Holiday rentals with a kayak in St. James City

Guest house in Fort Myers

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.

4.98 out of 5 average rating, 201 reviews

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!

4.93 out of 5 average rating, 99 reviews

Two vibrant blue Adirondack chairs are positioned on a covered porch, inviting relaxation. A welcome sign is displayed nearby, and a potted plant adds a touch of greenery. A decorative rug with a palm leaf design creates a cozy atmosphere on the outdoor space.

Flat in Saint James City

Island Castaway--Free Kayaks

This is the perfect place to sit back, relax and enjoy the view. You have the privacy of a one-bedroom apartment with small kitchen and bath. We are close to great restaurants and some of the best music on the island. Open water and excellent fishing are minutes away. Two kayaks are set up for fishing and are available for guests to use so bring your fishing rod. Pine Island has no beachs, but Ft Myers Beach is about an hour away or take a ferry ride from Bokeelia to Cayo Costa for the day.

A renovated home in a vibrant shade of green features a covered porch with outdoor seating. Palm trees provide a tropical ambiance, while a gravel area surrounds the property. Large windows allow natural light to enter, creating a welcoming entrance for guests.

4.98 out of 5 average rating, 59 reviews

Enjoy the Salt Life w/Gulf Access Dock＋Kayak＋Bike

The "Pinfish", Gulf Access Island Home w/ Boat Dock. Located in the BEST area of Saint James City! Only a few minutes to open water. Perfect for those who want a relaxing stay and boaters with easy & quick access to fishing, shelling, or beaching. A Floating Dock for the included Kayaks & Paddleboards. This Renovated upgraded 2/1, sleeps 5, has everything you need. Fish from the dock, say hi to the Manatees that visit, bike/walk to the amazing local restaurants. Experience true Old Florida.

A serene outdoor space features a pool surrounded by a screened-in enclosure, with a hot tub adjacent to it. The area is enhanced by a Tiki Hut in the background, with views of the calming canal waters. An American flag is visible, gently waving overhead.

4.92 out of 5 average rating, 51 reviews

Tropical Paradise! Gorgeous 3/3 Pool Home!

Zuzu’s Fancy is a wonderful 3 bedroom, 3 bathroom home in a quiet St. James City. This home is sure to please with its beautiful coastal décor and comfortable furnishings. Dolphins are often seen playing in the back canal while manatees swim in the front canal by the fire-pit. This home offers a screened in porch overlooking the canal, with a large Tiki Hut and large outdoor area. Bring your boat! You’ll find a great canal side dock complete with water and electric. *Pet friendly $150 applies

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, 239 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!

The backyard features a hot tub in the foreground, with a clear view of a pool in the background. Colorful adirondack chairs are arranged around the pool area, and a spacious house is visible with a screened porch. String lights are seen overhead, enhancing the outdoor ambiance.

4.98 out of 5 average rating, 116 reviews

April Deals! Hot Tub+Ping Pong+Just 5 min to Town

-5 min to Downtown Cape/10 min to Yacht Club Beach, 20 min to Causeway Beach, 25 min to Ft Myers & Sanibel Beach -Tropical fenced backyard w/ pool, hot tub, gas firepit, swing chair, hammock & Blackstone grill -Beach essentials, boogie boards, umbrellas, beach wagon, cooler & chairs -Board games, ping-pong, corn-hole, darts, 2 kayaks+life jackets -2 Beach Cruiser bikes + helmets -Relaxing enclosed covered patio + string lights, neon sign & grass wall -Canal access for kayak launch 5 min away!

An inviting outdoor area showcases a pool and spa, surrounded by lush greenery. The sky is tinted with vibrant pink and purple hues at sunset. A pink flamingo float rests in the water, adding a playful element to the serene setting.

4.99 out of 5 average rating, 108 reviews

5 Star Paradise Plus/Canal/Pool/Spa/KayaksSp.offer

This renovated luxurious, charming 4 bedroom home has stunning updates. It is a former model home. It has 2 master bedroom suites/private bathrooms & sliding glass doors leading out to the pool & spa area & 2 bedrooms share a bathroom. We love hosting baseball players, pickle ball enthusiasts & families who enjoy the Waterpark or Mini Golf all minutes away. Just a short walk to The Courts which is new with 32 Pickleball courts & 12 tennis courts. Play either from 1-3 PM for FREE.cahis

4.95 out of 5 average rating, 140 reviews

A serene beach scene showcases smooth, soft sands meeting the gentle waves of a turquoise ocean. A piece of driftwood rests in the foreground, complementing the clear blue sky and tranquil waters that stretch into the horizon.

