
Vacation 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!

17 Night Heron · Elegant, Stylish Beach Cottage
We had an awesome week at an awesome place. This spot is beautiful. Looking forward to coming back soon.

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!

Heated Pool/Fenced Yard, Golf Cart rental - 79
With us and children’s families we had plenty of room and things to do right on the property for 6 adults and 5 grandchildren from 2 to 10 years old! We had a blast: plenty of beds, bathrooms, big kitchen and den, indoor swimming pool, game room, hot tub, fire pit, short street for bikes, garage. On raining periods or at night the house was great for eating, play and family time! We got the golf cart and biked minutes from Folly Field beach and also to Island beach which were great beaches. Biking on the beaches and the innumerable wonderful trails throughout Hilton Head is amazing for those who take advantage of it. Besides the beach adventures we also took advantage of the horseback riding at Lawton Stables and the Pirates of Hilton Head kids pirate ship adventure at Harbor Town which was something the kids and adults will not forget. We ate most of the time in our great kitchen but some did get to enjoy two fabulous seafood restaurants. Hilton Head is a beautiful island!
Condo rentals with a pool

OceanFront Upscale 1 Bdrm Condo/HeatedPool/Sleeps6
Nick’s place was perfect for our family. The bunk beds were great for the kids, and the king bed was comfortable. The view from the balcony is beautiful with nice patio furniture to lounge in. The kitchen had everything we needed. Nick was very responsive and helpful!

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.

5 Star Location! Pool, Walk to Shops/Dining
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 !

Oceanfront Luxury! KING BED 65"TVs Pickleball BAR!
Condo was super easy to get to on the first floor and definitely oceanfront. Although we were on the first floor, we could still see 98% of the ocean over the dunes and easily hear the waves crashing from the balcony. We got to see a family of rabbits hopping through the dune grasses and 99.9% of the time no one is seen between our balcony and the ocean… giving the feeling of seclusion in a populated area. Everything worked as it should in every room in the condo… fantastic TVs, extremely good shower heads, sturdy beach chairs, stout beach umbrella w/ anchor, comfortable plush leather sofa, and a very comfy form fitting memory foam king bed with plenty of pillows for even the finicky sleeper. 99% of my kitchen needs were met…i’ll remember the cooking spray next time. The plush white sand was a pleasant surprise as well as how level and firm the sand gets when the tide goes out, great for bocce ball! BTW, just about any kind of tent, wind shade or popup is allowed on the beach.

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!!!

Beach Haven, Ocean Front Resort!
It is a clean safe place. Would definitely stay agin it is conveniently located. I was there for the heritage golf tournament Would like to come back and enjoy the beach more Highly recommend
Quick stats about vacation rentals with a pool in Hilton Head Island
Total rentals
5.5K properties
Nightly prices starting at
G$2,090 GYD before taxes and fees
Total number of reviews
120K 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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