIN, FL, 3469...
Community: Pinehurst Village
Timber Oaks 11311 DOLLAR LAKE DR 6, PORT RICHEY, FL,..., Port Richey, FL 34668
$159,000

2 beds

|

2 baths

|

1,210 sq ft

|

Condo

11311 DOLLAR LAKE DR 6, PORT RICHEY, FL,...
Community: Timber Oaks
Cindy Certified
3087 JACKSON DR, HOLIDAY, FL, 34691, Holiday, FL 34691
$549,000

4 beds

|

2 baths

|

1,787 sq ft

|

House

3087 JACKSON DR, HOLIDAY, FL, 34691
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.
Timber Greens 6016 COUNTRY RIDGE LN, NEW PORT RICHEY, ..., New Port Richey, FL 34655
$399,000

2 beds

|

2 baths

|

1,820 sq ft

|

House

6016 COUNTRY RIDGE LN, NEW PORT RICHEY, ...
Community: Timber Greens
Heritage Lake 4704 TIBURON DR, NEW PORT RICHEY, FL, 34..., New Port Richey, FL 34655
$270,000

2 beds

|

2 baths

|

1,638 sq ft

|

House

4704 TIBURON DR, NEW PORT RICHEY, FL, 34...
Community: Heritage Lake
Key Vista Villas 2514 SANDY HILL CT, HOLIDAY, FL, 34691, Holiday, FL 34691
$355,900

2 beds

|

2 baths

|

1,555 sq ft

|

House

2514 SANDY HILL CT, HOLIDAY, FL, 34691
Community: Key Vista Villas
Summertree 11030 PARADISE POINT WAY, NEW PORT RICHE..., New Port Richey, FL 34654
$356,900

3 beds

|

2 baths

|

1,844 sq ft

|

House

11030 PARADISE POINT WAY, NEW PORT RICHE...
Community: Summertree
Cindy Certified
13735 HOMERIDGE CT, HUDSON, FL, 34667, Hudson, FL 34667
$317,990

3 beds

|

2 baths

|

1,501 sq ft

|

House

13735 HOMERIDGE CT, HUDSON, FL, 34667
Scotsdale Cluster Condominiums 1307 STONEHAVEN LN, DUNEDIN, FL, 34698, Dunedin, FL 34698
$374,900

2 beds

|

2 baths

|

1,110 sq ft

|

Condo

1307 STONEHAVEN LN, DUNEDIN, FL, 34698
Esplanade at Starkey Ranch 11149 EGERIA DR, ODESSA, FL, 33556, Odessa, FL 33556
$1,299,000

3 beds

|

3 baths

|

3,094 sq ft

|

House

11149 EGERIA DR, ODESSA, FL, 33556
Summertree 11508 BLOOMINGTON CT, NEW PORT RICHEY, F..., New Port Richey, FL 34654
$319,900

3 beds

|

2 baths

|

1,632 sq ft

|

House

11508 BLOOMINGTON CT, NEW PORT RICHEY, F...
Community: Summertree
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Summertree 12128 LOBLOLLY PINE DR, NEW PORT RICHEY,..., New Port Richey, FL 34654
$240,000

2 beds

|

2 baths

|

1,644 sq ft

|

House

12128 LOBLOLLY PINE DR, NEW PORT RICHEY,...
Community: Summertree
Highland Lakes on Lake Tarpon 978 MADRID DR, PALM HARBOR, FL, 34684, Palm Harbor, FL 34684
$339,950

2 beds

|

2 baths

|

1,190 sq ft

|

Villa

978 MADRID DR, PALM HARBOR, FL, 34684
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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