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Holiday rentals with a pool in Hilton Head Island

Find and book unique homes with a pool on Airbnb

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Popular amenities for Hilton Head Island rentals with a pool

House rentals with a pool

Top guest favourite
Home in Hilton Head Island
4.99 out of 5 average rating, 83 reviews

180º Ocean Views, Treehouse "Siren's Lookout"

PamRating, 5 stars1 week ago
Connie’s place was not only the perfect size and location but also just the perfect vibe. Every part of the treehouse matched what we were wanting out of our vacation and made our trip that much more enjoyable. Whether it was sitting outside drinking coffee in the morning or out by the fire at night, the view and peaceful surroundings along with the interior views created the perfect escape for us throughout our entire stay. Connie was responsive and beyond amazing with every question and help we needed. She was an amazing host and created the best space for our trip, we appreciated every big and small detail!
Guest favourite
Home in Hilton Head Island
4.95 out of 5 average rating, 79 reviews

5 Bedroom-Beach Access-Pool-Sleeps 14!

SydneyRating, 5 stars3 weeks ago
We had an amazing stay at Sur La Mar for our girls trip! The house was clean, spacious, and perfectly set up for a large group—it made everything so easy and comfortable. The location was ideal, close to the beach and had everything we needed, and we loved having the pool to relax and hang out together. Steven was incredibly responsive and helpful throughout our stay. Highly recommend this place for anyone planning a big group getaway or family vacation in Hilton Head.
Guest favourite
Home in Hilton Head Island
4.88 out of 5 average rating, 34 reviews

~Couples Paradise~Villa W/Pool~Beachfront Resort

JocelynRating, 5 stars2 days ago
We had a great time at Zach & Allison’s! This was our second time at Hilton Head and once again, we loved every bit of it! Condo was very clean, location was great, and host was always very attentive. Would definitely recommend!
Guest favourite
Home in Hilton Head Island
4.94 out of 5 average rating, 114 reviews

Cozy Coastal Chic - Beach, Pickleball, Golf, Pets

JanelleRating, 5 stars1 week ago
Lovely space! Beautifully decorated and with modern touches and comfortable beds. We hope to return soon. We enjoyed biking around the neighborhood and to the general store. It’s a peaceful, quiet resort neighborhood — but so close to many things to do. Recommend the free shuttle to the beach, especially with preschool/elementary children in tow who may not feel like walking 12 minutes to the beach. Thanks to Patricia and Veronica for a memorable trip!
Guest favourite
Home in Hilton Head Island
4.98 out of 5 average rating, 109 reviews

New Resort-Style Pool, Cute House 88 Steps to Sand

JohnRating, 5 stars2 months ago
Our family of 5 stayed at Rick’s place for a week for spring break and thoroughly enjoyed it. It was easy walking to the beach, very fun to play in the heated pool, biking to Coligny for food, playground. We did a cookout one night in the cabana by the pool. The kids loved the bunk bed. The easy indoor/outdoor living was a delight. The TVs and remotes worked great. I enjoyed going on runs in the morning on the beach or on the biking/walking trail across the street from the house. The house had everything we could want like a stool for our 3 year old to use the bathroom sink to plenty of pool toys, beach toys, chairs, beach wagon, etc. The house also came with a pass to Sea Pines which was an unexpected treat!
Superhost
Home in Hilton Head Island
4.79 out of 5 average rating, 24 reviews

17 Night Heron · Elegant, Stylish Beach Cottage

JackRating, 5 stars1 day ago
We had an awesome week at an awesome place. This spot is beautiful. Looking forward to coming back soon.
Superhost
Home in Hilton Head Island
5 out of 5 average rating, 4 reviews

Modern Beach Escape | Private Pool~Steps to Beach

CraigRating, 5 stars3 weeks ago
The host was fabulous and attentive throughout the booking and our stay. The home was impeccable, conveniently located and had everything you could possibly need for a comfortable and leisurely beach vacay!
Guest favourite
Home in Hilton Head Island
4.86 out of 5 average rating, 371 reviews

W2Bch*4TVs*1GIG I*PetsWC *WiFi*4King ßds*grill*gms

AmyRating, 5 stars3 weeks ago
We loved our stay at Marina's beach hut. We walked to the beach morning and evening and views on the beach were beautiful. Everyone was so friendly. Had plenty of space for our family to either be together or spread out in the house space. House was well stocked with beach and home supplies. Loved having space for our car in the garage. Master bath shower was luxurious! Neighborhood was quiet and felt very safe. Loved the keyless entry system!

