Hilton Head House Rentals With Private Pool

Stay in style with a private pool on Hilton Head Island. While vacationing on Hilton Head, there’s nothing more relaxing than enjoying the pool with your friends and family. Our Hilton Head vacation rentals with private pools give you a place to dive into a refreshing afternoon. Located in Hilton Head’s best neighborhoods, with great access to beaches, golf courses, and family entertainment, these special vacation homes are perfect for families and groups. Book your Hilton Head poolside vacation today!

You can filter by bedrooms, guests, pet friendly and much more! Looking for oceanfront rentals? Use the oceanfront filter to select all Hilton Head oceanfront rentals with pool.

Booking your dream vacation is easy. Simply browse our selection of Hilton Head oceanfront rentals, choose your dates, and secure your reservation online. Our friendly team is also available to help you find the perfect property to suit your needs.Stay in style with a private pool on Hilton Head Island. While vacationing on Hilton Head, there’s nothing more relaxing than enjoying the pool with your friends and family. Our Hilton Head vacation rentals with private pools give you a place to dive into a refreshing afternoon. Located in Hilton Head’s best neighborhoods, with great access to beaches, golf courses, and family entertainment, these special vacation homes are perfect for families and groups. Book your Hilton Head poolside vacation today!

You can filter by bedrooms, guests, pet friendly and much more! Looking for oceanfront rentals? Use the oceanfront filter to select all Hilton Head oceanfront rentals with pool.

Booking your dream vacation is easy. Simply browse our selection of Hilton Head oceanfront rentals, choose your dates, and secure your reservation online. Our friendly team is also available to help you find the perfect property to suit your needs.

Properties Available 184 properties available
Walk to the Atlantic Ocean and Coligny Plaza for dining and shopping... what more do you need!?? Three (3) bedrooms and two (2) full bathrooms offer sleeping arrangements for up to seven. Updated furnishings complete the look of this home, providing a "shore to please" vacation. Complete with a backyard oasis, including a private pool and screened-
sand-dollar Special
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Cheers to a wonderful holiday season! Book by December 2nd and enjoy 15% off your Hilton Head vacation!  *Not valid on existing reservations


1 Bittern Street
1 Bittern Street Rating 4.8 (7)
House
Bedding Breakdown
  • 1 King
  • 1 Queen
  • 1 Bunk
Bathrooms
  • 2 full baths
amenities
  • Near Ocean
  • Grill/BBQ - Private
  • *4 Adult Bikes
  • Pool Access
  • Private Pool
  • Beach Cart
1 Bittern Street 1 Bittern Street 1 Bittern Street 1 Bittern Street 1 Bittern Street 1 Bittern Street 1 Bittern Street 1 Bittern Street 1 Bittern Street 1 Bittern Street
1 Bittern Street
Forest Beach
Bedrooms 3 bedrooms
Bathrooms 2 full baths
Guests 7 guests
Rating 4.8 (7)
Look at this 3-bedroom home within minutes of Coligny Plaza, Celebration Park, and sandy beaches - providing the perfect island getaway! With all new bathrooms and updated decor throughout, this beach cottage is the relaxed lifestyle you want for either a quick getaway or an extended stay! Pets are allowed. (limit 40lb) There is a $300.00 non refun
sand-dollar Special
Holiday Cheer with 15% Off

Cheers to a wonderful holiday season! Book by December 2nd and enjoy 15% off your Hilton Head vacation!  *Not valid on existing reservations


1 Dove Street
1 Dove Street Rating 5 (7)
House Pet Friendly
Bedding Breakdown
  • 1 King
  • 2 Queens
Bathrooms
  • 2 full baths
amenities
  • Near Ocean
  • *4 Adult Bikes
  • Dogs Considered
  • Private Pool
  • Beach Cart
  • Grill/BBQ - Private
1 Dove Street 1 Dove Street 1 Dove Street 1 Dove Street 1 Dove Street 1 Dove Street 1 Dove Street 1 Dove Street 1 Dove Street 1 Dove Street
1 Dove Street
Forest Beach Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 full baths
Guests 7 guests
Rating 5 (7)
West Garrison is located in a quiet neighborhood within Sea Pines Resort. The main level of the house has a large living and dining area to accommodate all family gatherings. A second living area on the main level is perfect for watching TV. Both living areas have a queen sleeper sofa. The main level showcases a master bedroom with an en-suite bath
sand-dollar Special
Holiday Cheer with 15% Off

