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Is Clearwater Beach or Madeira Beach the Better Short-Term Rental Investment in 2026?

A regulation-first, data-cited comparison of nightly-rental legality, AirDNA and AirROI 2026 revenue, Florida condo reserve law (SB 4-D and SIRS), lifestyle drivers (Pier 60 vs John's Pass Village), and risk between two of the Pinellas Gulf Beaches' most-searched markets, applied to the Haydon SHORE™ STR Investment Framework by a Broker Associate who has closed 150+ vacation rental and STR transactions on this corridor.

Last Updated: August 6, 2026

Can You Short-Term Rent in Clearwater Beach vs Madeira Beach?

In Clearwater Beach, rentals of less than 31 days or one calendar month are prohibited in every residential zone (LMDR, LDR, ILR, MDR) under Clearwater Community Development Code Sections 1-104.B and 3-919. Legal nightly and weekly vacation rentals in Clearwater Beach are limited to Tourist (T) and Resort Facilities High (RFH) districts, condo-hotels such as Sandpearl and Hyatt, and roughly 31 pre-2007 grandfathered residential properties. In Madeira Beach, short-term rentals under 30 days are permitted with no city minimum stay in four zones (R-3 Medium Density Multifamily, C-1 John's Pass Village Activity Center, C-3 Retail Commercial, and C-4 Marine Commercial) under Madeira Beach Ordinance No. 2018-01, codified as Section 110-843, and prohibited in R-1 Single-Family Residential (6-month minimum) and R-2 Low Density Multifamily (3-month minimum).

For a short-term rental investor, that zoning fork changes almost everything downstream: the size of the buyable universe, the price of entry, financing options, insurance stack, and expected revenue per property. Clearwater Beach is a tightly gated STR market where compliant inventory is scarce and premium priced. Madeira Beach is a middle-path market where large portions of the city (the John's Pass corridor, medium-density multifamily, and commercial zones along Gulf Boulevard) permit nightly rentals, while single-family and low-density multifamily neighborhoods do not.

Because most content on the open web treats Madeira Beach as a single zoning entity and Clearwater Beach as a single tourism entity, this comparison focuses on which specific inventory is actually rentable in each city. Data sources: City of Clearwater Code Compliance (verified July 2026), Madeira Beach Municipal Code Chapter 110 as updated by Ordinances 2024-09 and 2024-12 (adopted September 11, 2024), Madeira Beach Community Development Department at (727) 391-9951, AirROI 2026 (May 2025 through April 2026), and StellarMLS closed-sale records compiled by Cyndee Haydon.

Short Verdict

Madeira Beach is the stronger choice for buyers who want a legal nightly Airbnb or VRBO in a condo or townhome inside the John's Pass Village Activity Center (new C-1 zone) or in R-3 multifamily along Gulf Boulevard, with 25.8 percent AirROI YoY revenue growth in 2026 signaling active demand recovery. Clearwater Beach is the better fit for buyers with the capital and patience to acquire a condo-hotel unit at Sandpearl or Hyatt, or a Tourist/Resort-zoned property that can legally rent nightly, and who want the #3 Florida beach ranking and Pier 60 sunset-crowd positioning at premium ADR. The decision comes down to two variables: which zone the property sits in, and whether the buyer wants John's Pass boardwalk product or Clearwater Beach premium-resort product.

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Sandbars to Sunsets Team with Future Home Realty was featured in 700+ media placements reaching 200M+ readers for expertise on Pinellas Gulf Beach vacation rental investment. RealTrends Verified 2026, #723 in Florida out of 232,000 Realtors, top 1.5% of residential professionals nationwide.

Key Takeaways: Clearwater Beach vs Madeira Beach STR Investment

Why Does the Legal Framework Matter More Than the Beach Ranking?

Clearwater Beach ranks #3 in Florida on the USA Today 10Best 2026 list, and Madeira Beach anchors the middle of the 26-mile Gulf Beach corridor around John's Pass Village and Boardwalk, one of Florida's most-visited waterfront villages. Beach ranking and destination brand favor Clearwater. Buyable STR inventory and mid-market entry price favor Madeira Beach. Both are true at the same time. For an investor, the fork is not "which beach is better," it is "which market lets me legally operate the property I can afford to buy."

Most competing content on this comparison, including the lifestyle guides currently indexed in Google's top three results, describes the difference in vibes (energy vs. village, resort vs. boardwalk) and stops short of naming the ordinances, statutes, and revenue benchmarks a buyer actually needs to underwrite the deal. This page names them, sources them, and dates them.

What Does the Lifestyle and Walkability Feel Like in Each Market?

Clearwater Beach delivers a resort corridor along three miles of white sand, anchored by Pier 60, the nightly Sunsets at Pier 60 festival (4:00 to 8:00 PM daily, weather permitting), the Beach Walk promenade, and a dense waterfront hotel and restaurant cluster (Sandpearl, Hyatt, Marriott Sand Key). Madeira Beach delivers a boardwalk-driven waterfront village anchored by John's Pass Village and Boardwalk at 12901 Gulf Blvd (open 7 a.m. to 10 p.m. daily), roughly 2.5 miles of Gulf shoreline, and a golf-cart corridor connecting Madeira to Redington Shores and Indian Shores on 35 mph roads. Both are connected to each other and the rest of the corridor by PSTA Route 555, the Suncoast Beach Trolley.