Apartment rentals with a pool

Guest favourite
Apartment in Hilton Head Island
4.93 out of 5 average rating, 55 reviews

1Min Walk to Beach/Ocean View Balcony/Huge Pool

WillieRating, 5 stars2 days ago
The condo was modern and very clean. Very short walk to the beach and pool. Balcony view was great for a morning cup of coffee. Lee was very responsive to all questions. We would stay with Lee in the future.
Top guest favourite
Apartment in Hilton Head Island
5 out of 5 average rating, 88 reviews

5 Star Location! Pool, Walk to Shops/Dining

ShalaynaRating, 5 stars1 week ago
Had the best time ever here!! Great location. Right by a trolley stop and very easily bailable to all other great attractions including the beach. Will absolutley be back !
Guest favourite
Apartment in Hilton Head Island
4.96 out of 5 average rating, 137 reviews

Luxury Couples Retreat

RitaRating, 5 stars1 month ago
I had a wonderful stay! Julia is a great host who responded very quickly when I had a question. The condo is very comfortable and nicely decorated. The resort is well maintained and I appreciated having security and maintenance staff available if needed. There is so much to do on Hilton Head Island, I could easily have stayed another week!
Superhost
Apartment in Hilton Head Island
4.84 out of 5 average rating, 176 reviews

Beach Time! Retro-Mod Family Beach Fun

JessicaRating, 5 starstoday
This was a great place to stay. It is very convenient to have beach assess and the pool just steps away. In addition, having restaurants on site was very convenient!
Superhost
Apartment in Hilton Head Island
4.7 out of 5 average rating, 227 reviews

Condo on Beachfront Resort

RyanRating, 5 stars1 month ago
Our stay was great and as expected! It's a cheap option to stay on Hilton Head right by the beach with the option to use the pool as well.
Superhost
Apartment in Hilton Head Island
4.9 out of 5 average rating, 118 reviews

BEach HAPPY HHI Ocean view and steps to the Beach

AmandaRating, 5 stars4 weeks ago
We had a wonderful stay at BEach Happy HHI! The location was the best! An easy walk to the beach and super convenient to walk back to the condo if needed. The pool was a nice bonus too! The unit is small, but just as described. There were only two of us so the unit was great for us! We didn't use the kitchen to cook, but it was stocked with what we needed. We would definitely visit again!
Superhost
Apartment in Hilton Head Island
5 out of 5 average rating, 5 reviews

Marriott Sunset Pointe - 2BD

TinaRating, 5 stars4 months ago
This place is very well maintained, I feel very safe to stay there. Inside is very clean and homely. I enjoyed my stay. The only thing is: when we check out, the front desk girl has very unfriendly attitude and act like that she does not want to see me. After few minutes of putting up with this,I told her: “ can you be more pleasant?”. Then she said : “ I cannot hear you”. I do not understand why this is happening, maybe because I am Asian? All the guests in lobby having breakfast are white. My English is fluent and people have no trouble to understand me,FYI. The front desk girl who has bad attitude towards me is Mexican, maybe she does not like to see Asian? I really don’t understand, but I did not do anything wrong to deserve this kind of treatment. There is a man working on the raffle desk told me : “Welcome staying with us”. I said : “Thank you so much, you are very pleasant!”Then I told him what happened to me. Hopefully this will not happen to other people in future again!!!
Guest favourite
Apartment in Hilton Head Island
4.88 out of 5 average rating, 112 reviews

Relaxing 2Br/2ba condo on HHI, minutes from beach

JohanaRating, 5 stars3 weeks ago
It’s a very nice place to stay, very comfortable

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

  • Total rentals

    5.5K properties

  • Nightly prices starting at

    ₹865 before taxes and fees

  • Total number of reviews

    1.2L reviews

  • Family-friendly rentals

    4.4K properties are a good fit for families

  • Pet-friendly rentals

    830 properties allow pets

  • Rentals with dedicated workspaces

    2.8K properties have a dedicated workspace

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