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Vacation 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

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!
Top guest favorite
A modern treehouse is framed by lush greenery, showcasing large windows that invite natural light. A ramp leads to a spacious deck, providing access to the entry. The surrounding area features mature trees and tropical plants, enhancing the serene environment.
Home in Hilton Head Island
4.99 out of 5 average rating, 82 reviews

180º Ocean Views, Treehouse "Siren's Lookout"

PamRating, 5 stars1 week ago
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!
Top guest favorite
A private residence is set among tall trees, featuring a spacious patio area with a circular pool at its center. A barbecue grill and poolside loungers are visible, surrounded by natural landscaping, creating a serene outdoor retreat.
Home in Hilton Head Island
5 out of 5 average rating, 18 reviews

Starfish Beach House with Pool and Bikes

SueRating, 5 stars4 weeks ago
Sherri was very responsive to our concerns. She had a person on site that was very accountable to our needs. Would definitely stay again.
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 stars6 days 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 starstoday
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 stars2 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!
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

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!
Guest favorite
An expansive beachside pool is featured, surrounded by lounge chairs positioned on a paved deck. The pool's clear water reflects the blue sky and nearby palm trees, creating a relaxing atmosphere. Umbrellas provide shaded seating areas, enhancing comfort for guests.
Condo in Hilton Head Island
4.93 out of 5 average rating, 55 reviews

1Min Walk to Beach/Ocean View Balcony/Huge Pool

WillieRating, 5 stars1 day ago
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.
Top guest favorite
A private pool area is nestled among lush greenery and towering trees. Sun loungers are arranged around the pool, providing a tranquil setting. A secure fence surrounds the pool, enhancing privacy and safety in this serene outdoor environment.
Condo in Hilton Head Island
5 out of 5 average rating, 88 reviews

5 Star Location! Pool, Walk to Shops/Dining

ShalaynaRating, 5 stars1 week ago
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 !
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, 175 reviews

Beach Time! Retro-Mod Family Beach Fun

AndreaRating, 5 stars2 weeks ago
Perfect Airbnb for five nights in Hilton Head. Would definitely visit again! Anne gave clear and detailed instructions.
Superhost
The spacious beachside pool is prominently featured alongside the sandy shore, offering sun loungers and shaded seating areas. The ocean's gentle waves meet the horizon under a clear blue sky, with beach umbrellas dotting the coast in the distance.
Condo in Hilton Head Island
4.7 out of 5 average rating, 227 reviews

Condo on Beachfront Resort

RyanRating, 5 stars1 month ago
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.
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!!!
Superhost
A spacious pool area is shown, featuring a hot tub surrounded by a tiled deck with multiple lounge chairs arranged nearby. The resort buildings rise in the background under a clear blue sky, with palm trees adding a tropical touch to the scene.
Condo in Hilton Head Island
4.86 out of 5 average rating, 118 reviews

Beach Haven, Ocean Front Resort!

RichardRating, 5 stars2 months ago
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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