Siesta Key Monthly Rentals: What a Month Costs by Season
Real rates for five Siesta Key condos that rent by the month, a February versus September comparison, and the tax and zoning rules that shape a 30-night stay.
Five furnished 2-bedroom Siesta Key condos that rent by the month cost $3,000 to $7,650 in rent for 30 nights in September 2027, and $5,460 to $10,920 for the 28 nights of February 2027. Each unit costs 1.3 to nearly 2 times as much per night in February as in September. Add 13% tax on any stay of six months or less, plus the manager's own fees.
Those numbers come from the published rate tables of five condos managed by Home & Condo Rentals and Realty, a local management company whose Siesta Key condos are listed on srq.rentals and booked on the manager's own site. We checked each table on the manager's site on October 19, 2026. Rates are what the manager charges per night, before taxes, fees and travel insurance.
February versus September, condo by condo
| Condo | Size and beach | February 2027, 28 nights | September 2027, 30 nights |
|---|---|---|---|
| The Inlet 39 | 2 bed, sleeps 4, 5-minute walk | $5,460 ($195 a night) | $3,000 ($100 a night) |
| Fishermans Haven 201 | 2 bed, sleeps 4, on the beach | $7,280 ($260 a night) | $3,990 ($133 a night) |
| Tortuga 203 A | 2 bed, sleeps 4, on the beach | $7,840 ($280 a night, 54-night minimum) | $4,800 ($160 a night) |
| Island Reef 204A | 2 bed, sleeps 4, on Turtle Beach | $6,720 ($240 a night) | $5,550 ($185 a night) |
| Gulf and Bay 107D | 2 bed, sleeps 8, on Crescent Beach | $10,920 ($390 a night) | $7,650 ($255 a night) |
With tax, The Inlet 39 comes to about $6,170 for February and $3,390 for September. Gulf and Bay 107D, the only unit in the group that sleeps 8, comes to about $12,340 and $8,645. Each condo also lists a condo association or application fee of $100 to $150.
How the season moves the price
All five tables follow a similar pattern. Prices climb in December, peak in February and March, and drop from May through November. The Inlet 39 goes from $90 a night for August to November 2026 to $125 in December, $150 in January, $195 in February and March, $135 in April and $100 from May 2027. Fishermans Haven 201 goes from $140 in December to $233 in January and $260 in February.
- January and February fill first. Tortuga 203 A asks for 55 nights in January 2027 and 54 in February, so a single winter month is not an option there.
- Some units barely move. Island Reef 204A on Turtle Beach charges $185 a night in September and $240 in February, while The Inlet 39 nearly doubles.
- Rate periods change on the first of most months, so a stay from mid-February to mid-March mixes two rates. Ask the manager for a quote on your exact dates.
The 13% tax and the six-month line
Sarasota County charges a 6% tourist development tax on rentals of six months or less, on top of 7% state sales tax, according to the Sarasota County Tax Collector. The tax also applies to fees included in the rent, such as cleaning and pet fees. A one-month, two-month or full-winter stay is taxed the whole way through.
A bona fide written lease for continuous residence longer than six months is exempt under Florida Statutes section 212.03(4). One Siesta Key home on srq.rentals is set up that way: the upstairs apartment between Siesta Beach and Siesta Village, a 2-bedroom, 1-bath unit the host lists at about $2,400 a month plus electric, partially furnished, with a 183-night minimum and tenant screening.
Why so many Siesta Key rentals are monthly
Much of Siesta Key is in unincorporated Sarasota County. The county's rental guide says leases in single-family (RSF) zoning must be at least 30 days. Residential multi-family (RMF) property on the barrier islands, including Siesta Key, may rent for less than 30 days. Condo associations and managers can set their own minimums on top of the zoning rule, and the units above all ask for at least 27 nights.
A portion of the island lies inside the City of Sarasota, according to the city's coastal islands plan, and the city sets its own rules. If a listing is in the city portion, ask the host which rules apply. Our Siesta Key rental rules page has the details.
How to book a month on Siesta Key
- Pick the month before the condo. Your dates decide the price more than the building does.
- Ask what the monthly total includes: electric, internet, parking and the association fee.
- For winter 2027, ask about minimum stays now. Tortuga 203 A already requires close to two months in January and February.
- If nothing fits, post your dates and budget on our housing request board and local hosts can reach out.
Frequently asked questions
How much does a monthly rental on Siesta Key cost?
For five 2-bedroom condos with published rate tables, 30 nights in September 2027 runs $3,000 to $7,650 in rent and the 28 nights of February 2027 run $5,460 to $10,920. Add 13% tax and the manager's fees.
What is the cheapest month to rent on Siesta Key?
In the rate tables we checked, May through November is the low season. The Inlet 39 charges $90 a night from August to November 2026 and $100 from May 2027, against $195 in February and March 2027.
Do I pay tax on a two-month Siesta Key rental?
Yes. Sarasota County charges 6% tourist development tax plus 7% sales tax (6% state and 1% county surtax) on rentals of six months or less, 13% in total. A bona fide written lease for continuous residence longer than six months is exempt.
Is there a 30-day minimum on Siesta Key?
In single-family (RSF) zoning in unincorporated Sarasota County, leases must be at least 30 days. Multi-family (RMF) property on the barrier islands, including Siesta Key, may rent for less, though condo associations and managers often set their own minimums.
When should I book a winter month on Siesta Key?
Early. February is the most expensive month in all five tables we checked (tied with March at The Inlet 39), and Tortuga 203 A already requires 55 nights in January and 54 in February 2027.