Clearwater Beach (Pier 60 anchor). Nationally recognized destination with hotel-scale amenity packages: pools, fitness centers, concierge service, structured parking, and an activated public realm from Pier 60 through the Beach Walk. Guests can arrive Thursday night and not touch the car until Sunday. Pier 60 hosts the Sunsets at Pier 60 daily festival with artisans, street performers, and live music every night the weather cooperates, per the official Sunsets at Pier 60 program. That energy is the product. Peak season, holiday weekends, and major events run at high volume, which supports higher blended ADR but also higher turnover and higher wear on the unit.

Madeira Beach (John's Pass anchor). Madeira Beach is a compact Gulf-front city (roughly 4,200 population, 2.5 miles of shoreline) whose entire tourism engine centers on John's Pass Village and Boardwalk, a historic waterfront district of restaurants, shops, dolphin-tour operators, deep-sea fishing charters, and the boardwalk itself at 12901 Gulf Boulevard, phone (727) 394-0756, open daily 7 a.m. to 10 p.m. John's Pass draws corridor-wide guest traffic without a hotel-tower skyline: the buildings are two- to four-story mixed-use, and the retail is largely local, not chain. The Madeira Beach golf-cart corridor extends the walkable footprint north to Redington Shores and south to Treasure Island on roads posted 35 mph or less. For a guest who wants a boardwalk, a fishing charter, and dolphin tours steps from the rental, Madeira Beach is the product. For an investor, that walkable-boardwalk demand is what supports 25.8 percent YoY AirROI revenue growth in 2026.

How Do Pier 60 and John's Pass Village Differ as STR Demand Drivers?

Pier 60 drives a hotel-adjacent, nightly-festival demand pattern that peaks in the two hours before sunset and disperses into Clearwater Beach's resort corridor. John's Pass Village drives a boardwalk-and-boat demand pattern spread across the full 7 a.m. to 10 p.m. operating day, with dolphin-tour, deep-sea-fishing, and dining traffic feeding rental demand in the surrounding R-3 and C-1 zones. Both are corridor-scale demand anchors, but they route guest spending differently.

Pier 60 (Clearwater Beach). Pier 60 Park sits at the base of Clearwater Beach's three-mile shoreline and hosts the Sunsets at Pier 60 daily festival two hours before sunset until two hours after (typically 4:00 to 8:00 PM), per the official Sunsets at Pier 60 program and Visit St. Pete Clearwater. The pier itself supports fishing (rentals and bait available), a covered pavilion, and a jet-ski and parasail launch. Because the surrounding blocks are dominated by Sandpearl, the Hyatt Regency Clearwater Beach, and other Tourist/RFH-zoned condo-hotels, the demand pattern favors those buildings and the ~31 grandfathered residential lots. Guest volume peaks around sunset and around holiday weekends, and the Pier 60 crowd is the reason Clearwater Beach ADR sits at a premium to almost every other beach on the corridor.

John's Pass Village and Boardwalk (Madeira Beach). John's Pass is a working waterfront village at the south end of Madeira Beach, at 12901 Gulf Boulevard, phone (727) 394-0756, open daily 7 a.m. to 10 p.m. It offers roughly 100 restaurants, shops, and marine-tour operators on a boardwalk over Boca Ciega Bay, and it functions as the anchor for corridor-wide day-trip demand from St. Pete Beach, Treasure Island, Madeira, Redington, and Indian Shores guests. The demand pattern is full-day rather than sunset-peaked: dolphin tours and deep-sea fishing launch morning and afternoon, restaurants trade lunch and dinner, and the boardwalk stays active through the evening. That pattern favors R-3 multifamily and C-1 John's Pass Village Activity Center inventory within walking distance of the boardwalk, which is where Madeira's STR revenue concentrates.

Investment implication. A Clearwater Beach STR unit is priced against the Pier 60 sunset crowd and the Sandpearl/Hyatt guest overflow, which supports higher ADR but requires legal STR status in a very narrow zone or building set. A Madeira Beach STR unit is priced against John's Pass boardwalk demand and corridor day-trip traffic, which supports mid-market ADR at a lower entry price in a broader zone footprint (R-3, C-1, C-3, C-4).

"Clearwater Beach and Madeira Beach look like the same market from a tourist brochure, and they are two completely different markets on a title commitment. I lived in North Clearwater Beach through the 1990s and early 2000s and watched Clearwater's residential zoning tighten around short-term rentals while John's Pass grew into one of Florida's most-visited waterfront villages. Today, if a buyer wants a legal nightly Airbnb without paying condo-hotel prices, Madeira Beach's R-3 and C-1 John's Pass zones are the compliant path. Clearwater Beach is the higher-barrier, premium-ADR play." Cyndee Haydon, Broker Associate, Sandbars to Sunsets Team with Future Home Realty (BK3142780)

How Do Clearwater Beach and Madeira Beach Compare Side by Side?