Cheers to a wonderful holiday season! Book by December 2nd and enjoy 15% off your Hilton Head vacation!  *Not valid on existing reservations


1 West Garrison
1 West Garrison Rating 5 (9)
House
Bedding Breakdown
  • 2 Kings
  • 2 Sofa Beds
  • 2 Bunks
Bathrooms
  • 3 full baths
  • 1 half bath
amenities
  • Near Ocean
  • Pool Access
  • *4 Adult Bikes
  • Grill/BBQ - Private
  • Hot Tub/Spa - Private
  • Private Pool
  • Beach Cart
1 West Garrison 1 West Garrison 1 West Garrison 1 West Garrison 1 West Garrison 1 West Garrison 1 West Garrison 1 West Garrison 1 West Garrison 1 West Garrison
1 West Garrison
Sea Pines
Bedrooms 3 bedrooms
Bathrooms 3 full baths & 1 half bath
Guests 10 guests
Rating 5 (9)
Your very own private retreat in the heart of Sea Pines! This 3-bed, 3-bath single-level home offers an open concept with multiple living spaces for the entire family. The Tommy Bahama décor throughout and Brazilian cherry wood floors are highlighted by the numerous skylights which allow an abundance of natural light in. Upon entering, you will fin
sand-dollar Special
Holiday Cheer with 15% Off

Cheers to a wonderful holiday season! Book by December 2nd and enjoy 15% off your Hilton Head vacation!  *Not valid on existing reservations


12 Deer Run Lane
12 Deer Run Lane Rating 5 (45)
House
Bedding Breakdown
  • 2 Kings
  • 2 Twins
Bathrooms
  • 3 full baths
amenities
  • Near Ocean
  • Beach Cart
  • Pool Access
  • *4 Adult Bikes
  • Hot Tub/Spa - Private
  • Tennis - Membership
  • Grill/BBQ - Private
  • Private Pool
12 Deer Run Lane 12 Deer Run Lane 12 Deer Run Lane 12 Deer Run Lane 12 Deer Run Lane 12 Deer Run Lane 12 Deer Run Lane 12 Deer Run Lane 12 Deer Run Lane 12 Deer Run Lane
12 Deer Run Lane
Sea Pines
Bedrooms 3 bedrooms
Bathrooms 3 full baths
Guests 8 guests
Rating 5 (45)
128 Dune is just steps away from the glimmering Atlantic Ocean! This 3 bedroom, 3.5 bath home with a private *heated pool has a prime location in North Forest Beach. Beautiful hardwood flooring in the living room, quartz countertops in the kitchen, and coastal chic furniture are just a few of the upgrades. The bathrooms have been completely redesig
sand-dollar Special
Holiday Cheer with 15% Off

Cheers to a wonderful holiday season! Book by December 2nd and enjoy 15% off your Hilton Head vacation!  *Not valid on existing reservations


128 Dune Lane
128 Dune Lane Rating 5 (19)
House
Bedding Breakdown
  • 2 Kings
  • 1 Queen
Bathrooms
  • 3 full baths
  • 1 half bath
amenities
  • Near Ocean
  • Pool Access
  • Private Pool
  • Beach Cart
  • Grill/BBQ - Private
  • *4 Adult Bikes
128 Dune Lane 128 Dune Lane 128 Dune Lane 128 Dune Lane 128 Dune Lane 128 Dune Lane 128 Dune Lane 128 Dune Lane 128 Dune Lane 128 Dune Lane
128 Dune Lane
Forest Beach
Bedrooms 3 bedrooms
Bathrooms 3 full baths & 1 half bath
Guests 6 guests
Rating 5 (19)
Looking for a backyard you will never want to leave? Then look no further than 14 Sea Lane. This 3-bedroom renovated home in Palmetto Dunes is near the ocean and provides lots of privacy, perfect for the entire group! When entering this ranch-style home, you will walk up just a few steps to the front door and immediately be greeted by a large famil
sand-dollar Special
Holiday Cheer with 15% Off

