Holiday rentals with a kayak in Hilton Head Island

The Singleton Estate

This beautiful property has big plans coming up! Available for rent beginning May 1, this exceptional 6-bedroom, 6-bathroom home at 87 Singleton is undergoing a comprehensive, top-to-bottom renovation scheduled for completion by April 30. With over $350,000 in planned improvements, the property will deliver a like-new, luxury living experience. The renovation includes a significantly expanded kitchen featuring brand-new Viking appliances, along with fully upgraded interiors throughout. Every bed

Coastal Breeze -Top Floor - Hilton Head Island

2BR/2BA-Top Floor- Corner Villa -Direct Beach Access-2 Outdoor Pools-Heated Indoor Pool &Hot Tub-Master Bedroom-1 King Bed,Guest Custom Twin loft over Queen + Foldout 4" Twin Mat. Private patio, Smart TVs, dining for 6, fully equipped kitchen, Drip & Keurig coffee maker, blender + separate water to fill water bottles, Wi-Fi, bath towels & bed linens provided. Extra USB plugs in guest bedroom for all your electronic needs. Beach supplies: beach wagon, beach chairs, paddle ball, boogie boards.

Marriott Harbour Club - 2BD

Nestled in Hilton Head Island's Sea Pines Resort, Marriott's Harbour Club overlooks scenic Calibogue Sound. This Marriott Vacation Club resort offers access to Hilton Head's natural beauty, hospitality, and activities, including championship golf courses and numerous tennis courts. Enjoy fine dining, shopping, yacht harbors, galleries, Harbour Town, horseback tours, ecotours, watersports, and museums. Marriott's Harbour Club provides an ideal seaside getaway with family-friendly activities.

Waterfront Paradise in the heart of the Lowcountry

Lovely home on the water near Beaufort, SC. This 4 bed, 3 bath home on an almost 1/2 acre lot is in the heart of the Lowcountry. It has unobstructed sunset views and private dock. This is the prime location for summer fun - fishing, boating, beaching, cooking out, and living slowly. It's just 20 minutes from down town Beaufort and 20 minutes from Fripp Island. The house is situated on Port Royal Sound, across the water from Paris Island and Hilton Head. It's truly a boaters paradise!

Marriott's Harbour Point - 2BR/2BA - Waterfront!

Next to picturesque Shelter Cove Harbour on Hilton Head Island, you will find Marriott's Harbour Point and Marriott's Sunset Pointe Resort, quite possibly one of the most underrated locations on HHI. Enjoy outstanding direct waterfront views of Broad Creek from your private balcony in the morning and amazing sunsets in the evening. Watch the boats entering and leaving Shelter Cove marina along with the opportunity to see local wildlife including dolphins and many varieties of birds.

ThisISOceanfront! ESA! PetsAllowed! 2BR/2BA condo

Enjoy breakfast, peace and luxury at this large oceanfront 2BR/2BA condo. ESA Pets allowed! While the whole family relaxes, see and hear the waves crashing on Hilton Head. Enjoy this ocean view and sound all day or enjoy the many amenities! Beach Toys! Large, family-size beach tent, umbrella, blanket, beach chairs, towels for 8, beach cart for the short 200 steps to private beach access. Private oceanfront sundeck. Pool. All provided at no extra charge! Yes!Free Beach Toys, too!

Ocean-View Treetop Escape w/ Fire Pit!

Plan your next getaway for a stay on the sandy shores of Hilton Head Island when you book this 2-bedroom, 2-bathroom vacation rental home. The treetop house features a private setting with gorgeous ocean views that can be seen from inside and outside of the property. Sway in the hammock with a good read or dine al fresco on the patio or deck. When you’re ready to explore the island, visit the Harbour Town Lighthouse or book a tee time at Harbour Town Golf Links.

MyStay at 7649 Huntington - Lagoon Views & Beach!

Escape to 7649 Huntington Villa—your perfect Hilton Head retreat! This stylish 3BR/3.5BA villa in Palmetto Dunes offers lagoon views, a short walk to an uncrowded beach, and access to a heated pool, hot tub, and more. Enjoy a fully stocked kitchen, comfy living space, and beach gear ready to go. Golf, bike trails, and waterfront dining are all nearby, plus a free resort shuttle. Book now and unlock your dream vacation—because you hold the key!

Tennis - King Bed - 3 Pools - Beach

Our newly renovated Villa features 2 bedrooms and 2 bathrooms, all new furnishings, luxury linens, smart TVs and charging stations. We are on the third floor (no elevator) and overlook the tennis courts and the indoor pool area. It is only a 7 min walk through the shaded lagoon area, past the two outdoor pools to the natural sandy beach! Our unit is ideal for two couples or a small family. We have sleeping for 8 available.

Oceanfront Villamare Condo | Palmetto Dunes

SNOWBIRD FRIENDLY Here at Beach House Boutique Vacation Rentals we believe in providing you with amenities you won't find anywhere else. See all this 2bedroom/2bathroom Oceanfront Villa has to offer! 1. Luxury bedding, Bath & Beach Towels 2.. Hair dryers in each bathroom 3. Both a KEURIG and Regular Coffeemaker 4. Gift bag with local treats 5. Beach Towels for guest use 6. Keyless Entry 7. Oceanfront 8. Ocean Views

Coastal 2Bdrm Stay | Pool Access, Walk to Beach

Experience Hilton Head at our cozy coastal townhouse, steps from the beach! Enjoy a shared outdoor pool, private patio with grill, and a fully equipped kitchen. Family- and pet-friendly with Pack N Play, dedicated workspace, high-speed WiFi, washer & dryer. Relax, unwind and make great memories. 2 bedrooms, 3 bathroom, perfect for your getaway!

Palmetto Dunes Luxury Oceanfront Gem w/ View -King

Welcome to 451 Captain’s Walk in Palmetto Dunes Resort! A Premier Hilton Head Island Oceanfront Location. Centrally located to everything on the Island. This beautiful oceanfront villa is just steps away from the beach. Walk in and be immediately welcomed by the ocean. Condo is on 4th of 5 floors with Elevator.