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

Top guest favorite
An outdoor living area features a private pool, complemented by modern lounge chairs and a grill area. The open space is shaded by a wooden overhang, with accent pillows adding color. A wall-mounted television is visible in the background.
Home in Hilton Head Island
4.99 out of 5 average rating, 76 reviews

6 BR, Sleeps 26, Beach Time

KelseyRating, 5 stars2 weeks ago
This home is absolutely beautiful! We loved staying here!! Such a great experience!
Guest favorite
A private heated pool is presented with crystal-clear water, surrounded by a deck featuring four lounge chairs. The pool area is framed by lush greenery and trees, creating a peaceful outdoor space for relaxation.
Home in Hilton Head Island
4.95 out of 5 average rating, 79 reviews

5 Bedroom-Beach Access-Pool-Sleeps 14!

SydneyRating, 5 stars3 weeks ago
We had an amazing stay at Sur La Mar for our girls trip! The house was clean, spacious, and perfectly set up for a large group—it made everything so easy and comfortable. The location was ideal, close to the beach and had everything we needed, and we loved having the pool to relax and hang out together. Steven was incredibly responsive and helpful throughout our stay. Highly recommend this place for anyone planning a big group getaway or family vacation in Hilton Head.
Guest favorite
Home in Hilton Head Island
4.94 out of 5 average rating, 114 reviews

Cozy Coastal Chic - Beach, Pickleball, Golf, Pets

JanelleRating, 5 stars1 week ago
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!
Guest favorite
Home in Hilton Head Island
4.98 out of 5 average rating, 109 reviews

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

JohnRating, 5 stars2 months ago
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!
Superhost
The entrance of the cottage features a light blue door surrounded by a wooden deck, framed by lush greenery and tall trees. A small sign reading 'Home' hangs next to the door, indicating a welcoming atmosphere.
Home in Hilton Head Island
4.79 out of 5 average rating, 24 reviews

17 Night Heron · Elegant, Stylish Beach Cottage

JackRating, 5 stars1 day ago
We had an awesome week at an awesome place. This spot is beautiful. Looking forward to coming back soon.
Superhost
A modern two-story home is nestled among lush trees, featuring a large outdoor pool surrounded by a paved deck. A spacious covered balcony offers seating, providing a view of the inviting pool area and landscaped grounds, perfect for relaxing or entertaining.
Home in Hilton Head Island
5 out of 5 average rating, 4 reviews

Modern Beach Escape | Private Pool~Steps to Beach

CraigRating, 5 stars3 weeks ago
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!
Guest favorite
Home in Hilton Head Island
4.86 out of 5 average rating, 371 reviews

W2Bch*4TVs*1GIG I*PetsWC *WiFi*4King ßds*grill*gms

AmyRating, 5 stars3 weeks ago
We loved our stay at Marina's beach hut. We walked to the beach morning and evening and views on the beach were beautiful. Everyone was so friendly. Had plenty of space for our family to either be together or spread out in the house space. House was well stocked with beach and home supplies. Loved having space for our car in the garage. Master bath shower was luxurious! Neighborhood was quiet and felt very safe. Loved the keyless entry system!
Top guest favorite
A two-story light blue house with gray shutters is shown, set within a wooded area. A six-passenger golf cart is parked in the driveway, adding convenience for guests. Surrounding landscaping includes mulch and native plants, creating a natural setting.
Home in Hilton Head Island
4.95 out of 5 average rating, 158 reviews

Heated Pool/Fenced Yard, Golf Cart rental - 79

RandallRating, 5 stars1 week ago
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

Superhost
A view of the outdoor pool area surrounded by palm trees and lush greenery can be seen from the balcony. The pool is shaped with defined edges and is complemented by numerous lounge chairs and a peaceful atmosphere.
Condo in Hilton Head Island
4.77 out of 5 average rating, 193 reviews

