Company and Contact Information - Island Palm Vacation Rental

At Island Palm Vacation Rentals, we’re more than just a property management company—we’re locals who love where we live and what we do. Rooted in the laid-back charm of Southwest Florida, we’re dedicated to sharing the coastal lifestyle with every guest who walks through our doors and every homeowner who trusts us with their property.

Our mission is simple: to make vacationing and owning in Southwest Florida effortless, enjoyable, and rewarding. We bring together thoughtful property care, hospitality-driven guest experiences, and a personalized approach that keeps things stress-free. Whether it’s helping travelers discover the perfect beach getaway or giving homeowners peace of mind through trusted management, Island Palm Vacation Rentals is here to connect people with the best of Florida living—one stay at a time.

CONTACT US

Island Palm Vacation Rentals

4017 Del Prado Blvd S
Cape Coral, FL 33904

239-240-8297

rentals@island-palm.com

Meet the Team

Kelly Cruz

Rental Manager

kcruz@island-palm.com

Kelly holds a Bachelor’s degree in Hospitality Management from Johnson & Wales University and began her career in luxury hotels, where she developed a strong foundation in service and operations. She later became part of the original Pine Island Realty Vacation Rentals team and was thrilled to help lead its evolution into partnering with John R. Wood Properties—a trusted household name in Southwest Florida—to bring vacation rental management to the next level. With a passion for creating memorable experiences, Kelly loves how vacation rentals allow her to combine professional hospitality with the flexibility and creativity of personalized travel. She takes pride in caring for each property and ensuring every guest feels right at home. Outside of work, Kelly treasures time with her family and two kids. Whether it’s a beach day under the Florida sun or a magical trip to Disney, she embraces every chance to make lasting memories together.

Brantley Woodward

Rental Coordinator

bwoodward@island-palm.com

A true Southwest Florida native, Brantley has always held a special connection to Pine Island—often called the “forgotten island.” After earning his degree in Business Administration from The College of the Florida Keys, he spent nearly 14 years in the luxury hotel industry, working in both the Keys and Tampa Bay. His career in high-end hospitality gave him a strong foundation in service, operations, and creating memorable guest experiences. Brantley’s path came full circle when he returned home to Southwest Florida and joined Island Palm Vacation Rentals. With deep family ties to the Pine Island rental market and a lifelong love for the area, he takes pride in helping homeowners and guests experience the unique charm of this coastal community. Outside of work, Brantley is passionate about aviation, travel, and all things on the water. Whether he’s kayaking, boating, or planning his next trip, he’s happiest in motion—exploring the world from both the sky and sea.

Cyndy

Accounting Assistant

Christine

Property Services Coordinator

Lexi

Social Media Specialist

Daniel Dennis

General Manager
JRW Vacation Rentals

daniel@theholidaylife.com

As General Manager of JRW Vacation Rentals, Dan leads the rental division with a hospitality-first mindset and a collaborative approach. He oversees operations across Island Palm Vacation Rentals, The Holiday Life, and Resort Harbour Properties, working closely with each team to deliver exceptional service, strong property performance, and memorable guest experiences. A native of upstate New York, Dan earned his BS in Marketing and Management from Siena College before heading south for an internship with Walt Disney World—an experience that sparked his passion for hospitality and ultimately led him to build his career in Florida. Prior to joining JRW, Dan managed a luxury boutique hotel in Naples, where he became known for exceeding expectations and crafting personalized guest stays. Today, he combines strategic leadership with hands-on care to elevate vacation rental management throughout Southwest Florida. Outside of work, Dan enjoys traveling, kayaking the region’s scenic waterways, and rooting for his Florida Gators and Miami Dolphins.

Sydney Allen

Listing Manager
JRW Vacation Rentals

sydney@theholidaylife.com

As Listing Manager of JRW Vacation Rentals, Sydney leads the strategy behind showcasing and growing our portfolio of luxury homes across Southwest Florida. With over 14 years of real estate experience, she partners closely with homeowners and real estate agents to design effective listing strategies, elevate presentation, and position each property for success—all while driving the division’s strategic growth and ensuring every home reflects the high standards of JRW’s hospitality-first approach. Originally from Indiana, Sydney brings Midwest warmth to the laid-back coastal lifestyle she now enjoys in Southwest Florida. Before joining JRW, she built a successful career across multiple facets of real estate, earning a reputation for professionalism, approachability, and always going the extra mile. Outside of work, she’s a proud cat mom, lifelong Disney fan, and die-hard Colts supporter (yes, even during rebuilding seasons). Most often, you’ll find her on the water, relaxing at the beach, or chasing one of Florida’s famous sunsets with friends and family.