Redington Beach sits right next door to where I live in Madeira Beach, close enough that I have watched it change firsthand. For years I told investors that Redington Beach was off the table for true short-term rentals, because its residential single-family homes were effectively locked into long stays. That changed in October 2025. The town adopted Ordinance 2025-02, which finally opened the door to registered short-term rentals in its residential districts, and it quietly created one of the most distinctive rules on the whole coast.
So here is the honest answer to which town is the better buy: Redington Beach is now a real, quieter single-family STR option with the lowest occupancy cap on the beach, while Madeira Beach remains the walkable, condo-heavy, John's Pass powerhouse with more guests, more parking, and more to do on foot. Neither is wrong. The mistake is buying one while expecting the other.
"For years I steered STR buyers away from Redington Beach because the rules simply did not allow it. That changed in October 2025, and now it is one of the most interesting emerging single-family STR markets on the Gulf Beaches. But the eight-guest cap and three-vehicle limit mean the right property matters more here than almost anywhere else on this coast."
Can You Legally Run a Short-Term Rental in Redington Beach, Florida?
Yes, as of October 1, 2025. The Town of Redington Beach adopted Ordinance 2025-02, creating a formal vacation rental registration program for residential Districts 2 and 3, where single-family homes are located. Before this change, short-term rentals of single-family homes under 181 days were treated as a prohibited transient use in those districts. Owners must register annually, hold a Florida DBPR transient public lodging license, remit state and county taxes, obtain a town business tax receipt, and maintain a 24/7 responsible-person contact. (Source: Town of Redington Beach, Ordinance 2025-02)
Madeira Beach takes a different shape. Short-term rentals there are generally permitted in the C-1 and C-2 commercial districts and the John's Pass overlay, while most single-family R-1 and medium-density R-2 residential neighborhoods restrict or prohibit stays under 30 days. That is why Madeira Beach's STR inventory skews heavily toward condos and condo-hotels near the beach and the Pass, while Redington Beach's opportunity is in single-family residential homes. (The Offer Sheet)
| Requirement | Redington Beach | Madeira Beach |
|---|---|---|
| STR ordinance | Ordinance 2025-02, effective Oct 1, 2025 | City zoning code, C-1/C-2/John's Pass overlay |
| Eligible property types | Single-family homes in Districts 2 and 3 | Condos and condo-hotels in commercial and tourist zones; most R-1 residential homes excluded |
| Annual registration | Required, one per property, valid one year | Pinellas County Certificate of Use required |
| Florida DBPR license | Required | Required |
| 24/7 responsible-person contact | Required | Required under Pinellas County rules |
| Florida sales tax (7%) | Required | Required |
| Pinellas County TDT (6%) | Required | Required |
| Combined tax rate | 13% | 13% |
Important for Redington Beach buyers: The ordinance is effective October 1, 2025, which means enforcement patterns and registration workflows are still new. Confirm all current registration steps with the Town of Redington Beach directly before closing, and verify the specific property address is within District 2 or 3. One block can make a difference on these narrow barrier islands.
What Is the Maximum Number of Guests Allowed in a Redington Beach Vacation Rental?
Redington Beach caps vacation rental occupancy at two guests per bedroom with a hard maximum of eight people total, the lowest cap on this stretch of the Pinellas Gulf Beaches. No additional common-area guests are allowed beyond the bedroom count. The property may also have no more than three vehicles at any time, and no on-street parking by guests is permitted. Madeira Beach follows the Pinellas County standard of two per bedroom plus up to two in a common area, capped at 10 total guests. (Sources: Town of Redington Beach, Ordinance 2025-02; Pinellas County Government)
| Occupancy Factor | Redington Beach | Madeira Beach |
|---|---|---|
| Per-bedroom limit | 2 per bedroom | 2 per bedroom |
| Common-area extra guests | None | Up to 2 additional |
| Hard maximum guests | 8 people total | 10 people total |
| Vehicle limit on property | 3 vehicles maximum | 1 off-street space per 3 occupants |
| On-street guest parking | Not permitted | Varies by street and zone |
| 4-bedroom income ceiling | 8 guests max | 10 guests max |
Here is what that two-guest difference actually means for your income. A four-bedroom home in Madeira Beach can sleep 10 guests. The same four-bedroom in Redington Beach tops out at eight. For larger groups and family reunions, that gap costs you a tier of bookings and a higher nightly rate. Run the occupancy math before you run the price math on any property in either town.
