Holiday rentals in Jenkins Island

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!

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!

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.

Two Homes · Walk to Old Town · Fire Pit · EV

Two homes. One backyard. Zero rules about which one you have to sleep in. Your group pulls up to a shaded Old Town street and there they are — a classic Charleston Single with a wraparound porch and a sleek contemporary cottage, side by side, sharing a private fenced yard with Adirondack chairs and a fire pit already glowing at dusk. Someone claims the porch swing. Someone else heads straight for the cottage. Tonight, everyone gathers around the fire. The May River is down the street.

Luxury 3-Bdrm HHI Art Loft Townhome

Located in the private Spanish Wells area of Hilton Head Island, one of the most sought after vacation destinations in the world. Eight minute drive to Hilton Head Island beaches, golf/tennis, restaurants, bars, bike trails, and countless shopping, entertainment, and outdoor exploration activities. Kick back and relax in this calm, stylish townhome with distinct spaces for everyone. Home Owners have appointed the home with original and collected art. Convenient to Savannah & Bluffton.

Marriott Sunset Pointe - 2BD

Immerse yourself in comfort at our villa resorts Picturesque Shelter Cove Harbour on Hilton Head Island is where you will find two delightful vacation ownership resorts: Marriott's Harbour Point and Marriott's Sunset Pointe. Part of the pleasure of vacationing at either of these water-side retreats, are swimming in our two sparkling outdoor pools and basking in the sun on a 2,400-square-foot sundeck, or playing a game of basketball or pickle ball with family or friends.

Coastal Fairways

Welcome to Coastal Fairways with private beach access on Hilton Head Island, a 2BR/2BA condo in Shipyard with beautiful golf course views from the unit. Enjoy a bright living space, full kitchen, in-unit laundry, and a dedicated workstation. The community pool is steps away with a covered hot tub and playground. Bike paths, golf, and paved beach access with restrooms and outdoor showers via Shipyard Beach Club are all conveniently located just minutes away.

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.

Waterfront Tree House | HT Pool | Private Office

One of our newest homes, see our over 1000 *5*-star reviews. Calibogue Escape-Harbour Town Treehouse in Sea Pines Sailboats, Dolphins, Sunsets, what else could you ask for? This treehouse offers floor-to-ceiling windows with unparalleled views and the perfect setting for a perfect escape. Located on a dead-end street on Deer Island, just steps from Hilton Head’s Harbour Town and the Yacht Basin, this hideaway could not be more perfect.

Harbour Town Marina Studio | Walk to Lighthouse

Cozy, bright studio with direct views of the Harbour Town Marina, just steps from the lighthouse, shops, dining, and golf. The space features a comfortable sleeping area with king bed, sitting space, kitchenette, and full bath with tub/shower combo. Enjoy the small private balcony, perfect for morning coffee or evening sunsets over the marina. Ideal for 1–2 guests looking to enjoy the Harbour Town lifestyle in Sea Pines.

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.