House holiday rentals in St. James City

An outdoor heated pool is enclosed within a screened patio, featuring a spacious deck with lounge chairs. Lush greenery surrounds the area, and sunlight fills the space, creating an inviting atmosphere for relaxation. The pool's clear water reflects the bright blue sky above.

4.95 out of 5 average rating, 115 reviews

McGregor’s Gem• Heated Pool 3BR/2BA River District

🌴 Welcome to McGregor’s Gem—your ideal Southwest Florida retreat! Dive into relaxation in your private heated pool, spread out across three bedrooms and two baths, and enjoy the perfect blend of peaceful tree-lined neighborhood living just minutes from the charming Downtown Fort Myers River District, world-class beaches, and top local attractions.☀️ Whether you’re traveling with family, friends, or on business, this home offers all the modern comforts you need for a relaxing, stress-free stay

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, 58 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.

5 out of 5 average rating, 4 reviews

Home in Matlacha

Lux Oceanfront Island Oasis Fish Kayak Paddleboard

Escape to this tropical Island Oasis perched on the Gulf. Watch dolphins from your balcony! This spacious oceanfront gem comfortably sleeps 8 - perfect for families or groups. Relax in this unique retreat, only steps from fishing, boating, kayaking, and the Old Florida charm of Matlacha's seafood, art galleries and restaurants. Enjoy stunning water views from every room, a fully equipped kitchen, two fully stocked coffee stations and modern amenities. Your ultimate waterfront getaway awaits!

A spacious living room is furnished with a sectional sofa and decorative pillows. A large window fills the space with natural light, surrounded by indoor plants. A flat-screen TV is positioned on a red table, offering local and national programming options.

4.81 out of 5 average rating, 310 reviews

Amazon Bungalow near Sanibel & Fort Myers Beach

Tropical setting. Peaceful/quite neighborhood. Bunche Beach 2 miles, Sanibel Island 3.5 miles, Fort Myers Bch 5 miles. Home is set up as a duplex, with TWO COMPLETELY SEPERATE & PRIVATE entrances, kitchens, living rooms, bedrooms, bathrooms & laundry rooms for COMPLETE PRIVACY. The Bungalow is a 1 King bed, 1 full bathroom & shower with large living room, kitchen & porch. Perfect for Couples! • 1/2 mile to Restaurants and Shopping • Close to Shellpoint Golf-Course • FREE Wi-Fi and Cable-TV

5 out of 5 average rating, 20 reviews

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.

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, 35 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, 210 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, 9 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!

4.94 out of 5 average rating, 365 reviews

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.

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

A spacious bedroom features a wooden bed with a light-colored blanket and accent pillows. Natural light streams through two windows and French doors, highlighting the wood flooring and area rug beneath the bed. A decorative lamp and a nightstand add to the room's charm.

4.94 out of 5 average rating, 188 reviews

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!

The screened-in pool area features a sparkling swimming pool surrounded by a spacious deck. Natural light filters through the mesh enclosure, reflecting off the water. Outdoor seating is provided by a small table and chairs, with trees framing the serene backdrop.

4.95 out of 5 average rating, 131 reviews

Waterfront Home w/ Pool. Minutes to Sanibel

Where prime location meets tropical paradise. Welcome to your very own lakefront, poolside oasis, less than 10 minutes from the beach! Close to Sanibel Island, Fort Myers Beach & Bunche Beach, as well as local shopping, amazing restaurants, fun nightlife in Downtown Fort Myers and the winter homes of Thomas Edison & Henry Ford. Fully renovated throughout. The perfect destination for a family or friends vacation!

Popular amenities for St. James City house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A covered outdoor space features a heated saltwater pool bordered by wide stone tiles. Comfortable lounge seating is seen under an umbrella nearby. Lush greenery and canal views are visible beyond the pool area, offering a serene setting for relaxation.

5 out of 5 average rating, 61 reviews

Coastal Cowgirl - Heated Pool

A spacious open-concept living area is showcased, featuring a modern kitchen with an island and sleek cabinetry. Large glass doors provide abundant natural light and views of the outdoors. Rustic wooden beams contrast with the contemporary décor, highlighting both elegance and comfort.

4.91 out of 5 average rating, 68 reviews

AquaLux Smart Home

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.

4.9 out of 5 average rating, 89 reviews

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

A clear blue pool is surrounded by a spacious patio, featuring comfortable loungers partially immersed in the water. The inviting outdoor space overlooks the serene canal, while the covered lanai offers additional seating options. Lush palm trees sway gently in the background under a bright sky.

4.97 out of 5 average rating, 128 reviews

Boater’s Paradise-Stunning Sunsets! Games Room!

4.9 out of 5 average rating, 119 reviews

Cape Serenity- Luxury Waterfront Residence

An aerial view showcases a spacious home surrounded by lush greenery and waterways. A screened pool is visible in the backyard, alongside ample outdoor space. Nearby canals meander through the neighborhood, highlighting the serene location with accessible waterfront and scenic views.

4.89 out of 5 average rating, 9 reviews

The Best Kept Secret! #SJC

The living room features a spacious sectional sofa, providing ample seating. Large glass doors open to the outdoor area, enhancing natural light. A mounted TV displays beach scenery, while a modern fireplace adds a touch of warmth. The room's design promotes comfort and relaxation for guests.