"The three-vehicle cap in Redington Beach is just as important as the eight-guest cap. I walk buyers through a parking audit before they make an offer. A home with a two-car driveway and a narrow side yard is not a three-car property, no matter how much you want it to be. That single detail shapes every family reunion booking you will ever take."
How Far Is the Beach from a Vacation Rental in Redington Beach vs. Madeira Beach?
Madeira Beach is the more walkable of the two towns, anchored by John's Pass Village and Boardwalk with 100+ shops, restaurants, and attractions within easy reach of beachfront condos. Redington Beach is a quiet, almost entirely residential town spanning roughly 10 blocks along Gulf Boulevard, with six public beach access points and limited public parking; the walk from a specific home to the nearest access point varies significantly by address and is the single most important factor in a Redington Beach listing's nightly rate and occupancy. (Sources: Town of Redington Beach; Tampa Bay Beaches Chamber of Commerce)
In Redington Beach, the distance from the front door to the sand is not a nice-to-have detail in your listing, it is the headline. Public parking is limited and many side streets are permit-only, so guests rely on the rental's driveway, which the ordinance caps at three vehicles. Because the six beach access points are spread across a 10-block stretch, a two-block walk and a six-block walk are genuinely different investment propositions. I tell buyers to physically walk it before they buy.
| Walkability Factor | Redington Beach | Madeira Beach |
|---|---|---|
| Primary guest draw | Quiet residential beach; natural setting | John's Pass Village, 100+ shops and restaurants |
| Beach access | Six access points spread over 10 blocks; limited public parking | Broader access near John's Pass and Archibald Park; more public parking |
| Guest car dependency | High; guests need a car or LSV to reach dining and nightlife | Low near John's Pass; guests can walk to most amenities |
| New development | Stable low-density residential | Active; new beachfront condo and condo-hotel projects near Archibald Park |
Can Guests Use Golf Carts to Get Around Redington Beach?
Standard golf carts are not currently permitted on Redington Beach streets, because the town has not designated any roads for golf cart use. What is allowed is a street-legal low-speed vehicle (LSV), a cart that is titled, registered, and insured, driven by a licensed driver on roads posted 35 mph or less. A properly registered LSV can travel from Redington Beach south through Madeira Beach to John's Pass without crossing a high-speed bridge. A basic golf cart cannot legally operate on Redington Beach streets. In Madeira Beach, standard street-legal carts have broader access across Gulf Boulevard and most side streets. (Sources: Town of Redington Beach; Beachin' It Cart Rentals)
That distinction matters for your listing. If you plan to market golf cart access as an amenity in Redington Beach, make sure the vehicle you are providing or recommending is a true LSV with title, registration, and insurance, not a basic golf cart. Madeira Beach has the edge on golf cart freedom overall, with nearly all of Gulf Boulevard and its side streets open to street-legal carts.
How Much Does a Vacation Rental Earn in Redington Beach vs. Madeira Beach?
Redington Beach vacation rentals averaged $46,161 in annual gross revenue at 41.6% occupancy and a $379 average daily rate, with 72.7% year-over-year revenue growth across 55 active listings for May 2025 to April 2026 (AirROI 2026). Madeira Beach has a larger and more established STR market, with broad entire-home averages near $33,000 annually, though well-positioned beachfront condos and John's Pass units significantly outperform that average (Awning). The Redington Beach market is newer, with less competition and strong early growth, but the eight-guest occupancy cap limits large-group booking upside.
