
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

Governor’s Quarters: Stately Sea Pines Stay on HHI

98 Sandcastle Ct

Palmetto Dunes Home on 1st Tee Fazio Golf Course

Cozy Coastal Chic - Beach, Pickleball, Golf, Pets

Hilton Lagoon by AvantStay | Designer Home + Pool

Walk to beach - 2BD/2BA retreat

Private pool/spa : pool heat available : Kg master

Marsh Views | Pool, HotTub, Game Room&Pet Friendly
Condo rentals with a pool

Breathtaking OCEAN VIEW/Top Floor/Pool & Coligny

5 Star Location! Pool, Walk to Shops/Dining

1st flr, Pools, Tennis, Pickleball & Beach Access

Coral Paradise, Ocean View, Pool, Walk to Dining

Beach condo in gated resort w/ tons of amenities!

Coastal King Beach Flat Convenient to Everything!

Beachside Hilton Head Villa Fully Renovated

Upscale 1st Floor Villa, Steps From Beach-Sleeps 4
Other holiday rentals with a pool

180º Ocean Views, Treehouse "Siren's Lookout"

Coastal Comfort! Condo in beachfront resort.

Oceanfront View! Luxury Villa w/ Pool, Hilton Head

Beachfront Escape w Balcony+Pool

Gorgeous Hilton Head Beach Condo

Luxury Waterfront Tree House | Harbour Town | Pool

Easy Walk to the Beach ~ Sleeps 6! TWO bathrooms

Beautiful Newly Renovated 2 Bedroom/2 Bath Condo
Quick stats about holiday rentals with a pool in Hilton Head Island
Total rentals
5.7K properties
Nightly prices starting at
$15 AUD before taxes and fees
Total number of reviews
138K reviews
Family-friendly rentals
4.6K properties are a good fit for families
Pet-friendly rentals
880 properties allow pets
Rentals with dedicated workspaces
3K properties have a dedicated workspace
Destinations to explore
- Central Florida Holiday rentals
- Orlando Holiday rentals
- Saint Johns River Holiday rentals
- Western North Carolina Holiday rentals
- Atlanta Holiday rentals
- Myrtle Beach Holiday rentals
- Kissimmee Holiday rentals
- Gatlinburg Holiday rentals
- Charleston Holiday rentals
- Four Corners Holiday rentals
- Charlotte Holiday rentals
- Pigeon Forge Holiday rentals
- Rentals with a kayak Hilton Head Island
- Serviced apartment rentals Hilton Head Island
- Hotel rentals Hilton Head Island
- Villa rentals Hilton Head Island
- Rentals with beach access Hilton Head Island
- Rentals with an EV charger Hilton Head Island
- Rentals with breakfast Hilton Head Island
- Rentals with a fire pit Hilton Head Island
- Fitness-friendly rentals Hilton Head Island
- Resort rentals Hilton Head Island
- Rentals with a hot tub Hilton Head Island
- Rentals with lake access Hilton Head Island
- House rentals Hilton Head Island
- Family-friendly rentals Hilton Head Island
- Beach house rentals Hilton Head Island
- Beach condo rentals Hilton Head Island
- Rentals with a fireplace Hilton Head Island
- Waterfront rentals Hilton Head Island
- Rentals with outdoor seating Hilton Head Island
- Condo rentals Hilton Head Island
- Mansion rentals Hilton Head Island
- Townhouse rentals Hilton Head Island
- Rentals with an accessible height toilet Hilton Head Island
- Rentals with a home theatre Hilton Head Island
- Beachfront rentals Hilton Head Island
- Rentals with a washing machine and dryer Hilton Head Island
- Luxury rentals Hilton Head Island
- Cottage rentals Hilton Head Island
- Rentals with a sauna Hilton Head Island
- Pet-friendly rentals Hilton Head Island
- Apartment rentals Hilton Head Island
- Rentals with a patio Hilton Head Island
- 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
- Harbour Town Golf Links
- Palmetto Dunes Oceanfront Resort
- The Westin Savannah Harbor Golf Resort & Spa
- Shipyard Beach Access
- Tybee Beach Pier and Pavilion
- Mid Beach
- Bradley Beach
- Harbor Island Beach
- Tybee Beach point
- Dolphin Head Golf Club
- Secession Golf Club
- Wormsloe Historic Site
- Congaree Golf Club
- Bull Point Beach
- Driftwood Beach
- Long Cove Club
- Seabrook Island Beach
- Bonaventure Cemetery
- Hunting Island Beach
- The Beach Club
- Things to do Hilton Head Island
- Tours Hilton Head Island
- Sightseeing Hilton Head Island
- Nature and outdoors Hilton Head Island
- Food and drink Hilton Head Island
- Things to do Beaufort County
- Nature and outdoors Beaufort County
- Sightseeing Beaufort County
- Tours Beaufort County
- Things to do South Carolina
- Entertainment South Carolina
- Sports activities South Carolina
- Sightseeing South Carolina
- Nature and outdoors South Carolina
- Tours South Carolina
- Food and drink South Carolina
- Art and culture South Carolina
- Things to do United States
- Sightseeing United States
- Entertainment United States
- Wellness United States
- Tours United States
- Food and drink United States
- Art and culture United States
- Sports activities United States
- Nature and outdoors United States