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

Superhost
Home in Hilton Head Island
4.85 out of 5 average rating, 125 reviews

Palmetto Dunes Home on 1st Tee Fazio Golf Course

SamanthaRating, 5 stars1 week ago
Great place for our group to stay during a local golf tournament. Bedroom layout was great for several couples and had a nice central living area. House has everything we needed for the weekend and more. Would stay here again.
Guest favorite
Home in Cannonborough - Elliottborough
4.97 out of 5 average rating, 239 reviews

2500SF Downtown 1849 home w/ pool!

BrandiRating, 5 stars2 weeks ago
Frank was a great host for our small group of mom’s. We enjoyed the space, sipping coffee and wine on the balcony. The place was near the King Street action but far enough to not be right in the mix.
Guest favorite
Home in Hilton Head Island
4.89 out of 5 average rating, 9 reviews

Luxurious Sea Pines home with saltwater pool

ChristyRating, 5 stars2 months 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 Isle of Palms
4.98 out of 5 average rating, 54 reviews

The Palma- New Build, Spa/Pool, Two Blocks Beach

BillRating, 5 stars1 week ago
Wonderful place, walkable to the beach. Not too far from IOP main attractions.
Top guest favorite
Home in Summerville
5 out of 5 average rating, 17 reviews

Caspian: family friendly haven with private pool

SaraRating, 5 stars2 weeks ago
This was the perfect space for my best friend’s bachelorette weekend! We were able to gather friends from across the country and Canada, enjoy the beautiful weather in the privacy of our own backyard and pool, and explore Charleston! The location allowed us to save money and have more room/time to enjoy the visit with everyone, and take advantage of some more local experiences. The house was so clean and well-stocked with toiletries and linens. Joseph was also very responsive, helpful, and friendly. I would absolutely recommend this property for any group trip!
Guest favorite
Home in Kiawah Island
4.83 out of 5 average rating, 135 reviews

Kiawah Island Home w/ Pool - 4 bedroom /4 bath

HeatherRating, 5 stars5 days ago
The location was beautiful! Jayne was very responsive and accommodating so we could check in early. She also recommended a lot of local of local spots including a fantastic restaurant in John’s island! The pool was fantastic! Awesome quick stay
Superhost
Home in Johns Island
5 out of 5 average rating, 6 reviews

14 Sweetgrass Lane 2 BR with a Pool. Sleeps 4

Dr PlantadaRating, 5 stars11 months ago
The home was incredibly beautiful, comfortable, neat and clean. The beds were extremely comfortable and planty of pillows and blankets available. Master bedroom opens up to the deck and pool which was so beautiful especially in the early morning. The bathrooms were spacious, clean and updated especially the master bedroom bathroom, to die for. The kitchen had everything you could need. Love the open kitchen and dining area. The backyard was spacious, beautiful, with plenty of seating. Great for pictures as well. The pool was large and very clean amd inviting. The pool alsp has a small spa which was great. We reached out to the host several times and the responses were fast. The host addressed all our questions and requests. Pricing was very reasonable considering all other homes in that area were proced quite high. Cleaning fee was reasonable. The area is beautiful, the natural environment was amazing, even with deer passing by. Definitely returning and picking this host and home.
Guest favorite
Home in Isle of Palms
4.78 out of 5 average rating, 9 reviews

Amazing Island Home, Pool, Close to the Beach!

MichaelRating, 5 stars7 months ago
We had an amazing week with our three adult kids and their significant others! The home was beautiful! Comfy, clean, crisp ... everything we had hoped for and more! We were able to relax (plenty of comfortable space) and come together and enjoy our time together making meals, playing games, and watching movies. The location was excellent. Close to beach and town, yet quiet and private nestled in a beautiful neighborhood. Many memories were made with the family. We have already passed along our experince to interested friends and hope to have our family return again in the future.

Condo rentals with a pool

Guest favorite
Condo in North Charleston
4.89 out of 5 average rating, 62 reviews

Pond Side Retreat

CarolRating, 5 stars4 days ago
Found most things to be within 15-20 mins of location with easy access to freeways. Pleasant neighborhood.. felt very safe.
Guest favorite
Condo in Hilton Head Island
4.92 out of 5 average rating, 133 reviews

Condo 2 Qbeds/indoor pool/picklebal/3 blocks beach

MorganRating, 5 stars7 months ago
Gloria was kind and responsive via text messages. The condo was perfect for a long weekend. We also enjoyed the pickleball courts!
Guest favorite
Condo in Hilton Head Island
4.9 out of 5 average rating, 101 reviews

Luxury Condo King bed Pool &Ocean views Jetted Tub

GeorgeRating, 5 stars1 week ago
We spent four nights in Laura’s place for spring break in April and it was ideal. Great location and convenient to everything. Really enjoyed her two bikes as well. Laura communicated very well with us and we would highly recommend her place.
Guest favorite
Condo in Hilton Head Island
4.93 out of 5 average rating, 133 reviews

Beach Ocean Front -Heated Pool

RebeccaRating, 5 stars9 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, 225 reviews

Condo on Beachfront Resort

DianneRating, 5 stars1 month ago
I enjoyed my 5 day stay. It was clean and had everything I needed. The walk to beach and pool area was an easy walk not too far. I do think the mattress could use an update and be more comfortable. But overall, it was great place.
Guest favorite
Condo in Hilton Head Island
4.88 out of 5 average rating, 107 reviews

Relaxing 2Br/2ba condo on HHI, minutes from beach

MarissaRating, 5 stars2 weeks ago
We had a wonderful stay at Kacie’s. It was a great place to be for a few days…close to the beach, safe, quiet, and clean. Kacie was extremely responsive, and we appreciated the ease of check in/out, using WiFi, and viewing her recommendations! Would stay there again!
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 stars3 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
4.76 out of 5 average rating, 169 reviews

Walk to Beach - 3 Pools - Central Location!

TamsinRating, 5 stars2 weeks ago
Booked this for a quick stay while we had friends from the UK staying. This was a great location for access to a beautiful beach and the pools were ideal for the kids! The space was a great size for the amount of days we stayed and for 5 people. Steve and Jenna were very proactive with their welcome messages and also very quick to respond when we had questions.

Quick stats about vacation rentals with a pool in Kiawah Island

  • Total rentals

    300 properties

  • Nightly prices starting at

    ﺩ.ﺇ551 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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