Holiday rentals in Sea Pines

CoCo's Island Treehouse

. Unwind in a cozy, character-filled treehouse nestled in nature, featuring open-beam construction & a peaceful, wooded setting. Within easy walking distance of the beach, shops, & restaurants of Harbortown, this retreat offers the perfect balance of convenience & seclusion. Head to the wide beaches of the Sea Pines Beach Club by car, bike trail, or trolley. After a day of exploring, relax in front of the 85-inch TV, prepare a home-cooked meal in the fully equipped kitchen, or fire up the grill.

Steps to Ocean & Marina in Sea Pines-bikes-pool!

Free Bikes-Pool-Tennis! 2 bedroom, 2 bath Bluff Villas condo located in the heart of South Beach within the Sea Pines Resort. Steps from the beach, marina, pool & famous Salty Dog Cafe. Both baths Newly tiled/renovated amenities: - 4 bikes to use on Sea Pines' perfectly maintained wide bike paths - Pool 3 min next door(incl)-open Mem Day wknd - 1 hour/day + free walk on time-tennis at So Beach Racquet Club - new world class Pickleball facility! (reas rates) - 4 beach chairs & wagon - Spectrum

MyStay at 1 Spanish Moss – Pool-Game Room-Pets OK!

Escape to a luxurious private retreat in the heart of Sea Pines, where modern comfort meets island charm. This spacious home boasts 5.5 bedrooms, 5 bathrooms, and a backyard oasis with a heated pool (fee applies) overlooking Heron Point Golf Course. Just minutes from Harbour Town, the beach, and top attractions, it’s perfect for families and groups. Enjoy Smart TVs in every room, high-speed Wi-Fi, a Sonos sound system, and a pet-friendly policy. Book now for an unforgettable Hilton Head escape!

Sea Pines-Pool, Prime Location & View, Pets OK

A flood of sunshine and a stunning golf view welcome you in this beautiful two bedroom in Wildwood Spa, a quiet neighborhood just 1/2 mile from the Sea Pines Beach Club. A well appointed kitchen, work area, on-site pool and tennis/pickleball courts, and a propane grill are just a few of the noteworthy points with this property. Pet friendly, nicely updated and spacious. Bonus loft with a sleeper sofa and curtains for privacy expands the space for a variety of uses-kids, games, extra sleeping.

Sea Pines Serenity!

LOCATION, LOCATION, LOCATION! If you want security and serenity, this home is for you! This stylish 3 bed, 2 bath house has EVERYTHING you need for a relaxing vacation. Walking distance (10 blocks) to the best beaches on the island, dozens of restaurants and amazing Harbour Town! The fabulous Beach Club has onsite parking Sea Pines guests. Spend the day on a dolphin or pirate cruise, and then spend the night relaxing on a huge patio with your fire pit while enjoying s’mores!

100 Fairway Lane, Sea Pines: A Luxury Villa Stay

Welcome to all NEW BESTNEST/Luxe: An Elevated Experience in Vacationing, and our newest Luxe property at Unit 100 Fairway Lane Villas in Sea Pines. (200 Fairway Lane for mapping) Enjoy the ultimate in vacation rental accommodations on Hilton Head Island, featuring a carefully curated collection of homes and villas, chosen with the discerning traveler in mind, fabulously stocked, outfitted, and equipped, and supported by your personal property concierge, available 24/7.

18 East Beach Lagoon @ Sea Pines | Steps to Beach

HOST & HOME presents… 18 East Beach Lagoon! Escape to this breathtaking oceanfront retreat in the prestigious Sea Pines Resort. Just steps from the sand, this home offers a private beach path and unmatched tranquility. Relax in a designer-decorated space surrounded by lush Lowcountry greenery, featuring a large brick patio with teak furniture for al fresco dining. Perfect for up to 8 guests seeking unique style, comfort, and proximity to the ocean. Learn more below ...

Charming Lagoon view Townhome near Harbor Town

With a picturesque lagoon view this two-bedroom townhome is perfect for getting away from the every hustle. Spacious living area to relax and enjoy the peaceful settings of the lagoon on the back patio. Two well appointed bedrooms upstairs each with their own full bath and TV's. Walking distance to the Harbor Town Golf Club and Tennis courts as well as the Harbor town to shop, eat and enjoy the beautiful sights of the marina. (Short Term rental lic no. 7524.)

5 Star Location-Pool, Walk to Dining/Shops/Marina

Escape to our luxury villa in Hilton Head's exclusive Harbour Town in the gated Sea Pines Resort! A short walk from Harbour Town Marina, which offers enertainment, dining, shopping, water sports, cruises, golf, tennis, and a pier. You will have access to The Sea Pines Beach Club, a short trolly, bike or car ride away. This private 3rd-floor impeccilbly appointed 'coastal chic' retreat does not share any walls and offers serene lagoon views from a private balcony.

Heart of Harbour Town - Beach | Pool | Golf | 2BR/2.5BA - Pool Access

In the Heart of Harbour Town Experience the best of Harbour Town living with exquisite harbour views in this recently updated 2 BR / 2.5 BA end unit just steps away from the waterfront. Villa is a short walk to pool, the pristine Harbour Town Golf Links, and the Sea Pines Trolley -- offering complimentary seasonal transport. Recently renovated with gourmet kitchen, elegant living area, and outdoor dining. Sleeps 8. Includes Harbour Town pool passes.

Luxury 4BR Home w/ Pool & Golf Views - Sleeps 12

Heritage House is a newly redecorated 4BR/4BA retreat in Sea Pines, offering luxury, comfort, and golf course views. Sleeps 12 guests with spacious living areas, a private heated pool, fire pit, and screened porch. Enjoy new high-end furnishings, Smart TVs, and an open-concept kitchen. Just 1.1 miles to the beach, with bike rentals available for an additional fee. Pool is heated for free in March-May and September-November. 31 Heritage Road

Spacious Harbor Town Condo!

Your perfect vacation begins when you walk out the door of this newly renovated condo into the Harbour Town marina with its boutique shops, gourmet restaurants, racquet club offering tennis and pickleball, famous PGA tournament golf course, and the iconic red and white lighthouse. The spacious 1-BR sleeps up to four guests. The master bedroom has a King-size bed and a large picture window that comes with blackout curtains for late sleepers.