Homes with Private Pools | Hilton Head Island

Beat the hot summer weather on Hilton Head Island with a premium Hilton Head house rental with a pool. These popular properties offer the ultimate private outdoor amenity, perfect for sunbathing, entertaining the kids, and enjoying the outdoors in comfort. A private pool adds essential luxury and privacy to your stay, transforming afternoon downtime into a refreshing, memorable experience. For the best coastal getaway, secure one of these highly sought-after Hilton Head Island vacation rentals. Our selection of Hilton Head vacation rentals with pools ensures you maximize your fun and relaxation. Plan your trip today and get ready to enjoy endless, sunny afternoons by your private pool.


Properties Available 54 properties available
Rest and relaxation await at South Live Oak 25, surrounded by tranquil lagoons on Hilton Head Island! This beautifully renovated 4-bedroom, 4-bathroom Hilton Head Sea Pines home offers a spacious open floor plan and a fantastic outdoor area, perfect for family gatherings. This stair-free home provides vacationers with two living areas, wood and til
Specials Tag Special
Monthly Rentals

Hilton Head monthly rentals are available from October 1st- April 1st. Avoid the cold weather and live like a local at one of our fully furnished properties. Please call 800.276.8991 for availability & monthly quotes.


Thankful Tides Thanksgiving Savings

Celebrate Thanksgiving with a refreshing Hilton Head Island getaway and save 10% on your vacation rental stay with Sunset Rentals. Gather your favorite people for beach walks, holiday meals, bike rides, and the relaxed pace of island life. Plan a family reunion, start a new coastal holiday tradition, or enjoy a peaceful escape in a vacation home with the space and comfort to make the week feel special.

Book a new online reservation by October 31, 2026, for an eligible stay of three nights or more between November 21 and November 28, 2026. Use promo code THANKS2026 at checkout to receive 10% off your November stay. 

*Offer is valid on new online bookings when you book by October 31, 2026 for 3+ night stays from November 21 - 28, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties. 

Bedrooms 4 bedrooms
Bathrooms 4 full baths
Guests 13 guests
Rating 5 (20)
Located in the heart of the highly desired North Forest Beach neighborhood of Hilton Head Island, Lark 2 is a spacious 4-bedroom and 3-bath pet-friendly Forest Beach home that exudes South Carolina Lowcountry beach cottage flare and easy access to Hilton Head’s top beaches and attractions. Just 4 rows from the beach, this stilted Forest Beach vacat
Hot HOT 38
Bedrooms 4 bedrooms
Bathrooms 3 full baths
Guests 8 guests
Rating 5 (29)
Nestled in the serene enclave of Sea Pines on Hilton Head Island, Otter Road 105 is your idyllic retreat for a memorable getaway. This charming 3-bedroom, 2-bathroom dog-friendly home exudes warmth and comfort, perfectly accommodating up to six guests. Upon entering, you'll be greeted by a spacious living area designed for relaxation and entertainm
Specials Tag Special
Monthly Rentals

Hilton Head monthly rentals are available from October 1st- April 1st. Avoid the cold weather and live like a local at one of our fully furnished properties. Please call 800.276.8991 for availability & monthly quotes.


Thankful Tides Thanksgiving Savings

Celebrate Thanksgiving with a refreshing Hilton Head Island getaway and save 10% on your vacation rental stay with Sunset Rentals. Gather your favorite people for beach walks, holiday meals, bike rides, and the relaxed pace of island life. Plan a family reunion, start a new coastal holiday tradition, or enjoy a peaceful escape in a vacation home with the space and comfort to make the week feel special.

Book a new online reservation by October 31, 2026, for an eligible stay of three nights or more between November 21 and November 28, 2026. Use promo code THANKS2026 at checkout to receive 10% off your November stay. 

*Offer is valid on new online bookings when you book by October 31, 2026 for 3+ night stays from November 21 - 28, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties. 

Bedrooms 3 bedrooms
Bathrooms 2 full baths
Guests 6 guests
Rating 5 (6)
This stunning 6-bedroom, 6.5-bath new construction home sits on a massive lot along the serene 11 Mile Lagoon in Palmetto Dunes. Don’t miss the opportunity to be among the first to enjoy this custom home with its plush furnishings and luxury accommodations! The main level of the home features an open-concept floor plan with cathedral ceilings and E
Specials Tag Special
Monthly Rentals

Hilton Head monthly rentals are available from October 1st- April 1st. Avoid the cold weather and live like a local at one of our fully furnished properties. Please call 800.276.8991 for availability & monthly quotes.


