Vacation rentals with a kayak in St. James City

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Top-rated kayak rentals in St. James City

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Top guest favorite

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.

Home in Saint James City

4.98 out of 5 average rating, 52 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.

Top guest favorite

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.

Home in Saint James City

5 out of 5 average rating, 11 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 the same canal, home has dock to tie up boat. Tandem Kayak + Paddle Board available

Guest favorite

A cozy outdoor entrance features double French doors framed by a decorative awning. A wicker chair sits alongside a potted plant and a lantern, while a small wicker table with a potted lemon tree adds a touch of greenery. The tiled patio offers a welcoming atmosphere.

Guesthouse in Fort Myers

4.89 out of 5 average rating, 105 reviews

1920s Private Charming Cozy Tiny Home

Discover this charming 1925 stand-alone house in a scenic river-view neighborhood, close to eateries & shops. Enjoy private parking, security system, Wi-Fi, &Smart TV. Just 2 miles from vibrant downtown river district with dining, art, shops, music, & museums. Nearby amenities include; public golf course (.5 mi), community pool (1 mi), laundry (2 mi), and several beaches (5 mi). Experience tranquility and modern updates in this cozy 366 sq ft home, discreetly located behind a private residence.

Top guest favorite

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

4.99 out of 5 average rating, 224 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!

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, 159 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!

Guest favorite

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

4.95 out of 5 average rating, 128 reviews

Steps To Private Beach Captiva Includes Golfcart

Relax and Reconnect at Our Charming 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 (with applicable fees), it’s easily accessible by ferry, boat, or plane. With beach gear, access to the club pool, and unbeatable proximity to the beach start making memories!!

Guest favorite

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

4.9 out of 5 average rating, 121 reviews

Blue Laguna - Vacation in paradise!

Beautiful and welcoming are just two words to describe this magnificent, 4 story home with heated private pool and sweeping 360 degree water views from the observation deck. Blue Laguna features 3 bedrooms and 3 full baths allowing this home to sleep up to 6 people. Two screened in lanai's so you can sit and enjoy the island breeze and leave the sliding doors open for a true island nature experience during the colder seasons. A golf cart for 4 persons is also included in the rental.

Guest favorite

A spacious pool area is viewed with a clear turquoise pool reflecting sunlight. Five lounge chairs are positioned around the pool, with a wooden dock extending towards the water. Lush greenery and potted plants add a natural touch to the surroundings.

Guest suite in Burnt Store

4.85 out of 5 average rating, 361 reviews

Moon Shell Hideaway

Private entrance to your one bedroom plus den (with queen size sleeper/sofa) apartment attached to main house. Direct access to the Gulf of Mexico. Bedroom has a queen size bed and the den has a queen size sleeper/sofa. The den doubles as your kitchenette and sitting area with double sliding glass doors that open up to the shared pool and dock area. Gas grill and microwave for cooking (no stove). Boat to five restaurants. Visit the Matlacha Art Galleries. Fish off the dock. WELCOME!

Top guest favorite

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.

Home in Pelican

4.97 out of 5 average rating, 114 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!

Top guest favorite

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.

Home in Saint James City

5 out of 5 average rating, 15 reviews

Brand New in Saint James City

Brand new sparkling clean 2/2 canal waterfront in desirable Cherry Estates/St. James Isles; use of boat lift included. additional landscaping, driveway upgrades, fencing and other minor updates planned for September, 2024 but not guaranteed; parking space for boat and trailer, room in shed for bikes, close to restaurants, boat ramp, general store, bait/tackle shops. Local boat and golf cart rentals available; no bridges boating to Sanibel, Cayo Costa and other beaches.

Top guest favorite

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 Matlacha

4.99 out of 5 average rating, 207 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.

Top guest favorite

A serene view of a heated pool reflects the warm colors of a sunset, framed by lush palm trees. The screened enclosure provides an unobstructed view of the natural surroundings, enhancing the private and tranquil atmosphere of the outdoor space.

Guest suite in Saint James City

4.98 out of 5 average rating, 115 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 canal. 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!