Holiday rentals with a pool in Hilton Head Island

Find and book unique homes with a pool on Airbnb

0 of 0 items showing
1 of 3 pages
0 of 0 items showing
1 of 12 pages

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, 5 reviews

30 Plantation Dr @ Sea Pines | Pool & Spa | Golf

TinaRating, 5 stars1 month ago
Host and Home was an excellent host! There was an unforeseen issue with the home we had booked, and Host and Home ensured we got moved to another beautiful home where we had an excellent stay. They were very accommodating, proactive and responsive. I look forward to staying in other Host and Home properties in the future.
Guest favourite
Home in Hilton Head Island
4.89 out of 5 average rating, 9 reviews

Luxurious Sea Pines home with saltwater pool

ChristyRating, 5 stars2 months ago
The house was perfect! It was very open with plenty of room! We loved the openness of the kitchen into the dining room and into the living room! That’s where we stayed the most! All the beds were so comfortable! It was wonderful experience!
Top Guest favourite
Home in South Beach
4.98 out of 5 average rating, 40 reviews

Sea Pines - S. Beach Charmer - Private Pool/Spa

RoseannRating, 5 stars6 months ago
We had a great stay! From the beginning, Nick was very responsive. Gave us great recommendations and restaurant options. We loved that this home was in the sea Pines community. It was very private and there’s so much to do. Definitely worth getting the pool and the hot tub heated. The first couple of days we had a couple of issues with the hot tub and the pool being heated, but Nick and Judy were so responsive and did everything to accommodate us and fix the problem. The house is very clean. And we even had cleaning service in the middle of our stay, which was nice. Would def come back!
Guest favourite
Home in Hilton Head Island
4.98 out of 5 average rating, 80 reviews

Private pool/spa : pool heat available : Kg master

MariaRating, 5 stars3 weeks ago
We really enjoyed our stay at Abigail’s place! Very comfortable with everything you may need. The kitchen was well stocked. We enjoyed the pool!
Guest favourite
Home in Savannah
4.95 out of 5 average rating, 129 reviews

Jungle Paradise! Perfect Location w/ Private Pool!

KaleighRating, 5 stars2 weeks ago
LuKa’s home was perfect. We loved the location, it was perfectly located between Tybee and Savannah giving us multiple options to go eat, explore, and be touristy. This house was perfect for our family with kids ranging from 7-14. They each had something fun to do that kept them busy and entertained, and of course the pool was a bonus! Even without the pool being heated, it had zero affect on how fun we all had. The home was cleaned and well stocked of everything we needed. We honestly cannot wait to come back!
Guest favourite
Home in Tybee Island
4.94 out of 5 average rating, 33 reviews

Villa Palms - 4 BR Beautiful Home w/ Private Pool

JoseRating, 5 stars9 months ago
Our stay in Anthony’s House was incredible!! This is an Amazing Place! Had high expectations with the amount of positive reviews and it totally met them. Anthony went above and beyond with communication and he stoped by to make sure we have everything we needed and also he recommend places to visit and stores around the island! We visited Tybee Island 15 years ago and feel like we were staying at the best spot on the Island. 8 adults and a kid stayed in this beautiful home!! The swim up bar and outdoor tv was a huge hit with the guys. The open kitchen and living room was great for cooking, chatting and dining. Each of the bedrooms provided comfort for each of us!! The home was everything we needed for staying on Tybee Island. Also there is more amenities like ping pong table, foosball table and much more!! Thank you Anthony!!!
Guest favourite
Home in Hilton Head Island
4.93 out of 5 average rating, 204 reviews

Heated Pool/Fenced Yard, Golf Cart rental-51

CaitlinRating, 5 stars1 week ago
Michael’s place was absolutely perfect for our group!! We really enjoyed having the loft with a bunch of extra beds so we didn’t have to bring any air mattresses. It’s about a 7-10 minute easy walk to the beach. Had everything we needed for cooking. Hot tub was a nice addition! We did have a little trouble with keeping it warm but that was probably more user error on our end than anything and we didn’t try trouble shooting. Absolutely recommend this place for a larger group and would definitely stay here again!
Top Guest favourite
Home in Hilton Head Island
5 out of 5 average rating, 28 reviews

Townhouse with Southern charm

DoreenRating, 5 stars2 days ago
The townhouse was in a great location central to everything Very peaceful setting Kevin and Dena were wonderful hosts very responsive to all our needs We would definitely rent this property again. We love HH and this property was perfect for our family get together! Thanhs Kevin and Dena!

Condo rentals with a pool

Guest favourite
Condo in Hilton Head Island
4.92 out of 5 average rating, 133 reviews

Condo 2 Qbeds/indoor pool/picklebal/3 blocks beach

MorganRating, 5 stars6 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 stars8 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, 224 reviews

Condo on Beachfront Resort

DianneRating, 5 stars1 month ago
I enjoyed my 5 day stay. It was clean and had everything I needed. The walk to beach and pool area was an easy walk not too far. I do think the mattress could use an update and be more comfortable. But overall, it was great place.
Guest favourite
Condo in Hilton Head Island
4.88 out of 5 average rating, 105 reviews

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

KayleeRating, 5 stars1 week ago
We had a great time staying at Kacie’s condo. The location was great and she was so quick to respond with any questions we had. Definitely recommend!
Guest favourite
Condo in Hilton Head Island
4.9 out of 5 average rating, 108 reviews

Upgraded peaceful villa ! 7 min walk to the beach

MikeRating, 5 stars3 months 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
4.9 out of 5 average rating, 49 reviews

Beachside Condo: 2 bedrooms, 2 bathrooms

ChristopherRating, 5 stars1 month ago
Tasha was a wonderful host. She reached out to me prior to checkin to ensure I received the door code. She also handled an extra parking price for my wife very quickly. Best customer service I have experienced using Airbnb or hotel room. Highly recommend!!
Superhost
Condo in Hilton Head Island
4.76 out of 5 average rating, 167 reviews

Walk to Beach - 3 Pools - Central Location!

AlRating, 5 stars1 week ago
Very nice place and also host is communicative .
Superhost
Condo in Hilton Head Island
4.79 out of 5 average rating, 229 reviews

Pool side condo just steps from beach boardwalk!

ChelseaRating, 5 stars6 months ago
Sheena was responsive and this place is perfect for a family with small kids. The indoor pool is perfect for cooler weather. The walk to the beach was gorgeous with a great little restaurant right by the beach. There was a convenient storage garage for all of our beach supplies and they had some beach supplies available to borrow. The bed was so comfortable we slept so well each night! Sheena even allowed us to book an extra day at the last minute. Shelter Cove is a 3 min drive - groceries, restaurants, shopping - EVERYTHING! We would definitely stay here again.

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

  • Total rentals

    5.5K properties

  • Nightly prices starting at

    $16 AUD 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

Destinations to explore