Winding Cypress, Florida Airbnb Market Data 2026: STR Report & Statistics
How much can you earn on Airbnb in Winding Cypress, Florida? Based on AirROI's 2026 dataset (April 2025 – March 2026), the short answer is $16,649 per year — at a $224 nightly rate, 31.9% occupancy, and a $85 RevPAR that reflects moderate rate-to-revenue efficiency with room to optimize.
With just 39 active listings, Winding Cypress is a micro-market where selective demand that rewards strong listing quality and pricing strategy. Supply grew 14.7% over the past year, yet revenue and nightly rates both trended upward — a signal that traveler demand is outpacing new inventory rather than being diluted by it. For hosts, pricing power remains intact even as competition increases.
Regulation is low with minimal registration requirements, pointing to an operator-friendly environment. In a market this size, differentiated listings with strong reviews can capture outsized returns relative to the competition.
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What Are the Key Airbnb Metrics in Winding Cypress?
In Winding Cypress, the headline Airbnb metrics are $16,649 in average annual revenue,31.9% occupancy, $224 ADR, and $85 in RevPAR, and guests book about 53 days in advance.
How Much Do Airbnb Hosts Earn Monthly in Winding Cypress?
Understanding the monthly revenue variations for Airbnb listings in Winding Cypress is key to maximizing your short term rental income potential. Seasonality significantly impacts earnings. Our analysis, based on data from the past 12 months, shows that the peak revenue month for STRs in Winding Cypress is typically February, while June often presents the lowest earnings, highlighting opportunities for strategic pricing adjustments during shoulder and low seasons. Explore the typical Airbnb income in Winding Cypress across different performance tiers:
- Best-in-class properties (Top 10%) achieve $5,936+ monthly, often utilizing dynamic pricing and superior guest experiences.
- Strong performing properties (Top 25%) earn $4,068 or more, indicating effective management and desirable locations/amenities.
- Typical properties (Median) generate around $2,953 per month, representing the average market performance.
- Entry-level properties (Bottom 25%) see earnings around $1,432, often with potential for optimization.
Average Monthly Airbnb Earnings Trend in Winding Cypress
What Is the Monthly Airbnb Occupancy Rate in Winding Cypress?
Maximize your bookings by understanding the Winding Cypress STR occupancy trends. Seasonal demand shifts significantly influence how often properties are booked. Typically, Februarysees the highest demand (peak season occupancy), while June experiences the lowest (low season). Effective strategies, like adjusting minimum stays or offering promotions, can boost occupancy during slower periods. Here's how different property tiers perform in Winding Cypress:
- Best-in-class properties (Top 10%) achieve 76%+ occupancy, indicating high desirability and potentially optimized availability.
- Strong performing properties (Top 25%) maintain 58% or higher occupancy, suggesting good market fit and guest satisfaction.
- Typical properties (Median) have an occupancy rate around 35%.
- Entry-level properties (Bottom 25%) average 20% occupancy, potentially facing higher vacancy.
Average Monthly Occupancy Rate Trend in Winding Cypress
What Is the Average Airbnb Nightly Rate in Winding Cypress?
Effective short term rental pricing strategy in Winding Cypress involves understanding monthly ADR fluctuations. The Average Daily Rate (ADR) for Airbnb in Winding Cypress typically peaks in February and dips lowest during July. Leveraging Airbnb dynamic pricing tools or strategies based on this seasonality can significantly boost revenue. Here's a look at the typical nightly rates achieved:
- Best-in-class properties (Top 10%) command rates of $345+ per night, often due to premium features or locations.
- Strong performing properties (Top 25%) achieve nightly rates of $259 or more.
- Typical properties (Median) charge around $210 per night.
- Entry-level properties (Bottom 25%) earn around $167 per night.
Average Daily Rate (ADR) Trend by Month in Winding Cypress
What Is the RevPAR for Airbnb in Winding Cypress?
RevPAR in Winding Cypress is currently $85. Because RevPAR combines nightly rates with realized occupancy, it is one of the cleanest ways to compare how efficiently listings turn demand into revenue across the market.
- Entry-level properties (Bottom 25%) see $38 RevPAR.
- Typical properties (Median) generate $71 RevPAR.
- Strong performers (Top 25%) earn $122 RevPAR.
- Best-in-class (Top 10%) achieve $164 RevPAR.
Average Monthly RevPAR Trend in Winding Cypress
RevPAR Insights for Winding Cypress
- The average RevPAR in Winding Cypress is $85. This metric combines nightly rates with realized occupancy, making it one of the best single-number indicators of market efficiency.
