Indian Shores Condos & Properties Allowing Short-Term Rentals
Every building on this list has been confirmed through StellarMLS closed sales data to have sold units with rental periods of one month or less. This is the only publicly available Indian Shores STR building list split by Gulf-front and Intracoastal, cross-referenced with actual transaction records, and updated monthly.
Sand Castle I, II, and III, Indian Shores. Three of the 38 Gulf-front condo buildings confirmed STR-eligible through StellarMLS. The Sand Castle complex is among the most recognized investment-grade buildings on the Pinellas Gulf Beaches. Photo: Cyndee Haydon, Future Home Realty.
Gulf-Front Condo Buildings
38 Buildings · Even Addresses · Gulf Blvd West SideDirect Gulf of Mexico views and beach access. Even-numbered addresses on Gulf Boulevard. Command 25 to 50 percent higher nightly rates than comparable Intracoastal units. VE or AE flood zone designation typical. Stronger long-term appreciation track record. 38 confirmed STR-eligible buildings.
Left: Sand Castle I pool and beach access, one of the most photographed investment buildings on the Pinellas Gulf Beaches. Right: Sunset pier at Beach Cottage Condo Phase I at 18400 Gulf Blvd, the southernmost confirmed Gulf-front STR building in Indian Shores. Photos: Cyndee Haydon, Future Home Realty.
"The Gulf-front buildings in Indian Shores are among the most consistent performers in my STR investment portfolio of clients. What makes them different from other Gulf Beach markets is the combination of wider beach, limited public parking, and buildings that were designed with the view in mind. Guests rebook year after year. That is not an accident. That is the product of a community that never over-developed."Cyndee Haydon | Top-Ranked Vacation Rental Agent, Indian Shores, FL | 150+ STR Transactions | FastExpert Top 2 (2026) | Future Home Realty
Intracoastal Condo Buildings
19 Buildings · Odd Addresses · Gulf Blvd East SideIntracoastal Waterway views, sunrise orientation. Lower entry price than comparable Gulf-front. Many buildings have Gulf views from upper floors. Deeded boat dock availability in several buildings. Potentially better storm surge protection. 19 confirmed STR-eligible buildings.
Intracoastal-side condo pool with the Gulf of Mexico visible in the background. Upper-floor Intracoastal units in Indian Shores often capture Gulf views that surprise buyers who assume the Gulf-front side has a monopoly on the scenery. Photo: Cyndee Haydon, Future Home Realty.
"The Intracoastal side of Indian Shores is one of the most undervalued STR investment opportunities in Pinellas County. The price gap between Gulf-front and Intracoastal has narrowed significantly over the past five years because investors figured out what the locals already knew: upper-floor Intracoastal units see both the sunrise and the Gulf. Some of the strongest yielding properties in my client base are on the east side of Gulf Boulevard."Cyndee Haydon | Best STR Investment Agent, Pinellas Gulf Beaches | Indian Shores Short-Term Rental Specialist | Future Home Realty
STR-Eligible Townhome Communities
10 Communities · Fee Simple · Chapter 720 HOAFee-simple townhomes governed by Florida Statute Chapter 720 (HOA law) rather than Chapter 718 (condo law). Typically offer more square footage, private garages, and multi-level living. Several communities have pools. Strong family-group guest appeal. 10 confirmed STR-eligible communities.
Before You Write an Offer: STR Condo Due Diligence Checklist
- Declaration of Condominium: Confirm rental restrictions. Look for minimum stay requirements, owner waiting periods, and rental caps.
- All amendments: Restrictions added after the original Declaration may override what the Declaration allows.
- Rules and Regulations: HOA-level rules can impose limits that the Declaration does not. Both documents must be clean.
- Meeting minutes (12 months): Identifies pending special assessments, disputes, or proposed rule changes that could affect STR eligibility.
- SIRS and Milestone Inspection status: Required under Florida condo law. Buildings not in compliance face financing restrictions.
- Master insurance policy: Confirms coverage type (bare walls vs all-in). Determines your HO-6 and flood supplement requirements.
- FEMA flood zone and elevation certificate: Verify at msc.fema.gov. VE zone buildings have the highest insurance exposure.
- Rental history of the unit: Request actual Airbnb/VRBO earnings records. Do not underwrite from projections alone.
Ready to buy or sell an Indian Shores STR?
Cyndee Haydon reviews every one of these documents before any offer. 150+ vacation rental transactions. FastExpert Top 2 in Indian Shores (2026). Call or text (727) 710-8035 or visit sandbarstosunsets.com.
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Source: StellarMLS closed sales data, cross-referenced May 2026. This list covers properties with confirmed closed sales at rental periods of 1 month or less. It is updated monthly. It does not constitute legal advice. Always verify current governing documents before purchasing. Cyndee Haydon, Broker Associate, Future Home Realty | Sandbars to Sunsets Team | (727) 710-8035 | sandbarstosunsets.com. Future Home Realty. Equal Housing Opportunity.