Vacation rentals with a pool in Kiawah Island

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Popular amenities for Kiawah Island rentals with a pool

House rentals with a pool

Top guest favorite
Home in Mount Pleasant
4.96 out of 5 average rating, 114 reviews

Private Entrance Suite w/ pool, 5 min from beach

MichelleRating, 5 stars1 week ago
My husband and I enjoyed our stay. The location is in a very nice neighborhood and very close to lots of Charleston's favorite things to do. Liz was a great host giving specific directions as well as checking in to make sure we had everything we needed. However, we did not need to request anything additional than what was provided. Check in and check out was an easy process. We will stay here again.
Top guest favorite
Home in Fripp Island
4.96 out of 5 average rating, 48 reviews

Located mid-island by tennis courts, marsh sunsets

AntoninaRating, 5 stars2 weeks ago
We had a very short but relaxing stay at Kathy’s place. We enjoyed how quiet and private yet walkable it is to some food options and morning coffee. Loved riding around on a golf cart exploring the island and meeting its beautiful deer everywhere! We definitely will be back!
Guest favorite
Home in Saint Helena Island
4.99 out of 5 average rating, 128 reviews

The Hampton House

BeauRating, 5 stars1 week ago
This is a nice house with a lot of really great perks. The golf cart, kayaks, fishing rods, beach equipment, and more made it easy to enjoy the week. The location is peaceful and ideal for fishing but not perfect for swimming or waves; we went to adjacent Hunting Island State Park for the kids to ride waves (a state park pass is included by the host). We enjoyed our week!
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!
Top guest favorite
Home in Seabrook Island
5 out of 5 average rating, 29 reviews

Hugging Tree Sea Cottage!

AmberRating, 5 stars1 week ago
Do not hesitate to stay at Hugging Tree Cottage - our entire experience from first booking to check out was seamless. I cannot say enough about our host, Kim. She was proactive in reaching out to us to see if we needed anything or had questions and was incredibly responsive and kind when we contacted her. The house is perfection, so so so clean, beautifully decorated, VERY comfortable beds, fabulous and cozy couch, and the golf cart option was amazing. The kitchen is beautiful and has everything you need and the location of the house was so easy to the pool, beach, Freshfields, etc. We were 3 moms and 4 teen girls and it was perfect for our group. We are so grateful to our amazing hosts for an unforgettable long weekend. Thank you! Can’t wait to come again.
Guest favorite
Home in Folly Beach
4.98 out of 5 average rating, 135 reviews

Luxury pool, incredible porch, 3/2center of Folly!

OliviaRating, 5 stars2 weeks ago
We had the most incredible time staying at Corrie’s place in Folly Beach for our moms getaway girls trip! The location is unbeatable—just a short walk to the beach, fun bars and restaurants, and a super cool 24/7 market. The house itself is a dream—spacious, luxurious, and designed with the perfect mix of indoor and outdoor lounge areas to relax and connect. The hot tub and pool were absolutely next level. Corrie was a fantastic host, and everything was seamless from start to finish. If you’re considering booking—stop looking and just do it!!!! We’d come back in a heartbeat!
Top guest favorite
Home in Isle of Palms
4.96 out of 5 average rating, 84 reviews

Gorgeous home one block from beach w/ heated pool

MimiRating, 5 stars1 week ago
It’s a beautiful, well appointed, clean and tastefully decorated home. The home is spacious with a great floor plan. We were 3 families. 6 adults and 5 children. The kids loved the pool. There were numerous pool toys to keep them entertained. The kitchen is a cook’s dream. Everything ( except a coffee grinder) was available. The long kitchen table easily accommodates 12. We enjoyed the porches. There are 3 but we did not use top balcony. ( that is where the fire pit is ) There are lots of steps, but the convenience of the elevator was wonderful. It was a great location as well. We had a lovely time.
Guest favorite
Home in Isle of Palms
4.94 out of 5 average rating, 33 reviews

Beach House with Backyard Oasis

JillianRating, 5 stars2 months ago
We throughly enjoyed our stay and the house was perfect for two families of four. The location is perfect - walkable to town and close to the beach but off the Main Street so quiet and not busy. We loved the pool and hot tub and outdoor seating and we made good use of the ping pong table room. We had small issues and questions throughout our stay and Frank was very responsive. Would definitely stay here again.

