Holiday rentals with a patio in St. James City

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

Island Retreat

Welcome to paradise in Pine Island, Florida! This stunning 3 bedroom, 2 bathroom house is the ultimate vacation rental for those seeking a tranquil and waterfront experience. Relax with the whole family at this peaceful retreat. Visit our IG page at PineIsland_Retreat for photos, information and vacation ideas. Long Stay Discounts applied for stays of 7 nights or more. Discounts vary by stay. Longer Stay, Greater Discounts! Early Bird Discounts available for 2026-2027 bookings. Book Today!

Tropical Island Paradise Awaits You

Discover Emerald Palms, a one-of-a-kind tropical retreat on historic Pine Island. Surrounded by lush gardens, seashell walking paths, and a sparkling private pool, this hidden gem feels like your very own island within the island. This custom cedar stilt home is thoughtfully decorated to evoke the timeless spirit of Ernest Hemingway’s island hideaways, offering a cozy, nostalgic ambiance with all the conveniences you need for a relaxing stay. More than a vacation home — it’s an experience.

Waterside Cottage

Enjoy our peaceful little island paradise nestled beneath sprawling oaks and scattered palms just minutes from St James City’s restaurants and bars. Nearly 1/2 acre is yours to enjoy. Watch the manatees and dolphins swimming in the canal while you grill your catch of the day, or your fresh pick of the day from St James Fish House just down the street! Inside enjoy a fresh new contemporary and stylish cottage with everything you will need to make your stay comfortable, enjoyable and fun!

Island Time Private Poolside Retreat !

Welcome to Island Time! Enjoy all that Pine Island has to offer from this comfy poolside, waterfront ground level apartment with private entrance and boat dock access. Enjoy lounging at the private pool or BBQing on the patio. 15 miles of bike/walking trails are accessible from the front door, and several waterfront tiki bars and restaurants are within walking distance. Captiva, Sanibel and Fort Myers Beach are a short boat ride away. Explore Cape Coral, Fort Myers and nearby state parks.

Waterfront Retreat• Sunsets • Pool• Dock•Kayaks

If you’re looking for a place to slow down and soak up the sun, where mornings start with coffee on the dock and evenings end with sunsets over the canal, this is your place. Welcome to Sprocket Boathouse, a beautiful waterfront retreat with panoramic canal views. Spot turtles, herons and iguanas from your own private dock, spend the day fishing and kayaking, or unwind in the heated pool made for lazy afternoons. It’s the kind of place that makes you want to stay just one more night.

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!

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!

Tranquility, pool, ocean access, boat lift

Mins to ocean, 2 BR + Den, 3 Baths, private pool, end of Monroe channel, boat lift for up to 21 ft, watch dolphins, fish right off the dock, kayaks, boat ride only mins from Sanibel and Fort Myers Beaches, all the amenities of home + board games, Playstation, 2 adult bikes with helmets. Unwind, enjoy the sunny outdoors with a bar and private pool deck – watch sunsets, sip cocktails, spot dolphins, fish from the docks. Come enjoy waterfront living at its finest!

Gulf getaway! Boat dock, heated saltwater pool

Welcome to @TheGulfGetaway an incredible canal-side home built to make memories. You'll enjoy the comfort of a fully equipped home and many outdoor activities. House is within walking distance from bars & restaurants and has quick access to the Gulf of Mexico & nearby islands of Sanibel, Captiva & Cayo Costa by boat. Centered in a quiet familial neighborhood, the location of the home makes it easy to get around. 1 hr from Ft Myers Airport

cozy 1st floor apartment

wonderful first floor efficiency. 400 sq ft. includes bedroom, bathroom with shower and livingroom with fridge, airfryer oven that bakes, toasts and reheats. induction burner with frying pan and stock pot. all utensils and dishes and drinking glasses. kuerig. under cover parking. kayaks, fishing poles and bikes right on the water. your own parking spot under cover right next to the apartment. the upstairs unit has its own driveway.

Pine Island canal home with boat access to Gulf.

Enjoy your morning coffee with spectacular sunrises looking down the canal. Typical Florida landscaping with palm trees, hibiscus, mango, avocado, orange, lime, lots of banana trees. Screened in Heated Pool and attached Spa. Private Dock with 7000 lb. boat lift. Direct access to Gulf of Mexico. Large kitchen, Enclosed patio with dining , 3 bedrooms 3 1/2 baths. large driveway with plenty of parking for cars, trailers.