Skip to content

Home 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.

Condo in Hilton Head Island
Harborfront Hilton Head Condo with Sunset Views!
Escape to the Lowcountry when you book this idyllic condo on the water! Complete with 1 bedroom, 1.5 bathrooms, a stunning view, and access to a community pool, this vacation rental boasts everything you need for a worry-free escape! Whether you choose to dine on seafood at nearby restaurants, tan at Coligny Beach Park, or golf at Harbour Town Golf Links, this Hilton Head Island condo awaits after sun-kissed days. Enjoy the sunset from the balcony overlooking the harbor to top off the ideal day!
$98 per night
SUPERHOST
Condo in Hilton Head Island
Ocean Front Resort Villa
Freshly decorated in coastal cottage decor, this 540 sq ft one bedroom villa sleeps up to 6 and is located within the activity-filled Hilton Head Beach and Tennis Resort. The villa was recently remodeled with all new kitchen, bathroom and fixtures and is just 50 steps to gorgeous beach. The views from the living room include ocean, oceanfront pool , beach bar and grill, and pond with fountain. The villa is full of amenities including beach towels, beach chairs, beach umbrella and much more.
$128 per night
SUPERHOST
Condo in Hilton Head Island
Elegant couples retreat - 2021 remodel oceanview!
Stylish beach retreat: Enjoy ocean views and comfortable, Scandinavian design from this newly renovated villa located steps from the beach and within walking distance to many shops, restaurants & entertainment. This well-appointed villa features a beautiful, stocked kitchen, new flooring, walk-in shower and separate bedroom with a desk perfect for getting a little work done. Enjoy ocean-view dining on the balcony or at the kitchen island. There are beach chairs and 2 bikes for your use.
$110 per night

House rentals with a pool

Home in Hilton Head Island
Luxe Treetop Escape w/ Fire Pit & Ocean Views!
$281 per night
SUPERHOST
Home in Hilton Head Island
Harbour Town Treehouse-Sea Pines-Calibogue Lookout
$263 per night
Home in Hilton Head Island
Airy Treehouse w/ Bikes; Walk to Harbour Town!
$260 per night
Home in Hilton Head
Comfy 1BR | Pool | Balcony | Washer/Dryer
$146 per night

Condo rentals with a pool

SUPERHOST
Condo in Hilton Head Island
Beach Resort-OceanView Villa-Stylish Total Remodel
$120 per night
Condo in Hilton Head Island
BEACHFRONT KING BED VILLA, PVT BALCONY, SELF CKIN
$108 per night
SUPERHOST
Condo in Hilton Head Island
Beach Resort 3rd NT FREE Partial OceanView KingBed
$148 per night
SUPERHOST
Condo in Hilton Head Island
1 minute walk to the beach!
$99 per night