Anna Maria Island, FL
Old Florida charm - Gulf Coast's most beloved island escape
Anna Maria Island is a 7-mile barrier island on Florida's Gulf Coast with one of the most loyal repeat-visitor bases of any STR market in Florida. The island's strict preservation of Old Florida character - no chain restaurants, no high-rises, golf cart culture - commands premium pricing relative to its size. Properties here rent at exceptional rates and hold value extremely well.
Across 42 active STR-viable listings analyzed this month, Anna Maria Island shows a 2.2% median cap rate at a $3.5M median list price, 48% occupancy, and $1,008/night. That ranks #43 of 57 markets in STRROI's live ranking. At typical prices, cash flow is tight: most listings only pencil out with a large down payment, a below-list purchase, or above-market nightly rates.
Anna Maria Island real estate market right now
As of October 16, 2026, STRROI is tracking 42 homes for sale in Anna Maria Island that could run as short-term rentals, at a median list price of $3,477,500. The middle half are priced between $1.9M and $5.5M. That works out to a median of $1,496 per square foot for a typical 2,472 square foot home. Homes here have been on the market 180 days on average, longer than the 101 days typical across the 56 markets in STRROI's ranking, which usually leaves more room to negotiate on price. 9 of them were listed in the last 30 days.
These numbers cover the homes for sale STRROI analyzes as potential short-term rentals in Anna Maria Island, mainly ZIP 34216. They are not every home sale in the area, so they can differ from MLS-wide figures. Month-by-month price history starts Oct 2026 and fills in as the market is re-checked each month.
What's for sale in Anna Maria Island right now
Of the 42 homes for sale we analyzed in Anna Maria Island, none project positive monthly cash flow with 20% down at a 7.5% rate, and none rate Buy or better on STRROI's 1-10 scale. 4-bedroom homes are the most common (16 for sale, median $4.5M). Returns are strongest in 3-bedroom homes at a 2.4% median cap rate, and weakest in 4-bedroom homes at 2.1%.
- Weak: 1
- Avoid: 41
| Beds | For sale | Median price | Cap rate |
|---|---|---|---|
| 3 | 14 | $1.9M | 2.4% |
| 4 | 16 | $4.5M | 2.1% |
| 5+ | 10 | $5.9M | 2.2% |
| Type | For sale | Median price | Cap rate |
|---|---|---|---|
| Single-family homes | 41 | $3.7M | 2.2% |
Top-ranked homes for sale in Anna Maria Island this month
Scored 1-10 against real Airbnb comps. Addresses, photos and the full underwriting are in the app.
- #1Weak · 3/104 bd · 4 ba multi-family propertyZIP 34216 · listed at $1.8M
- Cap rate
- 5.3%
- Cash flow
- -$2,115/mo
- Nightly
- $462 at 48%
- #2Avoid · 2/104 bd · 2 ba single-family homeZIP 34216 · listed at $1.7M
- Cap rate
- 4.6%
- Cash flow
- -$3,041/mo
- Nightly
- $794 at 48%
- #3Avoid · 2/103 bd · 2 ba single-family homeZIP 34216 · listed at $1.3M
- Cap rate
- 4.6%
- Cash flow
- -$2,257/mo
- Nightly
- $586 at 48%
How Anna Maria Island compares
Anna Maria Island ranks #15 of 21 Southeast markets in STRROI's live ranking; St. Augustine leads the region with a median cap rate of 5.7%. Its 2.2% cap rate is 0.7 points below the 2.9% median across all 57 ranked markets, and its $3.5M typical list price is pricier than the Southeast median of $633K.
| Rank | Market | Cap rate | Typical price |
|---|---|---|---|
| #33 | Pigeon Forge, TN | 2.6% | $450K |
| #40 | Destin, FL | 2.4% | $515K |
| #42 | Asheville, NC | 2.3% | $750K |
| #43 | Anna Maria Island, FL | 2.2% | $3.5M |
| #46 | Hilton Head Island, SC | 2.2% | $950K |
| #47 | Sarasota, FL | 2.1% | $1.2M |
| #49 | Miami Beach, FL | 1.8% | $2.4M |
Rank is national, by median cap rate across active STR-viable listings. Cash flow uses STRROI's default financing assumptions. See the full ranking
Estimated Annual Performance
* Estimates based on market averages. Individual property performance varies. Always run a full underwriting analysis.
Why Investors Choose Anna Maria Island
Anna Maria Island STR investing, answered
Is Anna Maria Island, FL a good short-term rental market?
Anna Maria Island is a Southeast STR market with a 2.2% median cap rate, 48% annual occupancy, and $1,008/night across STR-viable listings, based on 42 active listings. It ranks #43 of 57 markets by median cap rate in STRROI's live ranking. This month none of its 42 homes for sale rate Buy or better.
What is the average Airbnb occupancy rate in Anna Maria Island?
STR-viable properties in Anna Maria Island average about 48% occupancy across the year. Peak season is Dec - Apr (winter snowbirds), summer families. Occupancy here reflects availability-adjusted booking performance, not raw calendar occupancy, so it represents what a full-time operated rental can realistically achieve.
How much do short-term rentals earn in Anna Maria Island?
At $1,008/night and 48% occupancy, a typical Anna Maria Island STR grosses roughly $176,970 per year before expenses, leaving an estimated $106,182 in net operating income. Across analyzed listings the median cap rate is 2.2%. Individual results depend on property, amenities, and management.
What types of properties work best for STR in Anna Maria Island?
Among homes for sale right now, 3-bedroom homes post the strongest median cap rate by size (2.4%). With guests, the best-performing STR types here are Beach Cottage, Single Family, Gulf-front Home. Matching the local guest profile and the amenities that drive bookings matters more than raw square footage.
How many homes for sale in Anna Maria Island cash flow as an Airbnb?
0 of 42 STR-viable listings (0%) project positive monthly cash flow after the mortgage, assuming 20% down at a 7.5% rate on a 30-year loan. The top-ranked listing this month is a 4-bedroom multi-family property in ZIP 34216 listed at $1.8M, projecting a 5.3% cap rate and -$2,115 a month.
What is the median home price in Anna Maria Island, FL right now?
The median list price of the 42 homes for sale STRROI tracks in Anna Maria Island is $3,477,500, and the middle half are priced between $1.9M and $5.5M. The median price per square foot is $1,496. These are homes that could run as short-term rentals, mainly ZIP 34216, not every sale in the area. Against a 2.2% median cap rate, that price level sets the return baseline you'd underwrite against.
How long do homes stay on the market in Anna Maria Island?
Homes for sale in Anna Maria Island have been listed 180 days on average, longer than the 101 days typical across the 56 markets in STRROI's ranking, which usually leaves more room to negotiate on price. 9 of them were listed in the last 30 days.
Market averages, not guarantees. Cap rates, occupancy, and nightly rates are market-wide averages based on active STR listings and historical data. Individual property performance depends on location, amenities, management, and listing quality. Always run a full underwriting analysis before purchasing.Stats sourced from 42 active listings · last updated Oct 16, 2026
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