Thankful Tides Thanksgiving Savings

Celebrate Thanksgiving with a refreshing Hilton Head Island getaway and save 10% on your vacation rental stay with Sunset Rentals. Gather your favorite people for beach walks, holiday meals, bike rides, and the relaxed pace of island life. Plan a family reunion, start a new coastal holiday tradition, or enjoy a peaceful escape in a vacation home with the space and comfort to make the week feel special.

Book a new online reservation by October 31, 2026, for an eligible stay of three nights or more between November 21 and November 28, 2026. Use promo code THANKS2026 at checkout to receive 10% off your November stay. 

*Offer is valid on new online bookings when you book by October 31, 2026 for 3+ night stays from November 21 - 28, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties. 

Bedrooms 6 bedrooms
Bathrooms 6 full baths 1 half bath
Guests 12 guests
Rating 5 (18)
8 Governors Lane is where southern charm meets modern comfort. This beautifully renovated and newly outfitted 3 bedroom, 2.5 bathroom home offers a spacious, open floor plan, luxurious accomodations and a brand new pool and spa for the 2026 season!The living area is comfortably furnished and offers a large Smart TV. The space extends to a sun room
Specials Tag Special
Monthly Rentals

Hilton Head monthly rentals are available from October 1st- April 1st. Avoid the cold weather and live like a local at one of our fully furnished properties. Please call 800.276.8991 for availability & monthly quotes.


Thankful Tides Thanksgiving Savings

Celebrate Thanksgiving with a refreshing Hilton Head Island getaway and save 10% on your vacation rental stay with Sunset Rentals. Gather your favorite people for beach walks, holiday meals, bike rides, and the relaxed pace of island life. Plan a family reunion, start a new coastal holiday tradition, or enjoy a peaceful escape in a vacation home with the space and comfort to make the week feel special.

Book a new online reservation by October 31, 2026, for an eligible stay of three nights or more between November 21 and November 28, 2026. Use promo code THANKS2026 at checkout to receive 10% off your November stay. 

*Offer is valid on new online bookings when you book by October 31, 2026 for 3+ night stays from November 21 - 28, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties. 

Bedrooms 3 bedrooms
Bathrooms 2 full baths 1 half bath
Guests 9 guests
Rating 5 (10)
Experience the ultimate getaway at 7 Heron, a beautifully renovated single-level home located just seven houses away from the beach. Ideal for a family vacation or a retreat with friends, this luxurious 3-bedroom, 2-bathroom home seamlessly blends upscale comfort with relaxed coastal charm.Step inside to a spacious open-concept layout where everyon
Specials Tag Special
Monthly Rentals

Hilton Head monthly rentals are available from October 1st- April 1st. Avoid the cold weather and live like a local at one of our fully furnished properties. Please call 800.276.8991 for availability & monthly quotes.


Thankful Tides Thanksgiving Savings

Celebrate Thanksgiving with a refreshing Hilton Head Island getaway and save 10% on your vacation rental stay with Sunset Rentals. Gather your favorite people for beach walks, holiday meals, bike rides, and the relaxed pace of island life. Plan a family reunion, start a new coastal holiday tradition, or enjoy a peaceful escape in a vacation home with the space and comfort to make the week feel special.

Book a new online reservation by October 31, 2026, for an eligible stay of three nights or more between November 21 and November 28, 2026. Use promo code THANKS2026 at checkout to receive 10% off your November stay. 

*Offer is valid on new online bookings when you book by October 31, 2026 for 3+ night stays from November 21 - 28, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties. 

Bedrooms 3 bedrooms
Bathrooms 2 full baths
Guests 8 guests
Rating 5 (21)
Welcome to Port Tack 67, your premier vacation home in the heart of Palmetto Dunes on beautiful Hilton Head Island. This stunning four-bedroom, three-and-a-half-bathroom residence offers the perfect blend of comfort, style, and island living for families and groups seeking an unforgettable coastal escape. Spread across two welcoming floors, this th
Specials Tag Special
Monthly Rentals

Hilton Head monthly rentals are available from October 1st- April 1st. Avoid the cold weather and live like a local at one of our fully furnished properties. Please call 800.276.8991 for availability & monthly quotes.