Home in Captiva

Steps to Beach Captiva Includes CLUB & Golfcart

HOST PAYS AIRBNB FEE WINTER SPECIALS Golf Cart and Club amenities Included North Captiva Island Cottage! Just steps away from the Gulf's pristine shores, this cozy retreat offers a private hot tub, perfect for families and beach enthusiasts. Enjoy modern amenities, a well-stocked pantry, and a complimentary golf cart to explore the island. Pet-friendly(small fee) accessible by ferry, boat, or plane. With beach gear, access to the club pool, and unbeatable proximity to the beach STAY WITH US

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, 121 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!

4.99 out of 5 average rating, 210 reviews

A serene waterfront scene features two small boats gliding through calm waters, surrounded by lush palm trees. Nearby structures exhibit a mix of colors, with a sailboat anchored in the background, creating a peaceful atmosphere in the canal.

Home in Hamlet

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.

A screened lanai features a rectangular pool surrounded by tropical greenery. Outdoor dining furniture is visible near a glass table, offering a place to enjoy meals. Colorful pool floats and lounge chairs add to the inviting space, with the waterfront just beyond the pool area.

4.84 out of 5 average rating, 112 reviews

Peaceful Oasis

Enjoy the best of the Cape Coral Yacht Club neighborhood. We offer beautifully restored Terrazzo floors along with all new cabinetry, appliances and furniture. The interior of the house has been greatly improved since Hurricane Ian. The lanai, pool and waterfront offer you serene splendor and beauty that you will not want to leave. We provide the most convenient location in Cape Coral, just one mile from the downtown restaurant district.

Villa in Saint James City

A spacious villa surrounded by lush palm trees offers a welcoming facade. A large driveway leads to the entrance, while elevated decks provide views of the landscaped surroundings. Bright blue skies and scattered clouds create a cheerful backdrop to the inviting exterior.

4.8 out of 5 average rating, 5 reviews

Seaside Villa Destin In the heart of Pine Island

Our SEASIDE VILLA DESTIN is idyllically located on Pine Island off Cape Coral. Especially for boat lovers, the villa is therefore the perfect vacation home. The way to the Gulf of Mexico is not far and you can explore many beautiful islands around Pine Island and Cape Coral by boat. The boat dock may be used with pleasure. For further fun in the house there are kayaks, table tennis, table soccer and bicycles. Also for the little ones is provided.

Popular amenities for kayak rentals in St. James City

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

A spacious outdoor area showcases a private pool surrounded by a well-kept lawn. The patio features seating by the water, with a dock for boats visible along the canal. Palm trees provide a tropical backdrop under a bright blue sky.

5 out of 5 average rating, 31 reviews

Canal fun! Boat, Pool, Hot tub, Bikes & Kayaks

A screened-in outdoor space features a private swimming pool surrounded by tropical greenery and a waterfront view. Two loungers are positioned near the pool, each adorned with decorative cushions. Light blue pool toys float on the water, creating a relaxed atmosphere.

5 out of 5 average rating, 43 reviews

Waterfront home with pool-bikes-kayaks and 2 kings

4.97 out of 5 average rating, 36 reviews

The exterior of the property features a paver driveway leading to a two-car garage, framed by lush palm trees and manicured green lawn. The home's stucco facade is complemented by a terracotta tile roof and outdoor seating area, all set against a clear blue sky.

Home in North Fort Myers

Last Min Deal: Hot Tub, Firepit, Kayaks & Fishing

Two glasses of water are served with orange garnishes, resting on a metal side table. The screen-in lanai frames a view of a clear pool, surrounded by lounge cushions. Lush greenery and palm trees are visible beyond the pool.

4.93 out of 5 average rating, 89 reviews

Sunny Pool Beach/Island Escape in Comfy Canal Home

5 out of 5 average rating, 18 reviews

A welcoming outdoor living space is presented, featuring two red armchairs with patterned cushions and a small teal table. Brightly colored walls enhance the lively atmosphere, while a patterned rug is laid on the floor. Decorative elements include potted plants and string lights overhead.

