Vacation rentals with a kayak in Naples

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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

A serene canal scene features a wooden dock alongside lush greenery and native trees. A small boat is anchored nearby, with additional boats visible along the waterway. Stone pathways lead through the landscaped area, providing access to the peaceful waterway.

Apartment in Alva

4.98 out of 5 average rating, 49 reviews

River views, boat slip, sleeps 5, pet friendly

Relax with family, friends at this quiet place. Bring your boat, fishing poles or tubes, kayaks, bikes and marshmallows for the campfire. This above garage guest house has serene water views, bedroom, bathroom, washer, dryer, full kitchen, 22” queen, and small futon. Bring your boat for fishing, tubing, fossil hunting and exploring on the Caloosahatchee. Park your boat in the canal. Inside storage for fishing poles, tackle and bikes for the mountain biking park across the river. Dogs ok.

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!

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, 178 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.

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.

Superhost

Villa in Pelican

4.69 out of 5 average rating, 52 reviews

Island Time Luxury Villa- Heated Pool

Don’t just go on vacation take your friends and family on an adventure to Island Time Luxury Villa. This Villa is located in the heart of Cape Coral on a freshwater canal that opens up onto Lake Mojave. The Cape Coral yacht club is minutes away or forget the driving and enjoy the villas incredible amenities like the large tiki hut equipped with a fridge, grill and white sand beach. We have recently added a putting green and turf lawn for your enjoyment!

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.

Guest favorite

The studio features a queen size bed adorned with a patterned quilt and ample pillows. A cozy sofa sits opposite, next to a small dining table. Natural light fills the space through sliding glass doors leading to a private screened lanai.

Apartment in Saint James City

4.91 out of 5 average rating, 11 reviews

Waterfront Island Resort w/Full Kitchen

Our resort offers you that old world charm. Our studios have full size kitchens, a private screened in lanai, large patio for barbecuing and outside dining on the water. There’s a fire pit and lawn area to relax at. Don’t forget to bring your boat and trailer or rent one. We offer dockside mooring for your boat and trailer parking in our lot. We are pet friendly, so let’s not leave your best friend bring them along.