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.

4.98 out of 5 average rating, 55 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 spacious bedroom features a large bed with a textured white coverlet and decorative pillows. Soft lighting is provided by two bedside lamps. A wicker bench sits at the foot of the bed, adorned with rolled towels. Natural light enters through a window framed by sheer curtains.

5 out of 5 average rating, 9 reviews

Quiet Island Get Away - Fishing, Relaxation & Fun

Bring the family! Plenty of space for boat, RV, motorcycle or jetskis! Fully renovated. Small beach around the corner. Fishing, marinas, launching close by. TARPON capital! Aquatic Preserves are excellent for kayaking and canoeing. Community pool $2 for seniors. (Not on property) Take ferry to beautiful beaches of Sanibel, Captiva and Cabbage Key. Quiet - no noise, no crowds and no traffic. "Country living". This is NOT the 24/7 night life of Miami. Thirty minute drive to Ft. Myers.

4.92 out of 5 average rating, 863 reviews

The charming exterior of the cottage is highlighted by a blue facade with white trim. Flower boxes adorn the windows, filled with lush greenery. A red door serves as a welcoming entrance. The patio area features stone pavers, surrounded by various plants and comfortable seating.

Tiny home in Fort Myers

Garden Cottage - Tiny House

PLEASE NOTE: The cottage is separate from our house and living quarters. The bathroom is in the back of the main house, just a few steps from the cottage, private and not shared with anyone. We take special precautions to thoroughly clean and disinfect the bedroom and bathroom after each guest. You’ll love our place because of the location, the ambiance, the outdoor space, and the neighborhood. We have a dog and a cat. Our place is good for couples, solo adventurers, and business travelers.

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, 13 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, 19 reviews

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!

Cottage in Saint James City

5 out of 5 average rating, 61 reviews

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!

Guest suite in Matlacha Isles-Matlacha Shores

A spacious pool area is viewed with a clear turquoise pool reflecting sunlight. Five lounge chairs are positioned around the pool, with a wooden dock extending towards the water. Lush greenery and potted plants add a natural touch to the surroundings.

4.85 out of 5 average rating, 365 reviews

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!

A spacious outdoor area is presented, featuring a sparkling pool surrounded by lounge chairs. Lush greenery is visible, along with a shaded seating area nearby. The sunlit sky creates a vibrant atmosphere, emphasizing the serene environment of the poolside space.

4.91 out of 5 average rating, 33 reviews

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.

A serene waterfront scene features two small boats gliding through calm waters, surrounded by lush palm trees. Nearby structures exhibit a mix of colors, with a sailboat anchored in the background, creating a peaceful atmosphere in the canal.

4.99 out of 5 average rating, 209 reviews

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.

Aerial view of a spacious waterfront home surrounded by lush greenery. The property features a heated pool with a spa and a tiki hut, offering an outdoor kitchen area. The home's modern architecture and large windows provide ample natural light, while the nearby dock ensures easy access to the water.

5 out of 5 average rating, 7 reviews

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!

A serene waterfront view features private docks with blue canopies, providing shade for two green lounge chairs. A small white boat is visible, securely positioned at the dock. Lush palm trees and a clear blue sky enhance the relaxing outdoor atmosphere.

5 out of 5 average rating, 29 reviews

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!

The pool reflects the two-story house, which features a spacious terrace above with ceiling fans and outdoor seating. White railings outline the property, and palm trees are visible nearby. The scene conveys a bright and inviting outdoor space for relaxation.

5 out of 5 average rating, 46 reviews

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

Popular amenities for outdoor seating rentals in St. James City

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.98 out of 5 average rating, 56 reviews

Spacious 3/2 50’ Dock-HotTub-Walk 2 restaurants

4.93 out of 5 average rating, 15 reviews

A modern single-story home is showcased with a neatly manicured front yard, featuring a stone driveway. The house is complemented by a covered entryway with double doors and two garage doors. Clear skies and palm trees provide a tropical backdrop.

Home in Bokeelia

Pine Island paradise, priced right.

A tranquil outdoor space features a heated saltwater pool surrounded by a screened-in lanai. Comfortable seating areas and a dining table are positioned within, enriched by lush greenery visible through the screens.

5 out of 5 average rating, 18 reviews

Pine Island Beach House! *Gulf Access, Heated Poo

4.96 out of 5 average rating, 50 reviews

A light and airy living area features a plush sofa with neutral-toned cushions, accompanied by a cozy armchair. A checkered rug defines the space, while a small plant adds a touch of greenery. Sunlight filters through the window, illuminating the inviting atmosphere.

Home in Fort Myers

Best Beach Cottage #2

Superhost

The view features a serene canal surrounded by lush greenery and palm trees. A small boat is visible in the distance, illuminated by a gentle glow from the moonlight reflecting off the water. Soft clouds drift across the twilight sky, adding to the peaceful ambiance.

