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
Home in Hilton Head Island
4.86 out of 5 average rating, 104 reviewsPalmetto Dunes Home on 1st Tee Fazio Golf Course
Home in Hilton Head Island
4.85 out of 5 average rating, 206 reviewsCoastal Town Gallery House - live like a local!
Home in Hilton Head Island
4.96 out of 5 average rating, 125 reviewsPeaceful Harbour Town Treehouse with Marsh Views
Home in Hilton Head Island
4.97 out of 5 average rating, 108 reviewsLovely 3BR in Palmetto Dunes w/ new pool & spa
Home in Hilton Head Island
4.94 out of 5 average rating, 129 reviewsSpa/Fully Screened Heated Pool/Elevator/Fenced-79
Home in Hilton Head Island
4.87 out of 5 average rating, 104 reviewsBlue Sky Villa: Beach/pets/golf/tennis/pickleball
Home in Hilton Head Island
4.92 out of 5 average rating, 109 reviewsLuxe & Fun Family Gem ~ Walk to Beach ~ Pool ~ BBQ
Home in Bluffton
4.86 out of 5 average rating, 176 reviewsBluffton/Hilton Head Island/Savannah Vacation Home
Condo rentals with a pool
Condo in Hilton Head Island
4.93 out of 5 average rating, 120 reviewsHip Nautic Couples Beach Condo, Pickleball/Hot Tub
Condo in Hilton Head Island
4.88 out of 5 average rating, 163 reviewsHilton Head Hidden Gem
Condo in Hilton Head Island
4.96 out of 5 average rating, 117 reviewsBeach&Tennis, Stylish, Modern, Folly Field Beach!
Condo in Hilton Head Island
4.88 out of 5 average rating, 199 reviewsOur Villa by the Sea
Condo in Hilton Head Island
4.98 out of 5 average rating, 132 reviews"Beach Time" - a cozy HHI Condo, steps from beach
Condo in Hilton Head Island
4.88 out of 5 average rating, 182 reviewsCozy Hilton Head Island Condo
Condo in Hilton Head Island
4.84 out of 5 average rating, 155 reviewsS&A Getaway at Xanadu Villas
Condo in Hilton Head Island
4.99 out of 5 average rating, 154 reviewsReno’d 1st floor walk to beach, pools pickleball
Quick stats about holiday rentals with a pool in Hilton Head Island
Total rentals
4.8K properties
Rentals with dedicated workspaces
2.4K properties have a dedicated workspace
Pet-friendly rentals
670 properties allow pets
Family-friendly rentals
3.9K properties are a good fit for families
Total number of reviews
102K reviews
Nightly prices starting at
$16 NZD before taxes and fees
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