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/ nacht(excl. kosten & belastingen)
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 totaal voor 3 nachten

11–14 okt 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

$ 4.014,70 USD totaal voor 3 nachten

8–11 mrt 2027

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

$ 1.141,43 USD totaal voor 3 nachten

27–30 sep 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 totaal voor 3 nachten

27–30 sep 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

$ 877,21 USD totaal voor 3 nachten

11–14 nov 2026

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)

$ 1.089,92 USD totaal voor 3 nachten

10–13 okt 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 totaal voor 3 nachten

25–28 sep 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

$ 9.502,65 USD totaal voor 4 nachten

27 sep – 1 okt 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)
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 totaal voor 3 nachten

26–29 sep 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)

$ 3.330,00 USD totaal voor 4 nachten

27 sep – 1 okt 2026

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 totaal voor 3 nachten

2–5 jun 2027

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)

$ 6.721,50 USD totaal voor 7 nachten

27 okt – 3 nov 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 totaal voor 3 nachten

1–4 dec 2026

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 totaal voor 3 nachten

26–29 sep 2026

3 Min to Beach, Edisto Treehouse, Stunning Sunsets
3BR Edisto Treehouse | Steps to Beach | Boat Space image 19
Entry leads to open Living Room/Dining Room
Freshly painted exterior and decking for 2026!
3BR Edisto Treehouse | Steps to Beach | Boat Space image 118

3 Min to Beach, Edisto Treehouse, Stunning Sunsets

3 bedrooms·2 baths
Edisto Beach • South Carolina
5(112 reviews)

$ 1.625,00 USD totaal voor 3 nachten

25–28 sep 2026

Welcome to Seascape!
Open living room
Open kitchen and dining area
Kitchen
Dining table off of kitchen and living room

Walk 2 beach, Firepit, Boat parking, Pets welcome!

2 bedrooms·1 bath
Edisto Island • South Carolina
5(6 reviews)

$ 1.057,00 USD totaal voor 3 nachten

27–30 sep 2026

Spacious, 4-bedroom house at the end of a no-outlet road. Plenty of space for parking. Ideal for two families or a group of friends.
Our house name means "Seagull" in Russian. Pronounced like "Chai" you'd get at Starbucks, plus "kuh". The owners lived several years in Kazakhstan where they spoke Russian, so this connects them to those memories.
And we do mean "secluded"! This photo is taken from the lot across the street.
The Chaika kitchen got a whole redo in 2021 with granite counters, new facing, new drawers, and new backsplash.
The kitchen is spacious, well equipped with plenty of utensils and appliances.

Secluded, Spacious Edisto Beach Walk Home "Chaika"

4 bedrooms·2 baths
Edisto Beach • South Carolina
4.92(146 reviews)

$ 940,80 USD totaal voor 3 nachten

15–18 okt 2026

May 2022 - Livingroom with new 75" smart tv and new queen sleeper sofa
Balcony over looking small pond/marsh and golf course. Small table and chairs (seating for 4)
King bed in bedroom with small tv
Drifting to Driftwood ~ Cute Condo ~ New 75" TV! image 5
Drifting to Driftwood ~ Cute Condo ~ 75" TV!

Drifting to Driftwood ~ Cute Condo ~ 75" TV!

1 bedroom·1 bath
Edisto Island • South Carolina
4.92(118 reviews)

$ 699,95 USD totaal voor 3 nachten

7–10 okt 2026

Exterior
Exterior
Exterior
Pool
Exterior detail

Lowcountry Luxury and Charm on Edisto Beach

4 bedrooms·3 baths
Edisto Island • South Carolina

$ 1.769,00 USD totaal voor 3 nachten

27–30 sep 2026

Up The Creek
Up The Creek
Up The Creek
Up The Creek
Up The Creek

Up The Creek

3 bedrooms·2½ baths
Edisto Island • South Carolina

$ 6.658,39 USD totaal voor 7 nachten

25 sep – 2 okt 2026

Edisto License to Chill image 1
Edisto License to Chill image 2
Edisto License to Chill image 3
Edisto License to Chill image 4
Edisto License to Chill image 5

Edisto License to Chill

3 bedrooms·2 baths
Edisto Island • South Carolina

$ 1.614,36 USD $ 1.294,48 USD totaal voor 3 nachten

25–28 sep 2026