
Holiday rentals with a pool in Hawaiian Islands
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Top-rated rentals with a pool in Hawaiian Islands
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Popular amenities for Hawaiian Islands rentals with a pool
House rentals with a pool

Waikiki Gem, Stunning Ocean View, Parking Included
I had a great stay at this beautiful apartment! The space was clean, well-maintained, and exactly as described. Check-in was super easy with clear instructions provided ahead of time. Charlie was communicative and helpful throughout the stay. I would definitely recommend this place and would happily stay here again! Mahalo nui!

Kai Malolo - Amazing Eco-friendly Oceanfront Home!
The view alone is worth the price! Everything was so lush and beautiful! We felt like we were in our very own private resort. We enjoyed the spacious house itself and the outdoor area. The pool was great and the beds were super comfortable! This was a great base to explore the entire Big Island of Hawaii! I would recommend this home to anyone! Just book it already!

Private Pool - 180° Ocean View - Minutes to Beach
We had a wonderful 7 day stay. Our 3 boys (16, 13, and 10) spent hours on the diving board and in the pool. Sandra’s place had everything we needed for beach trips, including beach chairs, wagon, umbrella, cooler and beach towels. I was so happy to have a washing machine to wash out the sandy towels and suits after our beach trips. It was a 5-10 minute trip for Costco,-target and Walmart and a 30-40 minute trip to Hāpuna Beach (don’t miss the Malsada stand on the highway on your way). We would come back to the house to cook supper, swim more in the pool, and watch the sunset from the beautiful yard. We also got a lot of use out of the basketball net in the driveway, and volleyball net in the side yard. Sandra was extremely helpful with all aspects of our stay, including local recommendations. Would definitely stay again if on the Big Island!

Poipu Custom Home, Central AC & Pool/Gym
Absolutely beautiful! A wonderful place to stay with all the amenities you could ask for - everything down to finite details made this place a peaceful place to stay. We will be back.

Kalo Homes - Makaha's Hidden Gem
In one word, AMAZING!!! Everything was exceptional, the only negative thing I can say is that now I have to buy a new bed at home because the bed at this place was incredible. The home was exactly as advertised, the views of the ocean were sensational. There were even extras for the beach such as coolers, snorkels, umbrellas, boogie boards and much more. Friendly and responsive hosts were there for us, even before we needed them. As long as you know where you are staying and are prepared for the drive, this place is a premium slice of heaven in heaven. Thank you for being part of our adventure.

Milolii Whale House With Ocean Views and Pool!
Beautiful and peaceful location. Watch gorgeous sunsets with panaromic voews pf the ocean right from the deck! Great snorkeling close by if you're comfortable getting in from rocks. Private pool to enjoy when you've had enough salt water for the day.

Kula Jewel - Pool, Hot Tub & Awesome Views!
Pamela was a fantastic host. She was responsive and so friendly. She truly loved the area and making guests feel at home. The space itself was such a dream. It had everything we needed and then some. The location and views were stunning. we sat on the porch almost every night just to take it all in. We loved staying at the Kula Jewel and would stay here again!

Ocean, Sunset, Mountain & Celestial Views
Tarek was awesome. Super responsive and very kind. 10/10 recommend his place to stay at when visiting Big Island. House was packed with much needed living amenities (paper towels, board games, laundry facilities). Loved the living conditions I got the chance to stay in!
Apartment rentals with a pool

~The Surfshack~ with breathtaking ocean views!!
Absolutely wonderful place to stay, exceptionally clean, beautiful and comfortable unit packed with Aloha! All of the descriptions and photos are accurate, and the place looks even better in person. A perfect home base for exploring the garden island! We will return for sure.

38th FLR- Luxe King Boutique Studio 1000 Cranes
Great view and very clean. Loved the modern amenities and the host was very responsive! Would love to stay and book again!

Million $ View on Gorgeous Secluded Beach!
Amazing view of the ocean. Nice beach and beach gear for kids.

Spectacular ocean-view at luxurious resort
The Cliffs is a great place to stay on the north end of the island. Bryant and Jane’s unit has a gorgeous unobstructed view of the ocean and sunset. The lanai was the best one there! There were plenty of beach chairs, mats etc to take on local excursions. The bed was comfortable. We liked that each night and/or morning there was a food truck available for guests. We have no reservations recommending their place.

32nd Floor Penthouse. 3min walk to Waikiki Beach
we thought this place was great. was close to everything g and just a few blocks from the beach.

SEArider TWO at Turtle Bay (1 bedroom / 1 bath)
We had a great stay! The home was clean, comfortable, and had all the essentials we needed — fridge, microwave, washer/dryer, and a small AC unit that kept things cool. The host was very responsive and accommodating throughout our stay, which we really appreciated. Overall, a great experience and we’d definitely stay again!

Luxury Mahana 1bd/2ba-Great Views-Free Park/WiFi
Dianne’s oceanfront condo in Kaanapali is an absolute gem—hands down one of the most stunning vacation rentals we've experienced. The panoramic ocean views from both the living room and bedroom are nothing short of breathtaking, offering an immersive front-row seat to the Pacific. The space itself is immaculate and thoughtfully designed, blending elegant décor with ultimate comfort. It’s fully stocked with everything you could possibly need, and the bed was exceptionally comfortable. Falling asleep each night to the soothing sound of waves crashing just outside was pure serenity. The location is unbeatable—just a short walk to the local food truck yard, grocery store, and an array of fantastic restaurants. On top of all that, Dianne is a phenomenal host: responsive, accommodating, and truly committed to making your stay perfect. If you’re looking for the ultimate Kaanapali escape, this is it!!

Ocean View Studio | 2 Minute Walk to Waikiki Beach
We stayed at the Pacific Monarch from May 20–28 and had a great experience. The unit was clean, spacious, and well-stocked with everything we needed for the beach—including umbrellas, backpack chairs, and boogie boards, which were incredibly convenient. While the listing mentioned an ocean view, it's worth noting that it’s more of a partial side ocean view—but still lovely to wake up to. Check-in was seamless, and we appreciated the ease of having on-site parking, which cost $35/day. One of our favorite features was the rooftop area. It offers fantastic panoramic views, a nice pool, a small jacuzzi, and even a sauna and lounge area—great spots to relax after a day out. The location is unbeatable. We were walking distance from lots of amazing food spots, and everything we needed was close by. A special shout-out to IYASUME Musubi, located right next to the hotel—it became our go-to breakfast grab on the way to the beach. Overall, a very enjoyable stay and we’d definitely consider re
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