Vacation rentals with a pool in Hilton Head Island

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Popular amenities for Hilton Head Island rentals with a pool

House rentals with a pool

Superhost
Home in Hilton Head Island
5 out of 5 average rating, 4 reviews

Stunning Sea Pines Retreat | Fantastic Pool & Spa

BradRating, 5 stars9 months ago
Fantastic home, lovely pool, private, well furnished kitchen. Would definitely consider coming back. Home And Home was extremely responsive prior and during the visit with any questions we had. We heated the pool and it was a must for early season. This is an extra cost that is posted in Additional Rules. You can check but I do not believe that the Spa will be heated unless you pay for heat. Once again, really enjoyed this AirBNB.
Guest favourite
Home in Hilton Head Island
4.97 out of 5 average rating, 78 reviews

Private pool/spa : pool heat available : Kg master

RamonRating, 5 stars4 months ago
best choice we made. beautiful place to relax and spend family time. Abigail was the best and always ontop of everything. fast answers
Guest favourite
Home in Hilton Head Island
4.9 out of 5 average rating, 10 reviews

FREE Pool Heat - Luxury Home - Pet Friendly

LuanneRating, 5 stars1 month ago
We had an excellent week at Hideaway in Sea Pines Hilton Head. The home was on a low-key street with no traffic. The home decor was updated and very attractive. The property was also pet friendly so our dog was able to enjoy a beach vacation as well.
Superhost
Home in Hilton Head Island
5 out of 5 average rating, 3 reviews

Island Getaway - an iTrip Hilton Head Home

AnaRating, 5 stars1 month ago
This home is spacious and well maintained. The open floorplan and ample living space allowed our family of 5 adults to each do their thing while having family time. The indoor pool was an added bonus and the location is perfect for accessing local shops, restaurants, beaches, and landmarks. Plenty of bike trails, golf courses, and tennis courts. It made for an ideal winter getaway!
Guest favourite
Home in Hilton Head Island
4.93 out of 5 average rating, 197 reviews

Heated Pool/Spa/Fenced Yard, Golf Cart rental-51

BrendaRating, 5 stars1 month ago
Michael was very responsive and flexible, the house was perfect for my big family and would highly recommend this home.
Guest favourite
Home in Hilton Head Island
4.87 out of 5 average rating, 52 reviews

SeaPines - Private Beach Path, Private Pool, Bikes

DougRating, 5 stars1 month ago
My wife and our four grown kids thoroughly enjoyed our stay at Jessica's place in late December. Jessica was absolutely fantastic to work with. The home was a perfect fit for our needs - spacious, clean, nicely appointed. It has everything we needed. We had our dogs with us and it was nice to have the backyard as well as the enclosed courtyard out front. The location is great - it's a short walk on the private walk to the beach. We often stay further down the beach closer to S Beach Marina and Calibogue Sound where the beach is wide at low-tide but kind of narrow at high-tide. Here, there is still a lot of beach even at high-tide and at low-tide it is super-wide. Great for all the sunrise, sunset and moonlight walks we did. Not crowded on the beach at all that time of year. Ideal location within Sea Pines - short-drive or bike ride to restaurants, shops, other parts of the island. Such an great week and loved Jessica's place - we hope to be back one day!
Guest favourite
Home in Hilton Head Island
5 out of 5 average rating, 24 reviews

Townhouse with Southern charm

MarilynRating, 5 stars2 months ago
We had a wonderful stay at this beautiful home in Hilton Head! The house was absolutely spotless and provided everything we needed for a memorable Thanksgiving dinner. The kitchen was well-equipped, and the spacious dining area made it perfect for gathering and enjoying a festive meal. The location was ideal—just a short walk to the beach, which we still enjoyed even though the weather was a bit chilly. The owner was incredibly helpful, providing detailed and clear instructions for getting in and out of the house, making our arrival and departure seamless. We loved the outdoor spaces, including the patios, and we can only imagine how great it would be to enjoy them in the warmer months. The proximity to the outdoor pool is also a big plus. We’ll definitely be back to experience it again in the summer! Highly recommend this home for anyone looking for a relaxing, comfortable stay in Hilton Head.
Superhost
Home in Hilton Head Island
5 out of 5 average rating, 3 reviews

New build marsh home with a private pool!

