
Home rentals with a pool near Kailua Beach
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Top-rated rentals with a pool near Kailua Beach
Guests agree: these stays are highly rated for location, cleanliness, and more.

"Endless Summer" Beachfront Condo w/ Full Kitchen!
Welcome to the beach! Your little piece of paradise! 1 bed w/ king bed & queen bed in the living room too! Directly on a beautiful white sandy beach that is great for swimming, snorkeling, fishing & kayaking! Sea turtles & tropical fish are right out front! Fully equipped kitchen, washer/dryer in the condo & private lanai looking out at a spectacular beach with amazing ocean views! Enjoy incredible sunrises too! Pool, gym, BBQ area & WIFI. Close to may attractions like PCC, Kualoa Ranch & More!
4.77 out of 5 average rating, 168 reviews
Best Kept Secret on Oahu! and WE ARE LICENSED!!!
Hawaii’s Best Kept Secret! The cottage is next to sandy coves, driftwood, shells, and Polo ponies in forested pastures. The ocean is excellent for snorkeling and fishing; there are 2 surf spots, & world-class windsurfing within 2 mile. Mountains behind us offer good hiking trails. The Colony has a nice pool, and a Pickle Ball court. We have TV and WiFi. LICENSE NO. 90/TVU-0108. GE-142-964-5312-01. TMK:1-6-8-009-001-0021. Note: We have NO Air Conditioner, 3 ceiling fans, 2 desk fans & ocean
4.88 out of 5 average rating, 164 reviews
Dreamy Beachfront Home (Car & Parking Available)
* Aloha! Welcome to our happy place - our beachfront home! * Featuring a direct ocean view from an entire wall of windows, where you can see the ocean, beach, lagoon, surfers, whales, sunsets, and more. The location is right on Waikiki Beach. You are within minutes of walking distance to almost everything - beaches, restaurants, bars, surfing lessons, boat tours, grocery stores, shopping malls and more. Every time I come to Hawaii, I am happy. I hope our place can bring you happiness too. :-)
4.9 out of 5 average rating, 107 reviews
Luxury Waikiki Condo w/ Retro Charm & FREE Parking
Welcome to this renovated 20th-floor condo in the iconic Marine Surf, a former 1960s Waikiki hotel. Enjoy vintage charm with modern luxury, including a partial ocean view, FREE underground parking, ultra-fast 1-gigabit internet, AC and a 65" smart TV with Apple TV. Relax in the pool or explore nearby world-class shopping, dining & beaches. With a queen bed and sofa bed, it’s perfect for couples or families. Reserve your slice of paradise today and discover the essence of Waikiki’s island luxury.
4.98 out of 5 average rating, 116 reviews
Beach 6 Min|BBQ|Community Pool+Gym|Peaceful+Gated
Discover your dream vacation, just 2 miles from the world-famous Makaha Beach. This pristine rental is perfect for those seeking an authentic Hawaiian experience! ~Stunning Views: From every room including the backyard! ~Culinary Delights: Create island feasts in our fully equipped kitchen. ~Cozy Comfort: Rest easy in plush bedrooms designed for ultimate relaxation. ~Adventure Awaits: Surfing, fishing, & more are within easy reach. Don't miss out on making memories that will last a lifetime!
4.99 out of 5 average rating, 133 reviews
Beachfront Getaway - Hawaiian Princess Condo
Mesmerizing sunset views from this sandy beach front condo. Nothing separates you from sparkling turquoise waters but footprints in the sand. Balcony is ideal height for turtle watching. From Nov- April you may spot a whale. This vibrant land is full of surprises. Even dolphins spin by now and then. Escape the crowds of Waikiki to experience a real Hawaiian lifestyle. Snorkel, boogie board or surf right out your door. Awakening to the rhythm of the ocean can change your life forever.
4.97 out of 5 average rating, 343 reviews
Turtle Bay Corner Condo With A Fairway View!
Resort-style amenities at your doorstep, including snorkeling beach access, pool, tennis courts, & 2 world-class golf courses. East Side of Kuilima Estates, on the Fazio 17th with cool breezes, washer & dryer, and Split A/C in bedroom & living room for comfort. The unit is locally owned and operated by longtime North Shore residents. After you have experienced all of the attractions O’ahu has to offer, check out our place on Molokai. Relax and enjoy a true authentic Hawaiian experience!
4.88 out of 5 average rating, 273 reviews
Legal STR: Aloha at Turtle Bay w/ Loft
TMK #570010270107 STR license # 51 Quiet upstairs unit with loft. Cooling trade breezes drift from the lanai through to the master bedroom. Walk to golf, restaurants and the beaches at the Ritz Carlton Oahu at Turtle Bay. 2 swimming pools, tennis and pickleball on site. Has beach toys and gear, tennis and pickleball rackets. WiFi, cable and Smart TV’s. Drive to North Shore beaches and local shopping. Gated, 24 hour security. One parking spot included. 2nd parking spot with permit.
4.89 out of 5 average rating, 261 reviews
Cottage Nene - Luxury Home by Beaches & Mountains
Modern luxury meets valley tranquility. Built in 2022, this spacious 3-bed, 2.5-bath cottage hosts up to 8. Enjoy an airy living room with 14ft ceilings, premium furniture, and smart TVs. Step outside to a fully landscaped tropical yard with the best mountain views in the community, perfect for morning coffee or evening stargazing. Enjoy community pool, jacuzzi, and gym, all while being minutes away from world-class west-side beaches and hiking trails. Guaranteed cancellation in 48 hrs.
4.98 out of 5 average rating, 121 reviews
Beautiful OceanView&Sunset @IlikaiResort w/Parking
🌴 BRAND NEW LISTING. NO RESORT FEES. FREE PARKING! 🌴 ✨ This ocean front condo is located at the iconic Ilikai Hotel & Luxury Suites. Your perfect getaway on the 9th floor offering beautiful ocean, sunset, & harbor views everyday! 💎 Immerse yourself in the beauty of Hawaii with just steps away from the pristine beach & lagoon. 🏝️ This inviting studio condo provides an exceptional experience surrounded by a vibrant neighborhood filled with shops, eateries, & fun filled activities!
4.94 out of 5 average rating, 100 reviews
Amazing Waikiki Beach Views!!
Perfect vacation getaway, with amazing views of Waikiki Beach and Lagoon!! Best location, walking distance to many points of interest, Ala Moana Mall/Designer stores and many restaurants! Enjoy visiting Oahu - there's sightseeing, swimming, hiking, surfing or shopping etc! Enjoy watching the fireworks every Friday nights from the patio, sponsored by Hilton Hawaiian Village! There’s 2 Ilikai pool iavailable for our guests. Also accepting long term stays at special rates.
4.88 out of 5 average rating, 233 reviews
Modern 1 Bedroom Condo in Downtown Honolulu
Aloha and welcome! Newly remodeled, clean and cozy 1 bedroom, 1 bathroom condo is in the heart of downtown Honolulu. Enjoy the views of the harbor and the city. We are a quick 10 min drive to beautiful Waikiki. Come explore all Oahu has to offer - surfing, swimming, snorkeling, relaxing on the beach, hiking, shopping, fine dining and more! Then unwind and relax in the comfort of the condo. We welcome you and hope you enjoy paradise at an affordable price.
4.98 out of 5 average rating, 283 reviewsPopular amenities for rentals with a pool near Kailua Beach
House rentals with a pool