BEACHFRONT KING BED VILLA, PVT BALCONY, SELF CKIN

DianneRating, 5 stars1 month ago
Close walk to the beach and Coligny. The bed is super comfortable. The AC works really good. The kitchen is small, but has all the essentials. The little shampoo/conditioners were nice because we forgot to pack ours. The condo is decorated nicely and is quite cozy and comfortable.
Guest favorite
A balcony view reveals a serene ocean scene, with calm blue waters meeting the sky. Below, a heated pool surrounded by lounge chairs invites relaxation, complemented by lush greenery that frames the area. Sunlight brightens the landscape, enhancing the tranquil ambiance.
Condo in Hilton Head Island
4.92 out of 5 average rating, 182 reviews

OceanFront Upscale 1 Bdrm Condo/HeatedPool/Sleeps6

EmilyRating, 5 stars2 weeks ago
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!
Top guest favorite
A living area is characterized by a comfortable seating arrangement, featuring a light-colored sofa and a patterned armchair. A wooden coffee table is placed centrally, and a television is mounted above a decorative fireplace. Large windows provide views of the outdoor deck and surrounding greenery.
Condo in Hilton Head Island
4.97 out of 5 average rating, 114 reviews

1BR/2BA condo w/private beach access in Shipyard

ZackeryRating, 5 stars2 weeks ago
This was our 4th trip to Hilton Head Island and our 2nd time staying on the island itself. LeDesa’s place was one of our favorite stays so far. The location was perfect—quiet, private, and tucked away in the Shipyard area, but still close to everything we needed. The walk to the beach wasn’t bad at all, even with a 2-year-old and a wagon. It was a little longer than we would have liked, but totally manageable. The home was spotless and extremely comfortable. We were impressed with how well-stocked it was—plenty of linens, towels, kitchen supplies, and cookware. It truly felt like home. We had a small maintenance issue during our stay, and the host responded immediately and had someone out to fix it right away. We felt well taken care of the entire time. I would highly recommend this Airbnb to anyone visiting Hilton Head. It has everything you could need, and we’re already looking forward to coming back next year!
Top guest favorite
A bright dining area with views of the ocean through sliding glass doors. A round table is set with a decorative bowl, while outdoor seating can be seen on the balcony. Lush greenery frames the coastline beyond.
Condo in Hilton Head Island
4.97 out of 5 average rating, 296 reviews

Oceanfront Luxury! KING BED 65"TVs Pickleball BAR!

Kent and CandyRating, 5 stars1 week ago
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.
Superhost
A swimming pool is surrounded by a spacious deck featuring numerous lounge chairs. Shade is provided by an umbrella over some seating areas. Lush greenery and tall trees frame the area, adding to the resort's relaxing atmosphere.
Condo in Hilton Head Island
4.84 out of 5 average rating, 176 reviews

Beach Time! Retro-Mod Family Beach Fun

JessicaRating, 5 starstoday
This was a great place to stay. It is very convenient to have beach assess and the pool just steps away. In addition, having restaurants on site was very convenient!
Guest favorite
Condo in Hilton Head Island
4.89 out of 5 average rating, 165 reviews

Book Now & Save! 3 blocks beach/pool/pickleball

JoshRating, 5 starstoday
We had a great time. The place was very clean and centrally located. Gloria was great and stayed in touch.
Superhost
A serene beachfront scene is captured, featuring a wooden boardwalk leading toward the water. Lush greenery and trees frame the view, offering a peaceful atmosphere. The sandy shore and distant water create a calming backdrop against a clear blue sky.
Condo in Hilton Head Island
4.86 out of 5 average rating, 140 reviews

Beach Front Villa Oak Tree Lined Views to Water

KevinRating, 5 stars1 week ago
Exceptional host. There are cats walking around property which made me raise an eyebrow but during stay they added to the charm! We maybe saw 5 different cats while there so not many at all. David was always responsive and checking in and answered our questions immediately. Will stay again on his properties. The beach was our backyard and perfect for our very young grandkids. Property has been featured on HGTV in past years.
Superhost
A view of the resort's building complex is presented, featuring multiple balconies and terracotta roofs. The outdoor pool is visible, surrounded by greenery and lounge chairs. A tranquil waterway lies in the background, with natural landscapes of grass and trees framing the scene.
Condo in Hilton Head Island
5 out of 5 average rating, 5 reviews

Marriott Sunset Pointe - 2BD

TinaRating, 5 stars4 months ago
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!!!

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

  • Total rentals

    5.5K properties

  • Nightly prices starting at

    G$2,093 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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