Rentals with Private Pools

Looking for Hilton Head rentals with pools? Go for a BESTNEST! Our homes with private pools are the perfect choice for any vacation. Most pools are can be heated in the colder months and we always provide quality pool furniture, lots of towels, and plenty of poolside-safe dishes and glassware.

When it comes to our Hilton Head Island Rentals, BESTNEST provides comfort, cleanliness, and consistency. Rest easy in a NEST from BESTNEST!


Properties Available 21 properties available
Welcome to the BESTNEST at 4 Scaup Court in Sea Pines. Here\'s the skinny - just buzz us for more details! Our advertised rates are our very best rates and calendar shows real time availability. We encourage you to book online! - Spacious, 3 BR/3 BA home with 1 king, 2 queens, 2 twins. Each bedroom has en suite bath. - 3rd row Ocean--Stand on
4 Scaup Court: Sea Pines
House Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.9 (40)
Welcome to the BESTNEST at 60 Lawton Road in Sea Pines! Here\'s the skinny - just buzz us for more details: Our advertised rates are our very best rates and calendar shows real time availability. We encourage you to book online! COMPLIMENTARY POOL HEATING FOR ALL MARCH 2026 RESERVATIONS. - Beautifully renovated! Light filled, 5 BR/ 4 BA home wi
60 Lawton Road: Sea Pines
House Pet Friendly
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 12 guests
Rating 5 (6)
Welcome to the BESTNEST at 45 Deer Run in Sea Pines. Here\'s the skinny - just buzz us for more details: Our advertised rates are our very best rates and calendar shows real time availability. We encourage you to book online! 3 new bathrooms and new living room furnishings completed March 2025! - Super stylish, 4 BR/4 BA home. 2 main level bedr
45 Deer Run Lane: Sea Pines
House Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 10 guests
Rating 4.9 (48)
Welcome to the BESTNEST at 9 Wren Drive in Sea Pines. Here\'s the skinny - just buzz us for more details! Our advertised rates are our very best rates and calendar shows real time availability. We encourage you to book online! COMPLIMENTARY POOL HEATING FOR ALL MARCH 2026 RESERVATIONS. - Spacious, 5 BR/5.5 BA home with 2 kings, 4 fulls, and 4
9 Wren Drive: Sea Pines
House
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 14 guests
Rating 4.9 (69)
Welcome to the BESTNEST at 11 Black Tern in Sea Pines. Here\'s the skinny - just buzz us for more details: Our advertised rates are our very best rates and calendar shows real time availability. We encourage you to book online! - Super stylish, 3 BR/2.5 BA home - Fully renovated with open plan and gorgeous views - Sleeping includes 1 king, 2 que
11 Black Tern: Sea Pines
House Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 7 guests
Rating 4.9 (75)
Welcome to BESTNEST/Luxe: An Elevated Experience in Vacationing. Our NEW BESTNEST/Luxe property at 12 Woodbine Place in Sea Pines is a super stylish 4BR/4 BA home, just fully renovated with fabulous furnishings and heatable pool. - The heart of this home is the one level, open living plan with pool and golf views form nearly every vantage point.
12 Woodbine Place: Sea Pines
House
Bedrooms 4 bedrooms
Bathrooms 5 baths
Guests 9 guests
Rating 5 (3)
Welcome to the BESTNEST at 44 Stoney Creek in Sea Pines. Here\'s the skinny - just buzz us for more details: Our advertised rates are our very best rates and calendar shows real time availability. We encourage you to book online! - Super stylish, 3 BR/3 BA home, fully renovated and featuring open living plan, all on one level - Each of 3 bedroom
44 Stoney Creek: Sea Pines
House
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 7 guests
Rating 4.9 (73)
Welcome to the BESTNEST at 8 Heritage Road in Sea Pines. Completely renovated and conveniently close to Harbour Town. - Super stylish, 4 BR/3.5 BA home. 3 main level bedrooms and 1 upper level bedroom including 2 master suites - Designed and furnished in the signature BESTNEST style: completely comfortable, sophisticated chic! - Sleeping includ
8 Heritage Road: Sea Pines
House Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 5 (27)
Welcome to the BESTNEST at 63 South Sea Pines Drive in Sea Pines- with FENCED POOL AREA! Here\'s the skinny - just buzz us for more details! Our advertised rates are our very best rates and calendar shows real time availability. We encourage you to book online! - Supremely stylish, 4 BR/3 BA home with 2 kings, 2 queens, and 1 twin + trundle. Ne
63 South Sea Pines: Sea Pines
House Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.9 (39)
Welcome to the BESTNEST at 27 Hollyberry Lane in Sea Pines. Our advertised rates are our very best rates and calendar shows real time availability. We encourage you to book online! - Super stylish and beautifully renovated 4 BR/3.5 BA home. - Sleeping includes 3 kings and 2 twins. - Open concept plan with everything on one level, with the excepti
27 Hollyberry Lane: Sea Pines
House Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (25)
Indulge in BESTNEST/Luxe: the pinnacle of vacation rental luxury on Hilton Head Island, where a meticulously curated selection of homes and villas awaits the discerning traveler. Each property is exquisitely appointed, fully equipped, and thoughtfully outfitted, complemented by the dedicated services of a personal concierge available around the clo
14 N Live Oak: Sea Pines
House
Bedrooms 6 bedrooms
Bathrooms 6 baths
Guests 10 guests
Rating 5 (13)
Our BESTNEST/Luxe property at 23 South Beach Lagoon (A VRBO Top Ten in America, The famous Today Show and Bucket List Family house!) showcases the concept beautifully- this is a casually chic, and gracious home, resplendent with inviting indoor and outdoor spaces. This property requires a minimum 7-night stay in summer, with Saturday arrivals and d
23 South Beach Lagoon Dr: Sea Pines
House
Bedrooms 6 bedrooms
Bathrooms 8 baths
Guests 14 guests
Rating 4.9 (15)

Tell us what you're looking for and someone will contact you with available options.

I agree