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Holiday, FL 55+ active adult communities & homes for sale - Page 8

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


297 homes 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
Summertree
$200ks - $300ks
Summertree, New Port Richey, FL
Resale Only | 55+ age-restricted | Built 1974 - 2015 | 800 homes
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
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
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
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.
Esplanade at Starkey Ranc...
$300ks - $700ks
Esplanade at Starkey Ranc..., Odessa, FL
Resale Only | Age-targeted | Built 2016 - 2022 | 517 homes
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
Edgewater Arms
$400ks - $600ks
Edgewater Arms, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1970 - 1974 | 209 homes
Victoria Lakes
$800ks - $1Ms
Victoria Lakes, Odessa, FL
New Construction | Age-targeted | Built 2025 - present | 166 homes
Green Dolphin
$100ks
Green Dolphin, Tarpon Springs, FL
Resale Only | 55+ age-restricted | Built 1974 - 1990 | 315 homes
Briar Patch
$100ks
Briar Patch, New Port Richey, FL
Resale Only | 55+ age-restricted | Built 1986 - 1993 | 198 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
Imperial Pines Condominiu...
$100ks - $200ks
Imperial Pines Condominiu..., Clearwater, FL
Resale Only | 55+ age-restricted | Built 1985 - 1985 | 181 homes
Key Vista Villas
$300ks
Key Vista Villas, Holiday, FL
Resale Only | 55+ age-restricted | Built 2001 - 2005 | 170 homes
Pinehurst Village
$100ks
Pinehurst Village, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1973 - 1976 | 240 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
Scotsdale Cluster Condomi...
$200ks
Scotsdale Cluster Condomi..., Dunedin, FL
Resale Only | 55+ age-restricted | Built 1980 - 1983 | 148 homes
Heather Hills Villas
$100ks
Heather Hills Villas, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1971 - 1976 | 64 homes
Heather Ridge
$100ks - $200ks
Heather Ridge, Dunedin, FL
Resale Only | 55+ age-restricted | Built 1978 - 1987 | 273 homes
Country Oaks
$100ks
Country Oaks, Hudson, FL
Resale Only | 55+ age-restricted | Built 1981 - 1986 | 42 homes
Linkside Village
$200ks
Linkside Village, Port Richey, FL
Resale Only | 55+ age-restricted | Built 1981 - 1985 | 100 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
Highland Lakes on Lake Tarpon 2739 SHERBROOKE LN B, PALM HARBOR, FL, 3..., Palm Harbor, FL 34684
$230,000

2 beds

|

2 baths

|

1,000 sq ft

|

Villa

2739 SHERBROOKE LN B, PALM HARBOR, FL, 3...
Timber Oaks 8360 HIGH POINT CIR 3, PORT RICHEY, FL, ..., Port Richey, FL 34668
$139,900

2 beds

|

2 baths

|

1,372 sq ft

|

Condo

8360 HIGH POINT CIR 3, PORT RICHEY, FL, ...
Community: Timber Oaks
Highland Lakes on Lake Tarpon 1350 GLENGARRY DR, PALM HARBOR, FL, 3468..., Palm Harbor, FL 34684
$429,000

2 beds

|

2 baths

|

1,694 sq ft

|

House

1350 GLENGARRY DR, PALM HARBOR, FL, 3468...
Timber Oaks 8350 HIGH POINT CIR 3, PORT RICHEY, FL, ..., Port Richey, FL 34668
$150,000

2 beds

|

2 baths

|

1,372 sq ft

|

Condo

8350 HIGH POINT CIR 3, PORT RICHEY, FL, ...
Community: Timber Oaks
Royal Stewart Arms 5 GATESHEAD DR 107, DUNEDIN, FL, 34698, Dunedin, FL 34698
$328,900

2 beds

|

2 baths

|

1,175 sq ft

|

Condo

5 GATESHEAD DR 107, DUNEDIN, FL, 34698
Community: Royal Stewart Arms
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Key Vista Villas 2453 PLEASANT HILL LN, HOLIDAY, FL, 3469..., Holiday, FL 34691
$275,000

