Holiday rentals with a patio 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!

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.)

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!

Key West Style Home w/ Hot Tub & Boat Lift

KEY WEST style stilted waterfront home in the heart of Matlacha! Visit all there is offer - walking distance to Blue Dog and Perfect Cup. Take a boat ride to Cabbage Key, Cayo Costa or Boca Grande! Upstairs and downstairs are screened in. The second floor is peaceful and tranquil overlooking the water and treetops. Home is a 2 bedroom, 2 bathroom, with additional bonus space with trundle bed. Home is perfect for boaters with double driveway, complimentary boat lift and cleaning station.

Studio in Paradise

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 resort style pool surrounded by lush vegetation. See the beautiful wildlife that visits the property. Take a short drive to the best tiki bars with nightly live music, or drop the boat at the nearby ramp for some world class fishing and miles of pristine beaches.

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.

Waterfront Pool Home. Minutes to Sanibel & Beaches

Where prime location meets tropical paradise. Welcome to your very own lakefront, poolside oasis, less than 10 minutes from the beach! Close to Sanibel Island, Fort Myers Beach & Bunche Beach, as well as local shopping, amazing restaurants, fun nightlife in Downtown Fort Myers and the winter homes of Thomas Edison & Henry Ford. Fully renovated throughout. The perfect destination for a family or friends vacation!

Private Hot Tub | King Bed Loft | Hammock Swings

🛜500mbps+ WiFi 🏠Fully private + Private entrance 🌴Hammock Swings ☀️ Outdoor Patio 🦩Private Hot Tub 🥑Kitchenette w/ electric hot plate 😴King Size Bed Loft 📚Work Desk 📺 55 inch Smart TV + Roku ❄️ Cold A/C 🚘 1 parking space NOTE: Accessing the bed requires climbing a ladder. While sturdy and secure, it may not be suitable for guests with mobility limitations, so please consider this before booking.

Matlacha Waterfront Home | Gulf Access & Pool

Experience Matlacha from this stunning waterfront home with direct Gulf access, a heated private pool, a spacious dock, and a boat lift. Bright, refined, and deeply relaxing, it’s the perfect coastal escape for families and friends. Wake up to still waters, enjoy warm swims under the sun, and end each day with the kind of peaceful, unforgettable evenings that make you never want to leave.