Sun-Drenched Pool Terrace With Endless Ocean Breezes
35 Ruddy Turnstone - Oceanfront Estate Framed by Palmettos & Ancient Oaks
Bird’s-Eye View of Your Secluded Beach Walkway
Your Private Path to the Shore
Unlock Hilton Head – Guest-Only Deals on Excursions & Rentals

35 Ruddy Turnstone

5 bedrooms·7 baths
Hilton Head Island • South Carolina

37.844,53 $ USD totale per 7 notti

26 giu – 03 lug 2027

Cancellazione gratuita
Backyard Bliss: Poolside Fun & Fireside Nights
Backyard Bliss: Poolside Fun & Fireside Nights
The 19th Hole Loft – An Entertainment Escape with Games, Music & More!
The Heart of the Retreat: Spacious, Sunlit, and Designed for Connection
The Ultimate Bunk Suite: Sleep, Play & Unwind

1 Spanish Moss Road

5 bedrooms·5 baths
Hilton Head Island • South Carolina

3.692,48 $ USD totale per 5 notti

14–19 set 2026

Living room
Welcome!
Welcome to our bright and open home.
Foyer
Living room

Coastal Chic at Inland Harbour

2 bedrooms·2 baths
Hilton Head Island • South Carolina
5(95 reviews)

2.930,28 $ USD 2.796,63 $ USD totale per 7 notti

08–15 set 2026

821 Ketch Court
821 Ketch Court
Enjoy Access to Harbour Town Pool Plus the Sun Deck Cafe!
View of Harbour Town Marina Across the Street
Across the Street from Lighthouse and Access to Marina Pathways

821 Ketch Court

3 bedrooms·3 baths
Hilton Head Island • South Carolina

1.074,57 $ USD totale per 3 notti

08–11 set 2026

Spacious first floor living and dining with sliding door to the deck
54" wall mounted TV, ceiling fan and layered lighting for evening wind down time.
Open floor plan for a great flow and great vacation. Island Song Villa will feel like your own personal villa.
The dining table easily seats 6 for meals.
View from the bottom of the stairs to the dining, kitchen, front door and 1st floor bedroom.

Island Song Villa

2 bedrooms·2 baths
Hilton Head Island • South Carolina
5(121 reviews)
$220 – $390/ notte(escl. spese e tasse)
Heart of Harbour Town - Beach | Pool | Golf | 2BR/2.5BA - Pool Access
Heart of Harbour Town - Beach | Pool | Golf | 2BR/2.5BA - Pool Access
Heart of Harbour Town - Beach | Pool | Golf | 2BR/2.5BA - Pool Access
Heart of Harbour Town - Beach | Pool | Golf | 2BR/2.5BA - Pool Access
Heart of Harbour Town - Beach | Pool | Golf | 2BR/2.5BA - Pool Access

Heart of Harbour Town - Beach | Pool | Golf | 2BR/2.5BA - Pool Access

2 bedrooms·2½ baths
Hilton Head Island • South Carolina
4.98(103 reviews)

3.445,00 $ USD totale per 3 notti

08–11 set 2026

Community Pool
Upstairs Primary Suite
Living Room
Dining Room
Patio with Grill and Golf Course Views

2227 Heritage Villa

3 bedrooms·3 baths
Hilton Head Island • South Carolina
$999/ notte(escl. spese e tasse)
Bright Living and Dining Area with Room for Everyone
Private patio with seating just steps from the pool
Community Pool Just Steps from Patio!
Private patio with seating just steps from the pool
The MyStay Extras!

2203 Heritage Villa

4 bedrooms·4 baths
Hilton Head Island • South Carolina

1.146,44 $ USD totale per 3 notti

08–11 set 2026

Best of Harbour Town - Beach | Pool | Golf | 3BR/3BA - Book for Summer - Pool Access
Best of Harbour Town - Beach | Pool | Golf | 3BR/3BA - Book for Summer - Pool Access
Best of Harbour Town - Beach | Pool | Golf | 3BR/3BA - Book for Summer - Pool Access
Best of Harbour Town - Beach | Pool | Golf | 3BR/3BA - Book for Summer - Pool Access
Best of Harbour Town - Beach | Pool | Golf | 3BR/3BA - Book for Summer - Pool Access

Best of Harbour Town - Beach | Pool | Golf | 3BR/3BA - Book for Summer - Pool Access

3 bedrooms·3 baths
Hilton Head Island • South Carolina
4.95(81 reviews)