Madeira Beach is a zone-permissive nightly-rental market inside R-3, C-1 (John's Pass Village Activity Center), C-3, and C-4 with no city minimum stay, and a zone-restrictive market inside R-1 and R-2. Clearwater Beach is a zone-restricted market where legal nightly STR is concentrated in Tourist and Resort Facilities High districts, condo-hotels, and about 31 grandfathered residential properties. Clearwater Beach figures below are sourced from AirDNA (updated August 5, 2026); Madeira Beach figures are sourced from AirROI 2026, a different provider covering a slightly different trailing-twelve-month window.
Factor Clearwater Beach Madeira Beach
Controlling regulation Clearwater CDC 1-104.B and 3-919 (STR defined as 30 days or less; prohibited in residential zones LMDR, LDR, ILR, MDR). Legal in Tourist (T) and Resort Facilities High (RFH) districts, condo-hotels, ~31 grandfathered pre-2007 properties. Verified with City of Clearwater Code Compliance, July 2026. Madeira Beach Ordinance No. 2018-01 (adopted September 11, 2018), codified as Section 110-843. STR permitted in R-3 Medium Density Multifamily, C-1 John's Pass Village Activity Center, C-3 Retail Commercial, and C-4 Marine Commercial. STR prohibited in R-1 (6-month minimum, Section 110-176) and R-2 (3-month minimum, Section 110-201). Ordinance 2024-09 replaced the prior C-1 Tourist Commercial District with C-1 John's Pass Village Activity Center on September 11, 2024. Ordinance 2024-12 repealed the former C-2 John's Pass Marine Commercial District on the same date.
Minimum stay 31 days or one calendar month, whichever is less, in all residential zones. No minimum in T, RFH, condo-hotels, and grandfathered properties. Sand Key condos typically 2-week or monthly minimums depending on the building declaration. No city minimum stay in R-3, C-1, C-3, C-4 (nightly permitted). 3-month minimum in R-2. 6-month minimum in R-1. Individual condo declarations may impose stricter minimums than the ordinance, so verify the current declaration on the specific building.
Typical annual revenue $41,200 (AirDNA, updated Aug 5, 2026; blended figure includes condo-hotel inventory, down 5.3% YoY) $35,963 (AirROI 2026, up 25.8% YoY)
Average Daily Rate (ADR) $361 (AirDNA, up 2.1% YoY) Not yet published by AirROI for Madeira Beach
Occupancy 59 percent (AirDNA, down 8.8% YoY) Not yet published by AirROI for Madeira Beach
Active listings 1,900 (AirDNA, down 9.2% YoY) Not yet published by AirROI for Madeira Beach
YoY revenue growth -5.3 percent (AirDNA) +25.8 percent (AirROI 2026)
Buyable STR-eligible inventory Narrow: condo-hotels (e.g., Sandpearl, Hyatt), Tourist/RFH-zoned buildings, ~31 grandfathered residential properties. Moderate: R-3 medium-density multifamily along Gulf Boulevard, C-1 John's Pass Village Activity Center inventory (including the six Character Districts: Boardwalk, John's Pass Resort, Low Intensity Mixed Use, and others created by Ordinance 2024-09), plus C-3 Retail Commercial and C-4 Marine Commercial parcels. R-1 single-family and R-2 low-density multifamily are STR-restricted.
Signature demand anchor Pier 60 and the nightly Sunsets at Pier 60 festival (4:00 to 8:00 PM daily, weather permitting), plus the Beach Walk promenade and hotel-corridor amenity density. John's Pass Village and Boardwalk at 12901 Gulf Blvd, open daily 7 a.m. to 10 p.m., with roughly 100 restaurants, shops, dolphin tours, and deep-sea fishing charters on the boardwalk over Boca Ciega Bay.
Ideal investor profile Higher-capital buyer targeting premium ADR, brand-name Clearwater Beach positioning, and condo-hotel or Tourist-zoned inventory. Comfortable with portfolio or specialty financing on condo-hotels. Cash-flow-focused buyer wanting a compliant nightly rental in a John's Pass-adjacent condo or R-3 multifamily unit, with conventional or DSCR financing on standard product.
Tax stack (combined) 13 percent (7 percent Florida sales tax + 6 percent Pinellas Tourist Development Tax). 13 percent (7 percent Florida sales tax + 6 percent Pinellas Tourist Development Tax).
2026 beach ranking #3 Florida beach (USA Today 10Best 2026). Not ranked in USA Today 10Best 2026 top Florida list. Anchored by John's Pass Village, one of Florida's most-visited waterfront destinations, and adjacent to Treasure Island (#2 Florida on USA Today 10Best 2026) across John's Pass Bridge.

What Five Questions Does Every Serious Buyer Ask Before Choosing Between These Two Markets?

Most Clearwater vs. Madeira lifestyle guides pose lifestyle questions and answer them qualitatively. Here are the same five decision questions answered with the ordinance, statute, and data a buyer actually uses to close.

1. Would you use a Clearwater Beach condo-hotel personally, or does a Madeira Beach John's Pass condo with no owner-use cap fit better?