- The gap between the top 10% ($164) and bottom 25% ($38) is $125, indicating significant performance disparity driven by property quality, pricing strategy, and location.
- RevPAR peaks in Feb and bottoms out in Jun, mirroring the broader seasonal demand pattern and suggesting opportunities for dynamic pricing.
Recommendations for Hosts
- Track your own RevPAR monthly against these Winding Cypress benchmarks. If your RevPAR falls below the median of $71, examine whether low occupancy or low ADR is the primary drag.
- Top-quartile listings achieve $122+ RevPAR through a combination of competitive pricing, strong reviews, and strategic amenities. Target this tier through incremental improvements.
- Use RevPAR rather than revenue alone when comparing properties of different sizes — it normalizes for available nights and gives a more accurate picture of performance.
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When Is the Peak Season for Airbnb in Winding Cypress?
Winding Cypress's peak Airbnb season falls in February, March, January, while the softest stretch is May, June, September. Overall, the market shows highly seasonal trends requiring careful strategy, which should guide pricing, minimum stays, and cash-flow planning.
Peak Season (February, March, January)
- Revenue averages $5,984 per month
- Occupancy rates average 52.4%
- Daily rates average $277
Shoulder Season
- Revenue averages $2,379 per month
- Occupancy maintains around 37.3%
- Daily rates hold near $213
Low Season (May, June, September)
- Revenue drops to average $1,644 per month
- Occupancy decreases to average 30.0%
- Daily rates adjust to average $195
Seasonality Insights for Winding Cypress
- Airbnb seasonality in Winding Cypress is pronounced. Revenue swings sharply between peak and low months, which means pricing strategy, minimum-stay settings, and cash reserves all need to account for extended slower periods.
- During the high season, the absolute peak month showcases Winding Cypress's highest earning potential, with monthly revenues climbing to $8,704, occupancy reaching 68.9%, and ADRs peaking at $284.
- Conversely, the slowest single month marks the market's lowest point — revenue may dip to $1,515, occupancy could drop to 26.3%, and ADRs may adjust to $192.
- Lower occupancy paired with meaningful seasonality means hosts in Winding Cypress need to maximize every peak-season booking and seriously consider whether off-season pricing adjustments or minimum-stay changes can capture incremental revenue.
Seasonal Strategies for Maximizing Profit
- Peak Season: Maximize revenue through premium pricing and potentially longer minimum stays. Ensure high availability and consider tightening cancellation policies to reduce last-minute gaps.
- Low Season: Offer competitive pricing, extended-stay discounts, and flexible cancellation policies. Target off-season travelers like remote workers, budget-conscious guests, and travelers with flexible schedules.
- Shoulder Seasons: Implement dynamic pricing that bridges peak and low rates. Target weekend travelers, local events, and business visitors. Slightly more flexible terms than peak season can help maintain occupancy without deep discounting.
- In a highly seasonal market like Winding Cypress, building a cash reserve during the top months is essential for covering fixed costs during the slow period. Automated pricing tools can help capture demand shifts in real time.
Do You Need a License for Airbnb in Winding Cypress?
Low regulation and minimal registration activity in Winding Cypress, Florida, United States point to an operator-friendly environment. That said, even low-regulation markets may have tax collection requirements, safety standards, or HOA rules that affect short-term rental operations. Always verify the latest short-term rental regulations and Airbnb license requirements directly with local government authorities for Winding Cypress to ensure full compliance before hosting.
(Source: AirROI data, 2026, finding no licensed listings among those analyzed)
What Are the Best Neighborhoods for Airbnb in Winding Cypress?
With a compact short-term rental market, Winding Cypress gives early-mover hosts an advantage in the right neighborhoods. The areas listed below are where guest demand and local attractions converge — a useful lens for investors evaluating whether to enter this market and where to position their listing.
