Hilton Head Vacation Rentals & Beach Rentals with Swimming Pool - 747 Rentals Available.
747 Vacation rentals
Filters applied: Swimming pool
Totally renovated OCEAN VIEW w WIFI and fitness
Hilton Head Apartment
- 1 bedroom 1
- 1 bathroom
- Sleeps 4 4
- 3 nights min
- Beach/lakeside relaxation
- Nearest beach 0.2 mi
- Swimming pool
$109
from $109 / night
Sea Pines Resort, 13 Black Skimmer. Beach View!
Hilton Head House
- 5 bedrooms 5
- 6 bathrooms
- Sleeps 21 21
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$500
from $500 / night
Ocean View Villa..75 Yds from beach-from $350/wk
Hilton Head Villa
- 1 bedroom 1
- 1 bathroom
- Sleeps 6 6
- Min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$60
from $60 / night
Gated community condo 200/300 steps to beach
Hilton Head Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- 5 nights min
- Beach/lakeside relaxation
- Nearest beach 0.2 mi
- Swimming pool
$70
from $70 / night
Sea Pines Central Location! - Walk to Beach/Golf- Private Pool- GOLF VIEW!
Hilton Head Villa
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 7 7
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$208
from $208 / night
Sun, Sand, Pools, Beach, Tennis, Bicycle Trails
Hilton Head Villa
- 1 bedroom 1
- 1 bathroom
- Sleeps 4 4
- Min stay varies
- Beach/lakeside relaxation
- Nearest beach 0 mi
- Swimming pool
$69
from $69 / night
Steps to Beach & Golf - Newly Renovated Home
Hilton Head House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$250
from $250 / night
3 houses, 75yds to beach, great pool NFB
Hilton Head House
- 6 bedrooms 6
- 5 bathrooms
- Sleeps 16 16
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$568
from $568 / night
Oceanfront on HHI's Best Beach New 5 Bedroom Home
Hilton Head House
- 5 bedrooms 5
- 6 bathrooms
- Sleeps 12 12
- Min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$650
from $650 / night
216 Barrington OCEANFRONT Booking Winter and Spring NOW!!
Hilton Head Villa
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 7 7
- 7 nights min
- Beach/lakeside relaxation
- Nearest beach 0 mi
- Swimming pool
$169
from $169 / night
5 Bdrm, Renov, Walk to Beach, Pool, Golf views
Hilton Head House
- 5 bedrooms 5
- 4 bathrooms
- Sleeps 12 12
- 5 nights min
- Swimming pool
- Ask about children
- Air conditioning
$571
from $571 / night
2nd Row, Tropical 7BR/5BA Pool & Hot Tub
Hilton Head House
- 7 bedrooms 7
- 5 bathrooms
- Sleeps 14 14
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$550
from $550 / night
Sea Pines Resort, Huge Beach Home !
Hilton Head House
- 7 bedrooms 7
- 7 bathrooms
- Sleeps 20 20
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$400
from $400 / night
Coligny Villas Forest Beach Condo
Hilton Head Condo
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 5 5
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$100
from $100 / night
A Great Escape
Hilton Head House
- 7 bedrooms 7
- 8 bathrooms
- Sleeps 20 20
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$499
from $499 / night
Lg Pool, handicap friendly sleeps 14
Hilton Head House
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 14 14
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$264
from $264 / night
Sea Pines Resort, 3rd Row Beach Walk, 5 Bedrooms
Hilton Head House
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 15 15
- Min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$550
from $550 / night
Resort Condo - Beach, 3 Pools, Tennis, Restaurants, Fitness, Hot Tub, Sauna!!
Hilton Head Villa
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$69
from $69 / night
BRAND NEW Beach House w/Pool, Elevatr Ready In May
Hilton Head House
- 5 bedrooms 5
- 4 bathrooms
- Sleeps 16 16
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$450
from $450 / night
Hilton Head Sea Pines Walk2Beach/book online
Hilton Head House
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$214
from $214 / night
Lagoon Front, Palmetto Dunes, 5 min walk to beach
Hilton Head Villa
- 3 bedrooms 3
- 4 bathrooms
- Sleeps 13 13
- Min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Ask about children
$225
from $225 / night
Resort Condo - Beach, 3 Pools, Tennis, Restaurants, Fitness, Hot Tub, Sauna!!
Hilton Head Villa
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$69
from $69 / night
Spacious 3BR/3BA Home with Private Pool in Palmett
Hilton Head House
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$195
from $195 / night
Oceanfront, Sea Pines, 22 Black Skimmer Rd. - Pool
Hilton Head House
- 6 bedrooms 6
- 7 bathrooms
- Sleeps 12 12
- Min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$550
from $550 / night
Beyond Luxury, Oceanfront 8 Bedroom Home w/ Salt Water Pools, Game Rm &
Hilton Head House
- 8 bedrooms 8
- 8 bathrooms
- Sleeps 20 20
- Min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$1655
from $1655 / night
Meticulous Oceanside Sea Pines Beach-house! 2nd Row with Ocean Views!
Hilton Head House
- 4 bedrooms 4
- 5 bathrooms
- Sleeps 16 16
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$768
from $768 / night
Newly Remodeled, on the Golf Course and Near the Beach!!
Hilton Head Villa
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$279
from $279 / night
335 Shorewood- Zero Entry Pool & Kiddy Pool. Oceanfront Views.
Hilton Head Villa
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$159
from $159 / night
258 Evian-Quick bike ride to beach. Pool & Tennis on-site
Hilton Head Villa
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$94
from $94 / night
Short Walk to the Beach, Private Pool/Spa, Near Coligny Plaza
Hilton Head House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$371
from $371 / night
1303 SeaCrest - 3rd Floor - Gorgeous Ocean Views & Walk to Shopping & Dining
Hilton Head Villa
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 8 8
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$159
from $159 / night
Direct Oceanfront Home, Private Pool/Spa
Hilton Head House
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 12 12
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$422
from $422 / night
52 N. Forest Beach-Brand NEW Beach Home. 5th row ocean w/elevator
Hilton Head House
- 7 bedrooms 7
- 8 bathrooms
- Sleeps 16 16
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$505
from $505 / night
77A Dune-New Homes with Awesome Views. 7/8 & 7/15 Weeks Available.
Hilton Head House
- 5 bedrooms 5
- 6 bathrooms
- Sleeps 16 16
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$633
from $633 / night
Steps to Beach, Private Pool/Spa and Pool Bar, 5 Minute Walk to Coligny
Hilton Head House
- 6 bedrooms 6
- 6 bathrooms
- Sleeps 16 16
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$436
from $436 / night
Southern Beach Living, Private Pool & Spa, Short Walk to Beach
Hilton Head House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$571
from $571 / night
Spectacular Oceanfront Beach Home with Extra Large Pool
Hilton Head House
- 6 bedrooms 6
- 5 bathrooms
- Sleeps 16 16
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$714
from $714 / night
12 N. Live Oak-8 min easy walk to beach
Hilton Head House
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 10 10
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$187
from $187 / night
Short Walk to Harbor Town, Lagoon Views, Onsite Pool/Tennis
Hilton Head Villa
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$193
from $193 / night
Newly remodeled, Private Pool, Minutes from beach
Hilton Head House
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$479
from $479 / night
What is Certificate of Excellence?
TripAdvisor gives a Certificate of Excellence to accommodations, attractions and restaurants that consistently earn great reviews from travelers.