Match the vehicle to the use. In Clearwater Beach, a condo-hotel unit at Sandpearl or Hyatt legally rents nightly and often imposes owner-use caps (14 to 30 days per year is common). In Madeira Beach under Ordinance No. 2018-01, an R-3 or C-1 (John's Pass Village Activity Center) condo can be used personally without a use cap and still legally rent nightly, as long as the specific condo declaration matches the ordinance.

2. How does Clearwater Beach's Pier 60 crowd volume compare to Madeira Beach's John's Pass boardwalk traffic?

Clearwater Beach absorbs national holiday-weekend and event volume (Pier 60 sunset draws crowds nightly, hotel-corridor volume peaks year-round). Madeira Beach receives high John's Pass day-trip traffic during operating hours (7 a.m. to 10 p.m.), but rental blocks along Gulf Boulevard step back from that intensity a few streets north. Higher volume in Clearwater supports higher ADR and turnover, which raises operational cost and wear. Madeira's steadier boardwalk-driven pattern supports lower turnover-cost economics.

3. Is STR income the primary goal in Clearwater Beach's zoned inventory or Madeira Beach's R-3 and C-1 zones?

If income is primary, verify the specific unit's legal STR status before offer, and do not work backward from a projected income number. In Clearwater Beach, that means confirming Tourist (T) or Resort Facilities High (RFH) zoning, condo-hotel status, or grandfathered-property confirmation from City of Clearwater Code Compliance. In Madeira Beach, it means confirming the parcel sits in R-3, C-1, C-3, or C-4, and pulling the current City of Madeira Beach Vacation Rental Restriction Map and the Community Development Department at (727) 391-9951.

4. Have you reviewed SB 4-D and SIRS compliance for a condo in Clearwater Beach or Madeira Beach?

For any condo in either market, request the current Milestone Inspection (required for 3+ story buildings at 30 years, per Florida SB 4-D) and the Structural Integrity Reserve Study (SIRS) under Florida Statute §718.112(2)(g). As of budgets adopted on or after December 31, 2024, associations can no longer waive or reduce SIRS-component reserves. Read both reports plus 24 months of board minutes before offer.

5. Are flood, wind, and insurance costs comparable in Clearwater Beach and Madeira Beach?

Both markets sit on Pinellas County barrier islands in FEMA flood zones with meaningful post-Hurricane Helene exposure. Madeira Beach single-family and multifamily typically quote $2,500 to $8,000+ per year for flood coverage and $3,000 to $15,000+ for wind (Sandbars to Sunsets 2026 client quote comparisons). Clearwater Beach premiums vary widely between low-rise residential and high-rise condo-hotel construction. Always quote the specific property, not a corridor average, through FEMA NFIP and a private wind carrier.

How Does Florida's Condo Reserve Legislation Affect Both Markets?

Florida SB 4-D (2022) and follow-on legislation impose two overlapping requirements on all condo buildings of three or more habitable stories: a Milestone Inspection at 30 years of age and a Structural Integrity Reserve Study (SIRS) every 10 years under §718.112(2)(g). Since December 31, 2024, unit owners can no longer vote to waive or reduce SIRS-component reserves. Both Clearwater Beach and Madeira Beach have older Gulf-front and John's Pass-adjacent inventory that must comply.

Under Florida Statute §718.503, revised effective July 1, 2025, a buyer's condo-document review period is 7 business days (previously 3). Use those days. Read the Milestone Inspection report, the SIRS, the current-year budget, the last two years of financials, and 24 months of board minutes for the words milestone, SIRS, reserve, assessment, and loan. A building past its statutory Milestone deadline with no completed inspection is a red flag. A building with a SIRS-funding gap disclosed in minutes is a special-assessment risk that must be priced into the offer.

Practical impact on this comparison: Clearwater Beach's older Sand Key high-rises and Madeira Beach's older Gulf-front R-3 buildings and John's Pass area condos both fall under SB 4-D. Clearwater Beach's newer condo-hotels (Sandpearl 2007, several 2010s+ product) and Madeira's newer C-1 John's Pass Village Activity Center product carry less near-term Milestone exposure but still require SIRS.

Which Market Produces Higher STR Revenue Per Property?

Clearwater Beach reports the higher blended average at $41,200 versus Madeira Beach's $35,963, but the trend lines run opposite directions: Madeira Beach revenue grew 25.8 percent year-over-year (AirROI 2026) while Clearwater Beach revenue fell 5.3 percent (AirDNA, updated August 5, 2026). Clearwater's figure is also inflated by condo-hotel inventory that most investors cannot finance conventionally.

Madeira Beach's 25.8 percent year-over-year revenue growth (AirROI 2026) tracks the corridor's post-Hurricane Helene demand recovery, John's Pass boardwalk foot traffic normalizing, and the compliance shakeout as more R-3 and C-1 owners registered legal STRs following the 2024 zoning update (Ordinances 2024-09 and 2024-12). Clearwater Beach's AirDNA numbers include Sandpearl, Hyatt, and other condo-hotel product where nightly rates run several multiples of a typical Gulf Beach condo, alongside a broader listing base where occupancy (-8.8% YoY) and active supply (-9.2% YoY) both contracted even as ADR rose 2.1 percent, a signal of softening demand rather than a pricing opportunity. That is a real revenue tier, but it is a different asset class with different financing (portfolio or cash), different insurance requirements, and different owner-use rules. When you strip out condo-hotels, the residual pool of legally rentable Clearwater Beach residential properties is small: the ~31 grandfathered lots plus Tourist and Resort Facilities High-zoned buildings.

