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.

Tropical Paradise! Gorgeous 3/3 Pool Home!

Zuzu’s Fancy is a wonderful 3 bedroom, 3 bathroom home in a quiet St. James City. This home is sure to please with its beautiful coastal décor and comfortable furnishings. Dolphins are often seen playing in the back canal while manatees swim in the front canal by the fire-pit. This home offers a screened in porch overlooking the canal, with a large Tiki Hut and large outdoor area. Bring your boat! You’ll find a great canal side dock complete with water and electric. *Pet friendly $150 applies

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!

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!

Waterfront 5 Star Getaway With Dock and Lift

Enjoy a peaceful stay at this 2-bedroom house in Saint James City. The cozy bedrooms feature 2 queen beds, perfect for a good night's sleep. RV & Trailer parking. With amenities like a washing machine&dryer, WiFi, and AC, guests can relax and unwind. Bring your boat, or enjoy dock in Saint James City. Bring your boat and fishing rods. Snook, Redfish, Snapper and Tarpon off our dock. Manatees and dolphins occasionally.Boat dock and included. Also there is a wheelchair elevator lift.

Matlacha Paradise! NEW Waterfront Home-Free Kayak

Matlacha is for LOVERS! Lovers of relaxation, fishing, art, friends, social scenes and enjoying Life in a beautiful location ON THE WATER! There could be occasional Post Hurricane construction noise on surrounding properties during February and March. Should there be any issues we will work with you in resolving them. Enjoy the water in Matlacha & the Barrier Islands. Fish, Sun and Kayak from our 8'X22' FUN & SUN deck docked in the back canal with picnic table & loungers.

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!

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!

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.