| Neighborhood / Area | Why Host Here? (Target Guests & Appeal) | Key Attractions & Landmarks |
|---|---|---|
| Winding Cypress | A beautiful gated community in Naples with a focus on nature and outdoor activities. Ideal for those seeking a peaceful retreat in sunny Florida, attracting families and retirees alike. | Nature trails, Lakeside clubhouse, Resort-style pool, Fitness center, Tennis courts |
| Naples Beach | One of Florida's most desirable beach destinations known for its beautiful white sand beaches and upscale dining and shopping. A prime area for attracting vacationers wanting a luxurious beach experience. | Naples Pier, Tin City, Clam Pass Park, Fifth Avenue South, Crayton Cove |
| Downtown Naples | The heart of Naples, featuring vibrant shopping, dining, and cultural experiences. Extremely popular with tourists and offers numerous upscale options for accommodation. | Naples Art Association, The Baker Museum, Naples Botanical Garden, The Village Shops on Venetian Bay, Cultural events year-round |
| Marco Island | A popular island destination close to Winding Cypress, known for its beautiful beaches and water activities. It's a favorite spot for families and beach lovers. | South Marco Beach, Tigertail Beach, Marco Island Historical Museum, Cape Romano, Watersports rentals |
| Golden Gate Estates | A vast area with a mix of residential properties and natural landscapes, suitable for guests looking for a more relaxed and private vacation experience. | Big Cypress National Preserve, Picayune Strand State Forest, Local farms and markets, Wildflower preserve |
| Vanderbilt Beach | A sought-after beach area known for upscale living and beautiful sunsets. Excellent for vacation rentals that cater to beachgoers. | Vanderbilt Beach Park, Delnor-Wiggins Pass State Park, Tennis facilities, Water sports rentals, Dining options by the beach |
| Pelican Bay | An upscale community that offers high-end homes and direct access to beautiful beaches. Attractive to those looking for a luxury stay. | Pelican Bay Beach, Artis—Naples, The Commons, Nearby shopping and dining, Nature preserves |
| Lely Resort | A luxury community known for its golf courses and resort-style amenities. Attractive for vacationers looking for leisure and relaxation. | Lely Resort Golf and Country Club, The Players Club and Spa, Nature trails, Community events, Swimming pools |
With 8 distinct neighborhoods showing meaningful short-term rental activity, Winding Cypress offers diversification within a single market. Investors can tailor their strategy — from high-turnover tourist zones to quieter residential areas that attract longer stays and remote workers.
What Types of Properties Are on Airbnb in Winding Cypress?
Room Type Distribution
Property Type Distribution
Market Composition Insights for Winding Cypress
- The Winding Cypress Airbnb market composition is heavily skewed towards Entire Home/Apt listings, which make up 100% of the 39 active rentals. This indicates strong guest preference for privacy and space.
- Looking at the property type distribution in Winding Cypress, Apartment/Condo properties are the most common (61.5%), reflecting the local real estate landscape.
- Houses represent a significant 38.5% portion, catering likely to families or larger groups.
Winding Cypress Airbnb Room Capacity Analysis (2026): Bedroom Distribution
Distribution of Listings by Number of Bedrooms
Room Capacity Insights for Winding Cypress
- The dominant room capacity in Winding Cypress is 2 bedrooms listings, making up 61.5% of the market. This suggests a strong demand for properties suitable for couples or solo travelers.
- Together, 2 bedrooms and 3 bedrooms properties represent 89.7% of the active Airbnb listings in Winding Cypress, indicating a high concentration in these sizes.
- A significant 30.8% of listings offer 3+ bedrooms, catering to larger groups and families seeking more space in Winding Cypress.
Winding Cypress Vacation Rental Guest Capacity Trends (2026)
Distribution of Listings by Guest Capacity
Guest Capacity Insights for Winding Cypress
- The most common guest capacity trend in Winding Cypress vacation rentals is listings accommodating 6 guests (46.2%). This suggests the primary traveler segment is likely larger groups.
- Properties designed for 6 guests and 4 guests dominate the Winding Cypress STR market, accounting for 77.0% of listings.
- 61.6% of properties accommodate 6+ guests, serving the market segment for larger families or group travel in Winding Cypress.
- On average, properties in Winding Cypress are equipped to host 5.5 guests.
How Do Listings in Winding Cypress Compare on Quality?
Listing quality in Winding Cypress can be approximated through presentation depth, bedroom count, and how often hosts disclose exact locations. These signals show how professionally the local supply base is merchandised.
Listing Quality Insights for Winding Cypress
- At 33.4 photos per listing on average, Winding Cypress hosts invest well in visual presentation. Listings with 20+ photos consistently outperform in search ranking and conversion.
- 20.5% of listings show their exact location. Lower disclosure rates can increase booking hesitation — guests want to know exactly where they are staying.
Recommendations for Hosts
- Enable exact location if possible — it removes a common source of guest uncertainty and can improve your listing's position in map-based searches.
- Use these quality indicators as a self-audit checklist. Listings that exceed the Winding Cypress averages across all three metrics are better positioned for premium pricing.
What Amenities Do Airbnb Guests Expect in Winding Cypress?
Amenity Prevalence
Amenity Insights for Winding Cypress
- Essential amenities in Winding Cypress that guests expect include: Air conditioning, Free parking on premises, Wifi, Pool, Kitchen, Washer, Smoke alarm, Dryer, TV. Lacking these (any) could significantly impact bookings.
