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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 stars1 week 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 Sea Pines
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 Sea Pines
5 out of 5 average rating, 18 reviews

Starfish Beach House with Pool and Bikes

SueRating, 5 stars3 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
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 stars2 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 Palmetto Dunes
4.94 out of 5 average rating, 114 reviews

Cozy Coastal Chic - Beach, Pickleball, Golf, Pets

JanelleRating, 5 stars3 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 Sea Pines
4.78 out of 5 average rating, 23 reviews

17 Night Heron · Elegant, Stylish Beach Cottage

AlexRating, 5 stars2 weeks ago
The home was perfect!! It can be so hard to find a place at the beach for just two people, but the cottage was wonderful. Comfortable, beautiful area, incredibly easy walk to the beach. The only thing worth noting is that the fridge is very small (basically an under counter drink drawer) so don’t expect to be able to load up on a full week of groceries. That said, there are so many grocery stores super close, so it was not a problem. I would absolutely come back for another relaxing weekend at the beach!!
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 stars2 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!

Condo rentals with a pool

Guest favorite
A sweeping view of the ocean is captured, highlighting the sandy shoreline and lush greenery in the foreground. A serene pond is visible, featuring a fountain that adds a tranquil element to the landscape, enhanced by a clear blue sky.
Condo in Hilton Head Island
4.94 out of 5 average rating, 65 reviews

HUGE Ocean View! 65"TV Pickleball BAR GYM & Tennis

KevinRating, 5 stars6 days ago
This was a great place: conveniently located, amazing resort amenities, and stress free. We would definitely stay again!
Top guest favorite
Condo in Hilton Head Island
4.9 out of 5 average rating, 134 reviews

Island House; First Floor Villa / Weekly discount

KellyRating, 5 stars1 month ago
We felt right at home immediately! Everything we could have possibly needed for our stay and more was readily available. The condo was cozy and very clean. The decor was beautiful! It was just wonderful all the way around! Will definitely be returning!
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 aerial view captures a large pool shaped like a star, surrounded by lounge chairs. The pool area is complemented by umbrellas and seating, with a sandy beach and the ocean visible in the background under clear blue skies.
Condo in Hilton Head Island
4.89 out of 5 average rating, 193 reviews

Easy Breezy at Hilton Head Beach & Tennis

TylerRating, 5 stars1 week ago
This place was great, exactly what our family needed for our stay at the beach! Erik was responsive and proactive and made sure we had everything we needed. The beach amenitites were a huge plus. The condo is in a great, private location. Would highly recommend!
Top guest favorite
The kitchen area features modern stainless steel appliances, including a refrigerator and stove. A wooden dining table with four chairs is positioned next to a window, which allows natural light to illuminate the space. White cabinets and a neutral backsplash complement the flooring.
Condo in Hilton Head Island
4.95 out of 5 average rating, 524 reviews

(5) Location! Walk to Coligny Beach Shops Dining!

CourtneyRating, 5 stars1 week ago
My family and I took a quick one day trip up to Hilton head Island from Atlanta to go to the beach. We were very pleased with this unit as it was only a couple blocks away from the beach so definitely within walking distance (less than a 10 minute walk), there were tons of restaurants and little shops nearby. The home was beautiful and clean and equipped with everything we needed, and they even had beach chairs and an umbrella and a wagon for us to use which was super helpful to have. The hosts were very communicative and even accommodated us getting there early from Atlanta. It was well worth the price in my opinion compared to other rentals, we will definitely be back to stay there again!
Guest favorite
A private balcony is shown, featuring a small table with a bottle and glass. Two beach chairs are propped against the railing, while a cooler is visible on the ground. The view includes a paved area with parking spaces and palm trees framed by clear blue skies.
Condo in Hilton Head Island
4.96 out of 5 average rating, 137 reviews

Luxury Couples Retreat

RitaRating, 5 stars1 month ago
I had a wonderful stay! Julia is a great host who responded very quickly when I had a question. The condo is very comfortable and nicely decorated. The resort is well maintained and I appreciated having security and maintenance staff available if needed. There is so much to do on Hilton Head Island, I could easily have stayed another week!
Superhost
A cozy living area is showcased, featuring a light beige sofa with blue accent pillows and a coffee table displaying colorful magazines. A kitchenette is visible to the left, with white cabinetry and essential appliances. Artwork hangs on the wall, adding a subtle touch to the serene space.
Condo in Hilton Head Island
4.91 out of 5 average rating, 138 reviews

HipNautic Couples Beach Escape Indoor Pool Jacuzzi

ClaireRating, 5 stars2 weeks ago
Really cute apartment with great amenities, conveniently located next to a connected Hilton Hotel so we my friends and I were able to take advantage of a few hotel perks ;) The hot tub and pool area were really nice too! Overall booking was made easy and the host was very responsive and helpful!
Top guest favorite
A circular pool is surrounded by a spacious deck adorned with lounge chairs. The pool area is framed by plantings and palm trees. The three-story building features multiple open balconies with wooden railings, providing a view of the pool and greenery.
Condo in Hilton Head Island
4.95 out of 5 average rating, 336 reviews

1 Minute walk to the beach *Amazing ocean view*

MarthaRating, 5 stars2 weeks ago
We could not have asked for a better host, excellent place to stay and so close to the beach. Paul had everything we needed for our stay, including all the equipment to enjoy our time on the beach. We will definitely be back.

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

  • Total rentals

    5.5K properties

  • Nightly prices starting at

    G$2,092 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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