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

Guest favourite
Home in Hilton Head Island
4.88 out of 5 average rating, 8 reviews

Luxurious Sea Pines home with saltwater pool

ChristyRating, 5 stars1 month 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!
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 days 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
4.94 out of 5 average rating, 127 reviews

Jungle Paradise! Perfect Location w/ Private Pool!

JianyingRating, 5 stars3 weeks ago
Our family had such a great time last Spring that we came back again this year! The place is just wonderful. It’s on a quiet street (great for early morning walks or jogs) but just a 10 minute drive to shops like Whole Foods, etc. Fifteen minutes and you’re in the center of Savannah and the same distance to Tybee Island. The house is perfect, bright and clean with all the amenities. The outdoor pool and backyard are gorgeous. The fuzeball and pool table kept our kids busy for hours. Host Luka is the best. Proactive and always responsive and helpful. We hope to be back again next year! Thank you, Luka!
Superhost
Home in Hilton Head Island
5 out of 5 average rating, 3 reviews

Island Getaway - an iTrip Hilton Head Home

AnaRating, 5 stars3 months ago
This home is spacious and well maintained. The open floorplan and ample living space allowed our family of 5 adults to each do their thing while having family time. The indoor pool was an added bonus and the location is perfect for accessing local shops, restaurants, beaches, and landmarks. Plenty of bike trails, golf courses, and tennis courts. It made for an ideal winter getaway!
Top Guest favourite
Home in Hilton Head Island
5 out of 5 average rating, 27 reviews

54 Folly Field Rd - Amazing Beach Home with Pool

TanangRating, 5 stars2 months ago
"We booked this Airbnb well in advance, and unfortunately, there was a double booking at our initial location upon arrival. However, the Oceanside team handled the situation with incredible professionalism and care. Within less than 10 minutes, they upgraded us to a better location that exceeded our expectations. The stay was absolutely amazing, and their attention to detail and dedication to guest satisfaction truly stood out. We’re so grateful for the exceptional service they provided and would highly recommend Oceanside to anyone looking for a seamless and enjoyable experience!"
Guest favourite
Home in Hilton Head Island
4.93 out of 5 average rating, 200 reviews

Heated Pool/Fenced Yard, Golf Cart rental-51

MelodyRating, 5 stars4 weeks ago
When we walked in the house was very clean and decorated very nicely. The best thing was the host had tons of cleaning supplies, dishware, pots and pans and even spices for cooking. The elevator was a plus, especially when going from the garage level to the top (4th) floor. The pool was nice and warm, even though we didn't have an opportunity to get in. But we did sit outside by the fire pit every night. The water went off for some reason, but Michael was proactive and sent us an alert before we even knew the water was off. It was back on again in no time. This was the perfect house for a getaway. We'll definitely be back
Guest favourite
Home in Hilton Head Island
4.87 out of 5 average rating, 54 reviews

SeaPines - Private Beach Path, Private Pool, Bikes

RachelRating, 5 stars3 days ago
Really beautiful home in Sea Pines, an easy walk to the beach and right alongside the bike paths. The house was even bigger than shown in the pictures, and super clean. I was amazed that even the inside of the oven was pristine! The beach is huge and uncrowded, the beds in the house are comfy, and the 3rd bedroom has 4 single beds which are perfect for kids. Plus, our dog was welcome (and very happy) in the home. We'd definitely recommend this home!
Top Guest favourite
Home in Hilton Head Island
5 out of 5 average rating, 25 reviews

Townhouse with Southern charm

MarilynRating, 5 stars4 months ago
We had a wonderful stay at this beautiful home in Hilton Head! The house was absolutely spotless and provided everything we needed for a memorable Thanksgiving dinner. The kitchen was well-equipped, and the spacious dining area made it perfect for gathering and enjoying a festive meal. The location was ideal—just a short walk to the beach, which we still enjoyed even though the weather was a bit chilly. The owner was incredibly helpful, providing detailed and clear instructions for getting in and out of the house, making our arrival and departure seamless. We loved the outdoor spaces, including the patios, and we can only imagine how great it would be to enjoy them in the warmer months. The proximity to the outdoor pool is also a big plus. We’ll definitely be back to experience it again in the summer! Highly recommend this home for anyone looking for a relaxing, comfortable stay in Hilton Head.

Condo rentals with a pool

Guest favourite
Condo in Hilton Head Island
4.93 out of 5 average rating, 132 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!
Top 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, 222 reviews

Condo on Beachfront Resort

LindaRating, 5 stars1 month ago
The condo was great for what was needed. We loved the distance from the beach, it was super convenient. The only recommendation I would have would be to have a few more basics kitchen items such as salt/pepper, aluminum foil, a food storage containers/bowls, etc. aside from that, it had everything we needed.
Guest favourite
Condo in Hilton Head Island
4.87 out of 5 average rating, 103 reviews

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

HannahRating, 5 stars1 week ago
Kacie’s condo was perfect for our family of four! It was comfortable, quiet, and had everything we needed. We enjoyed the short walk to beach, biking around the island, and the heated pool steps away from the condo. We will absolutely return!
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 stars2 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
4.92 out of 5 average rating, 48 reviews

Beachside Condo: 2 bedrooms, 2 bathrooms

ChristopherRating, 5 stars4 weeks 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, 165 reviews

Walk to Beach - 3 Pools - Central Location !

JasonRating, 5 stars2 weeks ago
The condo was exactly what we need for our Hilton Head stay. Being in the same building as the indoor pool was perfect for our daughter. Proximity to the beach was great and the whole area was walkable and bike able. We would definitely return!
Superhost
Condo in Hilton Head Island
4.84 out of 5 average rating, 122 reviews

Oceanside Resort. Heated Indoor Pool, Hot tub.

AnnaRating, 5 stars2 weeks ago
My friends and I had a beautiful stay here for our spring break. Mark answered my messages really quickly was very friendly. His place was accurately described in the captions and the resort was lovely. We already talked about going back again!

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

  • Total rentals

    5.3K properties

  • Nightly prices starting at

    $16 AUD before taxes and fees

  • Total number of reviews

    121K reviews

  • Family-friendly rentals

    4.3K properties are a good fit for families

  • Pet-friendly rentals

    800 properties allow pets

  • Rentals with dedicated workspaces

    2.5K properties have a dedicated workspace

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