Waterfront 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 the same canal, home has dock to tie up boat. Tandem Kayak + Paddle Board available

Gorgeous & Spacious 3/3.5, Incredible Water Views!

Incredible 3 bedroom 3.5 bath home with endless water views! This brand new renovated home offers so much space for the whole family. Two primary suites with king size beds, guest bedroom with 2 queens one with a twin trundle, back den with a foosball table, ping pong table that converts into a pool table, large lot with plenty of space for boat trailers and a small boat house with a lift that can hold up to 8k lbs and 20' boat or smaller and so much more! No pets if less than a week, $150 fee.

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.

Moon Shell Hideaway

Private entrance to your one bedroom plus den (with queen size sleeper/sofa) apartment attached to main house. Direct access to the Gulf of Mexico. Bedroom has a queen size bed and the den has a queen size sleeper/sofa. The den doubles as your kitchenette and sitting area with double sliding glass doors that open up to the shared pool and dock area. Gas grill and microwave for cooking (no stove). Boat to five restaurants. Visit the Matlacha Art Galleries. Fish off the dock. WELCOME!

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!

Blue Agave - *Ask About Summer Specials!*

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!

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.