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!

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.

Sun Fish Island Retreat

Relax and enjoy the sun and serenity of this tranquil getaway. Bring your boat and take advantage of the boat ramp and slips on the Henley canal. Enjoy the local restaurants and live music or use the complete kitchen and grill to make your own special meals. Spend the day exploring the local attractions, or bring your water toys and explore the local waterways and islands. Very close to Matlacha, Great Calusa Blueway, The Colusa Heritage Trail, Galt preserve, and so much more!

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.

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! Matlacha had damage from Ian. Our new home - none. You can still walk to great restaurants, shops and the fishing bridge. Enjoy the water in Matlacha & the Barrier Islands. Use our 1 person kayak for fun or fishing from our 8'X22' FUN & SUN deck docked in the back canal with picnic table & loungers. Relax, sun, grill and fish.

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!

Whole cozy house

Entire cozy house just for you friends and family. Perfect to spend a pleasant and relaxed moment. If you plan to have a party or event, this place is NOT for you. The neighbors are very strict in terms of noise and large groups of people. Well maintained house. CLEAN POOL BUT NOT HEATED. Walk in to a living area and separated dining. 20 minutes to airport, 25 minutes to the beach, fine dining and entertainment. For a virtual tour, click on the cover photo twice.

Gulf getaway! Boat dock, heated saltwater pool

Welcome to @TheGulfGetaway an incredible canal-side home built to make memories. You'll enjoy the comfort of a fully equipped home and many outdoor activities. House is within walking distance from bars & restaurants and has quick access to the Gulf of Mexico & nearby islands of Sanibel, Captiva & Cayo Costa by boat. Centered in a quiet familial neighborhood, the location of the home makes it easy to get around. 1 hr from Ft Myers Airport

Dive into Luxury: Stunning Tropical Home & Pool

Escape to a tropical paradise in this stunning 1952 midcentury modern home, perfectly located in the heart of historical McGregor Boulevard - home to the famous palm trees planted by Thomas Edison. Indulge in delicious meals at local restaurants like McGregor Cafe and McGregor Pizza, or tee off at the nearby public golf course. And if you're looking to hit the beach or explore downtown, both are just a short drive away.

Surfside Elegance SW Cape Coral Luxe Vacation home

This elegant spacious 3 Bedroom + Den, 3 Bathroom house with split floor plan and large living room will truly make you feel home! High ceilings, a lot of natural light, large rooms, amazing Florida canal view, large heated pool. Fully remodeled in 2017 and feels like new. Location is amazing, close to Marina, Cape Harbour, restaurants. Excellent, beautiful and safe neighborhood. This home is perfect for your vacation!