Vacation rentals with a kayak in Naples

The living area features a comfortable sofa arrangement under a ceiling fan, with large windows allowing natural light. The spacious bedroom showcases a four-poster bed, sleek furniture, and warm lighting. An enclosed patio displays a dining setup with colorful tableware, adjacent to a heated pool visible through expansive screen panels.

5 out of 5 average rating, 104 reviews

WF Oasis~Htd Pool~Spa~Pets4Free~BBQ~Big Lanai~Dock

Step into the spacious and entertaining 3BR 2Bath nestled in a tranquil canal front area close to many restaurants, shops and attractions. Explore the city or lounge the day away under the fairy-tale tiki hut next to the swimming pool and the private dock. 🐕Pets Stay Free! ✔ 3 Comfy BRs ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Patio (Heated Pool & Spa, TV, Lounges) ✔ Yard (Tiki Hut, BBQ, Dining, Lawn) ✔ Private Dock and boats ✔ Smart TVs + PS4 + SONOS ✔ High-Speed Wi-Fi ✔ Free Parking

4.97 out of 5 average rating, 226 reviews

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 Iona

Waterfront Hideaway

This picturesque Airbnb is a hidden gem nestled along a canal, 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. Close to Sanibel & Fort Myers Beach. Bring your boat & dock it on the seawall, ready to set sail whenever your heart desires. Book now - your coastal paradise awaits!

4.94 out of 5 average rating, 149 reviews

A spacious deck extends over the canal, surrounded by lush palm trees. Comfortable seating is arranged around a fire pit, with a paddleboard propped nearby. A BBQ grill is visible, inviting outdoor dining in a serene waterfront setting.

Home in East Naples

Boaters Bayshore Bungalow w/HOT TUB view of water.

BRING YOUR BOAT! This ranch home is located on a canal with direct access to the Gulf/Naples Bay(no bridges). Amazing water sports access. In the cool/hip Bayshore Arts district! Great restaurants, Naples Botanical Gardens, boating, 3 miles to DT Naples and 4 to the best beaches. This is a perfect family/friends vacation spot. We have all the gear to enjoy this location. Quiet neighborhood/newly renovated/great views. Coffee on the deck with sunrise in front of you or drinks at sunset. Serenity

The screened-in pool area features a serene swimming pool with shimmering water, two blue lounge chairs positioned nearby, and views of a wide canal. A thatched-roof Tiki hut can be seen across the water, surrounded by lush greenery.

4.99 out of 5 average rating, 251 reviews

LUX Villa w/ Private Salt Water Pool, Lanai, Canal

Are you looking to swim, relax outdoors, fish and take in beautiful sunsets on a wide gulf access canal? If so you will fall in love with this stunning newly constructed custom built home! The 2750 square foot home is bright & airy with two main bedroom on-suites & a separate family wing! The gourmet kitchen, dining room & great room open via large sliders to the lanai & pool w/ views of the canal in much desired SW Cape! Beach inspired villa! Large captains walk & Tiki! Check out our reviews!

4.95 out of 5 average rating, 192 reviews

Home in East Naples

Naples Cottage for two- your own private home

Welcome to your own, private waterfront home close to restaurants, coffee shops, parks and Naples beaches! This perfect tropical cottage for two comes with a stunning view of a natural lagoon. Fish and kayak right from the back yard! Two Kayaks & bikes provided! Lush, tropical setting. Relax on the back porch where there's always a breeze! Bike over to the Botanical Gardens, Pickle Ball courts or shops near by! Short drive to famous 5th Ave & Naples beaches! Lots of fun things to do near you!

A sandy backyard features a fire pit surrounded by several black chairs, with a canal lining the edge. Lush greenery and palm trees provide a tropical setting, while a spacious home stands in the background, framed by clear blue skies.

