Historic Home near the Beach w/ Pool | 306 Charleston Blvd | Roosevelt Retreat - Vacation rental home in Isle of Palms, SC

Welcome to 306 Charleston Roosevelt Retreat by AvantStay, a rare Isle of Palms gem where coastal ease meets rich American history. Constructed in 1958 by Nicholas G. Roosevelt—a cousin of Franklin D. Roosevelt and a direct descendant of the architect of the U.S. Capitol—this striking home carries a legacy that sets it apart. Once owned by beloved Charleston author Emily Whaley, the property blends timeless Lowcountry character with casual beach living, making it especially meaningful for history lovers and coastal wanderers alike.

Set just moments from Isle of Palms’ pristine shoreline, this getaway places you steps from sun-filled beach days, ocean breezes, and everything that makes this barrier island so special. Spend your mornings strolling toward the waves, your afternoons calming by the private pool, and your evenings grilling beneath wide-open Carolina skies.

Inside, sunlight fills the casual and colorful living room, anchored by a enormous TV and plush seating—ideal for movie nights or unwinding after a day at the beach. The open dining area comfortably seats six for shared meals, while the entirely equipped kitchen, complete with all the essentials and a cheerful breakfast nook, makes cooking feel simple and social. A second living space with a comfortable couch offers even more room to spread out and relax.

Five thoughtfully arranged bedrooms provide comfort and privacy for the entire group. The primary suite features a king bed and a private ensuite bath. Additional queen bedrooms offer serene spaces to recharge, while the bunk room with a twin-over-full setup—also with its own ensuite—is ideal for kids or teens. Another queen suite adds additional convenience, bringing the home to 5 bedrooms, 4 bathrooms, and sleeping space for up to 11 guests.

Outdoors, Roosevelt Retreat really shines. Appreciate slow mornings on the screened porch, sunny afternoons poolside, and warm evenings gathered around the outdoor dining area with a grille, lounge chairs, and space designed for lingering conversations. The backyard feels private and calming—ideal for families, friends, and multi-generational stays.

Located on the coveted south end of Isle of Palms, you’re close to local eateries, the IOP Marina, Isle of Palms County Park, and the laid-back appeal of close by Sullivan’s Island. Historic downtown Charleston—with its world-class dining, culture, and architecture—is just a short drive away.

Whether you’re drawn by the history, the beach, or the space to reconnect, Roosevelt Retreat offers a stay that’s as meaningful as it is relaxing.

Your beach week—rooted in history—starts here.

AvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like refrigerator stocking, private chefs, massages, transportation, special occasion celebrations, infant gear units, ski gear, beach gear, and more.

Just off the coast of Historic Charleston, Isle of Palms offers a striking six-mile stretch of white, sandy beaches. Spend the day chartering a boat and paddleboarding in the Atlantic, or discover the broad wildlife within the area's marshes and creeks. Isle of Palms is also the ideal place to decompress, with acclaimed spas, appealing eateries, and sweeping golf courses. All this and more await you in the jewel of South Carolina's Lowcountry.

Local Attractions: Isle of Palms Beach, Barrier Island Ecotours, Deep Water Vineyard, Acme Lowcountry Kitchen, Charleston Fun Park, Mount Pleasant Town Centre, Tidalwave Watersports, Fly In Helicopter Tours, Cafe Paname.

Home Truths:
- This home accepts up to 2 family pets (max. 25 lb) for a $250 fee; undisclosed pets brought without AvantStay’s approval may result in a $500 fine per pet.
- Please note that pool heat is offered at $100 per day; mininum of 3 nights.

Parking Details:
- Parking is available for up to 5 cars.

This is a smoke-complimentary property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.

As part of our commitment to being good neighbors, occupancy limits and peaceful hours (9pm-8am) are stringently enforced. No speakers or sound systems will be supplied for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation.

Events or events are not allowed without prior written approval and an additional fee. Any unauthorized events or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and costs.

There is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking additional care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.

As a reminder, we do work with 3rd event vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.

IDs will be requested for verification after booking. All bookings over 28 days require a security deposit.

We report and prosecute all Credit Card Fraud.

This is a smoke-complimentary property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.

As part of our commitment to being good neighbors, occupancy limits and peaceful hours (9pm-8am) are stringently enforced. No speakers or sound systems will be included for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation.

Events or events are not allowed without prior written approval and an additional fee. Any unauthorized events or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and costs.

There is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking additional care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.

As a reminder, we do work with 3rd event vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.

IDs will be requested for verification after booking. All bookings over 28 days require a security deposit.

We report and prosecute all Credit Card Fraud.

STR: P-00812