| Income Metric | Redington Beach | Madeira Beach |
|---|---|---|
| Average annual revenue | $46,161 (AirROI 2026, May 2025–Apr 2026) | ~$33,000 entire-home avg (Awning); beachfront units significantly higher |
| Average daily rate (ADR) | $379 (AirROI 2026) | Higher ceiling on beachfront and John's Pass condo-hotel units |
| Occupancy rate | 41.6% (AirROI 2026) | Varies widely by zone and property type |
| Revenue growth YoY | 72.7% (AirROI 2026) | Established market; growth more incremental |
| Active listings | 55 (AirROI 2026) | Larger market; more competition |
| Market maturity | Emerging; opened Oct 2025 | Established, proven STR track record |
| Property type that performs | Quiet single-family homes, beach-close | Beachfront condos, condo-hotels, John's Pass units |
| Financing options | Conventional, DSCR, portfolio loans | Residential condos: conventional or DSCR; true condo-hotels: portfolio or cash only |
Sources: AirROI 2026; Awning. Averages blend all property types in each market. Top-performing properties exceed these figures in both towns.
On Madeira Beach condo-hotel financing: Madeira Beach has a significant share of true condo-hotel properties, particularly near John's Pass. True condo-hotels do not qualify for conventional or DSCR loans. Portfolio lenders and cash are the primary financing paths. Confirm the legal property designation before assuming standard financing is available.
How Does the Haydon SHORE™ Framework Compare These Two Towns?
The Haydon SHORE™ STR Investment Framework is my five-factor evaluation method for every vacation rental purchase on the Pinellas Gulf Beaches. Here is how Redington Beach and Madeira Beach compare across each factor.
Redington Beach: 55 active listings, emerging market, 72.7% YoY revenue growth (AirROI 2026). Very limited competition in a brand-new STR environment.
Madeira Beach: Larger, established inventory concentrated in condo zones. More competition, especially near John's Pass beachfront.
Redington Beach: Ordinance 2025-02 effective Oct 1, 2025. Districts 2 and 3 only. Annual registration, DBPR license, 8-guest cap, 3-vehicle limit, no on-street parking.
Madeira Beach: C-1/C-2/John's Pass overlay only for STRs. Most residential homes excluded. Condo HOA docs are the gatekeeper on associations.
Redington Beach: $46,161 avg revenue, $379 ADR, 41.6% occupancy (AirROI 2026). 13% combined tax. Conventional and DSCR financing available for single-family homes.
Madeira Beach: Beachfront units can far exceed averages. Condo-hotel financing is portfolio or cash only. 13% combined tax.
Redington Beach: Ordinance is months old; enforcement patterns still settling. Eight-guest cap and 3-vehicle limit leave little room for error. Beach-access distance and parking are primary income risks.
Madeira Beach: Zoning risk is primary. Buying in a restricted residential zone creates a property you cannot legally rent short-term. HOA docs govern condos more strictly than city zoning in some cases.
Redington Beach: Quiet, family repeat-guest profile. Beach-walk distance and LSV access to Madeira Beach are top listing differentiators. First-mover advantage in a newly opened market.
Madeira Beach: Walkable, attraction-driven guest experience. John's Pass proximity commands premium ADR for well-positioned units.
What Are the Biggest Risks of Buying an STR in Redington Beach vs. Madeira Beach?
In Redington Beach, the primary risks are the newness of the ordinance (enforcement patterns still developing), the tight eight-guest and three-vehicle caps that punish properties with poor parking or long beach walks, and the possibility of future rule changes on an ordinance that is less than a year old. In Madeira Beach, the primary risk is zoning: buying a property in a restricted residential zone that cannot legally operate as a short-term rental, and for condos, HOA documents that may impose stricter rules than the city. Both towns carry standard Gulf Beaches risks including flood insurance escalation, the FEMA 50% substantial improvement rule on older structures, and hurricane exposure.
We watched nearby Indian Rocks Beach pass one of the state's strictest STR ordinances in 2023, then move to loosen it amid legal challenges in 2025, proof that rules on these barrier islands are living documents. A Redington Beach ordinance that is less than a year old deserves extra due diligence. (FOX 13 Tampa Bay)
How Do You Decide Between Redington Beach and Madeira Beach for a Short-Term Rental Investment?