- Popular amenities like Hangers are common but not universal. Offering these can provide a competitive edge.
Recommendations for Hosts
- Ensure your listing includes all essential amenities for Winding Cypress: Air conditioning, Free parking on premises, Wifi, Pool, Kitchen, Washer, Smoke alarm, Dryer, TV.
- Prioritize adding missing essentials: Air conditioning, Free parking on premises, Smoke alarm, Dryer, TV.
- Consider adding popular differentiators like Hangers to increase appeal.
- Highlight unique or less common amenities you offer (e.g., hot tub, dedicated workspace, EV charger) in your listing description and photos.
- Regularly check competitor amenities in Winding Cypress to stay competitive.
Which Airbnb Amenities Boost Revenue in Winding Cypress?
Not every amenity matters equally. This table focuses on the amenities most associated with higher revenue in Winding Cypress, which makes it more useful for prioritizing upgrades than a simple popularity list alone.
| Amenity | Prevalence | Revenue With | Revenue Without | Revenue Uplift |
|---|---|---|---|---|
Fire extinguisher | 84.6% | $18,692 | $5,415 | 245.2% |
Elevator | 28.2% | $29,924 | $11,434 | 161.7% |
Pack ’n play/Travel crib | 17.9% | $32,092 | $13,271 | 141.8% |
Hot tub | 64.1% | $21,037 | $8,814 | 138.7% |
Clothing storage | 71.8% | $19,807 | $8,612 | 130.0% |
Exterior security cameras on property | 15.4% | $30,963 | $14,047 | 120.4% |
First aid kit | 71.8% | $19,466 | $9,479 | 105.4% |
Long term stays allowed | 74.4% | $19,150 | $9,399 | 103.7% |
Bathtub | 71.8% | $19,341 | $9,797 | 97.4% |
Pets allowed | 15.4% | $27,261 | $14,720 | 85.2% |
Revenue Impact Insights for Winding Cypress
- Fire extinguisher tops the revenue impact list with a 245.2% uplift — listings with this amenity earn $18,692 vs. $5,415 without it.
- Fire extinguisher — while widespread — still correlate with meaningful revenue gains, making it table stakes rather than true differentiators.
Recommendations for Hosts
- Focus your upgrade budget on amenities in the top half of this table. Below-median amenities may improve guest experience but contribute less to revenue growth.
- Highlight revenue-impacting amenities prominently in your listing title, photos, and description — guests can't value what they don't notice.
Dive Deeper: Advanced Winding Cypress STR Market Data (2026)
Ready to unlock more insights? AirROI provides access to advanced metrics and comprehensive Airbnb data for Winding Cypress. Explore detailed analytics beyond this report to refine your investment strategy, optimize pricing, and maximize your vacation rental profits.
Explore Advanced MetricsWinding Cypress Airbnb Guest Demographics & Profile Analysis (2026)
Guest Profile Summary for Winding Cypress
- The typical guest profile for Airbnb in Winding Cypress consists of primarily domestic travelers (77%), often arriving from nearby Toronto, typically belonging to the Post-2000s (Gen Z/Alpha) group (50%), primarily speaking English or Spanish.
- Domestic travelers account for 77.0% of guests.
- Key international markets include United States (77%) and Canada (8.2%).
- Top languages spoken are English (76%) followed by Spanish (12%).
- A significant demographic segment is the Post-2000s (Gen Z/Alpha) group, representing 50% of guests.
Recommendations for Hosts
- Target domestic marketing efforts towards travelers from Toronto and Kentville.
- Tailor amenities and listing descriptions to appeal to the dominant Post-2000s (Gen Z/Alpha) demographic (e.g., highlight fast WiFi, smart home features, local guides).
- Highlight unique local experiences or amenities relevant to the primary guest profile.
- Consider seasonal promotions aligned with peak travel times for key origin markets.
What Are Airbnb Guest Ratings in Winding Cypress?
Listings in Winding Cypress average 4.91 out of 5 overall, with about 14.9 reviews per active listing and 25.6% of listings carrying the Guest Favorite badge.
Rating Breakdown by Category
Guest Rating Insights for Winding Cypress
- With an overall rating of 4.91, Winding Cypress listings meet an exceptionally high bar. Guests consistently report strong satisfaction, which drives repeat bookings and referral traffic.
- The strongest subcategory is Communication (4.94), while Value (4.84) trails behind — a useful signal for hosts looking to prioritize upgrades.
- 25.6% of listings carry the Guest Favorite badge, a strong trust signal that can meaningfully lift click-through and booking rates.