JohnRating, 5 stars7 months ago
The house was super clean, new/updated throughout, and perfect size for our group of 13! Kitchen was large and had a nice big table and island for everyone to hang at. The living room was comfy and right next to the kitchen so it felt like one big room. Just a short drive to a few beaches and parking wasn’t an issue at the beach, and also a short drive to tons of restaurants. If adults are going to get in the pool it might make sense to pay to have it heated, but for us the kids didn’t mind the cooler water temperature. The host company was very responsive and friendly. We’d definitely stay there again if we’re back in HHI with a big group..hands down 5 stars!

Condo rentals with a pool

Guest favourite
Condo in Hilton Head Island
4.93 out of 5 average rating, 131 reviews

$99 nite Jan & Feb1BR/1BA Qbeds/ind pool/picklebal

MorganRating, 5 stars4 months ago
Gloria was kind and responsive via text messages. The condo was perfect for a long weekend. We also enjoyed the pickleball courts!
Guest favourite
Condo in Hilton Head Island
4.93 out of 5 average rating, 133 reviews

Beach Ocean Front -Heated Pool

RebeccaRating, 5 stars6 months ago
My Husband and I loved this gem of a place. The location is perfect. Beautiful views of the ocean from the 3rd floor. The condo was very clean. The bed and linens were comfortable. Craig was kind and responsive. This place surpassed our expectations and we truly had a wonderful vacation!
Superhost
Condo in Hilton Head Island
4.7 out of 5 average rating, 221 reviews

Condo on Beachfront Resort

EricRating, 5 stars3 weeks ago
Great place and responded quickly to anything asked.
Guest favourite
Condo in Hilton Head Island
4.9 out of 5 average rating, 107 reviews

Upgraded peaceful villa ! 7 min walk to the beach

MikeRating, 5 stars1 month ago
Absolutely PRISTINE and extremely comfortable! Little thoughtful touches included an amazing gift bag and a detailed, thorough welcome binder chock full of helpful local suggestions and lodging/complex details. Quite obvious that the hosts truly care about providing an enjoyable experience to their guests! We would stay here again if we have the good fortune to visit beautiful Hilton Head Island again!
Guest favourite
Condo in Hilton Head Island
4.91 out of 5 average rating, 45 reviews

Beachside Condo: 2 bedrooms, 2 bathrooms

NickcoletteRating, 5 stars1 week ago
Me and my friends had a great time thank you to the hosts and I would definitely recommend.
Superhost
Condo in Hilton Head Island
4.75 out of 5 average rating, 162 reviews

Walk to Beach - 3 Pools - Central Location !

LizaRating, 5 stars1 month ago
We really enjoyed our time in Steve and Jenna apartment. Great location and access to the beach.
Superhost
Condo in Hilton Head Island
4.84 out of 5 average rating, 117 reviews

Oceanside Resort. Heated Indoor Pool, Hot tub.

CrystalRating, 5 stars1 month ago
I traveled to SC for work. The location was great, nice walk to the beach via the boardwalk, amenities of the association were great and I had all the comforts of home.
Guest favourite
Condo in Hilton Head Island
4.98 out of 5 average rating, 40 reviews

Lovely 2 bed condo with in/outdoor pool+hot tub

ChristineRating, 5 stars4 days ago
Thank goodness there was an indoor pool. It rained a bunch of days we were in SC so there still something for the kids to do. Condo was clean and was as described. Nice layout when your vacationing with 2 kids and a grandma. We each had our own space. One thing that can make an improvement is an extra TV in the 2nd bedroom.

Quick stats about vacation rentals with a pool in Hilton Head Island

  • Total rentals

    5.1K properties

  • Nightly prices starting at

    $14 CAD before taxes and fees

  • Total number of reviews

    120K reviews

  • Family-friendly rentals

    4.2K properties are a good fit for families

  • Pet-friendly rentals

    750 properties allow pets

  • Rentals with dedicated workspaces

    2.4K properties have a dedicated workspace

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