Your Gateway to Unforgettable StaysWhere we host
At Pierhead Vacations, we believe every getaway should be more than just a trip—it should be an experience to remember. Our diverse portfolio of vacation rental properties spans some of the most exciting destinations in the U.S., offering comfort, convenience, and style for every type of traveler.
1.
Florida
A wide range of properties in some of the Sunshine State’s most sought-after markets:
Daytona Beach – Classic coastal charm and vibrant beachfront living.
Orlando – Family-friendly homes near world-renowned theme parks and attractions.
Fort Myers Beach – Relaxed island vibes and Gulf-front serenity.
Cape Coral – Waterfront living with access to boating, beaches, and endless sunshine.
Daytona Beach
Orlando
Fort Myers Beach
Cape Coral
2.
Chicago, Illinois
Modern city escapes with world-class dining, culture, and entertainment at your doorstep.
Wicker Park
Why Stay With Pierhead Vacations?
We pride ourselves on delivering the highest quality vacation experiences for our guests. From beautifully maintained properties to thoughtful touches that make you feel at home, we go above and beyond to ensure your stay is seamless and stress-free. Whether you’re planning a family vacation, a couples’ retreat, or a solo escape, our homes are designed to provide the perfect balance of comfort and adventure.
RSPS Certification
Aaron May is Resort & Second-Home Property Specialist Certified with the National Association of Realtors!
We are very happy with Aaron and his team! He helped us every step of the way from searching for the perfect locations with excellent potential, to closing the deal alongside local experts and beyond! We now have completed several rounds of real estate deals with his assistance and have been satisfied every time!
- Rachel Ralya, Repeat Client
Book Your Next Vacation
Discover the difference of staying with Pierhead Vacations—where every detail is crafted with care, and every stay is designed to be memorable.