Cheers to a wonderful holiday season! Book by December 2nd and enjoy 15% off your Hilton Head vacation!  *Not valid on existing reservations


14 Sea Lane
14 Sea Lane
House
Bedding Breakdown
  • 1 King
  • 2 Queens
  • 1 Sofa Bed
  • 2 Fulls
Bathrooms
  • 3 full baths
amenities
  • Near Ocean
  • Grill/BBQ - Private
  • *4 Adult Bikes
  • Beach Cart
  • Private Pool
14 Sea Lane 14 Sea Lane 14 Sea Lane 14 Sea Lane 14 Sea Lane 14 Sea Lane 14 Sea Lane 14 Sea Lane 14 Sea Lane 14 Sea Lane
14 Sea Lane
Palmetto Dunes
Bedrooms 3 bedrooms
Bathrooms 3 full baths
Guests 12 guests
This bright and spacious home with beautiful beach decor is only steps away from the ocean. The first floor offers an open living room and kitchen with large windows and high ceilings. A separate dining room, bar seating, and a card/breakfast table exist. A king bedroom and 2 full baths are also on this floor. The upper floor hosts two guest bedroo
sand-dollar Special
Holiday Cheer with 15% Off

Cheers to a wonderful holiday season! Book by December 2nd and enjoy 15% off your Hilton Head vacation!  *Not valid on existing reservations


15 Ibis St
15 Ibis St Rating 5 (22)
House
Bedding Breakdown
  • 1 King
  • 1 Queen
  • 2 Twins
Bathrooms
  • 3 full baths
amenities
  • Near Ocean
  • *4 Adult Bikes
  • Private Pool
  • Pool Access
  • Grill/BBQ - Private
  • Beach Cart
15 Ibis St 15 Ibis St 15 Ibis St 15 Ibis St 15 Ibis St 15 Ibis St 15 Ibis St 15 Ibis St 15 Ibis St 15 Ibis St
15 Ibis St
Forest Beach
Bedrooms 3 bedrooms
Bathrooms 3 full baths
Guests 6 guests
Rating 5 (22)
Welcome to this beautiful ranch-style beach house, perfect for your next getaway! Complete with a backyard oasis, including a private pool and screened-in porch... it\'s ideal for your island escape. There are three (3) bedrooms and two (2) full bathrooms, offering sleeping arrangements for eight. The furnishings complete the look of this home, pro
sand-dollar Special
Holiday Cheer with 15% Off

Cheers to a wonderful holiday season! Book by December 2nd and enjoy 15% off your Hilton Head vacation!  *Not valid on existing reservations


15 Pelican
15 Pelican Rating 5 (21)
House
Bedding Breakdown
  • 1 King
  • 1 Queen
  • 2 Twins
  • 1 Sofa Bed
Bathrooms
  • 2 full baths
amenities
  • Near Ocean
  • Private Pool
  • Beach Cart
  • Grill/BBQ - Private
  • Pool Access
  • *4 Adult Bikes
15 Pelican 15 Pelican 15 Pelican 15 Pelican 15 Pelican 15 Pelican 15 Pelican 15 Pelican 15 Pelican 15 Pelican
15 Pelican
Forest Beach
Bedrooms 3 bedrooms
Bathrooms 2 full baths
Guests 8 guests
Rating 5 (21)
Overlooking the 10th tee of Harbour Town Golf Links, this beautifully decorated home features three bedrooms and 3.5 bathrooms. Take a short stroll to the Sea Pines Racquet Club, the Harbour Town Clubhouse, and the Harbour Town Yacht Basin. Stay in and enjoy the poolside views of the golf course from the living room, private den, and two of the mas
sand-dollar Special
Holiday Cheer with 15% Off

Cheers to a wonderful holiday season! Book by December 2nd and enjoy 15% off your Hilton Head vacation!  *Not valid on existing reservations


