Vacation rentals with a kayak in Naples

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in Naples

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Top guest favorite

Guest suite in Saint James City

4.98 out of 5 average rating, 104 reviews

Waterfront island private suite with private pool

Take it easy at this Island, PRIVATE, waterfront getaway! Enjoy a large PRIVATE electric heated pool, located directly on the water. Kayak dock and KAYAKS free with rental. Completely private entrance. Please be aware that Pine Island is a somewhat remote island without many commercial businesses and no public beaches but there’s more than plenty to do! 5 restaurants within 1 mile by car and many more within 8 miles. Located on a quiet residential street, directly on the water. Car is a must!

Top guest favorite

The image captures a two-story island home along a serene waterway, featuring a spacious dock with seating. A covered patio is seen on the ground level, while balconies are visible on the upper floor. Lush palm trees surround the property, enhancing its coastal setting.

Home in Matlacha

5 out of 5 average rating, 36 reviews

The White Egret On Matlacha

Island home with direct access to Matlacha Pass. A 2-story property equipped with a pool and spa, high-speed internet, smart TV's, and smart home applications. Enjoy the balconies with sunrise and sunset views. Kayak directly off the back dock from the properties private kayak launch . You can fish right off the back dock, bike, or walk to the local shops/restaurants and the world famous Matlacha bridge, which is less than half a mile away. 2 Kayaks and 2 bicycles are included in the rental.

Top guest favorite

Two bright yellow kayaks are positioned on a gravel surface beside a wooden fence. The kayaks are designed for versatility and stability, featuring storage compartments and padded seats, ready for water adventures in the nearby Pine Island Sound.

Home in Matlacha

4.98 out of 5 average rating, 44 reviews

Fisherman's Cottage at Matlacha

Take it easy at this unique and tranquil getaway. Incredible Pine Island Sound waterfront home on Matlacha Island in SW Florida. The absolute best sunset views in all of Florida. Watch the manatees and dolphins play under the pelicans, osprey, eagles and rosetta spoonbills. Catch snook, trout, tarpon and redfish off the dock or untie your boat and head out to some of the most beautiful, fish infested waters in the world! Don't have a boat? Hop on the provided kayak or our guide's boat.......

Top guest favorite

The modern kitchen is equipped with white cabinetry and stainless-steel appliances. A circular table with seating for four is positioned near a large glass sliding door that allows natural light and offers views of the outdoor space. A ceiling fan adds comfort to the room.

Guesthouse in Fort Myers

4.97 out of 5 average rating, 134 reviews

Waterfront Hideaway

This picturesque Airbnb is a hidden gem nestled along a canal with a one minute boat ride to the Caloosahatchee River. The living room, bathed in natural light is perfect for taking in the scenic views. The spacious bedroom has a king-size bed, ensuring a night of blissful rest. The full kitchen is equipped with all modern appliances. Bring your boat and dock it on the seawall, ready to set sail whenever your heart desires. (PLEASE NOTE-boats only) Book now - your coastal paradise awaits!

Guest favorite

A serene dock extends over calm water, featuring two brightly colored chairs in teal and light green. The reflection of the sky can be seen on the water's surface, while lush greenery outlines the distant shoreline.

Home in Cayo Costa

4.92 out of 5 average rating, 26 reviews

Cayo Costa Paradise Found

•This stunning home will be for sale as my wife and I transition to full retirement. • 360”views! • On the beach! • Artsy! .• Sleeps 6 (2 Queen, 2 Twin) • Additional unit on 1st fl. . Hot tub! • Beach combing! • kayaks! • Fishing poles! • Swimming, dolphins,manatees! . Books! . Grill, Utensils, fridge, microwave, plates, cups, glasses • 2 Full bath, 2 1/2 bath, 2 outside showers! • Towels, linens, soap, shampoo! • Fire pit!

Top guest favorite

The image captures a serene dock extending over a calm canal, surrounded by lush planting including tropical foliage. Seating is present on the dock, alongside a swim ladder. Soft lighting from overhead patio lights adds warmth to the peaceful scene, framed by natural greenery.

Home in Naples

4.98 out of 5 average rating, 177 reviews

Gulf Access Sanctuary, Kayaks, Bikes, ebikes

A renovated mid century modern house with natural peaceful views out of every window and slider. No detail spared, as it was going to be our forever home. Located on an ocean access canal, extremely safe, quaint and friendly neighborhood, just off 41. The backyard has a large shaded sitting area with a gas grill and fire pit. The dock hangs over the water with seating and swim ladder. 2 tandem kayaks, fishing rods & tackle, adult & children’s bicycles, beach chairs, and so much more.

