
Vacation rentals with a pool in Kailua
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Kailua

Total vacation rentals
Explore 80 vacation rentals in Kailua

Nightly prices starting at
Kailua vacation rentals start at €60 per night before taxes and fees

Verified guest reviews
Over 1,430 verified reviews to help you choose

Family-friendly vacation rentals
70 properties offer extra space & kid-friendly amenities

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
80 of Kailua vacation rentals include wi-fi access

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

4.8 Average rating
Kailua stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated rentals with a pool in Kailua
Guests agree: these homes with a pool 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!

HawaiianaLuxe_Townhouse at Turtle Bay_Hale LuLu
Come to escape to this newly renovated 1,150SF 2 bedrooms/2.5 bathroom townhouse for a soul comforting Northshore stay! Away from hustling downtown, Hale Lulu sits peacefully a few minutes away from iconic Turtle Bay Hotel and the most beautiful secluded beaches and trails! This unit is the biggest model in Kulima West. We offer 2 king size beds and 1 queen bed in three different bedrooms for your restful stay. The best cleaning crew was hired for your luxurious staying experience in Hawaii.

Oceanvw, walk 2 beach, $0 cleaning & park, kitchen
Whether you are planning a perfect romantic getaway or a much deserved quality family time vacay for FOUR, this high floor apartment w/ocean views checks all the boxes. The 1 bedroom with the KING BED is ideal for the parents, while the kids share the QUEEN SLEEPER SOFA in the living room. The kitchen is fully stocked w/everything you will need to prepare meals, drinks and snacks. It's a 4 minute walk to the beach. There is 1 FREE PARKING spot and there's NO RESORT FEES. Close to shops & food.

9K Hawaiian Princess - Alii Hale Aina
Beautiful remodeled Hawaiian Princess unit on one of the best beaches on Oahu. The view is nothing less than spectacular. The condo has been remodeled with the best of everything. You will not find a better place on the island if you are looking for a beach vacation away from the crowds of Waikiki. This unit has an NUC and is permitted rental Feel free to message me (scroll to the bottom) if you cannot find availability on the calendar. I have other listings on island that may be available

Makaha Hale - Serene 3 BR Home
Escape to the beautiful Makaha Valley in Hawaii and experience a truly unforgettable stay at our 3-bed 2.5-bath house. This enchanting Airbnb, nestled within a secure gated community offers a getaway for those seeking tranquility amidst the breathtaking beauty of the island. Enjoy breathtaking views of the Makaha Valley mountainside, modern amenities, and a serene ambiance. Indulge in nearby pristine beaches and immerse yourself in the beauty of the island. Your dream Hawaiian getaway awaits!

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.

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!

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.

Best Kept Secret on Oahu! and WE ARE LICENSED!!!
Hawaii’s Best Kept Secret: The cottage is next to sandy coves, driftwood, shells, and forested pastures filled with polo ponies. The ocean is excellent for snorkeling and fishing; there are two surf breaks within one mile, windsurfers get wind most afternoons, and the mountains behind us offer good hiking trails. The Colony has a nice pool and a large grass chipping green, and a tennis court. We have TV and WiFi. LICENSE NO. 90/TVU-0108. GE-142-964-5312-01. TMK:1-6-8-009-001-0021.

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.

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.

♥ North Shore Paradise at Turtle Bay ♥
For the discerning traveler, a designer curated space with every luxury detail thought of. When you step inside, you can feel the love poured into this space, and the exquisite detailed craftsmanship throughout. Nestled on the 3rd green of the famous Georgia Fazio course at Turtle Bay Kuilima Estates West on the North Shore of Oahu. A perfect spot to vacation, honeymoon, or spend some quality relaxation time. This magical space welcomes you with aloha.
Popular amenities for Kailua rentals with a pool
House rentals with a pool

Private SPA, Sleep 12, Beach 5 min

Large family home 5 min from beach- with pool

Slice of Paradise-3BR- Sleeps10-Same$ for 10 as 2

Oahu Ocean View • Sleeps 14, Pool, Hot Tub, Beach!

Waikiki Gem, Stunning Ocean View, Parking Included

Lanikai Ohana Hale: Tropical Cottage w/Pool, Lanai

Lani Kai Ocean View Villa Sleeps 12 Pool + Hot Tub

Le'ale'a by AvantStay | Ocean + Mountain Views!
Condo rentals with a pool

NEWLY RENOVATED (2021) Turtle Bay Haven!

Turtle Bay Condo Lilinoe

Modern & Contemporary North Shore Oahu Condo

2Turtle Bay Condo. Cozy retreat for two.

Turtle Bay Condo, 2 Bedroom, sleeps 6

#3103 2BR/2BA|Beachfront, Free Parking, Gym & Pool

Modern 1 Bedroom Condo in Downtown Honolulu

RusticLuxe — Go Fully Custom at Turtle Bay
Other vacation rentals with a pool

High FL-Upscale Ocean View w/ Easy Beach Access~

Island Jewel, North Shore Bliss

Sunset Hale

North Shore Hideaway

Ilikai Penthouse-Luxury Oceanview 2BR/2BTH/Parking

Aloha Surf Condo - Turtle Bay - AC + 2 E-Bikes

(Golden Week) Nr beach! Imperial Resort

Wake Up to Ocean Views! 2queen Apt w/ Free Parking
When is the best time to visit Kailua?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €430 | €322 | €301 | €315 | €315 | €322 | €433 | €430 | €344 | €322 | €322 | €327 |
| Avg. temp | 22°C | 22°C | 23°C | 24°C | 24°C | 26°C | 26°C | 27°C | 26°C | 26°C | 24°C | 23°C |
Destinations to explore
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- Waikiki Beach
- Lanikai Beach
- Kailua Beach
- Kualoa Ranch
- Waimea Bay Beach
- Ala Moana Beach Park
- Kapiolani Park Beach
- Honolulu Zoo
- Banzai Pipeline
- Kailua Beach Park
- Polynesian Cultural Center
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- Wet 'n' Wild Hawaii
- Kepuhi Beach
- Ko Olina Golf Club
- Kalama Beach Park
- Bishop Museum
- Hanauma Bay Nature Preserve
- Sharks Cove
- Hawaii Convention Center
- Ala Moana Center
- Dole Plantation
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- Turtle Bay Golf
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