Vacation rentals with a kayak in Hawaii

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Top-rated kayak rentals in Hawaii

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Guest favorite

Guest suite in Pāhoa

4.86 out of 5 average rating, 514 reviews

Lava Lookout: Kāne / full equipped kitchen /

Lookout on aged lava flows in paradise with sunny days and pristine starry nights. Enjoy the Milky Way and luxury in an off-grid oasis with water catchment, solar, and fruit. Here on the frontier where the lava greets the sun is a weekly block party every Wed. & Kehena Black Sand Beach 5.8 miles away. The Kāne room is one of four private studios that include the shared kitchen and work well for large groups; check out our other listings (Paka’a, Nāmaka, Pele) to see more reviews and details.

Guest favorite

Condo in Lahaina

4.96 out of 5 average rating, 101 reviews

Beachfront Sands of Kahana Oceanfront withA/C

🌺 Your Hawaiian Paradise Retreat Awaits! Ocean/ Beachfront views at Sands of Kahana w/ Air Conditioning! 🏖️ Escape to NW Maui Ocean/Beachfront Resort with onsite dining. Enjoy spacious 2 bed 2 bath accommodations w/ breathtaking views, stunning sunsets over Molokai & Lanai. Enjoy whale and turtle watching, surfing, and strolls along the sandy beach. Unwind with tropical breezes and libations at the onsite BeachHouse restaurant. Amenities of 2 pools, 2 gyms, Pickleball courts. Book your stay!

Guest favorite

Home in Koloa

4.92 out of 5 average rating, 125 reviews

*NEW Poipu 2BR Retreat|Pool|AC & Athletic Club

Welcome to our Farmhouse Beach Cottage, perfect for families or couples. Just a half mile from the beach, this home features 2 bedrooms, 1 bath, 1 family room and 1 kitchen. Enjoy modern design, a serene outdoor lanai, well-equipped kitchen, cozy bathroom, A/C bedrooms and beach essentials for all ages. Listen to birds chirp as you walk the neighborhood or to nearby shops and restaurants. Plus access to the Poipu Beach Athletic Club with waterslide, pool, gym, pickleball, Bar & Grill and more!

Guest favorite

Guest suite in Kailua-Kona

4.9 out of 5 average rating, 211 reviews

Jasmine Studio; No Cleaning Fee. King Bed

Located conveniently 5 minutes from the airport and a short 15 min drive to downtown Kailua Kona. Vaulted ceilings, a cute lanai to enjoy your morning coffee, large bathroom with double vanity, and a kitchenette make this rental a real gem. The AC is powerful for when the tropical breeze isn't quite cool enough, The WIFI is reliable and there is a large screen TV with ROKU for when you just want to hang out. We offer automated check in, excellent room amenities and flexibility with booking.

Guest favorite

Home in Princeville

4.81 out of 5 average rating, 144 reviews

Paradise retreat! Plunge Pool, Hot Tub, AC!

Tropical Paradise in Princeville’s tucked between golf course and the ocean. 3 bedrooms, den and nook can accommodate 11 people. Window AC in every room, Bali style furniture and all memory form mattresses. Huge backyard with mountain views, plunge pool, hot tub, Hawaiian fruit trees, build in gas grill, outdoor hot/cold water shower. Beach gears, Paddle board, kayak, surf & bodyboards, bike and snorkeling gears! The rate is based on 6 guests; extra fee $30 per night per additional guest.

Guest favorite

Condo in Lahaina

5 out of 5 average rating, 124 reviews

Panoramic Views right on a Sandy Swimmable Beach

Zoned "Hotel/Resort" so no need to worry about our zoning. 4th Floor Corner unit on a sandy swimmable beach with A/C. The secondary bedroom also has huge windows, en-suite bath and its own (2nd) lanai. Perfect location for watching the beautiful sunsets, see our resident sea turtles and an excellent place for spotting whales during the whale migration season. Beach towels, boogie boards, 4 beach chairs, cooler and much more... Kiddie pool, family pool, pickle ball courts, tennis courts.

Guest favorite

Home in Makaha Valley

4.95 out of 5 average rating, 107 reviews

Kalo Homes ~ Makaha’s Hidden Gem!

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!

Guest favorite

Home in Kailua-Kona

4.91 out of 5 average rating, 121 reviews

Kona Mountain Home, 3/2, lanai, hot tub, sleeps 8

My home is a classic Hawaiian ranchette on the slopes of Hualalai, on 3 acres of beautiful Hawaiian forest. It has beautiful lanais, a deck with hot tub downstairs, along with a workout room and ping pong table. KMH is close to several of Kona's beautiful beaches, the Big Island's most challenging golf, and has great views of the Kona coast. It is also adjacent to a Nature Preserve where you can hike for miles through the Forest. My home will make you feel like you live in Hawaii!

Guest favorite

Home in Princeville

4.98 out of 5 average rating, 122 reviews

Princeville at Hanalei North Shore Modern Escape

Hale Laniakea ~Princeville at Hanalei 4 Bedroom Modern Retreat Our home, Hale Laniakea (Immeasurable Heaven) is located in a private cul-de-sac in the best part of the beautiful Princeville at Hanalei resort. You will love being able to walk to Queen's Bath, Hideaways Beach & snorkel spot, the Makai Golf Course & Tennis Club & Pu'u Poa Beach on Hanalei Bay. Walk to 1 Hanalei Hotel where you can dine & see live music with a spectacular view. Hanalei is five minutes down the road.

Guest favorite

Guesthouse in Captain Cook

4.99 out of 5 average rating, 109 reviews

Pebble Beach House- 2 Minute Walk to the Beach!

Come enjoy our guest house with Pebble Beach just a 2 minute walk down the road! Our piece of paradise is located in a peaceful neighborhood where you can see and hear whales spouting and slapping their tails (in season) and enjoy ocean sunsets. Pebble Beach is a great place to snorkel, kayak, or start a hike along the Kings Trail to volcanic formations or a hidden black sand beach. We are located approximately 45 minutes south of Kona, and 75 minutes to Volcanoes National Park.

Guest favorite

Condo in Kihei

4.95 out of 5 average rating, 169 reviews

Top 5% Home with King Bed + Steps to Beach & Shops

Exquisitely remodeled top floor condo in one of the most desirable condo complexes in South Maui. Enjoy sunsets and peekaboo ocean views from your private lanai, walk to some of the finest beaches, shops & restaurants and lounge in the multiple pools & hot tubs on property with this perfect Hawaiian oasis! Everything (and we mean everything) is fully remodeled. From a peaceful island getaway to your next Hawaiian adventure, Makana Condo is ready for your enjoyment!

Superhost

Guesthouse in Captain Cook

4.92 out of 5 average rating, 133 reviews

Mongoose Manor- Modern guesthouse / amazing views

Amazing ocean views, cool nights and gorgeous sunsets. We are centrally located between Hilo and Kona. Perfect for exploring the South end of the island. We Guesthouse is located about 1-1.5 hours from the Kona Airport, where we offer tranquility, starry skies and an escape from the big city. 400 Sq. feet, private deck, outdoor shower, Queen size bed as well as queen sized futon to sleep 4 guests. Security camera located on perimeter of property for your safety