Staycation on Hilton Head Island

Experience a Refreshing Escape Without Leaving the Island 

Home is where you work, care for your family, and manage life’s daily responsibilities. But sometimes, home can also be the best place for a vacation—especially when that home is Hilton Head Island! Instead of looking beyond the island for adventure, consider a staycation and rediscover all the beauty, relaxation, and excitement Hilton Head has to offer. Whether you're seeking luxury accommodations, scenic exploration, or well-earned relaxation, a staycation lets you see your hometown from a fresh perspective while saving time and travel expenses.


Upgrade Your Staycation with Luxury & Comfort 

Taking a break from the routine doesn’t mean you have to go far—just change the scenery! A luxury vacation rental through Hilton Head Properties can transport you into a refreshing retreat without ever leaving the island. 

  • Enjoy New Surroundings – Choose from properties that offer oceanfront views, private pools, and direct beach access for an upgraded home-away-from-home experience. 
  • Spacious & Stylish Living – Open floorplans, high ceilings, and large windows bring in natural light and create an airy, relaxing ambiance. 
  • Dine In or Out – Our fully equipped chef-style kitchens allow you to prepare home-cooked meals—a fun contrast if you typically dine out! 
  • Private Outdoor Spaces – Enjoy balconies, patios, and decks to sip your morning coffee or unwind under the stars.

Rediscover Hilton Head: Explore Like a Tourist 

Even longtime residents of Hilton Head often overlook some of the island’s best-kept secrets. Your staycation is the perfect time to experience new adventures right in your own backyard! 

  • Coligny Beach Park – Lounge in the sun, take a long walk along the shore, or challenge friends to a game of beach volleyball. 
  • Sea Pines Forest Preserve – Explore hidden trails, freshwater lakes, and ancient shell rings for a dose of nature and history. 
  • Coastal Discovery Museum – Take in the rich history, culture, and wildlife of the Lowcountry—all in one fascinating location. 
  • Bike the Island – With over 60 miles of bike trails, you can explore Hilton Head like never before!

Make Your Staycation Plans Today! 

You don’t have to travel far for a relaxing and unforgettable escape. Book a staycation with Hilton Head Properties and enjoy the best of island living with luxury accommodations, exciting adventures, and well-deserved relaxation.


Properties Available 117 properties available
3 BEDS / 2 BATHSCozy, secluded family home in Sea PinesDog friendly (Non-Refundable Pet Fee Required)Close proximity to the beachConcishare (Includes access to luxury concierge service)Xplorie - 2 Free Adult Bikes (Valid for 3-21 night stays)Welcome to your own private oasis in Sea Pines, Hilton Head Island. This charming 3-bedroom vacation ho
Home - 52 Night Heron, Sea Pines
Homes Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
2 BEDS, 2 BATHSCozy villa with a private balcony overlooking a pondOpen living space with comfortable furnishingsSteps from the beach and bike path in Palmetto DunesConcishare (Includes access to luxury concierge service)Xplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Welcome to your beautiful vacation home in Palmetto Dunes o
Villa - Barrington Park 706, Palmetto Dunes
Condos/Villas
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
2 BEDS, 2 BATHSSpacious, tastefully decorated two-story villaTwo suites with king beds for luxurious sleeping arrangementsShort 5-minute bike ride to the beach from the Disney ResortXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights) Welcome to our beautiful vacation home in Hilton Head Island! This spacious two-story villa offer
Villa - Turnberry 285, Palmetto Dunes
Condos/Villas
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
3 BEDS, 2.5 BATHSTastefully furnished villa in Palmetto DunesDeck for outdoor enjoymentSteps away from pool, tennis courts, golf course, restaurants, and beachProvides a relaxing and peaceful getaway.Xplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Welcome to our stunning three bedroom vacation home, nestled in the heart of the LowC
Villa - Queens Grant 683, Palmetto Dunes
Condos/Villas Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths , 1 Half
Guests 8 guests
2 BEDS, 2 BATHSBuilding Construction from Sep 2024 - May 2025, subject to changeTastefully designed with a coastal ambianceMaster suite with king bed, private bath, and balcony accessAccess to expansive and private oceanfront poolWide sandy beaches and gentle surfXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Welcome to our beauti
Villa - Sea Cloisters 108, Folly Field
Condos/Villas
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
1 BED, 1.5 BATHStunning villa perfect for a beach getawaySpacious open living space with comfortable furnishingsSpacious balcony with breathtaking ocean viewsWalking distance to the beachXplorie - 2 Free Adult Bikes (Valid for 3-21 night stays)Welcome to the luxurious one bedroom Barrington Villa, located on the third floor with stunning oceanfront
Villa - Barrington Court 309, Palmetto Dunes
Condos/Villas Pet Friendly
Bedrooms 1 bedrooms
Bathrooms 1 baths , 1 Half
Guests 4 guests
1BD, 1.5 BTHSBeautifully renovated villa in Palmetto DunesPerfect beach getaway for couplesWell-equipped kitchenAccess to community poolXplorie - 2 Adult Bikes (Valid for stays between 3-21 nights)Welcome to 1770 St. Andrews in Palmetto Dunes! This beautifully renovated and dog-friendly 1-bedroom, 1.5-bathroom condo is the perfect getaway for
Villa - St Andrews Common 1770, Palmetto Dunes
Villas Pet Friendly
Bedrooms 1 bedrooms
Bathrooms 1 baths , 1 Half
Guests 4 guests
2 BEDS, 1 BATHOpen and airy villa with a short walk to the beachStunning furnishings and contemporary designInviting back patio for relaxationLarge, shaded swimming pool for cooling off and relaxationXplorie - 2 Free Adult Bikes (Valid for stays between 3 -21 nights)Welcome to this beautiful beach-oriented villa in Hilton Head Island! Recently reno
Villa - Stones Throw 4, Folly Field
Condos/Villas Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 1 baths , 1 Half
Guests 7 guests
3 BEDS | 3 BATHSDog friendly family home in Sea PinesComfortable and inviting living spaceOutdoor deck perfect for relaxing and unwindingAccess to ccomplex pool and tennis courtsXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)78 Shell Ring is an elevated home all on one floor in Carolina Place community in Sea Pines Resort on Hilto
Home - 78 Shell Ring Rd, Sea Pines
Homes Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
2 BEDS, 2 BATHSPet friendly villa in prime location, Palmetto DunesSpacious living space with hardwood flooringAccess to complex amenities, such as a pool and tennis courtsWalking distance to beach, golf courses, and shopsXplorie - 2 Free Adult Bikes (Valid for stays from 3 -21 nights)Welcome to the Villa at 7830 Centrecourt, your perfect vacation
Villa - Centrecourt 7830, Palmetto Dunes
Condos/Villas Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
2 BEDS/ 3 BATHSTastefully decorated villa with a peaceful atmosphereSpacious rooms with comfortable furnishingsPrestigious location with easy access to beaches, golf, and amenitiesXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights) Welcome to Hickory Cove #24, your ultimate vacation home nestled in the prestigious Palmetto Dunes
Villa - Hickory Cove 24, Palmetto Dunes
Condos/Villas
Bedrooms 2 bedrooms
Bathrooms 3 baths
Guests 7 guests
3 BEDS, 3 BATHSPet Friendly  villa in Palmetto DunesOpen, comfortable living spacePrivate patio with a gas grillShort walk to the beach, dining, tennis and golfXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights) Welcome to 536 Queens Grant, your perfect vacation home in the heart of Palmetto Dunes! This spacious 3-bedroom vi
Villa - Queens Grant 536, Palmetto Dunes
Condos/Villas Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests

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