Rentals with Private Pools
Browse HHI Rentals with Pools
Enjoying a BESTNEST vacation rental with a private pool is simply the most fun for the whole family. Our homes and villas with private pools provide a little extra space, privacy, and luxury; and for those chilly evenings, most all of our pools can be heated. You deserve it!
(Cost varies by season and source of energy; i.e., electricity or propane).
Browse ou rentals with Private Pools below or check out all of our Hilton Head Island Rentals here
20 properties available
Welcome to the BESTNEST at 2 Green Wing Teal in Sea Pines, just steps from the beach!
- Super spacious, 5 BR/6.5 BA home with 3 kings, 2 queens, and 2 Twins plus 2 Twin Bunks.
- 4th Row Ocean - Stand on the sand in less than 3 minutes.
- Private pool and spa, heatable in cooler months, and gas grill just off the kitchen
- Three master suites, pl
Welcome to the BESTNEST/Luxe at 8 Gull Point in Sea Pines.
8 Gull Point is a wonderfully comfortable home, and we have filled it with every amenity we appreciate when we vacation. The sweeping view of the broad, tidal marsh is stunning and visible from nearly every room. Enjoy watching scores of birds as they feed and fly in this peaceful and tra
Welcome to the BESTNEST at 74 Baynard Cove Road in Sea Pines, where coastal charm meets vintage chic in a renovated stunner. Comfortable furnishings, aged wood and woven textiles have created a "livable" luxury home located on a sought after street near Harbour Town, and only a short bike ride to the beach.
- Super stylish, 5 BR/4 BA home. (3 K
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
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
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.
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Welcome to the BESTNEST at 26 Tupelo 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.
- Super stylish, 4 BR/4.5 BA home including guest house.
- Fully renovated and updated.
- 3 BR/3.5 in main house (1 k
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
Welcome to the BESTNEST at 8 Heritage Road in Sea Pines. Completed renovated and super 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 includes 2 kin
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
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
Welcome to BESTNEST/Luxe: An Elevated Experience in Vacationing.
Enjoy the ultimate in vacation rental accommodations on Hilton Head Island, featuring a carefully curated collection of homes and villas, chosen with the discerning traveler in mind, fabulously stocked, outfitted, and equipped, and supported by your personal property concierge, avai
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