4.95 out of 5 average rating, 106 reviews

Canal Home- Gulf Access- PET friendly-Fenced yard

Waterfront home with Gulf access. Recently renovated 3 BR, 3 BA home on a canal off the Imperial river. Two en-suite bedrooms. The home can comfortably sleep 8 guests. Kayaks, bikes, fishing poles, yard games, backyard beach, and fire pit available for your use. Fenced in yard. Centrally located about 20 minutes from the airport, Naples, Fort Myers and only 3 miles from the beach! Close to several breweries, wine loft, local coffee shop, cocktail lounge, parks, churches, and many restaurants.

4.98 out of 5 average rating, 205 reviews

A spacious outdoor seating area is featured, showcasing a glass-top table surrounded by six chairs. The patio is complemented by a gas grill on one side. Large sliding doors provide a view of the interior dining area and kitchen, blending indoor and outdoor settings.

Home in North Naples

Gulf Access Canal, Kayaks, Bikes, Dock, Wildlife

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.

4.99 out of 5 average rating, 109 reviews

A sunlit pool area is framed by palm trees, with views of the canal and neighboring homes in the background. Comfortable loungers are positioned along the poolside, inviting relaxation amidst the tranquil waterfront setting.

Home in Fort Myers Beach

Paradise on canal minutes to Ft Myers Beach/Gulf

Beautiful 3 Bedroom, 3 bath home on a canal with a dock! Bring your boat or jet skis! Enjoy a relaxing stay watching the dolphins and manatee right off the dock. This exquisitely updated home has everything you need for a fantastic vacation. Especially location! 5 minutes to Ft Meyers Beach. Enjoy the resort right in your own backyard. New pool with hot tub and sun shelf. Enjoy beautiful sunsets off the huge patio. Trolly to beach at neighborhood entrance or walk to in minutes.

4.9 out of 5 average rating, 277 reviews

A private heated saltwater pool is surrounded by vibrant palm trees, creating a lush outdoor oasis. White lounge chairs are positioned along the poolside, inviting relaxation under a clear blue sky. A well-maintained grassy area adds to the serene atmosphere.

Cottage in Naples Park

Cottage Close to Vanderbilt Beach Heated Pool

2023 Complete Remodel West of 41 .Private Heated Saltwater Pool w/ 6’ Privacy Fenced backyard. 1 miles to Vanderbilt beach Cottage with screened Lanai, 50 inch HD tv, gas blackstone grill w/ceiling fans and wet bar with refrigerator for outdoor living. Great house for small families or couples. Both rooms have king beds, so ideal for 2 couples. A sofa sleeper has been added to sleep 6. Quartzite countertops with travertine Marble floors. Beach chairs, coolers, towels, and sand toys

A covered outdoor seating area features a wooden sectional sofa facing a sparkling pool. Two ceiling fans provide a cooling breeze. The serene water views and lush greenery create a tranquil backdrop, with a red umbrella providing shade over the pool.

4.99 out of 5 average rating, 157 reviews

Luxury Canal Villa•Heated Pool•Dock•Fishing•Kayaks

Welcome to Sprocket Boathouse, a dream waterfront escape. Beautiful views, a sparkling heated pool overlooking one of the widest canals in Cape Coral, and with western sun exposure, the house gets ☀️ all day. Don’t miss the incredible sunsets and sunrises! You won’t be disappointed. Spend hours swimming, kayaking or fish off your own private dock (kayaks & rods included.) Make sure to keep a look out for all the wildlife! You can spot iguanas, turtles & herons on the waterfront.

4.99 out of 5 average rating, 177 reviews

An open living area features a cozy seating arrangement with a brown armchair and a textured ottoman. Wall art depicting botanical themes complements the neutral walls. A modern kitchen bar with three stools is visible, lending to the inviting and functional design of the space.

Home in Naples Park

Pool Bikes & Beach | Paddle Board Included

We welcome your family of up to 2 adults & 3 children. You will be close to sandy beaches, great restaurants and shopping at this great North Naples Location. Just a few minutes from Vanderbilt Beach and Wiggins Pass Park. You will love all the great amenities and be able to relax in this brand new clean apartment. Amenities, Bikes, paddle board, beach wagon and beach towels. Very easy to check-in, you will have your own private entrance and private one car parking available.

