
Vacation rentals with a pool in Kailua
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Kailua
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

32nd Floor Penthouse. 3min walk to Waikiki Beach
Welcome to HaleHinano Penthouse, Waikiki Beach. Enjoy this rarely find 1BR Penthouse on the 32nd floor with panoramic ocean views of the crisp Hawaiian waters. This condo is fully renovated with modern furnishings and decor. Just a few steps away, you’ll be at beach fronts of Waikiki beach. You’ll be surrounded with local favorite fine dining, shopping plazas. -In unit washer and dryer. -Top roof Pool, Jacuzzi, BBQ -3 min walk to the Waikiki beach. -$35/day parking attached to the building.

SEArider TWO at Turtle Bay (1 bedroom / 1 bath)
Our number one priority at SEArider is to provide our guests with a luxury Hawaiian experience. This unit has been completely renovated with our main focus being quality and comfort. Nestled in the condominiums that surround Turtle Bay, TWO has a luxurious but minimal feel with a mauka (mountain) inspired theme. Key features include locally made and dyed linens and waffle print towels. TWO sits directly below our other property, SEArider ONE (please search us on Air BnB for photos and reviews.)

Waikiki Gem, Stunning Ocean View, Parking Included
Wake up to breathtaking ocean views from our newly renovated 1BR, 1BA condo. Relax on the lanai, let in the gentle breezes, and soak in the picturesque surroundings. With enough space for up to 4 guests, this retreat is perfect for couples, small families, or close friends seeking solace and tranquility. Immerse yourself in the calming ambiance of modern furnishings and a soothing color palette. Convenient parking included. Discover a blissful sanctuary where serenity and relaxation harmonize.

Absolutely Oceanfront-60'Waterfall Pool-Legal
Kailua Absolutely Oceanfront Deluxe Vacation Rental The closest house to the Ocean in Kailua Hear waves breaking just outside Located in a quiet uncongested upscale neighborhood 60ft salt-sanitized waterfall lap pool Attached Ocean-View Deck 16-foot vaulted ceilings Wall-mounted Fujitsu air conditioning Tide pooling steps away Dramatic Sunrises Refreshing Tradewinds No Bedbugs here/Bed Bug Protective Queen Mattress and pillow covers Ozone sanitized between rentals NUC: Certificate 90-BB-0060

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.

Luxe Loft at Turtle Bay
Our Luxe Loft is located at Turtle Bay Kuilima Estates East on the North Shore of Oahu. Nestled in between the world famous Palmer Golf course, you will enjoy resort amenities with the comfort of condo living. The North Shore of Oahu is referred to as the 7 mile miracle, for its beautiful white sand beaches, world class waves and crystal blue waters. From Hale'iwa Beach Park to Sunset Beach, you will find the most beautiful shore line found anywhere on earth. It is truly a magical place.

The Turtle Bay Signature
Come enjoy this newly updated, designer inspired, spacious end-unit condo in beautiful Turtle Bay. It is as comfortable as it is beautiful. Whether it's breakfast in bed or a drink on the lanai swing, you may not want to leave this tropical paradise. Everything has been updated, including hand-picked pendants that can be dimmed to suit your mood. There is a nearby pool, beach and tropical walking trails. Restaurants and shops can be found at the newly renovated Turtle Bay hotel.

Free Parking/Ocean View/Steps to Beach & Mall 33F
Fully newly remodeled in April this year! Everything is brand NEW! Amazing sweeping ocean view! Located on 33rd floor of Waikiki city, just a few minutes’ walk to the famous Waikiki Kahanamoku Beach & Lagoon, Ala Moana Beach Park, Ala Moana Shopping Mall, many restaurants , Cafes and Bars - everything is within walking distance. FREE PARKING is a Big Plus with a designated parking spot in the garage. You’ll have a great time in this brand new home with a queen bed and a sofa to stay!

Floor-to-Ceiling Oceanfront Home (Car Available)
* Aloha! Welcome to the happiest place in the world. * Featuring a direct ocean view from an entire wall of windows, where you can see the ocean, beach, lagoon, surfers, whales, sunsets, and more. This beachfront home is 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 so happy. I hope our place can bring you some happiness too. :-)

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! Hotel pool is also available for our guests. Also accepting long term stays at special rates.

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.

*Serendipity on the Moana! - Legal & Beachfront!*
Gorgeous, Fully Furnished, Beachfront, legal one-bedroom condo with over 740 square feet in Maili on Oahu. Maili Cove is a hidden gem and has easy access to golf courses, amusement parks, restaurants, shopping centers, financial and medical facilities and other services located on the west side of the island. Just 15 minutes down the road is the Disney Resort & Ko Olina. Owner a licensed real estate agent. State #1990/NUC-2309. TMK870280170031.
Popular amenities for Kailua rentals with a pool
House rentals with a pool

3 BR, Near Beach, Free Prkng, 1 LVL, Pool/Spa, Gym

Large family home 5 min from beach- with pool

Lanikai Ohana Hale: Tropical Cottage w/Pool, Lanai

Golf Course Front Condo in Kahuku

Makaha Hale - Serene 3 BR Home

Family Ocean Oasis, Hot Tub, 5 min drive to beach

Slice of Paradise-3BR- Sleeps10-Max 8 Adults

Sunny Heaven 1 Bd Plus Loft
Condo rentals with a pool

Amazing Ocean & Beach Views - Only Steps to Beach!

Beach Front Waikīkī Condo- Free Parking

39F-High-FL Studio w/ Diamond Head & Ocean Views!

STUNNING PENTHOUSE - 100FT TO BEACH - LEGAL!!

43F-Island Colony Studio-Ocean & City Skyline View

North Shore Getaway - Newly renovated!

Waikiki Banyan Relaxing Ocean View Free Parking

Breathtaking Ocean view, free 1 parking
Other vacation rentals with a pool

Top FL-Luxury Ocean View King Suite-Waikiki Beach~

Beautiful OceanView&Sunset @IlikaiResort w/Parking

Penthouse Upscale Oceanview King Studio Near Beach

20F-High Floor Ocean View-Ilikai-1BR-Waikiki Beach

Spacious Honolulu Studio Retreat w/ Parking & AC

Kuilima Estates West at Turtle Bay with King Bed

Sunset Hale

*Scenic Views* Upscale and 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 | G$95,184 GYD | G$78,449 GYD | G$89,745 GYD | G$105,435 GYD | G$125,518 GYD | G$128,656 GYD | G$105,435 GYD | G$104,598 GYD | G$83,678 GYD | G$78,449 GYD | G$78,449 GYD | G$79,495 GYD |
| 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 |
Quick stats about vacation rentals with a pool in Kailua

Total vacation rentals
Explore 90 vacation rentals in Kailua

Nightly prices starting at
Kailua vacation rentals start at G$14,644 GYD per night before taxes and fees

Verified guest reviews
Over 1,540 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!
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- Waikiki Beach
- Kailua Beach
- Kualoa Ranch
- Waimea Bay Beach
- Lanikai Beach
- Ala Moana Beach Park
- Banzai Pipeline
- Honolulu Zoo
- Kepuhi Beach
- Kapiolani Park Beach
- Hanauma Bay Nature Preserve
- Waimea Valley
- Kailua Beach Park
- Bishop Museum
- Wet 'n' Wild Hawaii
- Kalama Beach Park
- Pyramid Rock Beach
- Ko Olina Golf Club
- Dole Plantation
- Iolani Palace
- Sharks Cove
- Waikiki Aquarium
- Polynesian Cultural Center
- Waimea Bay Beach
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