Holmes Beach, Bradenton Beach and Anna Maria Island, FL Vacation Rental Property Management

Smarter Technology, Bigger Returns

Earn more with a family-founded team that pairs data-driven pricing and proven marketing with genuine island hospitality. Claim your free property analysis and see what your home can really do.

Get Your FREE Property Analysis

Transparent Fees

5.0 Avg Rating

Industry-Low Commission

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Maximize Revenue With Smarter Technology

Click-Based Pricing

Track clicks per available day on your calendar and adjust pricing in real time to capture every dollar of demand.

A/B Split Testing

Test and refine listing photos, titles, and strategy to lock in the highest-performing marketing for your property.

Dynamic Market Data

Leverage deep AMI market insight and local data to keep your listing highly ranked and consistently booked.

Five-Star Stays That Keep Guests Coming Back

Property Care

24/7 Guest Communication

Deliver standout service with a 100% guest response rate guaranteed and under 5 minute average reply time.

Thoughtful Hospitality

Wow every guest with welcome gifts, snack baskets, and guest essentials that earn 5-star reviews.

Design & Staging

Make your property stand out with professional design and staging built to attract premium bookings.

"EasyStay has been AMAZING!! Our home is always spotless, guest reviews stay at 5 stars, and revenue has increased. Their expertise keeps the property highly ranked and consistently earning 5-star reviews. My only regret is not switching to them sooner!"

— Lori F.

"We're seeing consistently higher occupancy and revenue than we were getting from our previous manager. Charlie and Grace are meticulous, detail-oriented, and constantly on the lookout for ways to improve. 5 Stars!"

— Thomas T.

"Charlie's team is on the leading edge and I love that they lean and focus on local market data to help them make decisions that have helped me increase my revenue."

— Jeremey R.

Hands-On Care From a Local Family Team

Maintenance & Cleaning

Keep your home spotless and guest-ready with reliable local housekeeping and proactive upkeep.

Security & Safety

Protect your property with Super Hog identity verification, smart locks, noise sensors, and doorbell cameras.

Owner-Operated Expertise

Partner with Charlie, Grace, and a team carrying decades of combined real estate and hospitality experience.

Partner with a property manager you can trust

Let us show you what EasyStay can do. We’ll take it from here.

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Location

3437 Caravelle St. Sarasota, FL 34240

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