Home in Hamlet

The Funky Flamingo

4.75 out of 5 average rating, 4 reviews

Home in Bokeelia

Grande View - Large 3/3 Island Lakehouse w/Pool

An expansive waterfront view is displayed, featuring calm blue waters under a clear sky with scattered clouds. A grassy area meets the water's edge, where several vehicles are parked on a paved surface. Lush greenery surrounds the parking area, offering a natural setting.

4.9 out of 5 average rating, 10 reviews

Island Time - Kayaks & Access to Matlacha Pass

4.95 out of 5 average rating, 44 reviews

A scenic view showcases a private deck featuring a spa and circular seating area, positioned near lush greenery. The serene beach is visible in the background, leading to calm waters under a softly lit sky at sunset, creating a tranquil coastal atmosphere.

Home in Captiva

North Captiva Beachfront | 360° Views | Hot Tub

Cottage rentals with a kayak

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

4.65 out of 5 average rating, 51 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, 7 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 Hamlet

4.88 out of 5 average rating, 42 reviews

The Coqui Palace

4.29 out of 5 average rating, 7 reviews

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

Cape Lake House Lake Front

A lush green lawn is bordered by palm trees and shrubbery, with a charming house featuring large glass doors. A gentle rainbow arcs over the scene, enhancing the serene atmosphere. Soft lighting from pathway fixtures highlights the stone walkway leading up to the entrance.

Cottage in Fort Myers

Luxury Waterfront Villa + Guest House

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

4.72 out of 5 average rating, 200 reviews

Captains Cottage

4.97 out of 5 average rating, 66 reviews

An aerial view captures a serene coastal neighborhood surrounded by lush greenery, with the beach visible in the distance. The beach house is nestled among palm trees, indicating its close proximity to the shoreline and other scenic homes in the area.

Cottage in Captiva

The FlipFlopper Beach House - North Captiva Island

5 out of 5 average rating, 26 reviews

A heated saltwater pool reflects the evening sky, showcasing vibrant hues of orange and purple. Lounge chairs are positioned around the pool area, and a tranquil lakeside view is visible, accentuating a peaceful outdoor space.

Cottage in Cape Coral

Sunset Cottage: Lake Front

Other holiday rentals with a kayak

5 out of 5 average rating, 10 reviews

A screened-in pool area features a large, clear water swimming pool with a built-in spa. Surrounding palm trees offer shade, and a view of the canal is visible beyond the pool deck. Patio areas are designed for relaxation, framed by greenery.

Villa

Last Minute-Villa Cape Belle Vue - kayaks, billiards

5 out of 5 average rating, 14 reviews

A screened lanai frames a sparkling pool, reflecting the blue sky and water beyond. Lush greenery lines the pool area, enhancing the view of the calm river. The boat lift is visible, ready for water activities.

Holiday home in Hamlet

Nature Lover's Dream - Waterfront Living Matlacha

5 out of 5 average rating, 9 reviews

Coral Soleil Haus|Gulf Access|Full Sun|Game Room

5 out of 5 average rating, 55 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 Cape Coral

Luxury new construction Villa Ocean Kiss on canal

5 out of 5 average rating, 12 reviews

A screened-in patio features a rectangular table surrounded by several chairs, offering a view of the lush green lawn and the pool area. The ocean can be seen in the background, with palm trees lining the property. Beach gear is stored neatly on the wall.

Apartment in Sanibel

Sanibel Island - Steps From Beach - Sandalfoot 2B2

5 out of 5 average rating, 14 reviews

An aerial view of a coastal neighborhood reveals well-appointed homes bordering a serene harbor. Lush greenery surrounds the area, while boats are docked at a nearby marina. The tranquil water reflects the clear blue sky, contributing to a calming seascape.

Townhouse in Captiva

Sunrise-Waterfront Cottage

The exterior of the canal front home is depicted, featuring a spacious dock with a boat lift and outdoor seating areas. A screened lanai is visible, offering views of the water. Surrounding greenery and the clear sky complement the tranquil setting.

4.82 out of 5 average rating, 17 reviews

Tranquility Villa!!! ⚓️🛥🏝