A zone-level revenue breakout for Madeira Beach (R-3 vs. C-1 John's Pass Village Activity Center vs. C-3/C-4 commercial) and a property-type breakout for Clearwater Beach (condo-hotel vs. Tourist/RFH-zoned condo vs. grandfathered single-family) both await StellarMLS exports that do not exist yet for either city. Until then, treat the town-wide AirROI and AirDNA averages as market-wide signals, not per-zone or per-asset-class projections.

Which Market Carries More Regulatory and Insurance Risk?

Clearwater Beach carries higher regulatory risk because legal STR status depends on zoning classification or grandfathered status that can be challenged, verified only through City of Clearwater Code Compliance, and cannot be assumed from an MLS listing. Madeira Beach carries moderate regulatory risk because the C-1 John's Pass Village Activity Center zone was created in September 2024 (Ordinance 2024-09) and the former C-2 was repealed the same day (Ordinance 2024-12), so any pre-September-2024 zoning reference on a listing or old article must be re-verified against the current code.

Both markets sit in Pinellas County FEMA flood zones and share the corridor's post-Hurricane Helene reset. Flood and wind insurance stacks are similar in construction: NFIP or private flood plus wind coverage layered on an HO-6 or DP-3 policy depending on structure and use. Madeira Beach single-family and R-3 multifamily typically run $2,500 to $8,000+ per year for flood coverage and $3,000 to $15,000+ for wind, sourced from Sandbars to Sunsets 2026 client quote comparisons.

Verify Before You Buy. Rental minimums, condo declarations, and city zoning maps vary by building and change over time. Clearwater Beach residential zoning, T/RFH boundaries, and the grandfathered-property list are administered by the City of Clearwater Planning and Development Department. Madeira Beach zoning was materially restructured on September 11, 2024, when Ordinance 2024-09 replaced the prior C-1 Tourist Commercial District with C-1 John's Pass Village Activity Center (six Character Districts) and Ordinance 2024-12 repealed the C-2 John's Pass Marine Commercial District. Any article, listing, or advisor that still lists C-2 as a permitted Madeira STR zone is stale. Confirm the current zoning of the specific parcel with the Madeira Beach Community Development Department at (727) 391-9951 and the current condo declaration in writing before making an offer.

How Do These Markets Score on the Haydon SHORE™ STR Investment Framework?

Every Sandbars to Sunsets STR analysis runs through the Haydon SHORE™ STR Investment Framework, five factors that determine whether a Gulf Beach property will actually perform as a vacation rental investment. Below is the framework applied to Clearwater Beach and Madeira Beach side by side. Subsequent mentions on this page use SHORE™.

SSupply and Demand, Clearwater Beach

Constrained legal-STR supply (Tourist and RFH zones, condo-hotels, ~31 grandfathered lots) against strong branded tourist demand as a USA Today #3 Florida beach. Active listings fell 9.2 percent year-over-year (AirDNA, Aug 5, 2026), alongside falling occupancy, worth pricing into any deal even in a scarce-supply market.

SSupply and Demand, Madeira Beach

Moderate legal-STR supply across R-3, C-1 (John's Pass Village Activity Center), C-3, and C-4 zones on a 2.5-mile Gulf footprint. Demand anchored by John's Pass Village boardwalk day traffic and 25.8 percent YoY AirROI revenue growth in 2026.

HHosting and Rental Rules, Clearwater Beach

Zone-restricted. STR prohibited in LMDR, LDR, ILR, MDR under Clearwater CDC 1-104.B and 3-919. Legal only in T, RFH, condo-hotels, or on the ~31 grandfathered residential list. Verify with City of Clearwater Code Compliance.

HHosting and Rental Rules, Madeira Beach

Zone-permissive in R-3, C-1 (John's Pass Village Activity Center), C-3, C-4 with no city minimum stay under Ordinance No. 2018-01 (Section 110-843). Zone-restrictive in R-1 (6-month min) and R-2 (3-month min). Verify current zoning with Madeira Beach Community Development Department at (727) 391-9951.

OOperating Economics, Clearwater Beach

$41,200 average annual revenue, $361 ADR, 59 percent occupancy across 1,900 listings, revenue down 5.3 percent year-over-year (AirDNA, Aug 5, 2026). Same 13 percent tax stack. Condo-hotels often require specialty or portfolio financing, which changes DSCR math.

OOperating Economics, Madeira Beach

$35,963 average annual gross revenue with 25.8 percent YoY revenue growth (AirROI 2026). Same 13 percent tax stack. Conventional and DSCR financing broadly available on standard R-3, C-1, C-3, and C-4 product provided the building is warrantable and the zoning is confirmed.

