Waterfront holiday rentals 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.

View · River · Getting around

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

View · Beach · Nearby

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!

Beach · View · Indoor spaces

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, and outdoor seating. With a large living space, full kitchen, and walkable bars and restaurants, this getaway is perfect for fishing, relaxing, or exploring.

Beach · Kitchen · Hospitality

Waterfront Retreat, Sleeps 8, Resort Style Pool

🌴 In July a Lemonade – Your Perfect Island Escape in St. James City! Welcome to your perfect island escape in St. James City! This stylish waterfront home has everything you need for a relaxing and fun-filled stay. You’ll be just minutes from great local restaurants, local marinas, and right on the water for easy access to Pine Island Sound and beyond. Whether you’re boating, biking, or just lounging by the pool, this home is your ideal base for a laid-back Florida vacation.

View · Beach · Pool

​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.

Beach · View · Layout

Charming 2-BR Home w/ AC, Dock & Peaceful.

Discover this charming 2-bedroom waterfront home in peaceful Saint James City. Each bedroom features a comfortable queen bed, plus a cozy living room with a sofa bed for extra guests. With 2 full bathrooms, everyone enjoys space and privacy. The home offers air conditioning and heating for year-round comfort. Relax indoors, unwind by the water, or plan your next island adventure from this inviting home away from home. We’re always happy to share local recommendations.

View · Pool · Outdoor spaces

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.

Beach · View · Access

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.

View · Beach · Outdoor spaces

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.

View · Beach · Location

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.”

View · Beach · Kitchen

2 Bedroom Island Oasis Getaway

Hi to all of our past & future guests. Our home is such a great place to stay, we are just steps from the water, fishing & the beautiful sunsets. We have space for your boat or you can rent one locally. Completely remodeled home as of March 2022, there is a master bedroom and a 2nd bedroom along with a large bathroom. Guest will have access to the entire house including the lanai, patio, boat dock, boat ramp and parking.

View · Beach · Kitchen