4.98 out of 5 average rating, 121 reviews

2 Kings, Pool, Gulf Canal, Game Room and Kayaks

4.95 out of 5 average rating, 138 reviews

A serene beach scene showcases smooth, soft sands meeting the gentle waves of a turquoise ocean. A piece of driftwood rests in the foreground, complementing the clear blue sky and tranquil waters that stretch into the horizon.

Home in Captiva

Steps to Beach Captiva Includes CLUB & Golfcart

Weekly house rentals

The exterior of a charming home is showcased, featuring tropical palm trees and vibrant bougainvillea bushes. A large sliding door is present, allowing natural light to brighten the interior. The textured white walls contrast with the greenery, creating a relaxed atmosphere.

4.93 out of 5 average rating, 40 reviews

Sunny Island Cottage w/ Large Patio

A dining area features a white table surrounded by six chairs, topped with blue placemats. A decorative vase filled with flowers sits in the center. The walls are lightly colored and display a wall sign that reads 'RELAX.' Pendant lights provide warm illumination.

4.93 out of 5 average rating, 14 reviews

The Little Yellow Retreat with boat parking

A peaceful waterfront view is captured, featuring a wooden dock extending into deep water. The serene water reflects the blue sky and clouds above. Palm trees and nearby structures enhance the coastal scenery, creating a pleasant atmosphere for outdoor activities.

4.82 out of 5 average rating, 11 reviews

Priceless Waterfront Escape in Matlacha

A spacious deck is shown overlooking calm waters, with two reclining lounge chairs positioned for relaxation. Various homes and palm trees can be seen along the waterway, while a bright sky filled with wispy clouds creates a serene backdrop.

5 out of 5 average rating, 19 reviews

Matlacha waterfront home

A two-story house with a light-colored exterior and a metal roof is showcased under a bright blue sky. Lush tropical landscaping surrounds the property, including palm trees. A paved driveway leads to the two garage doors at the front of the home.

5 out of 5 average rating, 31 reviews

Peaceful Lakeview Retreat / Screened Porch & Bikes

A bright living area features a navy blue sofa positioned against a turquoise wall. A light-colored coffee table rests on a patterned rug, while decorative nets hang from the ceiling, adding texture. Colorful wall art and vibrant accents enhance the coastal theme of the space.

4.75 out of 5 average rating, 51 reviews

Funky fish house

An aerial view of the serene waterfront property showcases a south-facing pool and hot tub, framed by a screened-in lanai. The spacious dock features various seating arrangements, including loungers and a shaded area, all set against the tranquil canal backdrop, enhancing the outdoor experience.

5 out of 5 average rating, 15 reviews

Pool, Hot Tub, Kayaks, Dock & Canal w/ Gulf Access

A modern kitchen is showcased with white cabinetry and gray granite countertops. Stainless steel appliances, including an oven and microwave, are visible. Ample natural light enters through a window, complementing the open layout, which is designed for convenience and functionality.

4.83 out of 5 average rating, 12 reviews

Waterfront Gulf-Access Getaway With Dock and Lift

Private house rentals

An inviting outdoor space features a patio with comfortable wicker chairs arranged around a gas fire pit. Floor-to-ceiling screens provide a view of the sparkling pool and canal, enhancing the serene waterfront setting.

4.95 out of 5 average rating, 40 reviews

Gulf Coast Retreat: 3BR Waterfront | Heated Pool

An open-concept kitchen and living space are featured, with a spacious island that includes seating for four. Natural light fills the room through large windows. Light-colored cabinetry and tiled floors enhance the contemporary ambiance, while a welcoming decorative sign and fresh flowers add touches of warmth.

5 out of 5 average rating, 4 reviews

Charlie's of Bokeelia

A serene waterfront view features a calm canal with a covered boat lift in the foreground. Lush palm trees line the banks, and boats can be seen in the distance. The clear blue sky is adorned with soft white clouds, reflecting on the tranquil water surface.

4.98 out of 5 average rating, 64 reviews

Island Cottage in Matlacha, Amazing!

5 out of 5 average rating, 6 reviews

Home in Punta Gorda

Pirate's Cove

An open living area features a spacious arrangement of light-colored furniture, including a large leather sectional and armchairs. A modern fireplace and flat-screen TV are positioned on a textured feature wall. Natural light floods the space through expansive glass doors that overlook the pool area.

4.98 out of 5 average rating, 44 reviews

Villa Sunset Serenade II

An outdoor pool area features a thatched-roof structure providing shade. A spacious swimming pool reflects sunlight, while a person enjoys a swim. Surrounding seating areas include lounge furniture and a dining area, all set against a backdrop of palm trees and greenery.

4.94 out of 5 average rating, 31 reviews

Boater’s Paradise in Bokeelia!

A scenic view of the canal-side property showcasing a wooden dock with a boat lift, surrounded by lush tropical vegetation. Sun loungers are placed on a manicured lawn, and the house's screened-in porch is visible, highlighting the tranquil waterfront setting.

5 out of 5 average rating, 40 reviews

Waterfront Oasis with Boat Lift & Hot Tub