House holiday rentals in St. James City

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 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!

2/2 The Sea-Batical ~ Waterfront Dream Escape

Keep it simple at Sea-Batical’s waterfront 2/2 with den + a bonus flex-space garage 🌴 The Sea-Batical is beautifully designed and fully updated dream escape located in Saint James City. Surrounded by peaceful preserves and just a short drive to the local restaurants and bars. Wake up to dolphins 🐬 swimming in the backyard or eagles 🦅 flying above. Bring your boat - we’re located off the 8th Street Canal or just your suitcase because you’re sure to get a break here!

Island Fun In The Sun! Water on 2 Sides

Water front, bring your boat! . Sit on tiki deck and watch the sunrise with your first cup of coffee or the dolphins. Kayak through the canal ways of Pine Island. Book a fun kayak,canoe tour or rent a golf cart or set up a fishing excursion. Buy all your fresh Catch of the Day at Island Crab Seafood Mkt. Or fish off of our dock out front. Ft Myer & Sanibel beach is hour drive away. No parties or pets. Dock & open water access out front. Adults only due to water front

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!

Hidden Gem of South West Florida

Enjoy your gulf access waterfront paradise in quaint Saint James City, Florida. A beautiful community to bask in the sunshine, enjoy some fishing, hike a trail in the Galt preserve or enjoy dinner and music at local restaurants, just minutes away. 2 Kayaks and 2 bikes for your use to explore or fish. Enjoy the beautiful warm Florida day & catch breath taking sunsets from the dock. You may even catch some Manatees or Dolphins hanging out in our back yard.

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.

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.

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.

Lime Life Villa, Retro Escape with Hot Tub!

Lime Life Villa – Retro Waterfront Escape in St. James City Welcome to Lime Life Villa, your slice of laid-back island life in sunny St. James City, Florida! Just steps from Tropical Point Park, this charming off-water retreat blends vintage 70s Florida style with modern comforts — perfect for boaters, beach lovers, and anyone chasing that “lime life” vibe.