Historic Retreat near Beach w/ Pool | 306 Charleston Blvd | Roosevelt Retreat by Property Manager

Welcome to 306 Charleston Roosevelt Retreat by Property Manager, a rare Isle of Palms gem where coastal ease meets rich American history. Built 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 charming home carries a legacy that sets it apart. Once owned by beloved Charleston author Emily Whaley, the property blends timeless Lowcountry character with relaxed beach living, making it especially meaningful for history lovers and coastal wanderers alike. Set just moments from Isle of Palms’ pristine shoreline, this retreat 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 lounging by the private pool, and your evenings grilling beneath wide-open Carolina skies. Inside, sunlight fills the relaxed and colorful living room, anchored by a large TV and plush seating—perfect for movie nights or unwinding after a day at the beach. The open dining area comfortably seats six for shared meals, while the fully equipped kitchen, complete with all the essentials and a cheerful breakfast nook, makes cooking feel easy and social. A second living space with a cozy 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, whcih has its own entrance, adds extra convenience, bringing the home to 5 bedrooms, 4 bathrooms, and sleeping space for up to 11 guests. Outdoors, Roosevelt Retreat truly shines. Enjoy slow mornings on the screened porch, sunny afternoons poolside, and warm evenings gathered around the outdoor dining area with a grill, lounge chairs, and space designed for lingering conversations. The backyard feels private and peaceful—ideal for families, friends, and multi-generational stays. Located on the coveted south end of Isle of Palms, you’re close to local restaurants, the IOP Marina, Isle of Palms County Park, and the laid-back charm of nearby 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. Property Manager provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. Just off the coast of Historic Charleston, Isle of Palms offers a stunning six-mile stretch of white, sandy beaches. Spend the day chartering a boat and paddleboarding in the Atlantic, or explore the extensive wildlife within the area’s marshes and creeks. Isle of Palms is also the perfect place to decompress, with renowned spas, charming restaurants, 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:* - You must be 25 years or older to book this home. - Please note that Early Check-In (ECI) and Late Check-Out (LCO) services are not available from May to September. - This home allows up to 2 pets under 25 lbs each for a fee; undisclosed pets brought without Property Manager’s approval may result in a $500 fine. - The pool can be heated for $100/day (4 night min) with at least 24hrs notice, as long as the average outside temperature is over 55F. - Guests must supply their own beach towels. - Beach chairs/toys are not included at this property. All reservations between 4-28 nights come with a $250 beach gear credit with VaykGear.com. Guests will be able to reserve gear after booking. - Fireplaces are not for guest use. - Please note that due to natural coastal conditions, beach areas may experience periodic erosion that can affect shoreline size and accessibility. During periods of high tide, portions of the beach—or the entire beach—may be temporarily inaccessible. We are not able to guarantee identical beach conditions for future stays, and refunds or relocations will not be available due to these natural changes. *Parking Details:* - Up to 4 cars can park onsite. This is a smoke-free 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 quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided 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 parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. There is nothing more important to us at Property Manager than the health, safety, and experience of our guests & staff. We’ve enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions. As a reminder, we do work with 3rd party 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-free 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 quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided 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 parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. There is nothing more important to us at Property Manager than the health, safety, and experience of our guests & staff. We’ve enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions. As a reminder, we do work with 3rd party 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 Licence number: P-00812