Welcome to the 4BR/4.5BA BESTNEST at 26 Tupelo Road. Beautifully renovated and thoughtfully designed for gathering, this spacious four-bedroom Sea Pines home offers exceptional flexibility for families and friends vacationing together. With a separate guest house, private pool, golf course views, and inviting indoor and outdoor living spaces, 26 Tupelo Road provides the perfect setting for relaxing, reconnecting, and making lasting Hilton Head memories.

THE SETTING: Located along one of Sea Pines' quiet residential streets, 26 Tupelo Road overlooks the golf course while offering easy access to the beach, bike paths, and many of the island's most popular attractions. Spend your mornings enjoying coffee in the Carolina Room, afternoons by the private pool, and evenings gathered around the gas fire pit beneath the stars. Whether you're exploring the island or simply enjoying a slower pace at home, this property makes it easy to enjoy every part of your Hilton Head vacation.

THIS HOME IS IDEAL FOR: Extended families, multiple families vacationing together, golf groups, and friends who appreciate having generous gathering spaces along with private accommodations. The detached guest house provides additional flexibility while allowing everyone to enjoy both togetherness and privacy throughout their stay.

WHAT GUESTS LOVE MOST: Guests consistently tell us that the guest house is one of their favorite features, giving grandparents, teenagers, or another family their own comfortable space while remaining just steps from the main house. The open living areas, peaceful golf course views, Carolina Room, private pool, and beautifully landscaped backyard create countless places to gather throughout the day. Evenings often end around the gas fire pit, sharing stories after a day at the beach or exploring Sea Pines.

POOL: The private pool and patio create a welcoming outdoor retreat for guests of every age. Spend sunny afternoons swimming, relaxing poolside, or grilling dinner before gathering around the fire pit as the custom landscape lighting brings the backyard to life after dark. The pool and spa may be heated with propane during cooler months for additional comfort.

SLEEPING ACCOMMODATIONS INCLUDE: Sleeps 10 comfortably // Main House: 1 King bed // 1 Queen bed // 2 Twin beds // Guest House: 2 Queen beds with 2 Twin bunks. The main home offers three beautifully furnished bedrooms, each prepared with luxury BESTNEST linens and comfortable accommodations, while the detached guest house provides an inviting private retreat complete with additional sleeping space, its own living area, and a full bathroom. The flexible floor plan is ideal for families traveling across multiple generations or groups of friends vacationing together.

FULLY STOCKED KITCHEN: The beautifully renovated kitchen has been thoughtfully equipped with everything needed to prepare meals throughout your stay. Quality cookware, matching dinnerware, generous serving pieces, ample glassware, Keurig and traditional drip coffee makers, and generous workspace make everything from breakfast before the beach to holiday dinners feel effortless. The open floor plan keeps everyone connected from the kitchen to the dining area, family room, and Carolina Room.

ADDITIONAL HIGHLIGHTS INCLUDE: Detached guest house with private living area and full bathroom, Carolina Room overlooking the golf course, private pool and spa, full-time gas fire pit, custom landscape lighting, Sonos speaker, secure high-speed Wi-Fi, enhanced Spectrum cable, Smart TVs throughout, full-size laundry room, beautifully renovated interiors, gas grill, and peaceful golf course views.

BESTNEST GUESTS ENJOY: Thoughtful comforts designed to make vacation easy, including luxury linens and towels, beach towels, a fully stocked kitchen, Keurig and traditional drip coffee makers, beach chairs, umbrellas, beach toys, beach cart, cooler, bathroom essentials, laundry supplies, paper products for the duration of your stay, secure high-speed Wi-Fi, and responsive local Guest Services whenever assistance is needed.

PETS: This property does not permit pets.

VEHICLES/ATTACHMENTS: Denied entry to Sea Pines include motorcycles/scooters, any vehicle categorized as an RV (this includes vans with hook-ups), boats, jet skis, and trailers.

HOW FAR TO BEACH: Approximately a 10 minute bike ride to the Beach Club. During the peak season free trolley service is available from designated points throughout Sea Pines to the Beach Club. Overnight guests may park directly at the Sea Pines Beach Club from the day after Labor Day through mid-March.

POOL HEAT: The private pool and spa may be heated with propane for an additional fee of $350 for the first day and $150 for each additional day during March through May and September through November. Winter rates are available upon request. Please note that when heated, the spa maintains approximately the same temperature as the pool (approximately 88–90 degrees) rather than functioning as a separate hot tub.

PAYMENTS AND CANCELLATION POLICY: For reservations made thirty (30) days or fewer prior to arrival, payment in full is due at the time of booking. For reservations made thirty-one (31) days or more prior to arrival, a deposit of 25% of the total reservation amount, along with the full travel insurance premium if selected, is due when the reservation is made. The remaining balance is due thirty (30) days prior to arrival. Long-term winter reservation policies may differ; please inquire for details. Guests may cancel up to thirty-one (31) days before arrival and receive a full refund of their deposit. Cancellations made between fourteen (14) and thirty (30) days prior to arrival are eligible for a 50% refund of the total payment. Reservations become non-cancelable and non-refundable beginning thirteen (13) days prior to arrival. Travel insurance is highly recommended.

THE BESTNEST EXPERIENCE is designed to feel effortless from the moment you arrive. Every BESTNEST is professionally cleaned, thoughtfully prepared, and carefully inspected to meet our standards for consistency, comfort, and care. No matter which Nest you choose, you'll always find luxury linens and towels, beach towels, a fully stocked kitchen, bathroom essentials, laundry necessities, generous paper products, Keurig and traditional drip coffee makers, Bluetooth speaker, beach chairs, umbrellas, beach toys, and a cooler—allowing you to travel lighter and settle in with ease. Our responsive local Guest Services team is available throughout your stay, with after-hours emergency assistance whenever needed, so you can simply relax and enjoy your time on Hilton Head Island.

We look forward to welcoming you to the BESTNEST at 26 Tupelo Road!

STR Permit Number: 027922