Recommendations for Hosts
- Focus improvement efforts on Value — even small gains in the weakest subcategory can lift overall ratings and search ranking.
- Encourage guests to leave reviews after checkout. Listings with more reviews rank higher in search results and convert browsers into bookers more effectively.
- With only 25.6% of listings earning Guest Favorite status, hosts who consistently exceed expectations have a clear competitive advantage.
Winding Cypress Airbnb Booking Patterns (2026): Available vs. Booked Days
Available Days Distribution
Booked Days Distribution
Booking Pattern Insights for Winding Cypress
- The most common availability pattern in Winding Cypress falls within the 271-366 days range, representing 69.2% of listings. This suggests many properties have significant open periods on their calendars.
- Approximately 92.3% of listings show high availability (181+ days open annually), indicating potential for increased bookings or specific owner usage patterns.
- For booked days, the 1-30 days range is most frequent in Winding Cypress (35.9%), reflecting common guest stay durations or potential owner blocking patterns.
- A notable 7.7% of properties secure long booking periods (181+ days booked per year), highlighting successful long-term rental strategies or significant owner usage.
How Far in Advance Do Guests Book Airbnb in Winding Cypress?
Average Booking Lead Time by Month
Booking Lead Time Insights for Winding Cypress
- The overall average booking lead time for vacation rentals in Winding Cypress is 53 days.
- Guests book furthest in advance for stays during March (average 120 days), likely coinciding with peak travel demand or local events.
- The shortest booking windows occur for stays in September (average 25 days), indicating more last-minute travel plans during this time.
- Seasonally, Spring (91 days avg.) sees the longest lead times, while Summer (32 days avg.) has the shortest, reflecting typical travel planning cycles.
Recommendations for Hosts
- Use the overall average lead time (53 days) as a baseline for your pricing and availability strategy in Winding Cypress.
- For March stays, consider implementing length-of-stay discounts or slightly higher rates for bookings made less than 120 days out to capitalize on advance planning.
- Target marketing efforts for the Spring season well in advance (at least 91 days) to capture early planners.
- Monitor your own booking lead times against these Winding Cypress averages to identify opportunities for dynamic pricing adjustments.
What Is the Average Length of Stay for Airbnb in Winding Cypress?
Guests in Winding Cypress stay about 8.5 nights on average, generating roughly 314 reservations and 8.3 bookings per listing in the latest AirROI dataset. The most common check-in time is 4:00 PM and check-out is 10:00 AM.
Monthly Length of Stay in Winding Cypress
Check-in Time Distribution
Check-out Time Distribution
Stay Pattern Insights for Winding Cypress
- Longer stays mean fewer turnovers and lower cleaning costs per revenue dollar. This pattern also opens the door to monthly discount strategies that attract remote workers and extended-stay travelers.
- Stay lengths peak in Feb (15.2 nights) and shorten in May (6.2 nights). Adjust minimum-night requirements seasonally to match.
Recommendations for Hosts
- Leverage the longer-stay pattern by offering weekly discounts — even 5-10% off can convert browsing into bookings for guests considering an extended stay.
- Set your check-in time to match or beat the market standard of 4:00 PM. Offering early check-in flexibility can be a low-cost differentiator.
- Monitor length-of-stay seasonality to adjust minimum-night requirements — longer minimums during peak periods maximize revenue while shorter minimums fill gaps in shoulder seasons.
Winding Cypress Airbnb Minimum Stay Requirements Analysis
Distribution of Listings by Minimum Night Requirement
1 Night
4 listings
10.3% of total
3 Nights
1 listings
2.6% of total
4-6 Nights
10 listings
25.6% of total
7-29 Nights
16 listings
41% of total
30+ Nights
8 listings
20.5% of total
Key Insights
- The most prevalent minimum stay requirement in Winding Cypress is 7-29 Nights, adopted by 41% of listings. This highlights the market's preference for shorter, flexible bookings.
- Very short stays (1-2 nights) are less common (10.3%), suggesting hosts prefer slightly longer bookings to optimize turnover.
- A significant segment (20.5%) caters to monthly stays (30+ nights) in Winding Cypress, pointing to opportunities in the extended-stay market.
Recommendations
- Align with the market by considering a 7-29 Nights minimum stay, as 41% of Winding Cypress hosts use this setting.
- If feasible, allowing 1-night stays, especially midweek or during low season, could capture last-minute bookings, as only 10.3% currently do.
- Explore offering discounts for stays of 30+ nights to attract the 20.5% of the market seeking extended stays.
- Adjust minimum nights based on seasonality – potentially shorter during low season and longer during peak demand periods in Winding Cypress.
