Holiday rentals with outdoor seating in St. James City

A renovated home in a vibrant shade of green features a covered porch with outdoor seating. Palm trees provide a tropical ambiance, while a gravel area surrounds the property. Large windows allow natural light to enter, creating a welcoming entrance for guests.

4.99 out of 5 average rating, 70 reviews

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.

A serene waterfront scene showcases a vibrant sunset, illuminating the sky in shades of orange and pink. Reflections are seen on the calm water, with palm trees framing the view. A paddle board rests on the grass beside a small table and chairs, inviting relaxation.

5 out of 5 average rating, 17 reviews

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

5 out of 5 average rating, 29 reviews

Home in Saint James City

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.

5 out of 5 average rating, 10 reviews

Relaxing Paradise

Escape to peaceful St. James City in southwest Florida! This open-concept home sits on the quiet Henley Canal with direct Gulf access. Watch dolphins and manatees over morning coffee, then hop on your boat, Sanibel, Captiva, and Fort Myers Beach are just minutes away. Enjoy a private pool, private putting green, fire table, and outdoor seating. With a large living space, full kitchen, and walkable bars and restaurants, this getaway is perfect for fishing, relaxing, or exploring.

5 out of 5 average rating, 32 reviews

Home in Matlacha

Boater’s Paradise: No-Bridge Gulf Access & Pool

⚓ Direct Gulf Access (No Bridges): Cruise to open water! 🏊‍♂️ FREE Heated Pool: Waterfront views, zero daily heating fees. 🛏️ Group Oasis: 4BR | 3BA | 7 Beds (Sleeps 13 comfortably). 🎣 Outdoor Living: Fish from your dock, BBQ & spectacular sunsets! 🐾 Pets Welcome & Fast Wi-Fi! 🚙 Massive Parking: Room for boat trailers! 📍 Location: Heart of Matlacha, minutes to Cape Coral. ⚡ Prime season dates book fast. Lock in your direct water access and reserve your dates today.

5 out of 5 average rating, 15 reviews

Home in Saint James City

Fishing | Boating | Firepit | BBQ | King Beds

Escape to The Island, a newly renovated St. James City retreat near marinas, fishing, kayaking, boating, and ferry access to Sanibel & Captiva beaches. Unwind in the private backyard with a firepit, BBQ, and loungers, or relax inside with king beds, a modern kitchen, Smart TV, and coastal-inspired design. Plenty of parking for boats, RVs, and jet skis. Peaceful island living just 30 minutes from Fort Myers. If your dates are unavailable, explore our other nearby retreats.

A wooden dock extends over the calm water, lined with sturdy posts topped with black caps and ropes. The backdrop features a serene house with green grounds, surrounded by lush palm trees. A vibrant sunset casts warm colors across the sky.

4.97 out of 5 average rating, 70 reviews

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

A covered outdoor area features a thatched roof and a concrete floor leading to a waterfront. Noticeable are the boat lifts to the side, with calm waters reflecting the blue sky and clouds. Potted plants are positioned near the entrance, adding a touch of greenery.

4.9 out of 5 average rating, 40 reviews

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.

Superhost

A rectangular pool is featured in the foreground, surrounded by a spacious paved area. In the background, a wooden dock extends over the water, complemented by lush greenery and palm trees. Clear blue skies reflect over the tranquil water.

4.77 out of 5 average rating, 31 reviews

Beautiful 5/3 Pool, Saltwater Cove,Sleeps 10!

Luxury 5-Bedroom Home on Private Saltwater Cove with Stunning Views! Discover your dream waterfront retreat! This exquisite 5-bedroom home is perfectly situated on a private saltwater cove, offering breathtaking views and unparalleled tranquility. Step outside to your own brand-new pool and outdoor kitchen, perfect for entertaining. Enjoy alfresco dining and lounging in the beautifully designed outdoor space, complete with a TV for ultimate relaxation.

5 out of 5 average rating, 16 reviews

Seascape Casita. Gulf Access, Kayaks and Bikes

Welcome to Seascape Casita, your waterfront cozy getaway in the heart of Saint James City on Pine Island. Just 5 minutes to open water is the perfect place to enjoy the beautiful beaches like Sanibel and Captiva. Also enjoy natural wonders by kayak or get to know the city by using the bikes. The area is also well-known for excellent fishing 🎣 spots. “Watch our video 🎥 tour on YouTube — search for ‘Seascape Casita Airbnb tour’ on YouTube.”

A tranquil waterway is depicted with a wooden dock extending into the calm water. Lush green grass runs along the edge, complemented by blooming hibiscus flowers. Nearby houses can be seen in the background, framed by palm trees under a clear blue sky.

4.96 out of 5 average rating, 104 reviews

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.

A vibrant sunrise casts warm hues over the canal, reflecting the colorful sky on the still water. Lush palm trees frame the scene, with boats lined along the docks. The tranquil atmosphere suggests a peaceful start to the day.