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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, 76 reviews

6 BR, Sleeps 26, Beach Time

KelseyRating, 5 stars2 weeks ago
This home is absolutely beautiful! We loved staying here!! Such a great experience!
Top guest favourite
Home in Hilton Head Island
4.99 out of 5 average rating, 82 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!
Top guest favourite
Home in Hilton Head Island
5 out of 5 average rating, 18 reviews

Starfish Beach House with Pool and Bikes

SueRating, 5 stars4 weeks ago
Sherri was very responsive to our concerns. She had a person on site that was very accountable to our needs. Would definitely stay again.
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 stars6 days 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
5 out of 5 average rating, 4 reviews

Modern Beach Escape | Private Pool~Steps to Beach

CraigRating, 5 stars2 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
5 out of 5 average rating, 15 reviews

Marsh Views | Pool, HotTub, Game Room&Pet Friendly

SarahRating, 5 stars3 weeks ago
We really enjoyed our time at the home. It was easy to book; easy to communicate with the hosts; easy to get in; and easy to check out. The house was beautiful and looked out over a beautiful view. The street was quiet and the location was perfect for our family with everything just a quick bike ride away.
Top guest favourite
Home in Hilton Head Island
4.97 out of 5 average rating, 144 reviews

Peaceful Harbour Town Treehouse with Marsh Views

BonnieRating, 5 stars1 week ago
When we walked into the octagon treehouse, we couldn’t stop squealing, “how cool is this?!” Kim’s home is one of the most fun and interesting stays we’ve ever had the pleasure of visiting. Kim and her family obviously have natural talent for hosting because the house was perfectly furnished with practical, comfortable and beautiful furniture and amenities, which made us feel at home right away. I can’t say enough nice things about our stay. It was wonderful from top to bottom thanks in large part to Kim’s recommendations and beautiful home. FYI, our young kids were obsessed with this house. We hope to be back again!

Apartment rentals with a pool

Guest favourite
Apartment in Hilton Head Island
4.94 out of 5 average rating, 66 reviews

HUGE Ocean View! 65"TV Pickleball BAR GYM & Tennis

KevinRating, 5 stars1 week ago
This was a great place: conveniently located, amazing resort amenities, and stress free. We would definitely stay again!
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 stars1 day 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.
Superhost
Apartment in Hilton Head Island
4.84 out of 5 average rating, 175 reviews

Beach Time! Retro-Mod Family Beach Fun

AndreaRating, 5 stars2 weeks ago
Perfect Airbnb for five nights in Hilton Head. Would definitely visit again! Anne gave clear and detailed instructions.
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
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
4.91 out of 5 average rating, 125 reviews

Exclusive Oceanfront Decorator Decor Spacious Bdrm

MeghanRating, 5 starstoday
It was great. Very spacious and the proximity to the beach is unbeatable. The pools were great too. Grady was a responsive host. We had a great time!
Guest favourite
Apartment in Hilton Head Island
4.83 out of 5 average rating, 157 reviews

Updated Beach Villa Resort

IsabellaRating, 5 stars1 week ago
Our host was responsive during any issues and flexible. All necessary furniture and amenities were avaliable. The pricing was fair on the location and surrounding areas.
Guest favourite
Apartment in Hilton Head Island
5 out of 5 average rating, 32 reviews

Palmetto Dunes Luxury Oceanfront Gem w/ View -King

LauraRating, 5 stars1 week ago
We had a wonderful stay. The community and condo was very well maintained.

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

  • Total rentals

    5.5K properties

  • Nightly prices starting at

    ₹866 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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