
Holiday rentals with a pool in Hilton Head Island
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Hilton Head Island
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.
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Popular amenities for Hilton Head Island rentals with a pool
House rentals with a pool

6 BR, Sleeps 26, Beach Time
This home is absolutely beautiful! We loved staying here!! Such a great experience!

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

Starfish Beach House with Pool and Bikes
Sherri was very responsive to our concerns. She had a person on site that was very accountable to our needs. Would definitely stay again.

Cozy Coastal Chic - Beach, Pickleball, Golf, Pets
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!

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

Modern Beach Escape | Private Pool~Steps to Beach
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!

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

Peaceful Harbour Town Treehouse with Marsh Views
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

HUGE Ocean View! 65"TV Pickleball BAR GYM & Tennis
This was a great place: conveniently located, amazing resort amenities, and stress free. We would definitely stay again!

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

Beach Time! Retro-Mod Family Beach Fun
Perfect Airbnb for five nights in Hilton Head. Would definitely visit again! Anne gave clear and detailed instructions.

Condo on Beachfront Resort
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.

Marriott Sunset Pointe - 2BD
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!!!

Exclusive Oceanfront Decorator Decor Spacious Bdrm
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!

Updated Beach Villa Resort
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.

Palmetto Dunes Luxury Oceanfront Gem w/ View -King
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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- Coligny Beach Park
- Forsyth Park
- Hunting Island State Park Beach
- North Beach, Tybee Island
- Palmetto Dunes Oceanfront Resort
- Shipyard Beach Access
- Harbour Town Golf Links
- The Westin Savannah Harbor Golf Resort & Spa
- Mid Beach
- Dolphin Head Golf Club
- Harbor Island Beach
- Tybee Beach Pier and Pavilion
- Hilton Head Island Beach
- Congaree Golf Club
- Tybee Beach point
- Bradley Beach
- Bull Point Beach
- Secession Golf Club
- Wormsloe Historic Site
- Bloody Point Beach
- Islanders Beach Park
- Seabrook Beach
- Bonaventure Cemetery
- Hunting Island Beach
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