The living room features a spacious sectional sofa, providing ample seating. Large glass doors open to the outdoor area, enhancing natural light. A mounted TV displays beach scenery, while a modern fireplace adds a touch of warmth. The room's design promotes comfort and relaxation for guests.

4.98 out of 5 average rating, 135 reviews

2 Kings, Pool, Gulf Canal, Game Room and Kayaks

Unwind Cape Coral welcomes you to sunny southwest Florida, close to magnificent beaches, fishing, shelling, Minnesota Twins Spring Training & much more. Come enjoy this new construction home with heated pool, Kayaks, heated and cooled game room (PlayStation 5), gulf access - salt water canal, 4k oled tv's & many more refreshing amenities. You will love this clean & bright home with lovely décor. Located in the highly sought after Pelican neighborhood of Southwest Cape Coral!

Popular amenities for Naples kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

The outdoor area features well-maintained grass bordered by gravel and illuminated palm trees, enhancing the tranquil canal view. A dining table is set up for outdoor meals, while string lights provide soft lighting. The calm water reflects the colorful lights, creating a serene atmosphere.

5 out of 5 average rating, 48 reviews

Waterfront Family Retreat/Heated Pool/kayaks&Games

The outdoor area features a heated pool with illuminated waters, a spa, and a Tiki Hut. Soft lighting highlights the architecture of the home, including arched columns. Lounge chairs provide seating near the pool, with direct access to the indoor entertainment area visible in the background.

5 out of 5 average rating, 23 reviews

Luxury Oasis w/ Heated Pool, Theater Room & Dock!

5 out of 5 average rating, 26 reviews

Tiki, Kayaks, Heated Pool, Canals, Fishing, Fenced

A modern dining area features a large wooden table set for a meal, complete with plates, glasses, and decorative centerpieces. Stylish pendant lighting illuminates the space, while an adjacent kitchen with stainless steel appliances can be seen in the background.

5 out of 5 average rating, 27 reviews

Heated Pool, Hut Tub, Dock, Bikes, Beach Gear!

4.89 out of 5 average rating, 123 reviews

Cape Serenity- Luxury Waterfront Residence

5 out of 5 average rating, 7 reviews

Belle Rio Paradise - Pool Home near beach on canal

4.85 out of 5 average rating, 55 reviews

An enclosed screened patio showcases a heated pool surrounded by tropical greenery. Outdoor furniture is positioned for relaxation, and a gas grill is visible along one side. The open concept allows views into the house, enhancing the inviting, airy atmosphere.

Home in North Naples

Lush Paradise: Heated Pool, Near Beach, Sleeps 10

An aerial view of a serene residential neighborhood showcases a winding canal bordered by lush greenery and palm trees. The scene is enhanced by a sunset casting warm hues across the sky, with well-maintained homes lining the expansive properties along the water.

4.97 out of 5 average rating, 62 reviews

Golden Pearl | Luxury Villa | Pool | Dock | Games

Cottage rentals with a kayak

Cottage in Bonita Springs

A serene view of the Enchanted Cottage is showcased amidst lush tropical landscaping. Pathways with stone pavers lead towards the quaint entrance, bordered by various palms and flowering plants that enhance the peaceful garden setting.

4.99 out of 5 average rating, 75 reviews

The Enchanted Cottage on the Imperial River

The exterior of the villa features a light-colored façade with a sloped roof and a well-maintained lawn adorned with tropical plants. A driveway leads up to a garage on one side, while a double entrance door provides access to the home.

Cottage in Cape Coral

4.67 out of 5 average rating, 54 reviews

Villa The Island Hideaway 2

A tranquil waterway is visible, reflecting the surrounding structures and sky. A private boat dock extends into the canal, offering access to boats moored nearby. The scene features well-maintained properties lining the banks, framed by palm trees and grassy areas.

