| 1 | Sigsbee Charter School INC | Education | $13.2M | $28.2M |
| 2 | Wesley House Family Services INC | Human Services | $8.3M | $14.4M |
| 3 | Community Foundation of the Florida Keys | Philanthropy, Voluntarism & Grantmaking | $6.6M | $33.8M |
| 4 | The India Blake Foundation INC | Philanthropy, Voluntarism & Grantmaking | $5.6M | $5.6M |
| 5 | Florida Keys Educational Foundation INC | Unclassified | $5.5M | $10.9M |
| 6 | Ah of Monroe County INC | Diseases, Disorders & Medical Disciplines | $4.9M | $14.8M |
| 7 | Star of the Sea Foundation INC | Health Care | $4.5M | $5.9M |
| 8 | Florida Keys Society for the Prevention of Cruelty to Animals | Animal-Related | $4.4M | $11.8M |
| 9 | Monroe Association for Retarded Citizens INC | Human Services | $4.4M | $4.4M |
| 10 | The Studios of Key West INC | Arts, Culture & Humanities | $3.4M | $15.2M |
| 11 | Key West Art & Historical Society INC | Unclassified | $3.2M | $4.3M |
| 12 | Rural Health Network of Monroe County Florida INC | Health Care | $3.1M | $2.3M |
| 13 | Monroe County Education Foundation INC | Education | $2.4M | $16.8M |
| 14 | Habitat for Humanity of Key West and Lower Florida Keys | Housing & Shelter | $2.1M | $11.0M |
| 15 | Mel Fisher Maritime Heritage Society INC | Unclassified | $2.1M | $5.7M |
| 16 | Key West Literary Seminar INC | Unclassified | $1.9M | $5.1M |
| 17 | Montessori Childrens School of Key West INC | Education | $1.6M | $2.6M |
| 18 | Samuels House INC | Human Services | $1.6M | $2.6M |
| 19 | Womankind INC | Human Services | $1.5M | $1.7M |
| 20 | Florida Keys Outreach Coalition INC | Unclassified | $1.5M | $2.8M |
| 21 | Boys & Girls Clubs of the Keys Area INC | Youth Development | $1.5M | $1.4M |
| 22 | Florida Keys Healthy Start Coalition INC | Health Care | $1.5M | $853K |
| 23 | Performing Arts Centers of Key West INC | Unclassified | $1.3M | $1.1M |
| 24 | May Sands Montessori School INC | Education | $1.3M | $878K |
| 25 | Key West Lodge No 1760 Loyal Order of Moose | Mutual & Membership Benefit | $1.0M | $1.7M |
| 26 | Greater Key West Chamber of Commerce INC | Unclassified | $1.0M | $1.1M |
| 27 | Key West Players INC | Unclassified | $999K | $1.3M |
| 28 | Loreen and Robert Ramey Community Foundation INC | Philanthropy, Voluntarism & Grantmaking | $976K | $5.0M |
| 29 | Fleming Street Faith Center INC | Human Services | $956K | $3.1M |
| 30 | Monroe County Homeless Services Continuum-of-care INC | Housing & Shelter | $901K | $460K |
| 31 | Veterans of Foreign Wars of the United States Dept of Florida | Unclassified | $860K | $2.4M |
| 32 | Key West Film Society INC | Arts, Culture & Humanities | $855K | $1.2M |
| 33 | American Legion | Public & Societal Benefit | $833K | $646K |
| 34 | Key West Wildlife Center INC | Animal-Related | $820K | $2.6M |
| 35 | Old Island Restoration Foundation INC | Unclassified | $728K | $911K |
| 36 | Dion Banks Foundation | Philanthropy, Voluntarism & Grantmaking | $695K | $4.5M |
| 37 | Historic Florida Keys Foundation INC | Unclassified | $668K | $6.8M |
| 38 | Key West Theater and Community Stage | Arts, Culture & Humanities | $650K | $736K |
| 39 | Key West Association of Realtors INC | Unclassified | $614K | $624K |
| 40 | Association for Tourism Development | Unclassified | $590K | $112K |
| 41 | Red Barn Actors Studio INC | Arts, Culture & Humanities | $575K | $295K |
| 42 | Key West Womans Club INC | Philanthropy, Voluntarism & Grantmaking | $558K | $2.2M |
| 43 | Key West Police Athletic League INC | Unclassified | $533K | $511K |
| 44 | Key West Botanical Garden Society INC | Environment | $518K | $1.4M |
| 45 | Fringe Theater of Key West INC | Arts, Culture & Humanities | $501K | $324K |
| 46 | Reef Relief INC | Environment | $497K | $600K |
| 47 | The Clements Family Charitable Trust | Unclassified | $488K | $2.2M |
| 48 | American Federation of Teachers | Unclassified | $453K | $61K |
| 49 | Monroe Council of the Arts Corporation | Arts, Culture & Humanities | $395K | $218K |
| 50 | Lighthouse Christian Academy INC | Human Services | $384K | $56K |
| 51 | Miami-dade Historical Maritime Museum INC | Arts, Culture & Humanities | $382K | $596K |
