Holiday rentals in St. James City

Pine Island Beach House! *Gulf Access, Heated Poo

Welcome to the "Blue Marlin"! St. James City on Pine Island is a fishing and boating community with old Florida charm! This 2-bedroom, 2-bathroom canal front, direct Gulf access vacation home located in St. Jude Harbors features a fully equipped kitchen and wonderful outdoor space with a place to dock your boat to provide a true maritime experience. Spend your days lounging by the heated saltwater pool or rent a boat to head out on the water. At the end of the day grill some hamburgers or stea

Island Castaway--Free Kayaks

This is the perfect place to sit back, relax and enjoy the view. You have the privacy of a one-bedroom apartment with small kitchen and bath. We are close to great restaurants and some of the best music on the island. Open water and excellent fishing are minutes away. Two kayaks are set up for fishing and are available for guests to use so bring your fishing rod. Pine Island has no beachs, but Ft Myers Beach is about an hour away or take a ferry ride from Bokeelia to Cayo Costa for the day.

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.

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.

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!

The Green Cottage in Matlacha

The Matlacha Cottages been completely gutted and redone twice. Beautiful galley kitchen, new queen sized bed, panoramic sunset views, and a private bathroom with newly tiled shower. We offer Roku TV, and WiFi. Work remotely here and get inspired! Shared back yard and patio spaces to enjoy the water and sunset views! Close by is Pine Island Community Pool, $3 entry. Loungers available. BYO kayaks book airbnb.com/h/pinkmatlacha if this cottage isn’t available or if you need more space!

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.

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!

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.

Reel Teal – Luxe 2BR Waterfront Getaway

Reel Teal is a stunning 2BR/2BA retreat in St. James City, FL, designed for comfort and coastal living. Enjoy high-end finishes, a spacious screened lanai, and perfectly manicured landscaping. Boaters will love the private dock, fish cleaning station, and unbeatable access to open water and the Gulf. Whether you’re relaxing in style or setting out on a boating adventure, Reel Teal offers the perfect Pine Island getaway.