Winding Cypress Airbnb Cancellation Policy Trends Analysis (2026)
Super Strict 30 Days
1 listings
2.6% of total
Limited
1 listings
2.6% of total
Super Strict 60 Days
1 listings
2.6% of total
Moderate
6 listings
15.4% of total
Firm
18 listings
46.2% of total
Strict
12 listings
30.8% of total
Cancellation Policy Insights for Winding Cypress
- The prevailing Airbnb cancellation policy trend in Winding Cypress is Firm, used by 46.2% of listings.
- A majority (77.0%) of hosts in Winding Cypress utilize Firm or Strict policies, indicating a market where hosts prioritize booking security.
Recommendations for Hosts
- Consider adopting a Firm policy to align with the 46.2% market standard in Winding Cypress.
- With 30.8% using Strict terms, this is a viable option in Winding Cypress, particularly for high-value properties or during peak demand periods.
- Regularly review your cancellation policy against competitors and market demand shifts in Winding Cypress.
How Much Are Airbnb Cleaning Fees in Winding Cypress?
Cleaning fees in Winding Cypress are meaningful operating levers, not just pass-through charges. What matters most is how often hosts charge them, how high they run relative to market norms, and how large a share of gross revenue they consume.
Cleaning Fee Insights for Winding Cypress
- About 66.7% of Winding Cypress listings charge a cleaning fee — a mixed market where some hosts absorb the cost into nightly rates while others break it out.
- The gap between the average ($1,676) and median ($250) cleaning fee indicates some high-end properties are pulling the average up considerably.
- Cleaning fees represent 6.5% of gross revenue on average — a modest component of the overall booking price.
Recommendations for Hosts
- Price your cleaning fee competitively against the Winding Cypress median of $250. Fees significantly above market norms can deter bookings, especially for shorter stays.
- Monitor competitor cleaning fees regularly. Airbnb's search algorithm factors in total price, so a well-calibrated cleaning fee can improve your listing's ranking.
What Do the Top Airbnb Listings in Winding Cypress Look Like?
Benchmark your potential! Explore examples of top-performing Airbnb properties in Winding Cypressbased on Trailing Twelve Month (TTM) revenue. Analyze their characteristics, revenue, occupancy rate, and ADR to understand what drives success in this market.
Coral Falls Lely 2b/2b(South Naples) 1st floor
Entire Place • 2 bedrooms
Luxe Top-Floor Condo in Beautiful Lely Resort
Entire Place • 2 bedrooms
Fully Renovated Naples, FL Condo at Lely Resort
Entire Place • 2 bedrooms
5* Star Coral Falls, in Lely, Naples Florida
Entire Place • 2 bedrooms
Stylish Top-Floor w/ Elevator 2 Bed/2 Bath Condo!
Entire Place • 2 bedrooms
Immaculate Naples Condo! Close to Marco Island!
Entire Place • 2 bedrooms
Note: Performance varies based on location, size, amenities, seasonality, and management quality. Data reflects the past 12 months.
Who Are the Top Airbnb Hosts in Winding Cypress?
Learn from the best! This table showcases top-performing Airbnb hosts in Winding Cypress based on the number of properties managed and estimated total revenue over the past year. Analyze their scale and performance metrics.
| Host Name | Properties | Grossing Revenue | Stay Reviews | Avg Rating |
|---|---|---|---|---|
| Evolve | 3 | $90,221 | 61 | 4.88/5.0 |
| Chris | 1 | $59,230 | 22 | 4.86/5.0 |
| Sarah | 1 | $55,081 | 13 | 5.00/5.0 |
| Stefanie | 2 | $52,405 | 16 | 5.00/5.0 |
| Roompicks By Victoria | 3 | $51,928 | 169 | 4.75/5.0 |
| Constance | 1 | $37,072 | 43 | 4.95/5.0 |
| Angela | 1 | $36,051 | 18 | 4.94/5.0 |
| Chris | 1 | $34,257 | 15 | 4.93/5.0 |
| Melissa | 1 | $33,071 | 5 | 5.00/5.0 |
| Denis | 1 | $29,288 | 13 | 5.00/5.0 |
Analyzing the strategies of top hosts, such as their property selection, pricing, and guest communication, can offer valuable lessons for optimizing your own Airbnb operations in Winding Cypress.
Who Are the Airbnb Hosts in Winding Cypress?
Winding Cypress has a relatively balanced host base.
Host Profile Insights for Winding Cypress
- A 30.8% Superhost share is healthy — enough experienced operators to anchor quality without making the market impenetrable for newcomers.
- 20.5% of listings are professionally managed, reflecting a market still dominated by individual hosts.