4.89 out of 5 average rating, 85 reviews

🌴ISLAND TIME! DOCK⚓️POOL🏊🏻‍♀️KAYAKS🛶Boat to Beach🏖 Pets

4.9 out of 5 average rating, 160 reviews

Home in Fort Myers

Dive into Luxury: Stunning Tropical Home & Pool

A waterfront home elevated on stilts is shown, featuring a light-colored exterior and solar panels on the roof. Surrounding palm trees and shrubs enhance the outdoor space. A wooden boat dock extends into the water, providing access for boating activities.

4.94 out of 5 average rating, 64 reviews

Key West Style Home w/ Hot Tub & Boat Lift

Superhost

4.88 out of 5 average rating, 58 reviews

Sunset POOL Waterfront Kayak bikes fish from dock

Apartment rentals with outdoor seating

4.98 out of 5 average rating, 121 reviews

An open-concept living area features a light-colored sofa and dark gray armchair, arranged around a circular coffee table. A spacious kitchen with white cabinetry and modern appliances lines the back wall. Natural light filters through large windows, creating a bright and airy ambiance.

Flat in Fort Myers Beach

Fall Specials! Island Paradise Walk to the Beach

4.94 out of 5 average rating, 128 reviews

A spacious covered seating area features comfortable wicker furniture adorned with floral cushions. A small table sits in front, accompanied by a variety of tropical plants in the background, creating a relaxed outdoor atmosphere.

Flat in Fort Myers

Queen Palm-Lrg. 2nd flr. apt-Special Fall Price!

4.81 out of 5 average rating, 230 reviews

A welcoming entrance features a red door framed by green foliage and colorful flowering plants. A 'WELCOME' sign is positioned beside the steps leading to the door, inviting guests into the space.

Flat in North Fort Myers

Garden Villa

4.93 out of 5 average rating, 162 reviews

A bright and airy room features a spacious bed adorned with decorative pillows. A large window allows ample natural light and offers a view of the waterfront. Light-colored walls and furnishings create an inviting ambiance, enhancing the serene atmosphere of the space.

Flat in Cape Coral

Suite with lake view.

4.91 out of 5 average rating, 195 reviews

A screened-in pool area is visible, featuring a clear blue pool with a shallow entry. Sunlight reflects off the water, and a few chairs are arranged around the pool. A shaded outdoor kitchenette is in the background, with a fenced yard beyond.

Flat in Cape Coral

Private Apartment with sunny pool

4.96 out of 5 average rating, 206 reviews

The exterior of the duplex apartment is shown, featuring a well-maintained yard with grass and shrubs. A gravel driveway leads to a single-car garage, while a wooden fence adds privacy. The building is painted in a deep blue with a brown shingled roof under a clear blue sky.

Flat in Cape Coral

Debbie's

4.89 out of 5 average rating, 107 reviews

Flat in Fort Myers

Prime location, very private, nice & spacious

4.9 out of 5 average rating, 193 reviews

The entrance features a small front porch with two blue chairs and potted plants, enhancing the inviting appearance. The porch is accessed by three steps leading to a door with a decorative wall hanging. The green railing complements the natural surroundings of the yard.

Flat in North Fort Myers

Rabbit Hollow Charming guest house in the country

Apartment rentals with outdoor seating

4.88 out of 5 average rating, 192 reviews

An outdoor seating area is highlighted, featuring a table surrounded by four wicker chairs. A grill is positioned nearby, and the view opens to a serene waterway, complemented by lush trees and a bright sky scattered with clouds.

Apartment in Cape Coral

Lovely Gulf Access/Kayak, Beach, Tiki Bar & Grill.

4.95 out of 5 average rating, 63 reviews

Apartment in Punta Gorda

One bedroom condo - overlooking harbor!

4.83 out of 5 average rating, 115 reviews

A modern kitchen features light grey cabinetry and stainless steel appliances, including a coffee maker and microwave. Natural light illuminates the space through a window above the sink, which is complemented by a sleek blue faucet. The countertop provides ample workspace.

Apartment in Fort Myers

Cozy Coastal Escape. Close to FMB and Sanibel

4.89 out of 5 average rating, 250 reviews

A serene view of the Gulf of Mexico features soft waves lapping against a sandy shore, with clear turquoise water meeting an expansive blue sky. The adjacent image shows the condo's exterior with lush green landscaping, highlighting multiple units in a welcoming and well-maintained setting.

Apartment in Sanibel

Rare walkout condo on Sanibel beach-Fully Restored

4.93 out of 5 average rating, 106 reviews

The living area features a spacious light-colored sofa accompanied by a rustic coffee table. Large sliding glass doors allow natural light and views of palm trees outside. A flat-screen TV is positioned against a light-coloured cabinet, while a dining table for two is visible on the lanai.

Apartment in Captiva

South Seas Resort Beach Villa 🌴 On The Beach !

4.97 out of 5 average rating, 35 reviews

Apartment in Sanibel

Pickleball, beachfront, Amazing GULF VIEWS!

4.98 out of 5 average rating, 50 reviews

A spacious living area is defined by a soft area rug and wooden flooring. Furniture includes a light blue couch, white dining chairs, and a dining table set. Natural light filters through large sliding doors leading to a balcony, with decorative artwork enhancing the walls.

Apartment in Fort Myers

November special