Holiday rentals with a kayak in St. James City

Apartment in St. James City

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.

4.93 out of 5 average rating, 105 reviews

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.

Outdoor spacesLocationComfort

4.98 out of 5 average rating, 240 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!

Outdoor spacesValueAmenities

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.

4.99 out of 5 average rating, 70 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.

Outdoor spacesLocationWalkability

4.99 out of 5 average rating, 262 reviews

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.

Home in Pelican

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!

Outdoor spacesValueBeach

4.91 out of 5 average rating, 141 reviews

A two-story beach house features a bright blue exterior and large windows, surrounded by palm trees and lush greenery. A wooden staircase leads to the entrance, with a deck visible on the upper level. The sandy area offers a welcoming beach environment.

Home in Captiva

Blue Laguna - Vacation in paradise!

This bright, fully equipped welcoming three‑story home features a private heated pool and a rooftop observation deck with stunning 360‑degree water views. It offers three comfortable bedrooms and three full bathrooms for up to six guests, plus two screened lanais where you can relax in the island breeze and listen to the birds. A four‑seater golf cart is included, so you can easily explore the beaches and sandy paths of beautiful North Captiva Island. Also full access to Island Club amenities!

Outdoor spacesValueSolo travel

A serene waterfront scene showcases a vibrant sunset, illuminating the sky in shades of orange and pink. Reflections are seen on the calm water, with palm trees framing the view. A paddle board rests on the grass beside a small table and chairs, inviting relaxation.

5.0 out of 5 average rating, 17 reviews

Charming Waterfront Home on Main Canal

Welcome to our waterfront home with direct access to the gulf! Located in St.James City, Pine Island, this beautifully renovated home, offers a spacious open concept style with two bedroom (Bedroom 1: Queen Bed+Bedroom 2: Bunk Bed (Queen Bottom+Full Top) and two bathrooms. Den with a Queen Size pullout sofa. Sanibel and Captiva Beach are a short boat ride away, area features world class fishing. Marina located on same canal, home has boat lift and dock to tie up to. Paddle board + tandem kayak

ValueLocationLaundry

A waterfront home elevated on stilts is shown, featuring a light-colored exterior and solar panels on the roof. Surrounding palm trees and shrubs enhance the outdoor space. A wooden boat dock extends into the water, providing access for boating activities.

4.95 out of 5 average rating, 87 reviews

Key West Style Home w/ Hot Tub & Boat Lift

KEY WEST style stilted waterfront home in the heart of Matlacha! Visit all there is offer - walking distance to Blue Dog and Perfect Cup. Take a boat ride to Cabbage Key, Cayo Costa or Boca Grande! Upstairs and downstairs are screened in. The second floor is peaceful and tranquil overlooking the water and treetops. Home is a 2 bedroom, 2 bathroom, with additional bonus space with trundle bed. Home is perfect for boaters with double driveway, complimentary boat lift and cleaning station.

LocationValueBackyard

4.94 out of 5 average rating, 156 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

Last Minute Offers Beach + Golf Cart + Club

BOOKING FALL 2026 HOST PAYS AIRBNB FEE 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 proximity/ steps to the beach

Outdoor spacesValueNearby

A wooden dock extends over the calm water, lined with sturdy posts topped with black caps and ropes. The backdrop features a serene house with green grounds, surrounded by lush palm trees. A vibrant sunset casts warm colors across the sky.

4.97 out of 5 average rating, 75 reviews

Island Fun In The Sun! Water on 2 Sides

Water front, bring your boat! . Sit on tiki deck and watch the sunrise with your first cup of coffee or the dolphins. Kayak through the canal ways of Pine Island. Book a fun kayak,canoe tour or rent a golf cart or set up a fishing excursion. Buy all your fresh Catch of the Day at Island Crab Seafood Mkt. Or fish off of our dock out front. Ft Myer & Sanibel beach is hour drive away. No parties or pets. Dock & open water access out front. Adults only due to water front

Outdoor spacesLocationCleanliness

4.99 out of 5 average rating, 160 reviews

Home in Cape Coral

Tropical Sunset Villa•Pool•Dock•Arcade•Kayaks

Welcome to Sprocket Boathouse, a dream waterfront escape, overlooking one of the widest canals in Cape Coral.Beautiful views, a sparkling heated pool and with western sun exposure, the home gets ☀️ all day. Don’t miss the incredible sunsets and sunrises! 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.

LocationOutdoor spacesFamily

Superhost

A rectangular pool is featured in the foreground, surrounded by a spacious paved area. In the background, a wooden dock extends over the water, complemented by lush greenery and palm trees. Clear blue skies reflect over the tranquil water.

4.79 out of 5 average rating, 33 reviews

Beautiful 5/3 Pool, Saltwater Cove,Sleeps 10!

Luxury 5-Bedroom Home on Private Saltwater Cove with Stunning Views! Discover your dream waterfront retreat! This exquisite 5-bedroom home is perfectly situated on a private saltwater cove, offering breathtaking views and unparalleled tranquility. Step outside to your own brand-new pool and outdoor kitchen, perfect for entertaining. Enjoy alfresco dining and lounging in the beautifully designed outdoor space, complete with a TV for ultimate relaxation.

ValueLocationComfort

5.0 out of 5 average rating, 18 reviews

Seascape Casita. Gulf Access, Kayaks and Bikes

Welcome to Seascape Casita, your waterfront cozy getaway in the heart of Saint James City on Pine Island. Just 5 minutes to open water is the perfect place to enjoy the beautiful beaches like Sanibel and Captiva. Also enjoy natural wonders by kayak or get to know the city by using the bikes. The area is also well-known for excellent fishing 🎣 spots. “Watch our video 🎥 tour on YouTube — search for ‘Seascape Casita Airbnb tour’ on YouTube.”

