Holiday rentals with a pool in Hilton Head

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Popular amenities for Hilton Head rentals with a pool

House rentals with a pool

Top guest favourite
Home in Hilton Head Island
4.99 out of 5 average rating, 77 reviews

6 BR, Sleeps 26, Beach Time

DebbieRating, 5 stars4 days ago
Highly recommend this home for family’s with children. We had 8 adults and 6 children with plenty of room. The kids room with bunk beds was perfect! Covered pool area was nice in the afternoons for the kids after being at the beach in the mornings. Hosts were amazing! Julia went above and beyond to accommodate us. We needed a large pot for a crab boil and she bought one for us to use. If we had questions Josh responded in a very timely manner. We would go back and are recommending to our friends.
Guest favourite
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 favourite
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!
Guest favourite
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 favourite
Home in Hilton Head Island
4.97 out of 5 average rating, 144 reviews

Peaceful Harbour Town Treehouse with Marsh Views

BonnieRating, 5 stars1 week ago
When we walked into the octagon treehouse, we couldn’t stop squealing, “how cool is this?!” Kim’s home is one of the most fun and interesting stays we’ve ever had the pleasure of visiting. Kim and her family obviously have natural talent for hosting because the house was perfectly furnished with practical, comfortable and beautiful furniture and amenities, which made us feel at home right away. I can’t say enough nice things about our stay. It was wonderful from top to bottom thanks in large part to Kim’s recommendations and beautiful home. FYI, our young kids were obsessed with this house. We hope to be back again!
Guest favourite
Home in Hilton Head Island
4.93 out of 5 average rating, 207 reviews

Heated Pool/Fenced Yard, Golf Cart rental-51

KevinRating, 5 stars1 month ago
No complaints - place was awesome. Great location close to the beach and a great backyard set up!
Top guest favourite
Home in Hilton Head Island
5 out of 5 average rating, 62 reviews

Luxurious 4-BR Retreat w/ Pool & Steps to Beach!

JenniferRating, 5 stars3 weeks ago
We loved our family time at Sondra and Diane's place and can easily recommend it others. It was so relaxing, yet there was plenty to do. Having our own pool and easy access to a quiet, beautiful beach was incredible. The house was very family friendly with a pack and play, high chair, toys, and books all available and very welcome by my daughter and her baby. All communications were easy, clear, friendly, and accomodating. They really want their guests to be comfortable - they even asked what temperature we'd like the house to be set at upon our arrival! I've never had that before! It was a wonderful vacation, and we'd love to go back!
Top guest favourite
Home in Hilton Head Island
5 out of 5 average rating, 41 reviews

Walk2Beach~4BR~Pool~Putting Green~Yard~EV

LisaRating, 5 stars1 week ago
Clean, comfortable, nicely decorated. Pool and backyard were wonderful. Great house for our family. Hilton Head is so beautiful. We enjoyed the home.

Apartment rentals with a pool

Guest favourite
Apartment in Hilton Head Island
4.94 out of 5 average rating, 67 reviews

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

HeatherRating, 5 stars3 days ago
Beautiful place! Not far to walk to pool and beach. Very clean and updated. Will definitely stay again.
Guest favourite
Apartment in Hilton Head Island
4.93 out of 5 average rating, 55 reviews

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

WillieRating, 5 stars5 days 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.
Guest favourite
Apartment in Hilton Head Island
4.89 out of 5 average rating, 193 reviews

Easy Breezy at Hilton Head Beach & Tennis

TylerRating, 5 stars2 weeks 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 favourite
Apartment in Hilton Head Island
4.96 out of 5 average rating, 94 reviews

Beach Front Resort - Ocean View King Bed

RachelRating, 5 stars6 days ago
We had a great stay at Carolyn's place! It was clean and just as described. The pool & beach are not far, and we enjoyed the amenities of the resort. We ended up eating a couple times at the restaurant on site to avoid the long waits off property and were happy. The beach was more crowded then we are used to (we came prime time summer!) but we still had a great time. We saw some of the fireworks on a night walk on the beach (on Tuesdays) which was fun. We enjoyed the snacks & beach toys! Thank you for sharing your place with us!
Superhost
Apartment 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!!!
Guest favourite
Apartment in Hilton Head Island
4.9 out of 5 average rating, 110 reviews

Upgraded peaceful villa ! 7 min walk to the beach

PaulaRating, 5 stars3 weeks ago
This condo is amazing! Great, secure location and easy walk to beach. All the little touches made you feel right at home. We asked for an early check in and were able to arrive early. I would definitely stay here again. Thank you for a wonderful home away from home!!!
Guest favourite
Apartment in Hilton Head Island
5 out of 5 average rating, 72 reviews

THE SANDPIPER’s NEST Luxury direct Oceanfront

CherylRating, 5 stars2 months ago
This was our first time to Hilton Head Island and this place checked all the boxes! Oceanfront, beach, walking and biking paths, and very peaceful and quiet.
Guest favourite
Apartment in Hilton Head Island
4.88 out of 5 average rating, 34 reviews

Dream Paradise Oceanfront Steps to beach & pool

ShaneRating, 5 stars4 days ago
Loved my stay here. Nice, clean unit that is beautifully decorated. The location is amazing. You are just a couple minutes walk from the beach, pool and bar. Great hosts as well. Always quick to answer any questions and often provided helpful info before I had to ask. I wouldnt want to stay anywhere else when visiting Hilton Head Island.

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