Makaha Hale - Serene 3 BR Home
4.97 out of 5 average rating, 114 reviews
Condo near Turtle Bay w/pool, beach & BBQ
4.93 out of 5 average rating, 116 reviews
Private SPA, Sleep 12, Beach 5 min
4.94 out of 5 average rating, 155 reviews
Waikiki Gem, Stunning Ocean View, Parking Included
4.97 out of 5 average rating, 148 reviews
Large family home 5 min from beach- with pool
4.95 out of 5 average rating, 153 reviews
Slice of Paradise-3BR- Sleeps10-Same$ for 10 as 2
4.9 out of 5 average rating, 156 reviews
Oahu Ocean View • Sleeps 14, Pool, Hot Tub, Beach!
4.95 out of 5 average rating, 148 reviews
Lanikai Ohana Hale: Tropical Cottage w/Pool, Lanai
4.71 out of 5 average rating, 94 reviewsCondo rentals with a pool

SEArider ONE at Turtle Bay
4.89 out of 5 average rating, 385 reviews
2Bed/2Bath Waikiki Corner Penthouse & Ocean Views
4.89 out of 5 average rating, 215 reviews
North Shore Turtle Bay Renovated 2Bd/2Ba + Loft
4.93 out of 5 average rating, 157 reviews
Premier Diamond Head & Ocean Views 1BR Suite
4.98 out of 5 average rating, 177 reviews
Modern & Contemporary North Shore Oahu Condo
4.99 out of 5 average rating, 348 reviews
NEWLY RENOVATED (2021) Turtle Bay Haven!
4.91 out of 5 average rating, 357 reviews
2BR+Den Downtown w/ Ocean Views + Free Parking
4.81 out of 5 average rating, 136 reviews
Free Parking/Ocean View/Steps to Beach & Mall 33F
4.85 out of 5 average rating, 277 reviewsOther vacation rentals with a pool

High FL-Upscale Ocean View w/ Easy Beach Access~
4.96 out of 5 average rating, 182 reviews
32F-Penthouse Pacific Monarch Studio-Ocean View
4.96 out of 5 average rating, 131 reviews
Beautiful and Spacious.
4.81 out of 5 average rating, 263 reviews
Oceanvw, walk 2 beach, $0 cleaning & park, kitchen
4.95 out of 5 average rating, 121 reviews
Island Jewel, North Shore Bliss
5.0 out of 5 average rating, 92 reviews
8P - Hale Ohana Ali
4.82 out of 5 average rating, 51 reviews
North Shore Hideaway
5.0 out of 5 average rating, 30 reviews
Wake Up to Ocean Views! 2queen Apt w/ Free Parking
4.97 out of 5 average rating, 36 reviewsQuick stats about rentals with a pool near Kailua Beach

Total vacation rentals
Explore 30 vacation rentals in Kailua Beach

Nightly prices starting at
Kailua Beach vacation rentals start at $294 CAD per night before taxes and fees

Verified guest reviews
Over 420 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space and kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
30 of Kailua Beach vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Kailua Beach rentals

4.9 Average rating
Kailua Beach stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
- Waikiki Beach
- Lanikai Beach
- Kualoa Ranch
- Waimea Bay Beach
- Ala Moana Beach Park
- Kapiolani Park Beach
- Honolulu Zoo
- Banzai Pipeline
- Kailua Beach Park
- Polynesian Cultural Center
- Kalama Beach Park
- Kepuhi Beach
- Ko Olina Golf Club
- Wet 'n' Wild Hawaii
- Waimea Valley
- Bishop Museum
- Hanauma Bay Nature Preserve
- Sharks Cove
- Hawaii Convention Center
- Ala Moana Center
- Dole Plantation
- Waimea Bay Beach
- Turtle Bay Golf
- Iolani Palace





