Your Gateway to Unforgettable Stays

Where 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.

Book Our Properties.

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.

  • Rotonda West – Quiet mornings, tee times nearby, and sunsets on the lanai.

  • New Smyrna Beach - New Smyrna Beach is a laid-back surf town where miles of uncrowded beaches, charming local shops, and great dining create the perfect mix of relaxation and adventure. It’s Florida’s best-kept secret—authentic, scenic, and effortlessly cool.

Tall modern beige residential building with balconies, palm trees, and a clear blue sky.
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Daytona Beach

Backyard of a modern house with a swimming pool, hot tub, patio furniture, and lounge chairs under a partly cloudy sky.
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Orlando

Three-story beach house with light green exterior, white trim, two garage doors, and a balcony on the second and third floors. Paved driveway leading to the garage, paved walkway to the front door. Surrounded by palm trees and neighboring houses under a blue sky with clouds.
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Fort Myers Beach

View of a backyard pool overlooking a canal with a thatched-roof dock, palm trees, and houses in the distance under a clear blue sky.
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Cape Coral

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Front of a house with double black doors, white trim, two large palm trees on either side, and a gravel yard.
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Rotonda West

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Small indoor swimming pool with a colorful mural on the wall depicting a beach scene, a woman wearing sunglasses, and tropical elements.
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New Smyrna Beach

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Chicago, Illinois

Modern city escapes with world-class dining, culture, and entertainment at your doorstep.

Outdoor patio area with a fire pit, seating, a dining table, a grill, string lights, and a large tree, enclosed by brick walls and wooden fencing.
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Wicker Park

featured Home

Welcome to The Pelican Tidehouse. This spacious, stylish retreat offers nearly 3,000 sq ft and is just a 2-minute walk to the beach and a short stroll to lively Flagler Ave. With 5 bedrooms, 3 bathrooms, and two living areas, it’s ideal for families, couples, or groups wanting comfort, fun, and plenty of room to relax.

Explore Pelican Tidehouse

The pelican tidehouse

Pelican Tidehouse offers resort-style amenities to elevate your stay, including: A heated pool – with FREE pool heat and a relaxing hot tub, all within a fully screened enclosure. There is also a basketball hoop and a fountain which shoots continuously into the pool!

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.

Why Stay With Pierhead Vacations?

Colorful children's playroom with a castle-themed structure, purple and gold accents, wall murals of mountains and trees, a chandelier, and a mirror.
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Aaron May is Resort & Second-Home Property Specialist Certified with the National Association of Realtors!

Resort & second-home property specialist

RSPS Certification

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Pierhead is proud to be an Airbnb superhost, a guest favorite, and a VRBO premier host. We strive to provide a luxury experience.

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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.

Explore our properties