LocationCheck-inComfort

Popular amenities for St. James City kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a Kayak

4.94 out of 5 average rating, 188 reviews

Home in Pelican

Waterfront villa w/ heated pool & lake view.

LocationOutdoor spacesAccess

4.99 out of 5 average rating, 115 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

LocationValueAccess

5.0 out of 5 average rating, 35 reviews

Boater’s Paradise: No-Bridge Gulf Access & Pool

Outdoor spacesLocationFamily

A covered outdoor area features a thatched roof and a concrete floor leading to a waterfront. Noticeable are the boat lifts to the side, with calm waters reflecting the blue sky and clouds. Potted plants are positioned near the entrance, adding a touch of greenery.

4.9 out of 5 average rating, 40 reviews

Fisherman's island paradise - Southwest Florida

Outdoor spacesLocationFamily

A coastal-style house with a light blue exterior is seen from the driveway. Two garage doors are positioned beneath a covered entrance with steps leading to the front door. Palm trees and landscaping softly frame the home, complementing the inviting surroundings.

5.0 out of 5 average rating, 19 reviews

Island Getaway

LocationGetting aroundNearby

4.9 out of 5 average rating, 78 reviews

Sunset POOL Waterfront Kayak bikes fish from dock

ValueLocationBeach

A shaded seating area features a comfortable lounge chair accompanied by light drapery that softly filters sunlight. The backdrop reveals a view of palm trees and a canal, enhancing the serene outdoor environment. A ceiling fan is visible, contributing to airflow.

5.0 out of 5 average rating, 27 reviews

2023 Build in Saint James City

LocationValuePets

5.0 out of 5 average rating, 50 reviews

A scenic view of the canal-side property showcasing a wooden dock with a boat lift, surrounded by lush tropical vegetation. Sun loungers are placed on a manicured lawn, and the house's screened-in porch is visible, highlighting the tranquil waterfront setting.

Home in Bokeelia

Waterfront Oasis with Boat Lift & Hot Tub

LocationOutdoor spacesGetting around

Cottages with a kayak

4.95 out of 5 average rating, 55 reviews

An outdoor patio area is furnished with four black metal chairs, an orange-adirondack chair, and a small table. A barbecue grill is positioned nearby on a paved surface. The backdrop features calm water and a colorful sky at sunset.

Cottage in Matlacha

Waterfront Matlacha Cottage - Sunsets & Fishing!

ValueOutdoor spacesCleanliness

Superhost

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, 55 reviews

Villa The Island Hideaway 2

Outdoor spacesLocationCondition

4.94 out of 5 average rating, 83 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

Outdoor spacesLocationTV

5.0 out of 5 average rating, 36 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

Outdoor spacesLocationComfort

Cottage in St. James City

A screened-in deck features a circular dining table surrounded by two swivel chairs. Textured bamboo walls and wooden flooring enhance the space, while ceiling fans provide airflow. Large windows allow natural light and views of the surrounding area.

4.91 out of 5 average rating, 111 reviews

Waterfront/Kayaks/True Salt Life Bliss!

ValueOutdoor spacesFamily

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 St. James City

5.0 out of 5 average rating, 8 reviews

Flamingo Bay Cottage

ValueOutdoor spacesHospitality

Surrounded by tall palm trees, the cottage features a modern facade with large windows. A vibrant exterior showcases a blend of greenery and pebbled landscaping, creating a welcoming entrance. Colorful outdoor seating is positioned in the foreground for relaxation.

Cottage in Bokeelia

4.67 out of 5 average rating, 219 reviews

Captains Cottage

ValueLocationNearby

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

Outdoor spacesLocationNearby

Other holiday rentals with a kayak

4.73 out of 5 average rating, 81 reviews

A clear view of a private pool and dock is presented. Two blue lounge chairs are positioned beside the pool, offering a spot to relax. The dock extends into the water, with a boat tied nearby. Lush greenery and an open waterway create a serene backdrop.

Villa in Matlacha

"House by the Sea"

LocationValueHeating

Superhost

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.

Villa in St. James City

4.78 out of 5 average rating, 9 reviews

Seaside Villa Destin In the heart of Pine Island

Outdoor spacesLocationGetting around

Apartment in St. James City

A private screened-in lanai is depicted, featuring two chairs adorned with floral patterns and a small glass table. A metal wall art piece adds character, while views of the tranquil water and trees are visible through the screens.

4.94 out of 5 average rating, 16 reviews

Waterfront Island Resort w/Full Kitchen

LocationValueParking

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.

4.92 out of 5 average rating, 13 reviews

Island Time - Kayaks & Access to Matlacha Pass

LocationComfortFamily

The exterior of a spacious canal-front home is shown, featuring large windows that offer views of the water. A covered docking area is visible, designed for boating, with a solid structure along the waterfront, providing convenient access to the Intracoastal Waterway.

5.0 out of 5 average rating, 22 reviews

☀️Little paradise☀️

LocationOutdoor spacesWi-Fi

5.0 out of 5 average rating, 16 reviews

Quaint Matlacha Island Cottage

LocationOutdoor spacesCheckout

A private heated pool is showcased with a serene waterfall feature. Colorful lights illuminate the surrounding tropical plants and palm trees, creating a tranquil nighttime ambiance. A sun umbrella is positioned at the edge of the pool, complementing the curved design.

4.94 out of 5 average rating, 35 reviews

The Dolphin Villa

Outdoor spacesValueCleanliness