Top guest favorite

A covered dock area is displayed, featuring a wooden structure with seating space and a small table. A boat is securely docked, with a carpeted surface enhancing comfort. The tranquil canal is visible, surrounded by lush greenery and residential properties.

Home in Matlacha

4.99 out of 5 average rating, 200 reviews

Matlacha Paradise! NEW Waterfront Home-Free Kayak

Matlacha is for LOVERS! Lovers of relaxation, fishing, art, friends, social scenes and enjoying Life in a beautiful location ON THE WATER! Matlacha had damage from Ian. Our new home - none. You can still walk to great restaurants, shops and the fishing bridge. Enjoy the water in Matlacha & the Barrier Islands. Use our 1 person kayak for fun or fishing from our 8'X22' FUN & SUN deck docked in the back canal with picnic table & loungers. Relax, sun, grill and fish.

Superhost

Home in Matlacha

4.8 out of 5 average rating, 20 reviews

Paradise Pool Waterfront Kayak bike fish from dock

New POOL, waterfront gulf access. Upstairs unit 2 bedrooms 1 full bath kitchen washer/dryer. Sleeps 6 all pillow top beds 1 king 1 queen and 1 queen memory foam pull out pack/ play crib. In the heart of Matlacha walking distance to town. Bring your boat and dock it in the property. For use kayaks, canoe, bikes, fishing rods. Direct TV sports package, high-speed internet. Boat Ramp less than half mile. Guest favorite air conditioning enclosed lanai with table sits 10.

Guest favorite

Cottage in Goodland

4.97 out of 5 average rating, 106 reviews

Waterfront View Cottage

Come and stay at the only location on the island with the one of a kind exceptional view of the Everglades. Step right out to the waters edge of the Goodland Bay, where you will be able watch the dolphins right from your porch and private patio. The cottage has great sliding glass doors that hold the magnificent view of the water, right from the living room. A freshly remodeled fully furnished, up to date, 1 bedroom cottage. Dockage, kayaks, and bikes available.

Superhost

A screened-in porch features two comfortable lounge chairs facing a calm waterfront. The space is adorned with a thatched roof and offers unobstructed views of the boats docked outside. Large windows allow for natural light to fill the area while maintaining a tranquil atmosphere.

Home in Saint James City

5 out of 5 average rating, 3 reviews

Hidden Gem of South West Florida

Enjoy your gulf access waterfront paradise in quaint Saint James City, Florida. A beautiful community to bask in the sunshine, enjoy some fishing, hike a trail in the Galt preserve or enjoy dinner and music at local restaurants, just minutes away. 2 Kayaks and 2 bikes for your use to explore or fish. Enjoy the beautiful warm Florida day & catch breath taking sunsets from the dock. You may even catch some Manatees or Dolphins hanging out in our back yard.

Guest favorite

Home in Pelican

4.95 out of 5 average rating, 44 reviews

Sunny Gulf Access Villa with Pool Family Approved!

Cape Sunset: Waterfront Bliss with Pool & Kayaks! Enjoy this modern 3-bedroom retreat, complete with stylish coastal décor and new furnishings. Relax by the pool, kayak through scenic canals, fish off the backyard dock, or watch breathtaking sunsets. Bedrooms feature smart TVs, Tempur-Pedic mattresses, and cozy vibes. Play your favorite tunes on the vintage Marantz stereo. Conveniently close to Cape Coral’s beaches, attractions, shopping, and dining.

Top guest favorite

Two red kayaks are positioned on a green lawn beside a calm canal. Palm trees and waterfront homes are visible in the background, contributing to a serene outdoor setting. Safety vests are attached to the kayaks, indicating readiness for use.

Home in Punta Gorda

5 out of 5 average rating, 11 reviews

Stunning! Luxury waterfront home

STUNNING!! LUXURY WATERFRONT HOME - HEATED POOL- Close to Harbor/Fish Village -PREMIER HOST reviews averaging 5.0 since 2018 on other site. -Modern, newly updated home with open layout allowing for enjoyment of the cool waterfront breezes. -Boat dock with very close Harbor access within 10 minutes. -Southern exposure, full sun, heated pool, and waterfront. Oversized pool extends along large portion of rear of home.