Holiday rentals with a fire pit in St. James City

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!

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.

Private farmhouse stay at Dim Jandy Ranch.

Take it easy at this unique and tranquil getaway. A beautifully appointed bed and bath in a separate building from the house. We have goats, donkeys and chickens and a Highland cow, all super friendly. Sit and relax on your private, beautiful lanai or any of our farm tables placed around the property. Join us as we feed the animals. Or even join in one of our Goat Yoga classes! We're easily located close to I-75, airports, shopping, beaches, downtown. Perfect for couples or solo travelers.

Cozy Cottage on the Farm

*Adult Only* cozy cottage on a beautiful horse farm in St. James City, Pine Island, FL. Close to dining, and a variety of boating, fishing, & water activities. Visit the famous Matlacha Bridge to cast a line or take a stoll in one of the nature preserves right on the island. Grab a water taxi to visit surrounding sister islands with beautiful, secluded beaches. Check out our guidebook for places to eat, things to do, and best ways to get there. (Guests over 25 only; (2) persons max occupancy.)

Waterfront Matlacha views! 2/2 Heated Pool Home

Experience old Florida island living at this incredible waterfront cottage home on Matlacha Island featuring massive waterfront views, a huge private heated pool, an authentic Seminole Indian Cheekee hut, and your own private boat ramp. This is not just a canal cottage it’s a full waterfront lifestyle property designed for relaxation & entertaining with unforgettable views & memories! This "turnkey-furnished" 2-bedroom, 2-bath retreat blends comfort with classic Florida Keys island character.

Inn Season Cottage-Cozy Florida Living

Welcome to the Inn Season Cottage...where relaxation, family time, and sunshine are always "INN" season. Experience cozy Florida living in this newly renovated 1250 sq. ft. home located in the desirable McGregor Corridor. This home is nestled within a quiet neighborhood and provides a relaxing setting for your family to unwind and make memories together. It is the ideal location for seasonal visitors looking to stay during the winter months, a small family vacation, or a couples getaway.

The Sweet Escape

Welcome to a little slice of paradise… You’re on island time now. Tucked back in a quiet neighborhood, this perfect little getaway provides the ultimate relaxation. Soak up some sun and sip libations while laying out at the heated saltwater pool surrounded by lush vegetation. Enjoy all the beautiful wildlife that frequent the property. Visit the tiki bars with nightly live music, drop the boat at the nearby ramp for world class fishing and miles of pristine beaches, and catch an epic sunset.

Island Getaway

Bring the whole family to this great place with lots of room for fun. House directly on canal to ocean with manatee and dolphins right at the dock! Biking, walking trails, kayaking, bring your own boat or jet skis, access to ocean short trip from the back yard canal access. Sit and enjoy sunsets from dock nightly! Outside dining area and upstairs patio give you great views of all that nature has to offer! Bring your telescope to star gaze. Enjoy the ocean breeze and views from all rooms!

Relaxing Paradise

Escape to peaceful St. James City in southwest Florida! This open-concept home sits on the quiet Henley Canal with direct Gulf access. Watch dolphins and manatees over morning coffee, then hop on your boat, Sanibel, Captiva, and Fort Myers Beach are just minutes away. Enjoy a private pool, private putting green, fire table, BBQ, and outdoor seating. With a large living space, full kitchen, and walkable bars and restaurants, this getaway is perfect for fishing, relaxing, or exploring.

Fishing | Boating | Firepit | BBQ | King Beds

Escape to The Island, a newly renovated St. James City retreat near marinas, fishing, kayaking, boating, and ferry access to Sanibel & Captiva beaches. Unwind in the private backyard with a firepit, BBQ, and loungers, or relax inside with king beds, a modern kitchen, Smart TV, and coastal-inspired design. Plenty of parking for boats, RVs, and jet skis. Peaceful island living just 30 minutes from Fort Myers. If your dates are unavailable, explore our other nearby retreats.

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.”

Dive into Luxury: Stunning Tropical Home & Pool

Escape to a tropical paradise in this stunning 1952 midcentury modern home, perfectly located in the heart of historical McGregor Boulevard - home to the famous palm trees planted by Thomas Edison. Indulge in delicious meals at local restaurants like McGregor Cafe and McGregor Pizza, or tee off at the nearby public golf course. And if you're looking to hit the beach or explore downtown, both are just a short drive away.