Bedrooms 4 bedrooms
Bathrooms 3 full baths 1 half bath
Guests 8 guests
Escape to this beautiful home offering a serene retreat for your next Hilton Head getaway! The house offers relaxing golf and lagoon views, a pool, jetted hot tub, three bedrooms, three full baths and a loft with pull-out couch. It comfortably sleeps ten. From the entry, the coastal feeling dining room is to your right. With seating for six and a l
Specials Tag Special
Thankful Tides Thanksgiving Savings

Celebrate Thanksgiving with a refreshing Hilton Head Island getaway and save 10% on your vacation rental stay with Sunset Rentals. Gather your favorite people for beach walks, holiday meals, bike rides, and the relaxed pace of island life. Plan a family reunion, start a new coastal holiday tradition, or enjoy a peaceful escape in a vacation home with the space and comfort to make the week feel special.

Book a new online reservation by October 31, 2026, for an eligible stay of three nights or more between November 21 and November 28, 2026. Use promo code THANKS2026 at checkout to receive 10% off your November stay. 

*Offer is valid on new online bookings when you book by October 31, 2026 for 3+ night stays from November 21 - 28, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties. 

Bedrooms 3 bedrooms
Bathrooms 3 full baths
Guests 10 guests
Rating 5 (45)
Take solace in this bright and inviting 3 bedroom, 3 bathroom home located only a short distance to the beach in the lovely Palmetto Dunes Resort on Hilton Head Island. This alluring Palmetto Dunes home is pet-friendly with a private pool and waterfront dock on the Palmetto Dunes lagoon system.This popular waterfront Hilton Head home offers two liv
Specials Tag Special
Monthly Rentals

Hilton Head monthly rentals are available from October 1st- April 1st. Avoid the cold weather and live like a local at one of our fully furnished properties. Please call 800.276.8991 for availability & monthly quotes.


Thankful Tides Thanksgiving Savings

Celebrate Thanksgiving with a refreshing Hilton Head Island getaway and save 10% on your vacation rental stay with Sunset Rentals. Gather your favorite people for beach walks, holiday meals, bike rides, and the relaxed pace of island life. Plan a family reunion, start a new coastal holiday tradition, or enjoy a peaceful escape in a vacation home with the space and comfort to make the week feel special.

Book a new online reservation by October 31, 2026, for an eligible stay of three nights or more between November 21 and November 28, 2026. Use promo code THANKS2026 at checkout to receive 10% off your November stay. 

*Offer is valid on new online bookings when you book by October 31, 2026 for 3+ night stays from November 21 - 28, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties. 

Bedrooms 3 bedrooms
Bathrooms 3 full baths
Guests 10 guests
Rating 5 (38)
2 Jessamine Place is located in the historically renowned Sea Pines and offers 4 bedrooms and 3 baths. With modern updates, a great private pool and an easy 15-minute walk to the beach, you’ll experience a family vacation on Hilton Head like no other.The living area features cathedral ceilings, hardwood flooring and a huge flat screen, mounted TV w
Specials Tag Special
Monthly Rentals

Hilton Head monthly rentals are available from October 1st- April 1st. Avoid the cold weather and live like a local at one of our fully furnished properties. Please call 800.276.8991 for availability & monthly quotes.


Thankful Tides Thanksgiving Savings

Celebrate Thanksgiving with a refreshing Hilton Head Island getaway and save 10% on your vacation rental stay with Sunset Rentals. Gather your favorite people for beach walks, holiday meals, bike rides, and the relaxed pace of island life. Plan a family reunion, start a new coastal holiday tradition, or enjoy a peaceful escape in a vacation home with the space and comfort to make the week feel special.

Book a new online reservation by October 31, 2026, for an eligible stay of three nights or more between November 21 and November 28, 2026. Use promo code THANKS2026 at checkout to receive 10% off your November stay. 

*Offer is valid on new online bookings when you book by October 31, 2026 for 3+ night stays from November 21 - 28, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties. 

Bedrooms 4 bedrooms
Bathrooms 3 full baths
Guests 10 guests
Rating 5 (16)
Welcome to Planters Wood 48, a fully renovated 4-bedroom, 4-bathroom luxury home nestled in the highly sought-after Sea Pines community on Hilton Head Island. Designed to comfortably sleep eight guests, this property offers unparalleled convenience, being just minutes away from Harbour Town and the beach. Inside, you'll discover a bright, airy, and
Specials Tag Special
Monthly Rentals

Hilton Head monthly rentals are available from October 1st- April 1st. Avoid the cold weather and live like a local at one of our fully furnished properties. Please call 800.276.8991 for availability & monthly quotes.