- 0.0% of listings have Instant Book enabled. Lower Instant Book adoption means many guests must request approval, which can slow conversions.
- 38.5% of listings use Airbnb's simplified pricing (host-only fee), where the host pays the entire platform service fee and the guest sees one all-in price with no separate Airbnb service charge. Lower adoption suggests a market with more independent hosts managing listings directly through Airbnb.
Recommendations for Hosts
- Earning Superhost status can significantly improve search ranking and guest trust. Focus on maintaining high response rates, low cancellations, and strong reviews.
- Consider enabling Instant Book — it reduces booking friction and Airbnb's algorithm tends to favor Instant Book listings in search results.
- With 33.3% cohosted listings, there may be a growing local market for property management services.
- Benchmark your host metrics against these Winding Cypress averages regularly and adjust your hosting strategy based on what top performers do differently.
Top Professional Management Companies in Winding Cypress
These are the highest-grossing professional property management operations in Winding Cypress, ranked by total revenue across their portfolio. Their performance metrics offer a benchmark for what institutional-level hosting looks like in this market.
| Company | Listings | Revenue | ADR | Occ. | Rating |
|---|---|---|---|---|---|
| Evolve | 3 | $90,221 | $202 | 48.7% | 4.88/5 |
| Roompicks By Victoria | 3 | $51,928 | $316 | 32.8% | 4.75/5 |
| OneSeventyTwo | 1 | $9,881 | $310 | 19.7% | 5.00/5 |
| Neil | 1 | $6,193 | $218 | 22.1% | 4.80/5 |
Management Company Insights for Winding Cypress
- The leading management company, Evolve, operates 3 listings with $90,221 in gross revenue — a useful benchmark for what scale looks like in Winding Cypress.
- Top managers average 2 properties each, suggesting professional management in Winding Cypress still operates at a relatively boutique scale.
- Professionally managed listings in the top tier average 4.86/5 in guest ratings — demonstrating that scale and quality can coexist.
Recommendations
- Study how top management companies price, position, and maintain their portfolios — their ADR and occupancy rates reflect strategies refined across dozens of listings.
- If you're considering hiring a property manager, compare their portfolio performance against these benchmarks before committing.
How Does Winding Cypress's Airbnb Market Compare to Nearby Cities?
How does the Winding Cypress Airbnb market stack up against its neighbors? Compare key performance metrics like average monthly revenue, ADR, and occupancy rates in surrounding areas to understand the broader regional STR landscape.
Compared with Anna Maria, Winding Cypress has 21 percentage points lower occupancy and about $547 lower ADR. That helps frame whether this market is winning more on demand, pricing, or both.
| Market | Active Properties | Monthly Revenue | Daily Rate | Avg. Occupancy |
|---|---|---|---|---|
| Sailfish Point | 18 | $17,017 | $1719.65 | 47% |
| Bal Harbour Village | 37 | $9,174 | $854.18 | 35% |
| Anna Maria | 56 | $8,842 | $771.83 | 53% |
| Anna Maria island | 590 | $8,049 | $867.67 | 40% |
| Lake Clarke Shores | 24 | $6,740 | $538.69 | 44% |
| Boca Grande | 30 | $6,310 | $812.97 | 37% |
| Lighthouse Point | 69 | $6,094 | $511.21 | 47% |
| North Bay Village | 116 | $5,792 | $558.10 | 42% |
| Captiva | 297 | $5,450 | $689.36 | 36% |
| Bradenton Beach | 126 | $5,273 | $540.64 | 42% |
Frequently Asked Questions About Airbnb in Winding Cypress
These quick answers summarize the most common investor and operator questions using AirROI's latest market data for Winding Cypress.
How much do Airbnb hosts make in Winding Cypress?
Winding Cypress hosts earn about $16,649 per year on average, with an average nightly rate of $224 and RevPAR of $85. Those figures describe the typical revenue environment for active listings in Winding Cypress, Florida, not the ceiling for the best operators. Source: AirROI 2026 data, Winding Cypress market, April 2025 to March 2026.
What is the average Airbnb occupancy rate in Winding Cypress?
The average Airbnb occupancy rate in Winding Cypress is 31.9%. February is the strongest month and June is the softest, so hosts should expect demand to move meaningfully throughout the year rather than stay flat.
What is the average Airbnb daily rate in Winding Cypress?
Listings in Winding Cypress average $224 per night. The broader pricing spread also matters: lower-performing listings cluster closer to the lower quartiles, while premium homes can price materially above the city average when demand spikes or listing quality stands out.
How many Airbnb listings are active in Winding Cypress?
