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Saint Helena Island Holiday Vacation with Pools

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    Travellers to Saint Helena Island are booking March dates now. Secure your vacation rental today, and have the perfect trip.
    92 Matching Rentals in Saint Helena IslandView all 119 rentals
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    Dataw Island Villa on Ocean Waterway with Dock, Kayak, Bikes, WIFI, 4 TVs, Grill1 / 46
    (56)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Rooftop Deck with Ultimate 360 Degree Views of the Islands sunrise and sunset!1 / 25
    (36)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    3 King Masters W/Private Baths, Two Golf Carts, Game Room, View!!1 / 36
    (62)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Ocean Views AMENITY CARDS and GOLF CART AVAILABLE1 / 25
    (17)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Saint Helena Island, South Carolina 29920
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    5 BR With Spectacular Views!1 / 24
    (28)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Saint Helena Island, South Carolina 29920
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
    Peaceful, beachfront property.  Kid-friendly; pets welcome!1 / 27
    (38)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    Saint Helena Island, South Carolina 29920
    Condo/Apartment - 4 Bedrooms, 3 Bathrooms, Sleeps 11
    Monthly Winter Specials, Bali Retreat :180° Ocean/Hunting island views1 / 50
    (33)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    Saint Helena Island, South Carolina 29920
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 5
    Ocean&Marsh Views! 5BR/5BA, Golf Cart,Wi-Fi! Read Our Reviews!1 / 22
    (105)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Saint Helena Island, South Carolina 29920
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
    Beautiful Atlantic Sound and River Views ~Golf Cart And WiFi! Sand Dollar Sweet1 / 33
    (13)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Saint Helena Island, South Carolina 29920
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    JULY 4 CANCELLATION, Oceanfront, Fripp Island, 6BR/6BA, 24/7 Beach,1 / 24
    (55)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 22 Quick View
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    Saint Helena Island, South Carolina 29920 7315
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 22
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    Gorgeous Ocean & Marsh Views!!! Golf Cart Included1 / 43
    (11)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Saint Helena Island, South Carolina 29920
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Prestine Waterfront Overlooking Championship Golf Course and Jenkins Creek1 / 21
    (7)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Saint Helena Island, South Carolina 29920
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Best Beach Front on Harbor Island - Unobstructed Ocean View1 / 42
    (34)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    Saint Helena Island, South Carolina 29920
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 5
    Large Deck with Awesome Ocean & Marsh View! Free WiFi! Free Hunting Island pass!1 / 36
    (78)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Saint Helena Island, South Carolina 29920
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
    Ocean / Beach / River / Sunsets / Marsh & More1 / 28
    (103)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Saint Helena Island, South Carolina 29920
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Best Beach Front on Harbor Island - Unobstructed Ocean View1 / 33
    (46)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    Saint Helena Island, South Carolina 29920
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 5
    Family Beach House steps away from the ocean w/Golf cart!1 / 32
    (26)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Saint Helena Island, South Carolina 29920
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 12
    Summer 2019-Includes Golf Cart, 2 Cards, 48' Flat Screen TV, WIFI, and Bikes!!1 / 24
    (24)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Saint Helena Island, South Carolina 29920
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
    Oceanfront 2 Bedroom New Deck!1 / 23
    (54)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    Saint Helena Island, South Carolina 29920
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
    Tremendous Fripp Island Home w/ Ocean View. Game Room, & Golf Cart, great for Gr1 / 50
    (12)Excellent
    7 Bedrooms, 8 Bathrooms, Sleeps 23 Quick View
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    Saint Helena Island, South Carolina 29920
    Holiday Rental House - 7 Bedrooms, 8 Bathrooms, Sleeps 23
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    Spacious Condo On Beautiful Harbor Island, Sc1 / 20
    (56)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Saint Helena Island, South Carolina 29920
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
    Pelican Point Unobstructed Beach Views Beach Access out back door!1 / 33
    (14)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Saint Helena Island, South Carolina 29920
    Condo/Apartment - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Golf Cart and 5 Bedrooms! Sleeps 131 / 25
    (13)Very good
    5 Bedrooms, 5 Bathrooms, Sleeps 13 Quick View
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    Saint Helena Island, South Carolina 29920