3.465,00 $ USD totale per 3 notti

08–11 set 2026

Balcony and Gorgeous View of the Harbour Town Lighthouse
Welcome to MyStay at 1029 Caravel Court!
Primary Bedroom with Zero-Gravity Bed and Views of the Harbour Town Lighthouse
Enjoy Access to Harbour Town Pool Plus the Sun Deck Cafe!
Caravel Court Building with Direct Lighthouse Views and Access to Marina Pathways

1029 Caravel Court

1 bedroom·2 baths
Hilton Head Island • South Carolina

789,55 $ USD totale per 3 notti

11–14 nov 2026

Cancellazione gratuita
Balcony View of the Harbour Town Lighthouse
King Bedroom with Harbour Town Lighthouse View
Enjoy Access to Harbour Town Pool Plus the Sun Deck Cafe!
Caravel Court Building with Direct Lighthouse Views and Access to Marina Pathways
Living Room with Harbour Town Lighthouse View

1027 Caravel Court

2 bedrooms·2 baths
Hilton Head Island • South Carolina
5(41 reviews)

1.141,41 $ USD totale per 3 notti

19–22 set 2026

Dining
Dining
Dining
Dining
Living area

Newly Updated, Near Harbour Town 1st Floor 2 Bedroom 2Bath Villa

2 bedrooms·2 baths
Hilton Head Island • South Carolina
4.7(66 reviews)

1.221,00 $ USD totale per 3 notti

08–11 set 2026

Oceanfront Estate Along Hilton Head’s Iconic Shoreline
Oceanfront Estate Along Hilton Head’s Iconic Shoreline
Oceanfront Estate Along Hilton Head’s Iconic Shoreline
14 Laughing Gull
Alfresco Dining Terrace with Pool & Ocean Views

14 Laughing Gull

7 bedrooms·8 baths
Hilton Head Island • South Carolina

8.578,82 $ USD totale per 5 notti

08–13 set 2026

Amazing view of Harbour Town Links Course
Front of house. Driveway fits 6 cars
Hilton Head Island - Sea Pines House off Harbour Town Golf Links
Hilton Head Island - Sea Pines House off Harbour Town Golf Links
4 bikes included

Hilton Head Island - Sea Pines House off Harbour Town Golf Links

3 bedrooms·3 baths
Hilton Head Island • South Carolina
5(36 reviews)

1.918,00 $ USD 1.896,00 $ USD totale per 3 notti

08–11 mag 2027

Cancellazione gratuita
Fall Golf and Cozy Villa equals Perfect Escape! image 1
Cover
Fall Golf and Cozy Villa equals Perfect Escape! image 3
Fall Golf and Cozy Villa equals Perfect Escape! image 4
Fall Golf and Cozy Villa equals Perfect Escape! image 5

Spring and summer dates available!

1 bedroom·1 bath
Beaufort County • South Carolina
4.87(23 reviews)

753,50 $ USD totale per 3 notti

13–16 set 2026

SEA PINES 4 Bed + Loft
SEA PINES 4 Bed + Loft
SEA PINES 4 Bed + Loft
SEA PINES 4 Bed + Loft
SEA PINES 4 Bed + Loft

SEA PINES 4 Bed + Loft

4 bedrooms·4 baths
Hilton Head Island • South Carolina
4.9(188 reviews)
$425 – $825/ notte(escl. spese e tasse)
Aerial view
Front of home
Entryway
Entryway
Kitchen view into living area

Hilton Head Lagoon Paradise in Deer Run

5 bedrooms·5 baths
Hilton Head Island • South Carolina
5(4 reviews)

2.142,86 $ USD totale per 3 notti

02–05 giu 2027

Cancellazione gratuita
Tranquility By The Beach: 12th Row From the Water image 1
Tranquility By The Beach: 12th Row From the Water image 2
Take a dip in the evening
Tranquility By The Beach: 12th Row From the Water image 4
The dining table can accommodate the entire family

Tranquility By The Beach: 12th Row From the Water

5 bedrooms·3½ baths
Hilton Head Island • South Carolina
4.93(59 reviews)

6.666,00 $ USD totale per 7 notti

08–15 set 2026

Sunset view at our beach
Looking into the living room from the dining room.
Living room looking to kitchen/dining and outdoor patio
Large kitchen
Master bedroom with king size bed. Master bath to the right of the bed

Sea Pines at South Beach

2 bedrooms·2 baths
Hilton Head Island • South Carolina
5(1 review)

943,50 $ USD totale per 3 notti

01–04 dic 2026

Cancellazione gratuita
Kitchen
Kitchen
Kitchen
Kitchen
Dining Room

The Salty Villa

3 bedrooms·2 baths
Hilton Head Island • South Carolina
4.93(148 reviews)

1.087,50 $ USD totale per 3 notti

26–29 set 2026