21 Windjammer Court
21 Windjammer Court Rating 5 (21)
House
Bedding Breakdown
  • 2 Kings
  • 1 Queen
  • 1 Other
Bathrooms
  • 3 full baths
  • 1 half bath
amenities
  • Near Ocean
  • Private Pool
  • Pool Access
  • Grill/BBQ - Private
  • *4 Adult Bikes
  • Beach Cart
21 Windjammer Court 21 Windjammer Court 21 Windjammer Court 21 Windjammer Court 21 Windjammer Court 21 Windjammer Court 21 Windjammer Court 21 Windjammer Court 21 Windjammer Court 21 Windjammer Court
21 Windjammer Court
Sea Pines
Bedrooms 3 bedrooms
Bathrooms 3 full baths & 1 half bath
Guests 8 guests
Rating 5 (21)
This 3-bed, 3-bath traditional Sea Pines beach home with a private pool is just 3rd row from the ocean! This ranch-style home has a large open kitchen and Corian countertops. The kitchen area encompasses a nice dining area and a glassed-in Carolina room. Nearby to the Carolina room is a spacious living room that looks over the pool. Sliding doo
sand-dollar Special
Holiday Cheer with 15% Off

Cheers to a wonderful holiday season! Book by December 2nd and enjoy 15% off your Hilton Head vacation!  *Not valid on existing reservations


22 Surf Scoter
22 Surf Scoter Rating 4.5 (2)
House
Bedding Breakdown
  • 2 Kings
  • 2 Twins
Bathrooms
  • 3 full baths
amenities
  • Near Ocean
  • Beach Cart
  • Private Pool
  • Grill/BBQ - Private
  • Pool Access
  • *4 Adult Bikes
22 Surf Scoter 22 Surf Scoter 22 Surf Scoter 22 Surf Scoter 22 Surf Scoter 22 Surf Scoter 22 Surf Scoter 22 Surf Scoter 22 Surf Scoter 22 Surf Scoter
22 Surf Scoter
Sea Pines
Bedrooms 3 bedrooms
Bathrooms 3 full baths
Guests 6 guests
Rating 4.5 (2)
Experience coastal living at its finest in this exquisite home at 22 Windjammer, located in the prestigious Sea Pines community. This beautifully designed property features spacious interiors, elegant furnishings, and an abundance of natural light, creating a warm and inviting atmosphere. The open-concept layout includes a modern kitchen equipped w
sand-dollar Special
Holiday Cheer with 15% Off

Cheers to a wonderful holiday season! Book by December 2nd and enjoy 15% off your Hilton Head vacation!  *Not valid on existing reservations


22 Windjammer Court
22 Windjammer Court
House
Bedding Breakdown
  • 1 King
  • 2 Queens
  • 1 Twin
  • 1 Sofa Bed
Bathrooms
  • 2 full baths
  • 1 half bath
amenities
  • Near Ocean
  • Grill/BBQ - Private
  • *4 Adult Bikes
  • Beach Cart
  • Private Pool
22 Windjammer Court 22 Windjammer Court 22 Windjammer Court 22 Windjammer Court 22 Windjammer Court 22 Windjammer Court 22 Windjammer Court 22 Windjammer Court 22 Windjammer Court 22 Windjammer Court
22 Windjammer Court
Sea Pines
Bedrooms 3 bedrooms
Bathrooms 2 full baths & 1 half bath
Guests 8 guests
This charming 3-bed, 3-bath dog-friendly vacation home is in the South Beach area of Sea Pines. *Heated private pool, spa, and just a short walk to the beach; this house is perfect for families or small groups. Also close by are all the activities offered by the South Beach Marina, including charter fishing, water sports, shopping, entertainment, a
sand-dollar Special
Holiday Cheer with 15% Off

Cheers to a wonderful holiday season! Book by December 2nd and enjoy 15% off your Hilton Head vacation!  *Not valid on existing reservations


3 Scaup Court
3 Scaup Court Rating 5 (28)
House Pet Friendly
Bedding Breakdown
  • 2 Kings
  • 2 Fulls
Bathrooms
  • 3 full baths
amenities
  • Near Ocean
  • Grill/BBQ - Private
  • Dogs Considered
  • *4 Adult Bikes
  • Tennis - Membership
  • Pool Access
  • Private Pool
  • Beach Cart
  • Hot Tub/Spa - Private
3 Scaup Court 3 Scaup Court 3 Scaup Court 3 Scaup Court 3 Scaup Court 3 Scaup Court 3 Scaup Court 3 Scaup Court 3 Scaup Court 3 Scaup Court
3 Scaup Court
Sea Pines Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 full baths
Guests 8 guests
Rating 5 (28)

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