
Holiday rentals with a pool in Hilton Head Island
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Hilton Head Island
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Hilton Head Island rentals with a pool
House rentals with a pool

98 Sandcastle Ct

2nd Row - Private Pool ~ 4 King Bedrooms

5 Bedroom-Beach Access-Pool-Sleeps 14!

Hilton Head Island Beach House - Sea Pines Resort

Brand New Sea Pines Remodel - Minutes To Beach!

Cozy beach house w/Private Heated Pool near park

Lagoon & Tidal Marsh Views w/Screened-In Porch

54 Folly Field Rd - Amazing Beach Home with Pool
Condo rentals with a pool

Remodeled KING BED 1BR Oceanview Top Floor Villa

Ocean Front Resort Villa

Luxury Condo King bed Pool &Ocean views hot Tub

Oceanside Beach Retreat

Newly Renovated: Island Hideaway on Hilton Head

1 Minute walk to the beach *Amazing ocean view*

Beautiful Oceanfront Villa with Amazing Sunrises

$95/nt ~ KING Bed ~ Sleeps 7 ~ CLEAN ~ Big Pool
Other holiday rentals with a pool

Palmetto Dunes - Captains Walk, Penthouse View

212 Barrington Court - Ocean Front Palmetto Dunes

Steps to the Beach - Perfect All-Season Getaway

Sea Pines Villa•Steps to Beach•Coffee Bar•King Bed

Palmetto Dunes! Luxe 2B Beach Golf Pickleball Pool

Coastal Oasis - 200 yards to Beach! (Lower Unit)

Prime Waterview! Hilton Head Shelter Cove Marina

Oceanfront paradise just steps away to the beach.
Quick stats about holiday rentals with a pool in Hilton Head Island
Total rentals
5.7K properties
Nightly prices starting at
$17 NZD before taxes and fees
Total number of reviews
130K reviews
Family-friendly rentals
4.7K properties are a good fit for families
Pet-friendly rentals
860 properties allow pets
Rentals with dedicated workspaces
3K properties have a dedicated workspace
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- Rentals with a patio Hilton Head Island
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- Rentals with pools Beaufort County
- Rentals with pools South Carolina
- Rentals with pools United States
- Coligny Beach Park
- Forsyth Park
- Hunting Island State Park Beach
- North Beach, Tybee Island
- Palmetto Dunes Oceanfront Resort
- Harbour Town Golf Links
- Shipyard Beach Access
- Bradley Beach
- Tybee Beach Pier and Pavilion
- Mid Beach
- Harbor Island Beach
- Wormsloe Historic Site
- The Westin Savannah Harbor Golf Resort & Spa
- Dolphin Head Golf Club
- Congaree Golf Club
- Secession Golf Club
- Driftwood Beach
- The Beach Club
- St. Catherines Beach
- Tybee Beach point
- Bull Point Beach
- Seabrook Island Beach
- Long Cove Club
- Islanders Beach Park
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