Define your guest first. If you want walkable, restaurant-and-nightlife energy with beachfront condo upside, lean Madeira Beach near John's Pass. If you want a quiet, family-style single-family rental with first-mover advantage in a newly opened market, look hard at Redington Beach.
Confirm zoning and registration by exact address. In Redington Beach, verify the home is in District 2 or 3 and walk through the new registration steps with the town directly. In Madeira Beach, confirm the property is in a zone that legally permits short-term rentals; that single step rules out many residential homes.
Run the occupancy math before the price math. Count bedrooms against Redington Beach's eight-guest cap or Madeira Beach's 10-guest cap. That number, not the home's square footage, sets your income ceiling and your target guest profile.
Audit parking honestly in Redington Beach. Redington Beach allows no more than three vehicles on the property and no on-street guest parking. A home without a legitimate three-car driveway is a compliance problem and a booking problem. Confirm the parking plan before you make an offer.
Physically walk the distance to the beach. Measure the walk from the front door to the nearest beach access point, especially in Redington Beach where access points are spread across a 10-block stretch and public parking is limited. That number belongs in the first line of your listing description.
Pull real STR comps, not town averages. Redington Beach's market is brand new, so lean on nearby Madeira Beach and Indian Shores data to set expectations while tracking the emerging Redington Beach performance as listings accumulate. Look at actual performance for comparable properties, not broader city averages.
Budget for flood insurance and the 13% tax before you close. Get a flood insurance quote in writing during your inspection period. Both towns carry full Gulf Beaches flood exposure. The 13% combined tax (7% Florida sales tax plus 6% Pinellas County Tourist Development Tax) applies to every booking in both towns and belongs in your real return calculation.
Frequently Asked Questions: Redington Beach vs. Madeira Beach STR Investment
Can you do short-term rentals in Redington Beach, Florida?
Yes, as of October 1, 2025. Redington Beach Ordinance 2025-02 created a vacation rental registration program for residential Districts 2 and 3. Before this change, short-term rentals of single-family homes under 181 days were prohibited in those districts. Owners must now register annually, hold a Florida DBPR transient public lodging license, remit state and county taxes, and comply with the town's occupancy and parking rules. (Source: Town of Redington Beach, Ordinance 2025-02)
What is the maximum occupancy for a vacation rental in Redington Beach?
Redington Beach caps occupancy at two guests per bedroom with a hard maximum of eight people total, the lowest cap on this stretch of the Pinellas Gulf Beaches. No additional common-area guests are permitted beyond the bedroom count, and the property may have no more than three vehicles at any time with no on-street guest parking allowed. (Source: Town of Redington Beach, Ordinance 2025-02)
Can you do short-term rentals in Madeira Beach?
Yes, but only in the right zones. Madeira Beach permits short-term rentals in the C-1 and C-2 commercial districts and the John's Pass overlay, where stays under 30 days are generally allowed. Most single-family R-1 and R-2 residential neighborhoods restrict or prohibit short-term rentals, which is why most of Madeira Beach's STR inventory is condos and condo-hotels near the beach and the Pass. Always verify by exact address before buying. (Source: The Offer Sheet)
How much does a vacation rental earn in Redington Beach?
Redington Beach vacation rentals averaged $46,161 in annual gross revenue at 41.6% occupancy and a $379 average daily rate, with 72.7% year-over-year revenue growth across 55 active listings for May 2025 to April 2026 (AirROI 2026). Because the Redington Beach STR market only opened to residential properties in October 2025, these figures reflect early-market performance and are likely to shift as more properties enter the market.
Can guests drive golf carts in Redington Beach?
Standard golf carts are not currently permitted on Redington Beach streets because the town has not designated any roads for golf cart use. A titled, registered, and insured low-speed vehicle (LSV) may be operated by a licensed driver on roads posted 35 mph or less, including Gulf Boulevard. A proper LSV can travel from Redington Beach south into Madeira Beach and John's Pass. A basic golf cart cannot legally operate on Redington Beach town streets. (Source: Town of Redington Beach)
Is Redington Beach or Madeira Beach a better first STR investment?
