Did you buy a second home in Old Saybrook that sits empty for most of the year?
It is a place of pride, but have you thought about making it a high-return asset as well?
Waterfront homes, luxury estates, and well-appointed condominiums in Old Saybrook can all be transformed into active income properties with Waystay Luxury Property Management and Real Estate Services.
We manage every aspect, from guest readiness and property care to seamless operations that deliver consistent results.
You enjoy your Old Saybrook property when you wish, while we handle everything else to keep it profitable.

We are Your Luxury Vacation Rentals Specialist
Waystay is dedicated to working with homeowners and estate managers who want to elevate their luxury residences into top-performing vacation rentals.
We manage every aspect with care, ensuring the property is properly optimized, revenue is maximized, guests are consistently satisfied, and the investment continues to perform at its highest potential for long-term success.
Our Suite of Luxury Rental Services
Luxury property management is unlike managing ordinary rentals, as it calls for heightened attention, deeper expertise, and a more personal touch. We know this firsthand because we are owners as well, and we understand how important it is to safeguard both the value of the property and the quality of the guest experience. With that in mind, we take on the responsibility of handling all essential services with the utmost care so that your investment remains protected and your guests receive nothing short of excellence.
- Private Pools, Breathtaking Views - Expert Marketing is the First Step
- Comprehensive Booking and Concierge Services
- Premium Property Maintenance
- Financial Oversight and Legal Compliance
Private Pools, Breathtaking Views – Expert Marketing is the First Step
Marketing is the engine behind successful bookings, and we take a precise approach to ensuring your property is seen by the right audience who appreciates what it has to offer. That includes:- Property listings crafted with search engine optimized descriptions to make sure your home consistently appears in search results.
- High-end photos and cinematic video tours that highlight the property’s luxury amenities and lifestyle appeal, making it more desirable to travelers.
Comprehensive Booking and Concierge Services
Our approach begins with carefully vetting every guest who submits a booking request, including:- Detailed background and credit checks, as well as review of rental history.
- Conversations and interviews conducted before arrival.
- Thorough review of house rules and signed agreements to ensure compliance and security.
- Double-checking all check-in and check-out details to prevent overlapping reservations.
- Verifying extra services with the homeowner before they are confirmed.
- Full-time support and concierge-level care that provides a premium guest experience. We are equipped to arrange special accommodations such as fine dining with private chefs, personal drivers, or other tailored services designed to enhance their stay.
Premium Property Maintenance
Part of keeping your property profitable is ensuring it remains in excellent condition after each guest leaves, which is why our team carries out:- Detailed inspections paired with written reports so you are always aware of the overall property condition and any maintenance requirements.
- Exceptional housekeeping services with full linen management to guarantee that the property is refreshed and disinfected for each new rental period.
Financial Oversight and Legal Compliance
Waystay makes financial oversight a top priority, and our approach to dynamic pricing ensures that your property generates the highest possible revenue.- When luxury rental demand rises in your area, we respond by setting optimized nightly rates that maintain your home’s competitive edge.
- Through data analysis and property-specific strategies, we work to improve both occupancy and revenue, guaranteeing your home remains on a healthy financial path.
- Insurance policies with coverage limits up to one million dollars.
- Execution of repairs and maintenance in strict accordance with local codes.
- Securing the necessary permits and inspections whenever the law requires it during upkeep.
Contact Us Today for a Consultation
Let’s explore how your home in Old Saybrook, whether it is a coastal villa, a private luxury residence, or an elegant retreat, can begin delivering strong income month after month. Learn more about how our curated services can be personalized for your unique property and placed on Old Saybrook’s growing and profitable rental market.