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 13
    Spacious home on Canal with private dock and steps from ocean.1 / 41
    (8)Very good
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Saint Helena Island, South Carolina 29920
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    Renovated Ocean Front1 / 24
    (75)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Saint Helena Island, South Carolina 29920
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Saint Helena Island, South Carolina 29920
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Golf Cart Included!! Harbour Key Retreat1 / 8
    (11)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Saint Helena Island, South Carolina 29920
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    The Sea Breeze, Cabana Club Pools, Pet Friendly,  Golf Cart1 / 24
    (34)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Saint Helena Island, South Carolina 29920
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Saint Helena Island, South Carolina 29920
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Oceanfront Living at Ocean View Pricing-2nd Row with Big View and Boardwalk!1 / 35
    (21)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Saint Helena Island, South Carolina 29920
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    STUNNING SUNSETS- HARBOR RIVER VIEW1 / 21
    (11)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Saint Helena Island, South Carolina 29920
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    3 Bdrm 2 Bath Waterfront Villa on Dataw with Dock, Bikes, Pool and Beach Pass!1 / 17
    (7)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Saint Helena Island, South Carolina 29920
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Breathtaking Ocean & Island Views from Four Porches!1 / 17
    (12)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Saint Helena Island, South Carolina 29920
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Perfect oceanfront family hideaway, pet friendly with a private path to the beac1 / 29
    (13)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Saint Helena Island, South Carolina 29902
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
    Condo With Lovely Marsh Views and Steps to Water1 / 22
    (4)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Saint Helena Island, South Carolina 29920
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    5 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    Saint Helena Island, South Carolina 29920
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 11
    Pristine 3 Bedroom Dataw Bluff Villa1 / 18
    (17)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Saint Helena Island, South Carolina 29920
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Expansive Marsh and Water View1 / 50
    (6)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Saint Helena Island, South Carolina 29920
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
    Pet Friendly Cottage with Views of Pond & Golf Coarse/Golf Cart Included1 / 21
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Saint Helena Island, South Carolina 29920
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Lovely 3 bedroom home with ocean access; guest cards available1 / 28
    (10)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Saint Helena Island, South Carolina 29920
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Two Bedroom Bluff Villa Just Steps to Dataw Amenities!!1 / 38
    (6)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Saint Helena Island, South Carolina 29920
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Bonito home on the 17th fairway1 / 24
    (31)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Saint Helena Island, South Carolina 29920
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Beautiful updated home with Private Pool and Ocean Views, great for perfect vaca1 / 48
    (12)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Saint Helena Island, South Carolina 29920
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
    Four-Bedroom House with Great View! Pool Across the Street! Hunting Island Pass!1 / 16
    (14)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Saint Helena Island, South Carolina 29920
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    VIEWS VIEWS VIEWS! BEACHFRONT 4 Bdrm Home.  Pvt Boardwalk to Beach. Golf cart!1 / 49
    (41)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Saint Helena Island, South Carolina 29920
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 12
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Saint Helena Island, South Carolina 29920
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
    NEW LISTING!! BEACH HOUSE VILLA SCREENED PORCH WITH VIEWS1 / 50
    (10)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Saint Helena Island, South Carolina 29920
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
    Ocean Front, Renovated 2017 with Upscale Furnishings/1 / 23
    (7)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Saint Helena Island, South Carolina 29920
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Great View of Swimming Pool and Beach, Minutes Walk to the Beach1 / 19
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Saint Helena Island, South Carolina 29920
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Ocean Front D-Building - POOL ACCESS AND OCEAN VIEWS!!!1 / 26
    (25)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    Saint Helena Island, South Carolina 29920
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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