Vacation 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.
Vacation 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
4.96 out of 5 average rating, 123 reviewsPeaceful Harbour Town Treehouse with Marsh Views
Home in Hilton Head Island
4.97 out of 5 average rating, 107 reviewsLovely 3BR in Palmetto Dunes w/ new pool & spa
Home in Hilton Head Island
4.85 out of 5 average rating, 103 reviewsPalmetto Dunes Home on 1st Tee Fazio Golf Course
Home in Hilton Head Island
4.85 out of 5 average rating, 205 reviewsCoastal Town Gallery House - live like a local!
Home in Bluffton
4.86 out of 5 average rating, 176 reviewsBluffton/Hilton Head Island/Savannah Vacation Home
Home in Hilton Head Island
4.86 out of 5 average rating, 103 reviewsBlue Sky Villa: Beach/pets/golf/tennis/pickleball
Home in Hilton Head Island
4.9 out of 5 average rating, 10 reviewsStylishly Updated Beach Cottage Yards from Ocean!
Home in Hilton Head Island
5.0 out of 5 average rating, 14 reviews~Couples Paradise~Villa W/ Pool~Beachfront Resort
Condo rentals with a pool
Condo in Hilton Head Island
4.95 out of 5 average rating, 232 reviewsOcean View! Steps to beach! Remodeled HHBT Condo!
Condo in Hilton Head Island
4.94 out of 5 average rating, 427 reviews(5) Location! Walk to Coligny Beach Shops Dining!
Condo in Hilton Head Island
4.96 out of 5 average rating, 227 reviewsOceanfront Designer! KING BED 65"TV Bar Gym Tennis
Condo in Hilton Head Island
4.89 out of 5 average rating, 153 reviewsBeachfront property with ocean/sunrise view!
Condo in Hilton Head Island
4.85 out of 5 average rating, 234 reviewsCharming Sea Pines Villa with View on Hilton Head
Condo in Hilton Head Island
4.98 out of 5 average rating, 183 reviewsLost Tiki Lounge TOP Floor Oceanfront 322 Breakers
Condo in Hilton Head Island
4.96 out of 5 average rating, 213 reviewsCozy Oceanfront-Romantic Retreat-Mesmerizing Views
Condo in Hilton Head Island
4.88 out of 5 average rating, 196 reviewsOur Villa by the Sea
Quick stats about vacation 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
$10 before taxes and fees
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