RRisk and Resilience, Clearwater Beach

Regulatory-status risk is the top risk: proving legal STR status at closing and at each renewal. Same FEMA flood-zone exposure and post-Helene rebuild framework as the rest of the corridor.

RRisk and Resilience, Madeira Beach

Zoning-restructure risk is the top risk: the C-1 John's Pass Village Activity Center is new as of September 11, 2024 (Ordinance 2024-09), and the former C-2 zone was repealed the same day (Ordinance 2024-12). Any parcel described as C-2 in a pre-2024 document is stale. FEMA and post-Helene exposure comparable to Clearwater Beach.

EExperience and Earnings Potential, Clearwater Beach

Premium guest-experience positioning (Sandpearl, Hyatt, Pier 60, Sunsets at Pier 60), higher blended ADR, brand-name search visibility. Best fit for a buyer targeting premium-tier product, not a first STR.

EExperience and Earnings Potential, Madeira Beach

Boardwalk-village guest experience anchored by John's Pass Village and Boardwalk (12901 Gulf Blvd, 7 a.m. to 10 p.m. daily), local restaurants and marine-tour operators, plus a golf-cart-corridor connection to Redington and Indian Shores. Strong fit for a first or second STR investor targeting mid-market cash flow with John's Pass demand.

How Do You Decide Between Clearwater Beach and Madeira Beach?

Decide on legal buyability first, financing second, and revenue third. If you cannot buy inside Clearwater Beach's Tourist/RFH zones, condo-hotel inventory, or ~31-property grandfathered pool, Madeira Beach's R-3 and C-1 (John's Pass Village Activity Center) zones are the compliant path. If you can, and you want brand-name Clearwater positioning at premium ADR, Clearwater Beach fits.
  1. Confirm the property's STR status in writing before offer: for Clearwater Beach, request the zoning classification and, for a residential lot, the grandfathered-property confirmation from City of Clearwater Code Compliance. For Madeira Beach, confirm the parcel sits in R-3, C-1, C-3, or C-4 (not R-1 or R-2) with the Madeira Beach Community Development Department at (727) 391-9951 and the current Vacation Rental Restriction Map at madeirabeachfl.gov.
  2. For any Madeira Beach parcel described in a pre-2024 document as C-1 Tourist Commercial or C-2 John's Pass Marine Commercial, pull the current zoning classification. Ordinance 2024-09 replaced the old C-1 with C-1 John's Pass Village Activity Center on September 11, 2024, and Ordinance 2024-12 repealed C-2 entirely the same day.
  3. Match the market to your financing plan. Condo-hotels in Clearwater Beach typically require portfolio or cash. Standard Madeira Beach R-3 and C-1 condo product typically qualifies for conventional or DSCR loans provided the building is warrantable.
  4. Pull the current condo declaration, bylaws, and amendments for any condo purchase in either market and read the minimum-stay term as recorded, not as remarked in MLS. Individual condo declarations may impose stricter minimums than the city ordinance.
  5. Model the deal with the 13 percent combined tax stack (7 percent Florida sales + 6 percent Pinellas TDT) built in from day one, not netted out later.
  6. Compare AirROI revenue benchmarks side by side, but for Clearwater Beach, verify whether the figure includes condo-hotel inventory before using it as a projection. For Madeira Beach, cross-check the AirROI $35,963 average against a StellarMLS pull of similar-bedroom-count listings inside your target zone (R-3, C-1, C-3, or C-4).
  7. Stress-test the flood and wind insurance stack against 2026 quotes for the specific property, not a corridor average. FEMA exposure is comparable, but per-property premiums vary widely.
  8. Ideally, walk the property with a Realtor who has closed both Clearwater Beach and Madeira Beach STR transactions and can confirm rental legality, zoning classification, and condo declaration terms in the same visit.

Clearwater Beach vs Madeira Beach STR FAQ

Can I legally run an Airbnb in Clearwater Beach in a single-family home?

Only in the ~31 grandfathered pre-2007 residential properties or in Tourist (T) and Resort Facilities High (RFH) zoned lots. All other residential zones (LMDR, LDR, ILR, MDR) prohibit rentals of less than 31 days per Clearwater CDC 1-104.B and 3-919. Verify status with City of Clearwater Code Compliance before purchase.

Can I legally run an Airbnb in Madeira Beach in a single-family home?

No. Madeira Beach single-family residential (R-1) requires a 6-month minimum stay under Section 110-176. STRs under 30 days are permitted in R-3 Medium Density Multifamily, C-1 John's Pass Village Activity Center, C-3 Retail Commercial, and C-4 Marine Commercial under Ordinance No. 2018-01 (Section 110-843), so most legal STR inventory is condo, townhome, or mixed-use rather than detached single-family.

What is the average annual revenue for a vacation rental in Madeira Beach?

$35,963 average annual revenue with 25.8 percent year-over-year revenue growth per AirROI 2026. ADR, occupancy, and active listing counts are not yet published by AirROI for Madeira Beach specifically.

What is the average annual revenue for a vacation rental in Clearwater Beach?

