Vacation rentals with a pool in Hilton Head Island

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Popular amenities for Hilton Head Island rentals with a pool

House rentals with a pool

Guest favorite
Home in Savannah
4.88 out of 5 average rating, 68 reviews

Relaxing Pool Paradise - Private Oasis Sleeps 14

ErinRating, 5 stars1 week ago
We had the pleasure of staying at this beautiful home. It exceeded all expectations. Very clean and well-maintained home. Bathrooms were spotless, with plenty of fresh towels. The kitchen was well-equipped, which was perfect for making meals when we didn’t want to go out. Plenty of space through the home. Location was fantastic-quiet, yet conveniently close to local attractions and restaurants. Beautiful pool and patio. Overall, this was an amazing place to stay, and I would highly recommend it to anyone looking for a comfortable and clean spot to relax.
Guest favorite
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 favorite
Home in Hilton Head Island
4.98 out of 5 average rating, 80 reviews

Private pool/spa : pool heat available : Kg master

MariaRating, 5 stars2 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 favorite
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!
Guest favorite
Home in Tybee Island
4.94 out of 5 average rating, 33 reviews

Villa Palms - 4 BR Beautiful Home w/ Private Pool

JoseRating, 5 stars8 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!!!
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!
Guest favorite
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
Top guest favorite
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 favorite
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 favorite
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 favorite
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 favorite
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 favorite
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 vacation rentals with a pool in Hilton Head Island

  • Total rentals

    5.3K properties

  • Nightly prices starting at

    $10 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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