Holiday rentals 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.

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!

Beach House, Elevator, Sleeps 12

Stroll just a few steps from Fish Haul Beach to discover our haven of relaxation.This newly built beach house boasts 3 bedrooms and 2.5 baths complete with complimentary linens and bath towel sets.Enjoy a fully equipped kitchen, ample dining space,and 2 expansive balconies to soak in the coastal ambiance.Enhance your beach stay with included amenities such as boogie boards,backpack beach chairs and wagons.We've anticipated every need and are dedicated to ensuring your stay exceeds expectations!

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!

The Lookout - A Modern Beach Retreat (Oceanfront)

Welcome to The Lookout! The moment you step into this villa you will be greeted by an open floor plan, a fully stocked kitchen, & every amenity that you'll need for your stay. Take a seat on one of the high top adirondack chairs & enjoy your favorite beverage while overlooking the most popular beaches on the island. Truly - every square inch of this unit has been meticulously utilized to give you an unforgettable vacation. We look forward to hosting you at Seaside Villa's premier luxury villa!

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!

98 Sandcastle Ct

98 Sandcastle Ct Brand New 6 Bedroom Home near Beach with Pool, Elevator/ (Sleeps Up To 22 Guests ) 20 in beds & 2 in Queen Sofa Sleeper. Over 3200 sq feet, 6 Bedrooms, Heated Pool, Elevator & about .3 miles from the beach = Tons of Fun!!! * 6 Bedrooms * 4 Full Baths * Walking Distance to Ocean. * Heated Private Pool. (Free pool Heat :) * Elevator Available: Free use Adults Only. * Free Parking: 4-6 reg cars/mini vans.. LRG SUV's or LRG Vans = 4 parking spots. Note: 2 = garage 4 =driveway.

Bluffton Breeze-3BR Heart of Old Town Village Home

🌴 Welcome to Bluffton Breeze! Slow down, breathe in the salt-kissed air, and settle into Bluffton Breeze — a quintessential Lowcountry retreat in the heart of Old Town Bluffton. Just steps from beloved restaurants, quirky shops, and those iconic May River views, this charming 3-bedroom, 3.5-bath home blends Southern hospitality, breezy comfort, and modern luxuries. With space for up to 6 guests, it’s the perfect spot to relax, reconnect, and soak up everything that makes Bluffton special.

The Carriage House at The Grove

Come relax with family and friends at this charming cottage located on multiple acreage overlooking a private lake teaming with native wildlife. Let both the two-legged and four-legged kids run around in a fenced backyard underneath majestic live oaks. Located within a private equestrian community, conveniently located near The Grove at Stoney Creek and Hewitt Oaks, and very close to Savannah, HHI, and Oldtown Bluffton. An additional adjacent apartment may be requested by messaging host.

Pet friendly condo with amazing Broad Creek views

Watch fireworks from your balcony on Tuesdays in season (June-August). Walk to Sunset celebration Friday nights in the park (June - August) Pet friendly condo in the heart of Shelter Cove, with all the amenities of Palmetto Dunes! Get involved in a variety of activities such as bike riding, golf, children’s activities, boating, fishing, hiking, shopping and more. Relax on your balcony while watching amazing sunrises, sunsets and wildlife. Walk to restaurants and shops or bike to the beach.

Nautical Coastal Cottage

Kick back and relax in our chic Coastal Cottage! Classic navy and white nautical vibes throughout the house! You will definitely enjoy the light and airy rooms! Only 2 miles from Old Town Bluffton! The house is equipped with a full kitchen, whether you decide to stay in and cook or choose one of our local downtown Bluffton restaurants! If you want to venture off to Hilton Head it is a 10 minute drive over the bridge! A vacation getaway you will remember…

Cozy Carriage House Under Oaks | Old Town Bluffton

nook - /nʊk/ – a secluded or sheltered place or part. We welcome you to The Nook, a peaceful escape nestled beneath centuries-old oak trees and located steps away from the vibrant core of the Old Town Bluffton Historic District. Spend your days strolling tree-lined streets, dining at some of the Lowcountry’s best restaurants, and enjoying scenic parks overlooking the beautiful May River. Begin and end your day at your restful, coastal retreat.