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

*Remodeled Oceanfront in Waikiki - Ilikai Marina
Welcome to our oceanfront home offering stunning ocean views and Hawaiian sunsets, all within walking distance to the beach. Whether you're seeking adventure, family fun, or relaxation, this is the perfect destination while visiting Oahu. On Friday nights, enjoy spectacular fireworks right from your balcony. We look forward to sharing recommendations for local restaurants, beaches, and activities to make your time in Hawaii unforgettable. Book now and start planning your island getaway with us!

Classic Unit at the Waikiki Banyan
Welcome to your perfect Hawaiian getaway! This beautiful unit at Waikiki Banyan offers the ideal blend of comfort, convenience, and island charm just a short stroll from world-famous Waikiki Beach. Step into a bright and breezy space designed for relaxation after a day in the sun. You’ll enjoy a thoughtfully arranged layout, cozy furnishings, and everything you need to feel right at home. Note: The pool and recreation deck are currently under construction and will remain closed until summer 2026

Rare Waikiki Gem | FREE Parking + Walk to BEACH
Stay in a spacious 2-bedroom, 1 bath retreat just minutes from Waikiki Beach—one of the most sought-after locations in Hawaii. Enjoy the RARE convenience of FREE PARKING, a huge value in Waikiki. Perfectly located near Hilton HawaiianVillage, Ala Moana Center & top dining—yet tucked away for a QUIET and PRIVATE stay. ✔ Family friendly - Sleep 5-6 ✔ Pool, BBQ, Free WiFi & A/C ✔ Walk everywhere in Waikiki Book now and experience comfort, convenience & unbeatable value in the heart of Waikiki.

[Rare]Mtn View | Walk Score 95 | Parking | Kitchen
Experience the newly renovated corner unit at Waikiki Banyan, with stunning 270° views of the Koʻolau Mountains, Koko Head, Diamond Head, and the Honolulu skyline from a private 28th-floor lanai. Revel in breathtaking sunrises and vibrant rainbows. In the heart of Waikiki, the unit is just 1 block from Waikiki Beach, Kapiolani Park, and Honolulu Zoo. Walk Score 95, easy access to nearby grocery stores, coffee shops, restaurants, and shops. ★ "We can't wait to come back and stay here again!" ★

North Shore Turtle Cove - Beachfront Condo with AC
Watch Honu (Giant Hawaiian Sea Turtles) in your backyard! And fall asleep to the sound of the ocean. Or watch waterfalls draping down mountains across the street after heavy rain. Remodeled beachfront condo with floor to ceiling lanai window, partial ocean view, resort style building amenities and en suite washer & dryer. Comfortably sleeps 6 with multiple beds, including King size sleeper sofa. Immerse yourself in everything North Shore living has to offer while only 45 Min drive to Honolulu.

Support Local Pool Spa Gym Top 5% Family Friendly
🌺 Mahalo for choosing to support a local family! We know you have many options, but we promise you will be pleased with your decision to stay in our quiet, peaceful, and family-friendly home. Whether you are a small family or large group, our Hale (home) is the perfect fit for you. 3/26/2026 update: Our property has been unaffected by the recent historic flooding on O'ahu, and guests can enjoy a safe and comfortable stay. 💦💪🏽 Community Pool, Spa & Fitness center 8 minute walk away 🛁

Oahu Ocean View • Sleeps 14, Pool, Hot Tub, Beach!
Welcome to Ohana Paradise! Why guests love our cozy Makaha Valley home: Free parking for up to 4 cars (hotels charge $40–$100 per car) Full kitchen—cook your own meals and save on dining out 4-stage reverse osmosis drinking water—no need to buy bottled water Private backyard with a BBQ grill—perfect for outdoor dinners Washer and dryer in the garage—travel light! Gated community with pool, hot tub, gym, and scenic mountain views Uncrowded beaches, hiking trails, and great surf spots!

