Vacation 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!

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.

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.

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

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.

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!

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.

Blue Agave - 2/2 Pool w/Dockage

Experience laid-back Pine Island vibes at this newly renovated home! Relax with expansive waterfront views, a private pool with screened lanai, and a large dock with boat dockage available. Inside, enjoy a king bed in the master, queen bed in the guest room, and a sleeper sofa. With free laundry and a central location, it’s perfect for exploring local seafood, world-class fishing/boating, and the charm of St. James City. Book now for your tropical retreat!

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.

Tropical Sunset

Waterfront Retreat in Saint James City – 2BR/2BA Boater’s Paradise Welcome to your perfect getaway in sunny Saint James City, Florida! This charming 2-bedroom, 2-bathroom waterfront oasis that is on the 2nd floor is nestled on a peaceful canal with direct access to the Gulf—ideal for boaters, anglers, and anyone seeking relaxation by the water.