Family-friendly holiday rentals in St. James City

Mojito Island Cottage

Update: In September 2022 we were affected by Hurricane Ian. We had just over 5 feet of flooding in our treasured cottage. We have worked tirelessly to put everything back together. All new tile, walls, electric, lighting, furniture, and we even improved the bathroom! Spacious tropical home with water view from our back yard lanai. Boat Dock with Cleaning Fish Station, BBQ beautiful sunsets with fish jumping in our canal. New large kitchen and one block from art galleries, restaurants and bars.

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.

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

Luxury Canal Villa •Pool •Kayaks •Fishing •Arcade•

Sprocket Boathouse sits along one of Cape Coral’s widest canals, with beautiful western sun exposure. Spend your days lounging by the heated pool, (no extra fees), paddling through the canals with our complimentary kayaks, or casting a line off your own private dock. Keep an eye out for turtles and iguanas and enjoy unforgettable sunsets right from the backyard. Fire up the BBQ with propane ready to go, or head inside where you can enjoy our retro arcade games and vintage vinyl collection.

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!

Steps to Beach Captiva Includes CLUB & Golfcart

HOST PAYS AIRBNB FEE FALL 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

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!

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.

Casa Baybreeze - Luxury on Water

Escape to paradise in this spacious 3BR/2.5BA waterfront pool home in St. James City, FL! Features include a designer kitchen w/ gas range, coffee bar, luxe appliances, pool table, heated pool & spa w/ waterfall, tiki hut w/ outdoor kitchen, and gulf-access dockage—just 5 mins to open water! Enjoy world-class fishing, tropical vibes, and walkable island dining. The master suite boasts a private terrace, bath & walk-in closet. This is Pine Island living at its finest!