2BR Non-Ocean View at Oceanfront Hilton Resort
Escape to paradise at Hilton Grand Vacations Club Lagoon Tower! Your private 2-bedroom suite blends home comforts with resort luxury in Waikiki’s most iconic beachfront resort. A perfect family-friendly getaway, it is home to Duke Kahanamoku Beach, Best Beach 2024 winner. Enjoy access to pools, a beautiful saltwater lagoon, beach, watersports, and walkable dining, shopping, and activities. Whether unwinding, exploring, or celebrating, everything is designed for a relaxing, memorable stay.

Close 2 Beach Entire Guest Suite
Due to local regulations, this home can only be rented once in a 30 day period. *Please reach out to us prior to booking. Availability shown in the calendar is not guaranteed. Recently renovated, this unit is a four bedroom, two bathroom getaway with high speed WiFi internet, washer/dryer and air conditioning. The beach access point is less than a 4 minute walk away! You are also only a 5-10 min walk away from the Polynesian Culture Center, BYU-Hawaii Campus and the Mormon LDS Temple.

Nai’a Suite at La Bella’s-Walk to Beach-Licensed
La Bella’s B&B is a High End Luxury home filled with charm and a touch of farmhouse/beach elegance. Two Suites are available for booking. Owners live onsite. Starbucks, Safeway, Gas Stations and Eateries are right across the street. Nai’a (Dolphin) Suite Offers: -Kitchenette -Private Bathroom -Separate Entrance -AC and Powerful high end fan -King size bed w/luxury bedding If you want a beautiful garden, great host family and a short walk to the beach this is the place for you.

Beautiful home in Laie, 5 min walk to the beach!
Available for a couple weeks in June 2026 We love our sunny yellow home in Laie! One of the best things about our home is we are only a 5 min walk to our favorite beach. Close to the Polynesian Cultural Center, LDS temple, BYU Hawaii and beautiful North Shore beaches. Come and enjoy our freshly updated home. We provide beach chairs, umbrella, boogie boards, and beach towels. Up to 30 day rental. Availability questions?801/722/8214 or FB Cathy Erickson Kimball.

Condo near Turtle Bay w/pool, beach & BBQ
Experience laid‑back island living on Oahu’s North Shore, just steps from Turtle Bay and the beach. Relax on the patio with sunrise coffee or unwind after surf sessions. - Sleeps 4 | 1 bd + loft | 3 beds | 2 baths - Year‑round pool, tennis & pickleball courts - Beach access, beach essentials & kayak - Private patio/balcony w/ BBQ grill - Kitchen, Wi‑Fi, workspace & in‑unit washer/dryer - Family‑friendly: Pack ’n play, toys & board games
Popular amenities for kayak rentals in Kailua
House rentals with a kayak

Condo near Turtle Bay w/ pool & beach access

Townhome w/pool, beach & golf views

Ground‑floor condo w/beach access & pool

Townhouse w/pool, beach & golf view

Hale Mahina Beach House

Townhome w/golf views & pool

Townhome w/Turtle Bay, pool & beach access

Condo w/pool & beach kayak near Turtle Bay
Other holiday rentals with a kayak

Escape to Paradise at Lagoon Tower - Studio

Hilton's Lagoon Tower 1-Bd Plus Ocean View

Stunning View of Waikiki-1 Bedroom Suite-Near Icon

*Newly Renovated Oceanfront Waikiki- Ilikai Marina

Oceanfront condo w/pool, kayak & BBQ

Stunning Resort Near Waikiki Located Near Oceanfro

Beautiful Beachfront KoOlina Club,1BR Resort Villa

Cozy studio w/rooftop pool & balcony view
Quick stats about holiday rentals with a kayak in Kailua

Total holiday rentals
Explore 20 holiday rentals in Kailua

Nightly prices starting at
Kailua holiday rentals start at $154 SGD per night before taxes and fees

Verified guest reviews
Over 720 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Kailua holiday rentals include wifi access

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

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