| 52 | Key West Business Guild INC | Unclassified | $378K | $199K |
| 53 | Michelles Foundation INC | Education | $373K | $640K |
| 54 | Key West Art Center INC | Arts, Culture & Humanities | $368K | $510K |
| 55 | Monroe County Coalition INC | Mental Health & Crisis Intervention | $358K | $36K |
| 56 | Key West Garden Club | Environment | $349K | $1.4M |
| 57 | American Academy of Advertising | Community Improvement & Capacity Building | $336K | $1.6M |
| 58 | Key West Pre-school Co-operative INC | Education | $325K | $62K |
| 59 | Tree Institute International INC | Environment | $315K | $208K |
| 60 | Key West Community Sailing Center INC | Recreation & Sports | $311K | $382K |
| 61 | Lower Keys Friends of Animals INC | Animal-Related | $311K | $406K |
| 62 | Key West Harry S Truman Foundation INC | Arts, Culture & Humanities | $308K | $949K |
| 63 | Xena Fund of the Florida Keys INC | Animal-Related | $306K | $303K |
| 64 | Keys Learning Center INC | Education | $264K | $43K |
| 65 | Cancer Foundation of the Florida Keys | Health Care | $245K | $1.9M |
| 66 | Key West Rotary Club Foundation INC | Unclassified | $241K | $945K |
| 67 | American Legion | Public & Societal Benefit | $234K | $74K |
| 68 | Ancient & Accepted Scottish Rite of Free Masonry So Juris USA | Unclassified | $225K | $3.4M |
| 69 | The Lodging Association of the Florida Keys and Key West INC | Unclassified | $220K | $287K |
| 70 | Rotary International | Unclassified | $214K | $44K |
| 71 | Friends of the Monroe County Public Library in Key West Florida INC | Education | $213K | $877K |
| 72 | A H I Housing INC | Housing & Shelter | $208K | $891K |
| 73 | A Positive Step of Monroe County | Mental Health & Crisis Intervention | $193K | $38K |
| 74 | Anchors Aweigh Club INC | Mental Health & Crisis Intervention | $175K | $475K |
| 75 | Fraternal Order of Orioles | Unclassified | $157K | $4K |
| 76 | Key West Little Conch Baseball League INC | Recreation & Sports | $156K | $9K |
| 77 | Key West Cultural Preservation Society INC | Arts, Culture & Humanities | $145K | $17K |
| 78 | Literacy Volunteers of America Monroe County INC | Unclassified | $144K | $100K |
| 79 | Keys to Be the Change INC | Education | $141K | $127K |
| 80 | Kids Come First in the Florida Keys INC | Youth Development | $133K | $34K |
| 81 | Queer Keys INC | Human Services | $131K | $70K |
| 82 | Key West Impromptu Classical Concerts INC | Arts, Culture & Humanities | $130K | $384K |
| 83 | Sister Season Fund INC | Philanthropy, Voluntarism & Grantmaking | $129K | $475K |
| 84 | Sunrise Rotary Foundation of Key West INC | Philanthropy, Voluntarism & Grantmaking | $129K | $991K |
| 85 | Souternmost Hockey Club | Recreation & Sports | $128K | $194K |
| 86 | Key West Military Affairs Committee INC | Public & Societal Benefit | $105K | $219K |
| 87 | Doctors of Nursing Practice Professional Development INC | International, Foreign Affairs & National Security | $102K | $43K |
| 88 | Harry & Harriet Ruchman Charitable Foundation INC | Unclassified | $102K | $805K |
| 89 | 1213 William Street Corporation | Housing & Shelter | $99K | $543K |
| 90 | Kw Lady Conchs Softball Booster Club INC | Recreation & Sports | $96K | $96K |
| 91 | International Association of Fire Fighters | Unclassified | $94K | $95K |
| 92 | Bahama Village Music Program INC | Arts, Culture & Humanities | $93K | $163K |
| 93 | VFW Post 3911 Toys for Conchs and Relief for Veterans INC | Human Services | $93K | $37K |
| 94 | Todd Stuart Foundation INC | Philanthropy, Voluntarism & Grantmaking | $90K | $45K |
| 95 | Leadership Monroe County INC | Community Improvement & Capacity Building | $84K | $101K |
| 96 | Marine Preservation Society of the Florida Keys INC | Environment | $83K | $216K |
| 97 | Key Bridge INC | Mental Health & Crisis Intervention | $76K | $2.0M |
| 98 | Firmkeys INC | Public Safety, Disaster Preparedness & Relief | $74K | $144K |
| 99 | Sloppy Joes Foundation INC | Public & Societal Benefit | $70K | $53K |
| 100 | Keys Choral Arts INC | Arts, Culture & Humanities | $63K | $107K |