Holiday rentals with a kayak in Kitsap County

The Landing at Oyster Bay - Waterfront Home

The Landing at Oyster Bay is an aviation themed waterfront home in a prime location for kayaking, paddle boarding, hiking, touring Seattle, and exploring the Hood Canal and Mt. Rainier. Come for the location, but stay for all the amenities! From the provided kayak, SUP, yard games, an abundance of board games, and fun aviation décor this house will sure to keep the whole family entertained! The waterfront backyard provides constantly changing serene views as the tides fluctuate through the day!

McDonald Cove Cabin

Rustic cozy cabin. Open concept for easy entertaining with glorious views of the water. Main floor bedroom with Queen bed plus open loft with Queen bed. The cabin has one bathroom opposite the downstairs bedroom. Great outdoor living with two decks; front deck facing the waterfront. Use stairs to access the beach and boat house which houses two single kayaks, one double kayak, life jackets, and beach chairs for guest use. One exterior security camera, which monitors the driveway is present.

Sinclair Cottage ~ Cozy Coastal Retreat w/ Hot Tub

Amazing view from this cozy, 2-story, adorable beach cottage. Property is low bank waterfront with a dock, covered porch/hot tub/ barbecue & fire pit. New: Air conditioning *small pet friendly, with pre-approval and $100 pet fee Everything you’ll need ! Well appointed kitchen, 2 bedrooms on the upper floor. 2 TVs/Cable. Good wifi, desk, great little space to WFH or just relax! Quick drive to the waterfront town, 10 minutes to the Bremerton ferry. -Steep stairs -Expect some road noise

Weather-N-Heights Hood Canal Waterfront Retreat

Located just 60 miles north of Olympia on the on the scenic Hood Canal, Weather-N-Heights resort was lovingly built and enjoyed by my parents for many years. Recently updated to it's original splendor, it sits right on the shore with spectacular views looking south down the canal. This property has it all. Whether it is swimming, fishing or watching the local wildlife right from the deck or hiking, waterfalls and exploring everything the Olympic Peninsula has to offer within a short drive.

Peaceful Waterfront Cottage, Deck - Gorgeous Views

Our cozy cottage features stunning views of Dyes Inlet. The sunrise and sunset views are truly amazing & you can enjoy them on the nice big deck, or warm & cozy in bed. It is fully furnished & includes 1 BR with closet, 1 BA & a full kitchen/dining room with refrigerator, range, microwave, coffee maker, toaster oven & all the essentials. Amenities include TV, DVDs & player, books & games, wi-fi, grill, use of canoe, kayak, bikes & rubber boots. And there lots of animals to visit!

The Loft | Beach | Kayaks & Pickleball

The Loft at Black Pearl on Dyes Inlet — a garden-view retreat steps from the beach. Wake to coastal light, play pickleball, kayak the inlet, or unwind by the beachside firepit. A large grassy yard opens directly onto the pickleball court and a garden path leads down to your own private beach area. Full kitchen, kayaks, paddleboards, firepit, and pickleball court included. The Loft can be added to a Helm booking when available — inquire about compound availability.

Private Beach Access | Fire Pit | Sleeps 6

Escape to serenity with your loved ones at this tranquil 2-bedroom retreat nestled in the heart of Oyster Bay! Admire the breathtaking vistas of the bay from your private deck from the upper unit. Conveniently located near all the essentials in Bremerton, this charming abode offers the perfect blend of convenience and relaxation. Plus, enhance your stay with a discounted sailboat charter – the ultimate way to explore the beauty of the surrounding waters!

The Sound Landing w/ Beach Access & Theater Room!

This beautiful townhouse overlooking the Puget Sound offers an expansive, fully equipped kitchen, a cozy theater room, beach access with kayaks, and an outdoor firepit! It’s the perfect spot for a relaxing getaway. Plus, you’re centrally located to explore in any direction—whether it’s Downtown Seattle, Hood Canal, or Olympic National Park! For those visiting for work, we’re less than 10 minutes to Puget Sound Naval Shipyard and other military bases!

Luxury Waterfront w/ Private Dock + Kayaks

True waterfront on Point Monroe with private dock and panoramic Bay views. Launch the provided kayaks and paddleboards from your own shoreline, bring your boat, and unwind around the firepit as seals and eagles pass by. Newly remodeled with open-concept living that flows directly to the water. Walk to Fay Bainbridge Park and reach the Seattle ferry in just 15 minutes. A rare Bainbridge stay where the water isn’t just the view — it’s your backyard.

Tide Cove Beach House in Poulsbo

Nestled in the wooded Lemolo waterfront neighborhood in Poulsbo, this large 4 bedroom 2.5 bath vacation home is perfect for family and friends to gather. Stay and enjoy all the outdoor amenities of the home like the beach stocked with water toys, fire pit, large patio with grill, outdoor furniture and more. Or indoor amenities including the 65" 4k OLED TV, gaming room, large family dining room, huge soaking tub, 4 head shower and much more.

The Log House at Leaning Tree Beach

Located just south of Silverdale, this peaceful log cabin can be yours for the evening. Literally steps from the Puget Sound, you will sleep like a baby listening to the sound of the ocean waves and breeze through your window. Conveniently 10 minutes to the Bremerton/ Seattle ferry, and close to hiking trails and recreation in the Olympic Mountains. We have local recommendations available, and mooring options for boats.

The Little Guest House - Footsteps From Oyster Bay

The Little Guest House is a vintage 100 year old home nestled in a quiet neighborhood with all the modern conveniences to make your stay comfortable and relaxing. The living areas are inviting both inside and out. There is a cozy living and dining room, full kitchen with a charming breakfast nook, and a laundry room for your use. The bathroom is small with a shower (no tub).