Condo rentals with a pool

Top guest favorite
Condo in Hilton Head Island
4.98 out of 5 average rating, 116 reviews

Beach condo with pool and stunning nature views

JamesRating, 5 stars1 month ago
Loved our stay here. Condo very clean and comfortable, especially beds. Very communicative hosts Thank you for letting us stay
Top guest favorite
Condo in Seabrook Island
4.94 out of 5 average rating, 102 reviews

On the Beach-End Unit! Enjoy Dolphins & Sunsets!

MarkRating, 5 stars3 weeks ago
Pelican Watch is a beautiful place on Seabrook. The beach is a 2 minute walk from the backdoor with a great view from the back porch. You need a car to get to most restaurants but great places are 10-20 minutes away. Harris Teeter is well stocked nearby with great steaks and seafood as well as wine. I’d definitely stay here again.
Guest favorite
Condo in Hilton Head Island
4.96 out of 5 average rating, 294 reviews

Ocean View! Steps to beach! Remodeled HHBT Condo

SarahRating, 5 stars3 days ago
We loved our stay here, it’s a great location on the beach, we like this area of the island as it doesn’t seem as crowded. The resort is nice and has different activities going on, we love having the poolside bar area and ice cream stand right there. The place itself was nice, clean, made good use of space. Kids loved the hall bunks. Very easy to check in and out.
Top guest favorite
Condo in Hilton Head Island
4.98 out of 5 average rating, 259 reviews

HHBT Resort-OceanView-Remodeled-Steps to beach/bar

MegRating, 5 stars3 days ago
I’ve stayed at this resort multiple times but this room is by far the best! It was clean, had every thing we needed & more, and was a perfect location for a wagon haul to the beach. It was impressively stocked with things you may forget. We had a wonderful stay & will be staying in this room again for our next stay. Thank you!
Top guest favorite
Condo in Charleston
4.98 out of 5 average rating, 204 reviews

Little Oak Love | 5 Minutes to Folly | Marsh Views

MarthaRating, 5 stars2 weeks ago
Stunning views from an open deck and a super comfy screened deck. Quiet serene atmosphere. Great kitchen amenities. Would definitely like to return.
Guest favorite
Condo in Isle of Palms
4.95 out of 5 average rating, 332 reviews

Stylish Ocean Front Sanctuary

HeatherRating, 5 stars2 weeks ago
Everything was awesome. The only negative was we didn’t end up getting check-in access until about 5pm the first day, but we did get an hour later checkout. Would stay again for sure
Guest favorite
Condo in Isle of Palms
4.89 out of 5 average rating, 100 reviews

Sunrise Sea Cabin 137C - Isle of Palms, SC!

TinaRating, 5 stars2 weeks ago
My family and I thoroughly enjoyed this beach getaway—both for a wedding and for some much-needed relaxation. The location was excellent, with a very short walk to a private beach and pool. Nikki was extremely responsive and kind. She provided plenty of towels, beach chairs, and beach toys for the kids, which made our stay even more enjoyable. Only a few complaints. Nikki has all of the cooking appliances, but no cooking oil or seasoning. Shower pressure is uncomfortably hard. And the fan in the bedroom is loud, no matter what setting you have it on, other than that everything else was great stay.
Top guest favorite
Condo in Hilton Head Island
4.97 out of 5 average rating, 143 reviews

Luxury OceanView KING BED 65"TV Bar Pickleball GYM

PatrickRating, 5 stars2 weeks ago
C339 is a beautiful condo and great location. Can’t wait to go back. Mike was also very quick in answering questions.

Quick stats about vacation rentals with a pool in Kiawah Island

  • Total rentals

    300 properties

  • Nightly prices starting at

    G$31,383 GYD before taxes and fees

  • Total number of reviews

    2.2K reviews

  • Family-friendly rentals

    280 properties are a good fit for families

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with dedicated workspaces

    250 properties have a dedicated workspace

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