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

Total holiday rentals
Explore 80 holiday rentals in Kailua

Nightly prices starting at
Kailua holiday rentals start at $121 NZD per night before taxes and fees

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

Family-friendly holiday rentals
70 properties offer extra space and kid-friendly amenities

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
80 of Kailua holiday 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.

Honu Hideout at Turtle Bay
Come escape to Honu Hideout on the exclusive North Shore of Oahu, and enjoy this newly renovated ground floor unit situated just a short walk away from the iconic Turtle Bay Resort and the most breathtaking and secluded beaches on Oahu. Far away from the hustle and bustle of Honolulu, this unit offers the peacefulness of the country and the proximity to infamous attractions for the vacation of your dreams. Relax and restore or adventure and explore, you choose, all within minutes of your door.

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.

N Shore Turtle Bay Kuilima Condo Getaway! Reviews!
Ritz Carlton without the price, this vacation condo is just that! Enjoy resort convenience w/o the resort price! Quiet and tucked against the golf course, we have a beautiful pool & tennis court on site. Just a few minutes walk to Turtle Bay Ritz , which has great beaches to snorkel and swim, restaurants,bars, 2 golf courses, the Arnold Palmer &George Fazio, biking/walking trials. Sunset beach, Waimea Bay, Haleiwa, Banzai Pipeline, Polynesian Culture Center, world famous food trucks all near

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!

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 w/cool breezes, new washer & dryer, and 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 there and enjoy a true authentic Hawaiian experience!

Turtle Bay Condo Lilinoe
Ground floor end unit, located on the 18th hole of the world re-nowned Turtle Bay resort! King sized bed in bedroom, 1 queen Murphy bed and 1 queen sofa bed in living room. AC in both bedroom and living room. Screened-in lanai. Tennis courts, pool and bbq grills. Beach is 5 minutes walking distance. Short drive away from prime spots (sunset beach, pipeline, shark’s cove, Waimea) shopping, and food. Our condo is a legal short-term rental. Ask me about my other properties for larger parties.

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.

NEWLY RENOVATED (2021) Turtle Bay Haven!
NEWLY RENOVATED condo (2021) at Turtle Bay on Oahu's world famous North Shore. Enjoy more than 5 miles of secluded beaches, 2 private swimming pools, 2 private tennis & pickle ball courts, 2 PGA golf courses, horseback riding & fine dining all less than a 5 minute walk from your front door! The condo was completely remodeled in 2021 (Kitchen, Bathrooms, Flooring, decor as well as AC throughout). This 1Bed, 2Bath unit is one of the few Legal and licensed vacation rentals on the North Shore!

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.

3BR, Near Beach, Game RM, Private Spa, Pool, Gym
Escape to paradise in this beautiful vacation home located in Makaha Valley. Enjoy stunning panoramic ocean views and relax in the tropical backyard. Inside, you'll find a fully equipped kitchen, comfortable furnishings, and ample space for your group. Take a short drive to the beach and spend your days swimming, surfing, or lounging on the sand. Come back and enjoy a BBQ on the outdoor grill. Perfect for families or groups of friends, this vacation home is the ultimate Hawaii getaway!

SEArider ONE at Turtle Bay
~ You just found your Base Camp to explore the North Shore of Oahu ~ Our condo has just been completely remodeled and redecorated with two brand new bathrooms. We are situated alongside the Palmer Golf Course and are a short 5-10 minute walk to the ocean. Enjoy the resort amenities of Turtle Bay coupled with the comfort of condo living. Health and comfort are top priority. We pride ourselves on a clean home and have implemented additional measures for sanitization.
Popular amenities for Kailua rentals with a pool
House rentals with a pool

Ocean View Home for Family Fun Getaway Near Beach

Waikiki Gem, Stunning Ocean View, Parking Included

Le'ale'a by AvantStay | Ocean + Mountain Views!

Large family home 5 min from beach- with pool

Lanikai Ohana Hale: Tropical Cottage w/Pool, Lanai

Ocean View Exquisite Home at Cottages at Mauna Olu

Villa Aloha · 4 Bedrooms, Pool, Hot Tub Sleeps 12

Slice of Paradise-3BR- Sleeps10-Same$ for 10 as 2
Condo rentals with a pool

The Seascape at Turtle Bay

RusticLuxe — Go Fully Custom at Turtle Bay

2Turtle Bay Condo. Cozy retreat for two.

Magical Skies Hale at Turtle Bay

Secluded White Sandy beach just 30 steps away

North Shore Getaway - Newly renovated!

Ranked Top 1% Airbnb-Privacy & Luxury @ Turtle Bay

"Endless Summer" Beachfront Condo w/ Full Kitchen!
Other holiday rentals with a pool

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

Oceanvw, walk 2 beach, $0 cleaning & park, kitchen

Turtle Bay Designer Renovated Walk to Beach • Pool

Turtle Bay Bungalow- Parking, AC & Walk to Beach

[Rare] Diamond Head & Ocean Views 1BR Suite

Aloha Surf Condo - Private Deck - Pool - E-Bikes

Sunset Hale

North Shore Hideaway
When is the best time to visit Kailua?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $867 NZD | $650 NZD | $607 NZD | $874 NZD | $1,040 NZD | $1,066 NZD | $874 NZD | $867 NZD | $693 NZD | $650 NZD | $650 NZD | $659 NZD |
| 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 |
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- Waikiki Beach
- Kailua 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
- Bishop Museum
- Wet 'n' Wild Hawaii
- Hanauma Bay Nature Preserve
- Kepuhi Beach
- Waimea Valley
- Ko Olina Golf Club
- Kalama Beach Park
- Sharks Cove
- Hawaii Convention Center
- Ala Moana Center
- Dole Plantation
- Waimea Bay Beach
- Turtle Bay Golf
- Things to do Kailua
- Things to do Honolulu County
- Food and drink Honolulu County
- Sports activities Honolulu County
- Entertainment Honolulu County
- Sightseeing Honolulu County
- Art and culture Honolulu County
- Nature and outdoors Honolulu County
- Things to do Hawaii
- Nature and outdoors Hawaii
- Tours Hawaii
- Sightseeing Hawaii
- Sports activities Hawaii
- Wellness Hawaii
- Food and drink Hawaii
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- Things to do United States
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