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 55 properties available
Experience Hilton Head Island in luxury and comfort when you stay in this beautiful, 3 bedroom, 3.5 bath, Palmetto Dunes vacation home on Hilton Head Island. Beveled glass double entry doors make a distinctive first impression as you enter a home where the decor is a perfect blend of old and new, highlighted by original artwork and natural outdoor
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 1 half bath
Guests 8 guests
Look no further for your next family vacation home! 36 Kingston is a stunning 4 bedroom, 3 bathroom Shipyard Hilton Head pet-friendly rental with a private pool! This spacious home with an open floor plan features 2 living areas and a fantastic kitchen. With separate wings of the home on either side of the living areas, this 36 Kingston is perfect
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 9 guests
Rating 5 (28)
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
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)
Look no further for your new favorite Hilton Head Sea Pines vacation spot! 5 Indigo Lane provides a renovated, bohemian-inspired home, perfect for couples and families alike. This 4 bedroom, 3 bathroom home has laminate and tile flooring throughout, all new bathrooms and furnishings and fantastic outdoor space with a newly landscaped and refreshed
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 8 guests
Rating 5 (29)
If you're searching for fully updated vacation rentals on Hilton Head, SC with lots of space, amazing views, a large pool and close to the beach then look no further. This 7 bedroom, 6.5 bathroom Hilton Head SC home is located on a quiet private cul-de-sac in Palmetto Dunes Resort with views of both the 11-mile lagoon system and the Robert Trent Jo
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 7 bedrooms
Bathrooms 6 full baths 1 half bath
Guests 23 guests
Calm, cool, and relaxed is how you feel entering Kingston Road 29, a 4 bedroom, 4 bath, Hilton Head Shipyard home rental geared for your vacation. This stylish Shipyard home will sweep away your thoughts of work and have you dreaming of Hilton Head’s sunsets. Warm, neutral tones underlay the foyer and leads throughout the open floor. A formal dinin
Specials Tag Special
Featured Properties Special

We’ve handpicked some of our favorite vacation rentals and made them even better with a discount! Browse our featured properties and find the perfect place for your next getaway. Availability is limited, so book your stay today and use promo code FEATURED10 to save today!


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 12 guests
Rating 5 (23)
32 Crabline Court is an exquisitely decorated 5 bedroom, 4 bathroom home located in Hilton Head’s Singleton Beach rentals area. It offers a short walk, or bike ride, to Singleton Beach as well as quick access to the beautiful Chaplin Park, shops, restaurants and Hilton Head attractions and activities.Approximately 10 steps up lead to the porch, a g
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 5 bedrooms
Bathrooms 4 full baths
Guests 12 guests
Rating 5 (18)
Make cherished memories that will last forever when you treat your family to an island vacation in this 4 bedroom, 3 bathroom Hilton head home for rent in the beautiful Shipyard. Gloucester 79 is a beautiful Shipyard home that will not disappoint!Upon entering the home you will be greeted by a southern style front porch complete with rocking chairs
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 4 bedrooms
Bathrooms 3 full baths
Guests 10 guests
Rating 5 (9)
Welcome to 4 Gunnery Lane, a quintessential Sea Pines home! This beautifully outfitted five bedroom, five and half bathroom home offers the comfort and space you deserve for your next family vacation. With multiple living spaces, bedrooms spanning multiple levels and a perfectly private pool area, this home will soon become your go-to Hilton Head g
Specials Tag Special
Featured Properties Special

We’ve handpicked some of our favorite vacation rentals and made them even better with a discount! Browse our featured properties and find the perfect place for your next getaway. Availability is limited, so book your stay today and use promo code FEATURED10 to save today!


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 5 bedrooms
Bathrooms 5 full baths 1 half bath
Guests 12 guests
Rating 5 (5)
Dune Lane 127 is a 4 Bedroom 3 Bathroom Oceanfront Forest Beach Home on the beautiful island of Hilton Head. Upon entering the home, the main level of the home gives you direct access to the oceanfront pool and the sunning deck. The primary bedroom with private bath has a king bed, flat screen TV and sliding door out to the pool. Bedroom #2, also o
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
Guests 10 guests
Rating 5 (12)
Your Perfect Family Getaway!With spacious rooms, elegant furnishings, and an exceptional outdoor space, 26 Gloucester is the ideal retreat for your next family vacation.The open-concept living area offers plenty of seating, a large wall-mounted Smart TV, and sliding doors that open to an elevated deck. The deck showcases stunning views of the pool,
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 5 bedrooms
Bathrooms 4 full baths
Guests 14 guests
Rating 5 (3)

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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.