
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.

Cozy Studio in Waikiki w/ King bed &Canal view
Aloha! 🌺 Welcome to your Waikiki retreat. This newly renovated studio in the Hawaii Monarch offers a comfy king bed, canal views, and a stocked kitchenette. This studio will include beach gear (snorkels,umbrellas,chairs) and little extras past guests have left behind, so it feels like home for travelers! Steps from food trucks, a 10-min walk to Sheraton Beach & Royal Hawaiian shops—perfect for adventure by day and relaxation by night. Your island home awaits, with comfort and Aloha spirit! 🌴

New Rooftop Pool~ Gorgeous Ocean View 1b1b Suite
Find your paradise in this 1-bedroom suite in the heart of Waikiki! Stunning ocean view from lanai, cozy bedroom, spacious living room and kitchen, with access to rooftop pool, sauna, hospitality suite and more This hidden gem is ONE block from Waikiki beach, with everything within walkable distance. Perfect for couple’s getaways, remote work, and family vacations Under 5-minute walk to ✔ International Market Place ✔ Marugame Udon ✔ Kona Coffee Purveyors ✔ Maguro Bros ✔ Moku Hawaii Surf Shop

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.

38th FLR- Luxury King Boutique Studio 1000 Cranes
Welcome to our luxurious Hawaiian retreat on the stunning island of Oahu. This beautifully-appointed Airbnb offers an unforgettable vacation experience in one of the most sought-after destinations in the world. Located in a prime location on the island, our Airbnb boasts breathtaking ocean views, pristine beaches, and a wealth of local attractions and activities. The property features exquisite furnishings, upscale amenities, and elegant touches that create a serene and relaxing ambiance.

North Shore Oahu Getaway at Turtle Bay Resort
880 acres of Turtle Bay Resort while staying in our luxury condo. Our beach cottage is a perfect place to relax and unwind. Located at Kuilima Estates West in the Gold Coast "quiet corner" of the property, less car traffic. It's called the Gold Coast for a reason! Enjoy stunning views of the golf course and a peek a boo view of the ocean right from the windows of your living room. Our condo has 3 on site pools, charcoal BBQ pit, tennis courts, and basketball courts in this gated community

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.

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.

"Coconut Cottage by the Sea" Steps to the beach!
Aloha & Welcome to Punaluu! Enjoy a memorable visit when you stay in this unique sandy beachfront cottage! Important! Please keep reading for information about the renovations going on at the property. Incredible view of the ocean & you will love amazing sunrises right out your window! This special condo has a great little kitchen & new king bed. Perfect for swimming, snorkeling, paddleboarding & just relaxing on the beach! BBQ area, pool, gym, security & FREE parking!

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.

♥ 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

Waikiki Gem, Stunning Ocean View, Parking Included

Large family home 5 min from beach- with pool

Lanikai Ohana Hale: Tropical Cottage w/Pool, Lanai

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

4 BDRM, Near beach, Ocean Views, HotTub, Pool, Gym
Condo rentals with a pool

Turtle bay retreat

Panoramic OceanView/STEPS FROM BEACH/FreeParking

Modern & clean condo at Turtle Bay

Luxe Loft at Turtle Bay

Rated Top 5% Airbnb: Privacy & Luxury @ Turtle Bay

Elegant, Spacious Downtown Hideaway w/Parking

Relaxing amazing Ocean and Diamond Head View

Panoramic Ocean View/ Full Kitchen/2603A
Other vacation rentals with a pool

Penthouse Upscale Oceanview King Studio Near Beach

Villa 317 King bd Penthouse Ocean View TurtleBay

Spacious Honolulu Studio Retreat w/ Parking & AC

37F-Ultra Upscale Ocean View-Modern 1BR W/Parking!

Turtle Bay Top Floor Studio unit 164 with Split AC

Sunset Hale

Elegant Luxury OceanView&Fireworks@IlikaiResort+Park

*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 | $622 CAD | $513 CAD | $587 CAD | $689 CAD | $820 CAD | $841 CAD | $689 CAD | $684 CAD | $547 CAD | $513 CAD | $513 CAD | $520 CAD |
| 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 $96 CAD 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 and kid-friendly amenities

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
80 of Kailua vacation rentals include wifi 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
- Waimea Bay Beach
- Lanikai Beach
- Kualoa Ranch
- Ala Moana Beach Park
- Banzai Pipeline
- Honolulu Zoo
- Kapiolani Park Beach
- Hanauma Bay Nature Preserve
- Bishop Museum
- Kailua Beach Park
- Waimea Valley
- Wet 'n' Wild Hawaii
- Kalama Beach Park
- Polynesian Cultural Center
- Ko Olina Golf Club
- Dole Plantation
- Pyramid Rock Beach
- Sharks Cove
- Waikiki Aquarium
- Iolani Palace
- Waimea Bay Beach
- Turtle Bay Golf
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