Bedrooms 4 bedrooms
Bathrooms 4 full baths
Guests 8 guests
Rating 5 (8)
This fabulous 7 bedrooms, 6.5 bath Mooring Buoy vacation rental home in Palmetto Dunes sits on an 11-mile long lagoon and offers tranquil views, spacious interiors, two suites, a picturesque backyard, premium movie channels (included in the cable package) for movie nights and is just a few minutes walk to the Atlantic Ocean. 179 Mooring Buoy offers
Specials Tag Special
Monthly Rentals

Hilton Head monthly rentals are available from October 1st- April 1st. Avoid the cold weather and live like a local at one of our fully furnished properties. Please call 800.276.8991 for availability & monthly quotes.


Thankful Tides Thanksgiving Savings

Celebrate Thanksgiving with a refreshing Hilton Head Island getaway and save 10% on your vacation rental stay with Sunset Rentals. Gather your favorite people for beach walks, holiday meals, bike rides, and the relaxed pace of island life. Plan a family reunion, start a new coastal holiday tradition, or enjoy a peaceful escape in a vacation home with the space and comfort to make the week feel special.

Book a new online reservation by October 31, 2026, for an eligible stay of three nights or more between November 21 and November 28, 2026. Use promo code THANKS2026 at checkout to receive 10% off your November stay. 

*Offer is valid on new online bookings when you book by October 31, 2026 for 3+ night stays from November 21 - 28, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties. 

Bedrooms 7 bedrooms
Bathrooms 6 full baths 1 half bath
Guests 16 guests
Rating 5 (7)

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Hilton Head Island Vacation Rentals With Pool FAQs:

How does a home with a pool boost relaxation on Hilton Head Island?

After a day on the beach or riding around Hilton Head Island, nothing’s quite as refreshing as coming home and slipping into the pool. You can wade in or simply unwind by the edge embracing the peace—just you, the sunny blue sky, and the tranquility of the moment.

A pool offers a quiet retreat away from the crowds and the rest of the island while remaining immersed in the island’s beauty of nature. Having a pool at your Hilton Head Island home means there’s more space for you to relax, enjoy the moment, and make the most of your vacation.

 

What convenience does a pool provide for families visiting Hilton Head Island?

A private pool redefines the way your family relaxes on Hilton Head. If the ocean isn’t ideal for the day, you can take the pressure off of having to go to the beach for time in the water. The kids can splash and play right at home, giving parents the freedom to relax knowing everyone’s within reach.

Breaks are easy, the snacks are close by, and no one’s asking, “can we leave yet?” The pool offers a refreshing change of pace. It’s family fun without the hassle.

Your family can set its own pace during your Hilton Head Island stay, with the pool becoming the best part of your vacation routine.

 

How does a private pool offer a distinct swimming experience on Hilton Head Island?

A private pool offers what the beach can’t: no crowds, no unpredictable ocean conditions, and no messy sand to clean up. The pool is always easy and convenient: calm, clean, and ready to use anytime.

Swim whenever you want, anytime you want, with no stress about the things you can’t control. You still get the water, the tranquility, and the space. Nestled among swaying palms and quiet skies, a private pool becomes a cherished memory from your Hilton Head stay.

 

What social perks come with a pool at a Hilton Head Island Home?

The pool becomes your in-house hangout spot, an easy way to connect without having to go anywhere at all. It’s where kids gather and make games on the fly, and grownups gather without needing a plan.

No need to reserve space, dodge crowds, or pack up and go to the car; you’re just moments away from the kitchen or the grill. Whether you’re hosting a casual get-together or a full-on party under the sun, the pool is guaranteed to keep everyone entertained.

With a private pool, time flows a little differently, and you don’t have to go far to feel connected.

 

How does a pool pair with Hilton Head Island’s warm weather for guests?

When the island’s temperature begins to rise (especially during the summer), a pool at home gives you a relaxing way to cool down without heading to the beach. It’s a great way to stay outdoors longer without the heat cut your time short.

And in the milder spring and fall seasons, the pool keeps the outdoors fresh. With a pool, guests can take the weather in stride and turn it into something to enjoy on Hilton Head Island. Swim, lounge, repeat—that's the agenda for your vacation.