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205 rentals found
Family-Friendly Home w/Private Pool, Scr...
4.4
(30)

Gloucester 36Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Gloucester 36 offers everything you would want for your Hilton Head vacation: a great location...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
4 bed/3 bath home in Shipyard with peace...

A hidden gem in the heart of Shipyard! Only mins. to Shipyard’s private beach and mins. to Hilton Head’s most trendy public beaches, stores, and eateries! Upon entry you are greeted by a enchanting living room with a full wall of windows...

  • Hilton Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
Many Updates in this Large Four Bedroom ...
2.8
(5)

You're going to appreciate the many updates to this roomy 4 bedroom 3 Bathroom Fazio villa! The entire first floor features new floor throughout, giving the home a fresh and modern feel. The kitchen has been entirely modernized and now features...

  • Hilton Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Beautiful Colonial-style Home with Lagoo...

What's not to adore with this well thought out home and all it has to offer? All three bathrooms just finished remodel in April 2024! The first floor consists of a sizable living room with ample beach-modern furnishings providing seating for the...

  • Hilton Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
Beautiful home on the 11-mile lagoon sys...
4.8
(6)

Come savor this huge five bedroom and five bathroom home located on Palmetto Dunes' 11-mile lagoon system! Located within the heart of Palmetto Dunes Oceanfront Resort, this home has been gorgeously decorated throughout with wood floor and coastal...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
Beautiful lagoon views, new living room ...
4.0
(3)

Welcome to your coastal getaway in the heart of Palmetto Dunes Oceanfront Resort on Hilton Head Island! This gorgeously appointed 4 bedroom, 4 bathroom townhome offers the ideal blend of indoor comfort and outdoor tranquility, charmingly located...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 8
2 Min Walk 2 Beach Pickleball Golf Tenni...
5.0
(110)

One of the very best located properties in Hilton Head. Our 2026 bookings are filling up faster than ever before! Book before it is too late. Walk everywhere. Ideal vacation location! Two min. walk to tennis and pickleball courts, eateries and...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 12
14 Collier Beach, Oceanfront, Pool, Elev...
4.7
(18)

14 Collier Beach, Hilton Head Island is a striking oceanfront estate that offers a state-of-the-art chef's kitchen, an open-concept living and dining area leading to an oceanfront pool, deck, and grille. The home features a opulent master suite with...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 16
Sandcastle by the Sea - brand-new, priva...
4.6
(16)

Sandcastle 97Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located in a gated beachside community, Sandcastle by the Sea is a family-friendly 6BR/4BA...

  • Hilton Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 18
4 bedroom/4.5 bathroom home with private...

This striking Hilton Head home features a cavernous rooms, a huge private pool area, and great golf course vistas. The great room opens to the dining area and kitchen. A deck off the living area offers a table for outdoor dining and stairs leading...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 8
5th Row, Sea Pines-South Beach, Private ...
4.8
(114)

2 Cedar Wax Wing is a Sea Pines Hilton Head 4 bedroom with private baths home near the South Beach area. This single level home is very cavernous with two living areas and a handsome kitchen with granite counter tops, stainless steel appliances and...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 14
Beachfront beauty with pool access - fir...

Sea PointeOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'This handsome five-bedroom home is just steps away from Singleton Beach and the shared community...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 10
44 Bradley Beach, Close to Beach, Large ...
4.3
(19)

44 Bradley Beach is a 6 Bedroom, 4.5 Bathroom family vacation home that sleeps 15 and has a enormous 16' x 32' pool, and features an outdoor fire pit ideal for a nighttime hosting around the pool or a cool day in the fall! There is plenty of seating...

  • Hilton Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 15
Ideal Hilton Head vacation rental for fa...
3.0
(1)

This Hilton Head Island home rental features an open floor plan that is ideal for family gatherings - and you'll appreciate the private pool! The dining room has seating for eight and a wall of windows flanking a French door that opens to the...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
Oceanfront, Sea Pines, Pool & Private Be...
5.0
(65)

This oceanfront beach home is for a awesome family (or multi-family) holiday. It combines an original but refreshed beach "bungalow" with an extension that adds a master bedroom suite, office/study, formal dining room, powder room, elevator, and...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 12
Large Six Bedroom Custom-Built Home with...

This home is designed to fit your next family vacation! The kitchen comes completely equipped to meet your family's cooking needs with stainless steel appliances and bespoke cabinetry, including two ovens and microwave. The enormous kitchen island...

  • Hilton Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 11
Private Oceanfront Home with Private Poo...

You'll appreciate this six bedroom oceanfront home located in esteemed Palmetto Dunes Oceanfront Resort. Boasting numerous enormous windows facing the oceanfront, this home provides oceanfront vistas from nearly every room! As you enter, you are...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 14
Stunning oceanfront home offering privat...
5.0
(6)

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.This gorgeous 5-bedroom, 5.5-bathroom home is located in the heart of North Forest Beach. Ideally located, it features direct access to the pristine sandy...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 16