2 beds

|

2 baths

|

1,555 sq ft

|

House

2453 PLEASANT HILL LN, HOLIDAY, FL, 3469...
Community: Key Vista Villas
Edgewater Arms 632 EDGEWATER DR 238, DUNEDIN, FL, 34698, Dunedin, FL 34698
$349,900

2 beds

|

2 baths

|

1,220 sq ft

|

Condo

632 EDGEWATER DR 238, DUNEDIN, FL, 34698
Community: Edgewater Arms
Timber Greens 6543 PINE WALK DR, NEW PORT RICHEY, FL, ..., New Port Richey, FL 34655
$274,900

2 beds

|

2 baths

|

1,380 sq ft

|

Villa

6543 PINE WALK DR, NEW PORT RICHEY, FL, ...
Community: Timber Greens
Heritage Lake 9309 TROWBRIDGE CT, NEW PORT RICHEY, FL,..., New Port Richey, FL 34655
$185,000

1 beds

|

1 baths

|

723 sq ft

|

Villa

9309 TROWBRIDGE CT, NEW PORT RICHEY, FL,...
Community: Heritage Lake
Highland Lakes on Lake Tarpon 1609 WHITEBRIDGE DR C, PALM HARBOR, FL, ..., Palm Harbor, FL 34684
$149,400

1 beds

|

1 baths

|

964 sq ft

|

Condo

1609 WHITEBRIDGE DR C, PALM HARBOR, FL, ...
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.
Royal Stewart Arms 7 DUNOON PL 203, DUNEDIN, FL, 34698, Dunedin, FL 34698
$277,700

1 beds

|

1 baths

|

957 sq ft

|

Condo

7 DUNOON PL 203, DUNEDIN, FL, 34698
Community: Royal Stewart Arms
Heritage Lake 4719 CAVENDISH DR, NEW PORT RICHEY, FL, ..., New Port Richey, FL 34655
$298,900

2 beds

|

2 baths

|

1,646 sq ft

|

House

4719 CAVENDISH DR, NEW PORT RICHEY, FL, ...
Community: Heritage Lake
Heritage Lake 4658 WALLINGFORD CT, NEW PORT RICHEY, FL..., New Port Richey, FL 34655
$219,900

2 beds

|

2 baths

|

1,204 sq ft

|

Condo

4658 WALLINGFORD CT, NEW PORT RICHEY, FL...
Community: Heritage Lake
Highland Lakes on Lake Tarpon 2738 SHERBROOKE LN C, PALM HARBOR, FL, 3..., Palm Harbor, FL 34684
$140,000

1 beds

|

2 baths

|

814 sq ft

|

Villa

2738 SHERBROOKE LN C, PALM HARBOR, FL, 3...
Briar Patch 6421 REMUS DR, NEW PORT RICHEY, FL, 3465..., New Port Richey, FL 34653
$179,499

2 beds

|

2 baths

|

964 sq ft

|

Villa

6421 REMUS DR, NEW PORT RICHEY, FL, 3465...
Community: Briar Patch
Summertree 11248 MOLLYMAWK CT, NEW PORT RICHEY, FL,..., New Port Richey, FL 34654
$325,000

3 beds

|

2 baths

|

1,558 sq ft

|

House

11248 MOLLYMAWK CT, NEW PORT RICHEY, FL,...
Community: Summertree
Want to learn more about 55+ communities in Holiday? 55places can help!
Questions? Call us: (727) 800-3371
Heather Lake Condominiums 940 VIRGINIA ST 304, DUNEDIN, FL, 34698, Dunedin, FL 34698
$111,000

1 beds

|

1 baths

|

760 sq ft

|

Condo

940 VIRGINIA ST 304, DUNEDIN, FL, 34698

Frequently Asked Questions


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Call us: (727) 800-3371
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REIN updates its listings on a daily basis. Data last updated: Oct 09, 2026.
This application does not include information on all of the properties available for sale at this time.

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