Cottage in Saint James City

5 out of 5 average rating, 8 reviews

Flamingo Bay Cottage

A bright and inviting living area features pastel yellow walls complemented by an array of furnishings in varied hues. The space includes a dining table with chairs, a cozy seating area with a striped sofa, and decorative artwork adorning the walls.

Cottage in Matlacha

4.88 out of 5 average rating, 42 reviews

The Coqui Palace

Cottage in Bonita Springs

An outdoor seating area features a round black table surrounded by six metal chairs, set against a backdrop of white siding. A potted plant sits in the center of the table. Sunlight filters through the nearby window, enhancing the inviting atmosphere.

5 out of 5 average rating, 19 reviews

Quiet Riverside Cottage in Downtown Bonita Springs

Superhost

A serene outdoor space features a clear, heated saltwater pool surrounded by lush palm trees. Colorful kayaks are visible along the lakefront, while blue lounge chairs provide comfort for relaxing under the sun. The tranquil water reflects the blue sky and nearby greenery.

Cottage in Cape Coral

4.44 out of 5 average rating, 9 reviews

Cape Lake House Lake Front

A charming island cottage is surrounded by lush palm trees and tropical foliage. Two blue chairs are positioned on the gravel driveway, inviting relaxation. The entrance is framed by vibrant greenery, and a metal roof reflects the sunny skies.

Cottage in Bokeelia

4.69 out of 5 average rating, 213 reviews

Captains Cottage

The entrance of the bungalow is framed by lush tropical plants, with a welcoming pathway leading to double glass doors. The exterior walls are a soft pink hue, complemented by white window shutters. A decorative mat is positioned at the front door, enhancing the inviting appearance.

Cottage in Cape Coral

4.93 out of 5 average rating, 54 reviews

Boat Paradise Gulf Access 2,000 sf home 62 ft dock

Other vacation rentals with a kayak

5 out of 5 average rating, 56 reviews

An aerial view of the villa showcases a spacious property with a large custom heated saltwater pool, surrounded by a screened lanai. Two kayaks rest on the lush green lawn, and the private dock extends into the calm canal waters.

Villa in Pelican

Luxury new construction Villa Ocean Kiss on canal

4.97 out of 5 average rating, 74 reviews

Condo in Naples

85" TV, World Tennis Club, Beach 4mi, Sauna

A deck area is complemented by several blue Adirondack chairs arranged around a circular fire pit. Lush greenery surrounds the space, with palm trees and decorative planters visible. A kayak rests beside the deck, while a shaded pergola provides a relaxing area for outdoor enjoyment.

4.86 out of 5 average rating, 22 reviews

Private home resort on the river family fun

4.96 out of 5 average rating, 26 reviews

An outdoor seating area is featured on a wooden deck, with a cozy arrangement of chairs and a table. The sky is filled with vibrant colors as the sun sets, and tall palm trees provide a tropical backdrop. The boathouse architecture showcases large windows reflecting the evening light.

Guesthouse in Fort Myers

Sleep over the water- Boathouse with Private Dock

4.98 out of 5 average rating, 97 reviews

A serene pond is framed by lush greenery and tropical palm trees. Gentle fountains create ripples in the water, while a landscaped border of gravel and plants enhances the natural setting. The nearby two-story house is partially visible, providing a tranquil backdrop.

Treehouse in Naples

‘Treewater’ House (tree and lakehouse combo)

An aerial view shows a spacious house adjacent to water, featuring a private pool and a boat dock. Lush greenery surrounds the outdoor area, while multiple houses can be seen along the waterfront. A boat is tied up at the dock, emphasizing the water access.

5 out of 5 average rating, 45 reviews

Casa Marina

4.7 out of 5 average rating, 74 reviews

A two-story beach house is displayed, featuring a vibrant blue exterior with contrasting black railings. An exterior staircase leads to the upper level, where glass doors provide access to the wraparound deck. The house number is prominently displayed on the wall.

Home in Bonita Beach

Gulf Coast Gateway: 2/2, Steps from Bonita Beach!