Madeira Beach has the larger, established market with proven income history, higher occupancy ceilings, and strong beachfront condo performance, making it the lower-uncertainty established play. Redington Beach is the quieter, emerging single-family option with 72.7% year-over-year revenue growth (AirROI 2026), less competition, and first-mover potential, but a tighter eight-guest cap, brand-new rules, and the need for careful property selection. The right choice depends on your risk tolerance, target guest, and how much due diligence you are prepared to apply to parking and beach-access distance at the specific address.
Do I need a business license to rent on Airbnb in Redington Beach?
Yes. Operating a short-term vacation rental in Redington Beach requires annual registration under Ordinance 2025-02, a Florida DBPR transient public lodging license, a Redington Beach business tax receipt, and registration for Florida sales tax and Pinellas County Tourist Development Tax. Each registration is property-specific, valid for one year, and must be renewed annually. (Source: Town of Redington Beach, Ordinance 2025-02)
How much tax do I pay on a short-term rental in Redington Beach or Madeira Beach?
Both towns collect the same combined 13% on gross rental receipts: 7% Florida sales tax plus 6% Pinellas County Tourist Development Tax. Returns are due by the 20th of the following month, even in months with no bookings. Platforms like Airbnb and VRBO typically auto-collect and remit the Florida sales tax; owners are responsible for confirming county TDT remittance. (Source: The Offer Sheet)
Is conventional financing available for a short-term rental in Redington Beach?
Yes, for single-family residential homes. Redington Beach STR properties are standard residential homes in Districts 2 and 3, which generally qualify for conventional, DSCR, or portfolio financing. This is a meaningful advantage over Madeira Beach's condo-hotel inventory, where true condo-hotel units are typically ineligible for conventional or DSCR loans and require portfolio lenders or cash. Confirm property type and lender requirements before going under contract.
What happens to my Redington Beach STR if the rules change again?
Redington Beach Ordinance 2025-02 is less than a year old as of mid-2026, which means it carries more regulatory change risk than longer-established ordinances. Florida law provides some preemption protections for existing STR operators if rules change prospectively, but local governments have modified ordinances in ways that affect operations, as seen in nearby Indian Rocks Beach in 2023 and 2025. Buying in a newly opened market requires factoring this risk into your underwriting and maintaining full compliance at all times.
What parking is required for a vacation rental in Redington Beach?
Redington Beach Ordinance 2025-02 limits vacation rental properties to no more than three vehicles on the property at any time. On-street parking by guests is not permitted. A property that cannot physically accommodate three vehicles in its driveway or on its lot without using the street is not compliant. Verify the actual parking capacity of any property, not just the stated number of spaces, before purchasing. (Source: Town of Redington Beach, Ordinance 2025-02)
How does Redington Beach's beach access compare to Madeira Beach for vacation rental guests?
Redington Beach has six public beach access points spread across approximately 10 blocks of Gulf Boulevard, with limited public parking at most access points. The walk from a specific rental home to the nearest access point varies significantly by address and is a primary driver of nightly rate and occupancy in this market. Madeira Beach offers broader public beach access near John's Pass and Archibald Park, with more public parking available for guests, making it less dependent on the specific property's proximity to the sand.
RealTrends Verified 2026: #723 in Florida out of 232,000 Realtors, top 0.3% of Florida Realtors, top 1.5% nationally | 2022 Florida Realtors Associate Realtor of the Year | 2026 Florida Realtors Treasurer | 2026 NAR Regulatory Issues Forum Chair | FastExpert Top 2 in Indian Rocks Beach (2026) | HomeLight "Sells Homes Fast Florida" (2026)
I live in Madeira Beach and have watched Redington Beach open its STR market firsthand in October 2025. I have closed 150+ vacation rental and STR transactions across the Pinellas Gulf Beaches since 2005. I do not manage vacation rentals after the sale. My role is to help you find, evaluate, and close the right property using the Haydon SHORE™ Framework and 20+ years of on-the-ground knowledge of these specific markets. Call me at (727) 710-8035 or reach me through sandbarstosunsets.com.