$41,200 average annual revenue at a $361 ADR and 59 percent occupancy across 1,900 active listings, per AirDNA data updated August 5, 2026. This is a blended, market-wide figure that includes condo-hotel inventory, so it overstates what a standard residential or Tourist/RFH-zoned condo produces on its own. Revenue is down 5.3 percent year-over-year.

Why does this page use AirDNA data for Clearwater Beach and AirROI for Madeira Beach?

Madeira Beach and the rest of this site's core cities are benchmarked against AirROI 2026 (May 2025 through April 2026). A verified AirROI dataset for Clearwater Beach was not available at time of publication, so Clearwater Beach figures come from AirDNA (updated August 5, 2026) instead, a different provider covering a slightly different trailing-twelve-month window. Both sources are cited by name and date everywhere they appear so the two are never mixed silently.

Is short-term rental revenue growing or shrinking in Clearwater Beach and Madeira Beach right now?

The two markets are moving in opposite directions. Clearwater Beach STR revenue is down 5.3 percent year-over-year, with occupancy down 8.8 percent and active listings down 9.2 percent even as ADR rose 2.1 percent (AirDNA, updated August 5, 2026). Madeira Beach revenue is up 25.8 percent year-over-year (AirROI 2026), consistent with post-Helene demand recovery and John's Pass foot traffic normalizing.

Should I buy in Clearwater Beach or Madeira Beach for my first short-term rental?

For a first STR, Madeira Beach is often the lower-friction choice: a condo or townhome in R-3, C-1 (John's Pass Village Activity Center), C-3, or C-4 can legally rent nightly under Ordinance No. 2018-01, and conventional or DSCR financing is broadly available. Clearwater Beach fits a second or third STR when you have the capital and financing structure to enter Tourist-zoned, RFH-zoned, condo-hotel, or grandfathered inventory.

What zoning districts allow short-term rentals in Clearwater Beach?

Tourist (T) and Resort Facilities High (RFH) districts, together with condo-hotels and the ~31 grandfathered pre-2007 residential properties. Residential zones LMDR, LDR, ILR, and MDR prohibit rentals of less than 31 days or one calendar month under Clearwater CDC 1-104.B and 3-919 (STR defined as 30 days or less).

What zoning districts allow short-term rentals in Madeira Beach?

R-3 Medium Density Multifamily, C-1 John's Pass Village Activity Center, C-3 Retail Commercial, and C-4 Marine Commercial, with no city minimum stay under Madeira Beach Ordinance No. 2018-01, codified as Section 110-843. R-1 Single-Family Residential requires a 6-month minimum (Section 110-176) and R-2 Low Density Multifamily requires a 3-month minimum (Section 110-201).

What is the C-1 John's Pass Village Activity Center in Madeira Beach?

C-1 John's Pass Village Activity Center is the new mixed-use zoning district that replaced the prior C-1 Tourist Commercial District under Ordinance 2024-09, adopted September 11, 2024. It defines six Character Districts (Boardwalk, John's Pass Resort, Low Intensity Mixed Use, and others) around the John's Pass Village and Boardwalk waterfront, and it permits nightly short-term rentals with no city minimum stay under Section 110-843.

What happened to Madeira Beach's C-2 zoning district for John's Pass?

The former C-2 John's Pass Marine Commercial District was repealed in full by Ordinance 2024-12, adopted September 11, 2024. Any listing, article, or advisor that still references C-2 as a permitted Madeira Beach STR zone is stale. Current permitted STR zones are R-3, C-1, C-3, and C-4 only.

Are Sand Key condos in Clearwater Beach short-term rental friendly?

Sand Key sits within Clearwater's city limits, and most Sand Key condo buildings impose a 2-week or monthly minimum stay under the current condo declaration, not nightly. Rental terms vary building by building and change over time, so always confirm against the current declaration and amendments before offer.

Are condo-hotels in Clearwater Beach a better STR investment than a Madeira Beach C-1 condo?

Condo-hotels such as Sandpearl and Hyatt legally rent nightly and command higher ADR, but typically require portfolio or cash financing and impose owner-use limits. A Madeira Beach condo in a C-1 John's Pass Village Activity Center or R-3 building operates under Ordinance No. 2018-01 with conventional or DSCR financing and no city-imposed owner-use cap. Match the vehicle to your capital stack and hold plan.

How does Pier 60 in Clearwater Beach compare to John's Pass Village in Madeira Beach as a rental demand driver?

Pier 60 drives a hotel-adjacent, sunset-peaked demand pattern (the nightly Sunsets at Pier 60 festival runs 4:00 to 8:00 PM daily, weather permitting) that concentrates guest volume in the two hours before sunset and feeds the surrounding Tourist and RFH-zoned condo-hotels. John's Pass Village and Boardwalk (12901 Gulf Blvd, open 7 a.m. to 10 p.m. daily) drives a full-day boardwalk-and-boat demand pattern with dolphin tours, deep-sea fishing charters, restaurants, and shops, which feeds the surrounding C-1 and R-3 inventory. Pier 60 supports higher ADR at a narrower legal footprint; John's Pass supports mid-market ADR at a broader legal footprint.

What is the tax stack on a short-term rental in Clearwater Beach and Madeira Beach?