Winding Cypress currently has about 39 active Airbnb listings in AirROI's market dataset. That supply count helps explain how competitive the market is, how much depth there is for benchmarking, and whether the market behaves like a niche destination or a scaled urban market.
How strict are short-term rental regulations in Winding Cypress?
AirROI currently classifies the short-term rental regulation level in Winding Cypress as Low. The dataset also shows about 0.0% of listings with registration evidence. That is a market signal, not legal advice, so hosts should still confirm current licensing and compliance rules locally before listing.
What is the RevPAR for Airbnb in Winding Cypress?
RevPAR in Winding Cypress is about $85. That metric combines pricing and occupancy into one efficiency number, so it is often a better quick benchmark than ADR alone when investors want to compare how well listings convert nightly rates into realized revenue.
Is Airbnb profitable in Winding Cypress?
Occupancy of 31.9% means Winding Cypress is a more selective market. Profitability is achievable but requires careful cost management, premium positioning, or targeting longer stays to reduce turnover. Average annual revenue is $16,649, but individual returns depend on property type, location within the city, and the host's operating efficiency.
How far in advance do guests book Airbnb in Winding Cypress?
The average booking lead time in Winding Cypress is about 53 days — a longer planning horizon typical of destination or vacation markets where travelers book well in advance. Hosts who understand their market's booking cadence can adjust minimum stays and pricing windows accordingly.
What are the best neighborhoods for Airbnb in Winding Cypress?
Based on AirROI's analysis, some of the top neighborhoods for short-term rentals in Winding Cypress include Winding Cypress, Naples Beach, Downtown Naples. Each area attracts different guest profiles — from business travelers to leisure visitors — so the best location depends on the property type and target audience a host is aiming for. See the full neighborhood breakdown above.
What type of property performs best on Airbnb in Winding Cypress?
entire_home listings make up 100.0% of the active supply in Winding Cypress. The most common configuration does not always mean the most profitable — operators who identify underserved property types or bedroom counts can sometimes outperform the market average by filling a gap in local supply.
How does Winding Cypress compare to nearby Airbnb markets?
Among neighboring markets, Sailfish Point posts $204,199 in average annual revenue with 47.0% occupancy, compared to Winding Cypress's $16,649 and 31.9%. Comparing nearby markets helps investors understand whether a destination's performance reflects local demand or broader regional trends.
What is the average length of stay in Winding Cypress?
The average Airbnb stay length in Winding Cypress is about 8.5 nights. That matters for turnover, cleaning operations, and pricing strategy because shorter stays increase changeovers while longer stays can smooth occupancy and reduce operational friction.
What is the average Airbnb guest rating in Winding Cypress?
Airbnb listings in Winding Cypress average 4.91 out of 5 overall. About 25.6% of listings carry the guest favorite badge, which suggests a meaningful share of inventory is competing on review quality rather than price alone.
Which amenities boost Airbnb revenue in Winding Cypress?
Fire extinguisher and Elevator are among the strongest revenue-linked amenities in Winding Cypress. In AirROI's latest dataset, listings with these amenities outperform those without on average revenue, which makes amenities analysis useful for prioritizing investment and listing upgrades.
Do Airbnb hosts charge cleaning fees in Winding Cypress?
Yes. About 66.7% of active Airbnb listings in Winding Cypress charge a cleaning fee, and the average fee is $1,676. The more important operating benchmark is how much of gross revenue that fee consumes, not just the absolute dollar amount.
What percentage of Airbnb hosts are Superhosts in Winding Cypress?
At 30.8%, there is a healthy mix of experienced and newer hosts — earning Superhost status can still provide a meaningful visibility boost.
About AirROI Market Data
AirROI tracks over 20 million properties across 190+ countries and maintains 15+ years of historical performance data, making it one of the deepest Airbnb and STR intelligence platforms available. The analytics pipeline aggregates listing-level data monthly — revenue, occupancy, nightly rates, RevPAR, guest demographics, booking patterns, and competitive supply — so investors and operators can benchmark any market against its own history and against neighboring destinations.
Real estate investors, property managers, financial institutions, hedge funds, tourism boards, hospitality consultants, tech platforms, and academic researchers rely on AirROI data to underwrite acquisitions, optimize pricing, model macro trends, and conduct peer-reviewed research. Data is available through in-depth market reports like this one and the Airbnb API with 22 endpoints and an Airbnb MCP Server for AI agents.
AirROI proprietary analytics as of 2026-03-31. Metrics reflect trailing twelve-month aggregates from active listings. Revenue figures are market averages, not projections. Neighborhood descriptions are AI-generated and reviewed for accuracy. For full methodology, see the data methodology page.