Hilton Head Vacation Rentals & Beach Rentals with Swimming Pool - 105 Rentals Available.
105 Vacation rentals
Filters applied: Swimming pool
Oceanfront on HHI's Best Beach New 5 Bedroom Home HEATED POOL INCLUDED
Hilton Head House
- 5 bedrooms 5
- 6 bathrooms
- sleeps 14 14
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$802.00
from $802.00 / night
2306 Ocean View Condo - Beach, 3 Pools, Hot Tub, Sauna, Tennis, Restaurants, etc
Hilton Head Villa
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 2 hours 5 minutes
$102.00
from $102.00 / night
Gated community condo 200/300 steps to beach
Hilton Head Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Beach/lakeside relaxation
- Nearest beach 0.2 mi
- Swimming pool
Responds fast! Avg. 2 hours 47 minutes
$344.00
from $344.00 / night
1304 Ocean View Condo - Beach, 3 Pools, Hot Tub, Sauna, Tennis, Restaurants, etc
Hilton Head Villa
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 2 hours 5 minutes
$251.00
from $251.00 / night
Oceanside Family Resort-Boardwalk to Beach, Pools, Tennis!
Hilton Head Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 4 nights min
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 2 hours 35 minutes
$144.00
from $144.00 / night
Sunny, Updated Oceanfront Villa Steps to Beach & Pool/Beach Gear Incl! Golf Near
Hilton Head Villa
- 2 bedrooms 2
- 2 bathrooms
- sleeps 7 7
- min stay varies
- Beach/lakeside relaxation
- Nearest beach 0 mi
- Swimming pool
$294.00
from $294.00 / night
Spacious 3BR/3BA Home with Private Pool in Palmett
Hilton Head House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 10 10
- 7 nights min
- Nearest beach 1 mi
- Swimming pool
- Child friendly
$344.00
from $344.00 / night
Sea Pines Steps to Beach Book Online Bikes, Tennis, Pets, heated pool
Hilton Head House
- 4 bedrooms 4
- 4 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$500.00
from $500.00 / night
Resort Condo - Beach, 3 Pools, Tennis, Restaurants, Fitness, Hot Tub, Sauna!!
Hilton Head Villa
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 2 hours 5 minutes
$228.00
from $228.00 / night
Oceanside Family Resort-Boardwalk to Beach, Pools, Tennis!
Hilton Head Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 4 nights min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
Responds fast! Avg. 2 hours 35 minutes
$121.00
from $121.00 / night
3406 Resort Condo - Beach, 3 Pools, Hot Tub, Sauna, Tennis, Restaurants, Fitness
Hilton Head Villa
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 2 hours 5 minutes
$80.00
from $80.00 / night
Coligny Villas Forest Beach Condo
Hilton Head Condo
- 2 bedrooms 2
- 3 bathrooms
- sleeps 5 5
- 3 nights min
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 2 hours 37 minutes
$172.00
from $172.00 / night
Resort Condo - Beach, 3 Pools, Tennis, Restaurants, Fitness, Hot Tub, Sauna!!
Hilton Head Villa
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 2 hours 5 minutes
$240.00
from $240.00 / night
17 Dune - "The Cottage" - Oceanfront 7 Bedroom, North Forest Beach
Hilton Head House
- 7 bedrooms 7
- 7 bathrooms
- sleeps 16 16
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$901.00
from $901.00 / night
2 Bedroom Townhouse, Springwood Villas, Short Walk to Beach
Hilton Head House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$145.00
from $145.00 / night
2nd Floor Townhouse, Short Walk to Beach, FREE Gym & Tennis
Hilton Head Villa
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$143.00
from $143.00 / night
Short Walk to the Beach, Pet Friendly Shipyard Villa
Hilton Head House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$160.00
from $160.00 / night
Remodeled Kitchen, FREE Tennis & Gym, Onsite Pool, Short Walk to Beach
Hilton Head Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$161.00
from $161.00 / night
21 Heron - Oceanfront Home, Private Boardwalk
Hilton Head House
- 6 bedrooms 6
- 6 bathrooms
- sleeps 14 14
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$700.00
from $700.00 / night
Renovated Villa, Lagoon & Golf Course 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
$95.00
from $95.00 / night
Ocean Views, 2nd Row Home, Private Pool and Spa
Hilton Head House
- 7 bedrooms 7
- 7 bathrooms
- sleeps 16 16
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$750.00
from $750.00 / night
18 Gannet - 3rd Row Home with Easy Beach Access
Hilton Head House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 9 9
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$425.00
from $425.00 / night
688 Queens Grant, Short Walk to the Beach
Hilton Head House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 7 7
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$145.00
from $145.00 / night
Short Stroll to Beach and Coligny, Private Pool and Game Room
Hilton Head House
- 5 bedrooms 5
- 3 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$260.00
from $260.00 / night
Steps to the Beach, Private Pool
Hilton Head House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 9 9
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$226.00
from $226.00 / night
South Forest Beach Villa, Short Walk to Beach
Hilton Head Villa
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$170.00
from $170.00 / night
Perfect Family Vacation, Short Walk to the Beach, Springwood Villas
Hilton Head House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$164.00
from $164.00 / night
Haul Away 12
Hilton Head House
- 5 bedrooms 5
- 4 bathrooms
- sleeps 12 12
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$475.00
from $475.00 / night
14 Heron Street - 6 Bedroom Home Close to Beach with Jacuzzi!
Hilton Head House
- 6 bedrooms 6
- 6 bathrooms
- sleeps 19 19
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$525.00
from $525.00 / night
13 Sandpiper Street - Pet Friendly and Free Pool Heat Until May
Hilton Head House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$500.00
from $500.00 / night
Updated Villa, Private Balcony, Lagoon Views, Steps to the Beach
Hilton Head Villa
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$185.00
from $185.00 / night
Bright and Airy 2 Bedroom Pet Friendly, Queens Grant
Hilton Head Villa
- 2 bedrooms 2
- 2 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$165.00
from $165.00 / night
Modern Stand Alone Villa, Short Walk to Stunning Beach
Hilton Head Cottage
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$150.00
from $150.00 / night
High Water 9
Hilton Head House
- 7 bedrooms 7
- 6 bathrooms
- sleeps 22 22
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$583.00
from $583.00 / night
219 Cordillo - 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
$390.00
from $390.00 / 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
$245.00
from $245.00 / night
Short walk to the Beach, 2 Bedroom Renovated Forest Beach Villas
Hilton Head Villa
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$155.00
from $155.00 / night
23 Dune - Mimi's Place - Private Beach Access, Large Pool, Giant Pool Deck
Hilton Head House
- 7 bedrooms 7
- 7 bathrooms
- sleeps 18 18
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$850.00
from $850.00 / night
2 Bedroom Townhouse Shipyard, Sailmaster Commons
Hilton Head Villa
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$145.00
from $145.00 / night
Full Sweep 7
Hilton Head House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 9 9
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$260.00
from $260.00 / night
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