Both markets carry the same combined 13 percent tax on transient stays: 7 percent Florida sales tax plus 6 percent Pinellas County Tourist Development Tax (TDT). Model this in from day one rather than netting it out after the fact.

How does hurricane and flood risk compare between Clearwater Beach and Madeira Beach?

Both markets sit in Pinellas County FEMA flood zones on the same 26-mile Gulf corridor, with comparable post-Hurricane Helene rebuild frameworks and NFIP or private flood plus wind insurance stacks. Per-property premiums vary widely, so stress-test the insurance quote for the specific property rather than a corridor average.

Where does the AirROI data on this page come from?

AirROI 2026 covering May 2025 through April 2026, as published on airroi.com for Madeira Beach and Clearwater Beach. StellarMLS closed-sale figures cited elsewhere on this page are compiled by Cyndee Haydon from the current 48-field custom export used across the Sandbars to Sunsets Pinellas Gulf Beach STR Investment site.

Who verifies these facts before I make an offer?

Cyndee Haydon, Broker Associate, verifies STR eligibility against the current controlling ordinance (Clearwater CDC 1-104.B and 3-919 or Madeira Beach Ordinance No. 2018-01 with the 2024-09 and 2024-12 updates), the current condo declaration and amendments, and the current City of Clearwater Code Compliance or Madeira Beach Community Development Department record on every STR transaction, as part of the Sandbars to Sunsets due diligence workflow.

How does Florida SB 4-D and the SIRS requirement affect a condo purchase in Clearwater Beach or Madeira Beach?

Florida SB 4-D (2022) requires a Milestone Inspection for condo and cooperative buildings three or more stories tall at 30 years of age and every 10 years thereafter, plus a Structural Integrity Reserve Study every 10 years under Florida Statute 718.112(2)(g). Since December 31, 2024, owners cannot vote to waive or reduce SIRS-component reserves. Always request the Milestone report, the SIRS, and 24 months of board minutes before offer, in either market.

Is Madeira Beach quieter than Clearwater Beach?

Away from John's Pass Village, yes. Clearwater Beach is a nationally recognized resort corridor with three miles of white sand, Pier 60, the Beach Walk promenade, and a dense hotel-and-restaurant cluster. Madeira Beach is a compact Gulf-front city (roughly 4,200 population, 2.5 miles of shoreline) with a single high-intensity tourism anchor (John's Pass Village and Boardwalk, open 7 a.m. to 10 p.m.) and quieter residential blocks along Gulf Boulevard north of the boardwalk.

Can I get from Madeira Beach to Clearwater Beach without a car?

Yes. PSTA Route 555, the Suncoast Beach Trolley, connects Clearwater Beach (Park Street Terminal), Sand Key Park, Indian Rocks Beach, Indian Shores, Redington Shores, Madeira Beach, John's Pass, Treasure Island, and St. Pete Beach on a single route along Gulf Boulevard. The Madeira Beach golf-cart corridor also links Madeira to Redington Shores and Indian Shores on 35 mph roads.

What financing options work for a Clearwater Beach condo-hotel vs. a Madeira Beach C-1 STR condo?

Clearwater Beach condo-hotels such as Sandpearl and Hyatt typically require portfolio or cash financing because conventional and most DSCR programs exclude condo-hotel classification. Madeira Beach STR-eligible condos in C-1 (John's Pass Village Activity Center) or R-3 typically qualify for conventional loans, DSCR investor loans, or standard second-home financing, provided the building is warrantable and the zoning is confirmed.

Related Resources

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About Cyndee Haydon, Your Gulf Beach STR Investment Realtor

Cyndee Haydon, Clearwater Beach and Madeira Beach Short-Term Rental Investment Expert, Sandbars to Sunsets Team with Future Home Realty

Cyndee Haydon, CRS, ABR, SRS, RENE, RSPS, CLHMS, CIPS, SRES

Clearwater Beach & Madeira Beach STR Investment Expert · Broker Associate, Future Home Realty · BK3142780

RealTrends Verified 2026, #723 in Florida out of 232,000 Realtors, top 1.5% nationally · (727) 710-8035

Cyndee Haydon is Broker Associate with the Sandbars to Sunsets Team with Future Home Realty. She has closed 435+ residential transactions totaling $230M+ in sales since 2005, including 150+ vacation rental and short-term rental transactions and 62 STR-friendly properties sold in the past 5 years, 28 of them above $1M. She has been a Gulf Beaches resident since 1991, lived in North Clearwater Beach through the 1990s and early 2000s, and holds the CRS, ABR, SRS, RENE, RSPS, CLHMS, CIPS, and SRES designations. She is the 2026 Chair of the NAR Regulatory Issues Forum, 2026 Treasurer of Florida Realtors, and past NAR Insurance Committee Chair (2023).

Compare Clearwater Beach and Madeira Beach for Your Next STR Purchase

Tell Cyndee what you are looking for and she will send back a like-for-like analysis with current StellarMLS data and verified regulatory status for each property on your shortlist, including current zoning (Clearwater T/RFH or Madeira R-3/C-1/C-3/C-4) and condo declaration terms.