Holiday rentals with a kayak in St. James City

4.93 out of 5 average rating, 105 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 St. 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.

Outdoor spacesLocationAccuracy

4.98 out of 5 average rating, 246 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.

Guest house 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!

LocationOutdoor spacesGrill

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.

4.83 out of 5 average rating, 60 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

LocationValueNearby

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, 265 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!

Outdoor spacesLocationAccess

4.91 out of 5 average rating, 142 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!

LocationOutdoor spacesCheck-in

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

LocationOutdoor spacesDecor

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.

4.96 out of 5 average rating, 90 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.

Outdoor spacesLocationLaundry

5.0 out of 5 average rating, 38 reviews

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

⚓ Direct Gulf Access (No Bridges): Cruise to open water! 🏊‍♂️ FREE Heated Pool: Waterfront views, zero daily heating fees. 🛏️ Group Oasis: 4BR | 3BA | 7 Beds (Sleeps 13 comfortably). 🎣 Outdoor Living: Fish from your dock, BBQ & spectacular sunsets! 🐾 Pets Welcome & Fast Wi-Fi! 🚙 Massive Parking: Room for boat trailers! 📍 Location: Heart of Matlacha, minutes to Cape Coral. ⚡ Prime season dates book fast. Lock in your direct water access and reserve your dates today.

LocationOutdoor spacesCondition

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

Looking for peace and tranquility? Come visit and get to know Saint James City, FL. Beautiful sunset views right from the dock. Small town feel, where island time starts the minute you cross into the island. Bring your fishing rod and your boat or fish right from the dock. Don't care for fishing, then enjoy one of several local restaurants, where music, great food and drinks are plentiful. Or just relax under the tiki with a good book and a view of the water.

LocationOutdoor spacesSleep quality

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

Beach Getaway + Golf Cart & Club Access

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

LocationValueBeach

5.0 out of 5 average rating, 8 reviews

Tropical Sunset

Tropical Sunset is a 2-bedroom, 2-bath waterfront retreat in Saint James City, a true boater's paradise on the southern tip of Pine Island. Sip your morning coffee on the private balcony overlooking the canal, then head out to the Gulf from your private boat slip for a day of fishing, kayaking or island hopping. A fully equipped kitchen, washer and dryer, and parking for your vehicle and trailer make it an easy base for a laid-back Old Florida getaway.

Outdoor spacesLocationView

4.78 out of 5 average rating, 9 reviews

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

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.

Outdoor spacesLocationBathroom

Popular amenities for kayak rentals in St. James City

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

A serene waterfront view is captured from a dock, showcasing calm waters reflecting palm trees and houses along the shore. The dock is anchored with sturdy posts topped by black finials and surrounded by a gentle rope, emphasizing the peaceful ambiance.

4.97 out of 5 average rating, 168 reviews

Flirty Flamingo Gulf Access Cape Coral Home

ValueLocationCondition

4.94 out of 5 average rating, 188 reviews

Waterfront villa w/ heated pool & lake view.

Outdoor spacesLocationNearby

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, 141 reviews

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

LocationOutdoor spacesCondition

4.97 out of 5 average rating, 126 reviews

A serene waterfront view reveals calm waters reflecting the clear blue sky. Lush palm trees line the water's edge, and nearby homes with red and brown roofs create a peaceful atmosphere. The scene invites relaxation and appreciation of the natural surroundings.

Home in Cape Coral

“Red Sunset”Waterfront.Gulf Access Heated Pool.

ValueLocationCheck-in

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, 76 reviews

Island Fun In The Sun! Water on 2 Sides

Outdoor spacesValueDecor

5.0 out of 5 average rating, 13 reviews

Home in Captiva

NEW! Beachfront!3BR Suites Sustainable Home+Dock

Outdoor spacesValueCleanliness

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

LocationFamilyNearby

The view features a serene canal surrounded by lush greenery and palm trees. A small boat is visible in the distance, illuminated by a gentle glow from the moonlight reflecting off the water. Soft clouds drift across the twilight sky, adding to the peaceful ambiance.

4.88 out of 5 average rating, 98 reviews

🌴ISLAND TIME! DOCK⚓️POOL🏊🏻‍♀️KAYAKS🛶Boat to Beach🏖 Pets

Outdoor spacesLocationParks

Cottage rentals with a kayak

4.93 out of 5 average rating, 57 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!

ValueLocationCleanliness

4.94 out of 5 average rating, 84 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 spacesLocationAccuracy

4.67 out of 5 average rating, 55 reviews

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

Villa The Island Hideaway 2

LocationOutdoor spacesHospitality

5.0 out of 5 average rating, 38 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 spacesLocationBack garden

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!

Outdoor spacesLocationParking

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 spacesQuiet

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

4.66 out of 5 average rating, 222 reviews

Captains Cottage

Outdoor spacesLocationCheckout

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

LocationOutdoor spacesWalkability

Other holiday rentals with a kayak

4.75 out of 5 average rating, 12 reviews

An aerial view of the resort features a two-story building surrounded by lush palm trees adorned with soft lighting. A wooden dock extends alongside the water, providing access for boating. The outdoor seating area on the patio appears inviting, with clear views of the tranquil surroundings.

Flat in St. James City

Waterfront Island Resort w/boat docking

Outdoor spacesLocationPets

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

Outdoor spacesLocationGetting around

5.0 out of 5 average rating, 22 reviews

Home in Burnt Store

Canal Front Home Heated Pool Private Dock

Outdoor spacesLocationFamily

A private hot tub is set on a patio overlooking a waterfront canal. The tub features white interior with multiple jets and a control panel. Lush greenery and palm trees surround the area, complemented by a clear blue sky and water view.

4.97 out of 5 average rating, 73 reviews

3br 2bath Waterfront hot tub bikes kayaks and dock

ValueOutdoor spacesBathroom

A charming coastal home is presented with a gravel driveway and lush greenery in the foreground. The exterior features light yellow walls and blue accents. A variety of palm trees and outdoor decor items enhance the inviting entrance that leads to the waterfront view beyond.

4.99 out of 5 average rating, 75 reviews

Fisherman's Cottage at Matlacha

Outdoor spacesLocationTV

A glass dining table with colorful chairs is positioned on a balcony, overlooking a calm canal. The sky is filled with hues of orange and pink, reflecting on the water's surface. Palm trees and waterfront homes are visible in the background, creating a tranquil setting.

5.0 out of 5 average rating, 61 reviews

The White Egret On Matlacha

LocationOutdoor spacesNearby

5.0 out of 5 average rating, 22 reviews

NEW!Pelican Paradise Retreat - Gulf Access

Outdoor spacesLocationComfort