Holiday houses in Jenkins Island

Sea Pines house ~ Golf Sim / Putting Green / Games

Town of Hilton Head Island STR Permit Number: 064406 Centrally located in Hilton Head Island just within the gates of Sea Pines, with golf simulator, outdoor putting green, 2 game rooms, and a backyard area with games, outdoor dining, fire table & seating, this home is a one-of-a-kind experience. Sleeping up to 10 guests (2 kings and 4 doubles), this luxurious space will offer unparalleled comfort, amenities, and the perfect location for you to use as your central base to enjoy the best of HHI.

Wharf Street Coastal Escape - Premier Old Town 3BR

Experience the best of Old Town Bluffton, SC, in our stylish 3-bedroom, 2.5-bath coastal retreat. This posh residence features high-end finishes including marble baths, gourmet kitchen, large bedrooms, and a screened-in porch. Nestled in the heart of the Lowcountry, this spacious home blends comfort and luxury, offering a serene escape with Old Town's charming shops, restaurants and amenities just outside your door. Enjoy relaxation, adventure, and Southern hospitality steps from the May River.

Sunset on the May / Historic Old Town Bluffton

Spacious studio apartment sits above a detached garage with your own private entrance located in the heart of Old Town Bluffton. A short stroll to nearby restaurants, boutiques and unbelievable sunsets on May River. New king size bed, appliances and large sectional couch. Full kitchen with plenty of space to relax and store your things. Nice size bathroom, full shower and an abundance of amenities like private fire pit, outdoor grill and patio table for your enjoyment. HH Beaches minutes away!

Lux|Free Golf|Heated Pools|Free Bikes|Parris Is

Perfect for golf escapes, military families, or nearby family gatherings! • 2 Complimentary Rounds of Championship golf per day ($250 day value) • Free bike rentals • 3BR/2BA on beautiful Callawassie Island • Sleeps 6 with king, queen, and twins • 2 heated/cooled pools, tennis, and pickleball • 2 on-site restaurants • <30 mins to Beaufort • 30 mins to Bluffton & Parris Island • <60 mins to Hilton Head & Savannah • <90 mins to Charleston Discover charm, luxury, and adventure all in one place!

Guest House on Lawrence Street

UPDATED LUXURY, FASTIDIOUS CLEANLINESS in historic OldTown Bluffton’s coziest carriage house. OldTown’s vibe is just plain fun. Stoll 2 blocks to super restaurants, night life, art galleries, boutiques, antebellum homes & lush waterfront parks on the idyllic May River. New in 2018 w/ quartz counters, private bedroom w/ plush king-size bed, upscale bath w/ soaking tub, bright living/dining room, full kitchen & romantic rocking-chair porch up in moss-draped oaks. Read our Reviews—guests love it!

Ocean View & Steps to Beach! Remodeled HHBT Condo

Newly remodeled! Adorable beach front condo located in HH Beach & Tennis Resort. Watch & listen to the ocean waves right from your 2nd floor balcony! The condo is in a gated area within where guests will have access to a private beach, 2 pools, resort restaurants, tennis, pickleball, beach volleyball, playgrounds, cookout areas, bike rental, and a gym. We also provide beach chairs, coolers, boogie boards and coffee! It's all here! The getaway you've been waiting for and deserve! 💕

Alli B's Air B and B-Great Country access off 278

Your family will be close to everything when you stay at this centrally-located place. No gate fees or parking fees- right off of 278- central located between Bluffton and HHI under foot of bridge. Farm like experience -family owned 30 years . Quiet . Pet friendly . Beds-two twin -can pull together if wish -one couch(Not a sofa bed) and one mattress under a bed that can be moved out . Property has several buildings , Guest apt is above garage. NOTE: SEE Space info below

Penthouse Living | Marina Views in Shelter Cove

Experience elevated coastal living in this beautifully renovated Shelter Cove penthouse overlooking the marina. With 3 private balconies, enjoy sweeping harbor views, morning coffee, and sunset evenings from above it all. Relax by the resort-style pool and hot tub, or stroll to waterfront dining, shops, and adventures just steps away. Perfect for couples or small groups, this stay blends comfort, views, and walkable convenience for a memorable Hilton Head escape.

Hot Tub, Fire Pit, Savannah, Tybee

Amazing Location! This home sits in between Tybee Island and Savannah's Historic Downtown. A 10 minute drive to River Street and 15 minute drive to Tybee Island. This is the perfect home for families or couples wanting to visit the Wildlife Center located just 3 minutes away! Cozy hot tub and firepit, Beach chairs and towels, plush beds with luxurious linens, a fully stocked kitchen, and all the things you need to make a vacation complete are waiting for you.

Bluewater Resort & Marina - Large 3BR/3BA

Come delight in the beauty of the Intracoastal Waterway and savor stunning sunsets from the dock at Bluewater Resort & Marina located on Skull Creek. Bring your boat for free dockage or just relax and watch the boats and yachts go by. This resort has something for everyone, from water and nature lovers to golfers and loungers. This is also a great resort to enjoy the beauty of HHI without the crowds common to other areas of the island.

1mi to MCRD PI | Pinky's Palace | Cozy Bungalow

This peaceful 2BR bungalow in Mossy Oaks is the perfect home base for Parris Island graduations, Port Royal visits, and Lowcountry getaways. Minutes from Parris Island, downtown Beaufort, Port Royal, beaches, and the Spanish Moss Trail, guests enjoy a stress-free stay with renovated interiors, Smart TVs in every room, a fully equipped kitchen, and relaxing outdoor spaces. Quiet, convenient, and family-friendly with true Southern charm.

The Love Bird Suite

Located on the serene and historic Wilmington Island, this space was designed as a romantic couple’s getaway. Enjoy this spacious studio, equipped with a working indoor gas fireplace, a large soaking tub, floor to wall tiled shower, and an outdoor hot tub. Centrally located between Historic Savannah and Tybee Island, enjoy day trips to visit these amazing places and return to a relaxing and romantic retreat style stay.