House holiday rentals in St. James City

4.95 out of 5 average rating, 111 reviews

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.

Home in Fort Myers

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, 56 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.

The screened-in pool area features a serene swimming pool with shimmering water, two blue lounge chairs positioned nearby, and views of a wide canal. A thatched-roof Tiki hut can be seen across the water, surrounded by lush greenery.

4.99 out of 5 average rating, 232 reviews

LUX Villa w/ Private Salt Water Pool, Lanai, Canal

Are you looking to swim, relax outdoors, fish and take in beautiful sunsets on a wide gulf access canal? If so you will fall in love with this stunning newly constructed custom built home! The 2750 square foot home is bright & airy with two main bedroom on-suites & a separate family wing! The gourmet kitchen, dining room & great room open via large sliders to the lanai & pool w/ views of the canal in much desired SW Cape! Beach inspired villa! Large captains walk & Tiki! Check out our reviews!

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, 20 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!

5 out of 5 average rating, 17 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.

Superhost

A round outdoor table with four metal chairs is positioned on a concrete patio. Surrounding plants add greenery to the setting, creating a relaxed outdoor dining area. The ground features gravel and a few decorative stones, enhancing the natural ambiance.

5 out of 5 average rating, 3 reviews

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!

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.

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

A shaded seating area features a comfortable lounge chair accompanied by light drapery that softly filters sunlight. The backdrop reveals a view of palm trees and a canal, enhancing the serene outdoor environment. A ceiling fan is visible, contributing to airflow.

5 out of 5 average rating, 16 reviews

2023 Build in Saint James City

Brand new sparkling clean 2/2 canal waterfront in desirable Cherry Estates/St. James Isles; use of boat lift included: parking space for boat and trailer, room in shed for bikes, close to restaurants, boat ramp, general store, bait/tackle shops. Local boat and golf cart rentals available; no bridges boating to Sanibel, Cayo Costa and other beaches.

Popular amenities for St. James City house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.95 out of 5 average rating, 21 reviews

An aerial view captures the scenic coastline and sandy beach. A vibrant community is nestled along the shore, featuring lush greenery. Clear blue waters meet the horizon, while a tennis court and pool are visible within the community, enhancing the outdoor experience.

Home in Captiva

Sunset Captiva 10 - Private home just steps to the

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, 187 reviews

Surfside Elegance SW Cape Coral Luxe Vacation home

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, 125 reviews

Boater’s Paradise-Stunning Sunsets! Games Room!

A screened patio area showcases a heated pool, surrounded by concrete decking. A comfortable outdoor dining area is visible in the background, with a TV mounted on the wall. Lush greenery outside the patio adds a touch of nature to the serene setting.

4.99 out of 5 average rating, 104 reviews

Bella's Sunshine - 4 Bedrooms 2 Bath Heated Pool

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.

4.97 out of 5 average rating, 118 reviews

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

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, 43 reviews

Villa Sunset Serenade II

Superhost

Home in Hamlet

5 out of 5 average rating, 4 reviews

waterfront paradise

Weekly house rentals

5 out of 5 average rating, 16 reviews

A spacious screened-in patio offers views of the beach and ocean. Comfortable seating is arranged around a small table, complemented by decorative area rugs. Sunlight fills the space, and a palm tree is visible just beyond the railing, enhancing the coastal setting.

Home in Sanibel

Gorgeous Sanibel Surfside Oceanfront Residence

4.92 out of 5 average rating, 13 reviews

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.

Home in Bokeelia

The Little Yellow Retreat with boat parking

5 out of 5 average rating, 29 reviews

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.

Home in Bokeelia

Peaceful Lakeview Retreat / Screened Porch & Bikes

4.96 out of 5 average rating, 51 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

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.

4.9 out of 5 average rating, 10 reviews

Waterfront Gulf-Access Getaway With Dock and Lift

Superhost

Home in Punta Gorda

5 out of 5 average rating, 4 reviews

Pirate's Cove

5 out of 5 average rating, 18 reviews

A welcoming outdoor living space is presented, featuring two red armchairs with patterned cushions and a small teal table. Brightly colored walls enhance the lively atmosphere, while a patterned rug is laid on the floor. Decorative elements include potted plants and string lights overhead.

Home in Hamlet

The Funky Flamingo

5 out of 5 average rating, 25 reviews

A charming yellow house is framed by lush greenery and vibrant red flowers. The inviting porch features a railing, while a pathway leads to the entrance. Tropical palm trees sway gently in the background under clear blue skies.

Home in Bokeelia

Bountiful Bokeelia

Private house rentals

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, 59 reviews

Coastal Cowgirl - Heated Pool

A private pool area features a clear blue pool surrounded by a spacious stone patio. Two wooden lounge chairs are positioned near the pool, providing a comfortable spot to relax. Lush greenery and palm trees frame the space, enhancing the tranquil setting.

5 out of 5 average rating, 9 reviews

Florida, Cape Coral, SunShine

A bright sunroom is filled with modern wicker seating adorned with green and white cushions. Large glass doors provide a view of the outdoor space, while a patterned area rug complements the decor. Lush plants add a touch of nature to the inviting atmosphere.

5 out of 5 average rating, 47 reviews

Canal View! Walking distance to Marina Village

A spacious outdoor area is featured, showcasing a heated saltwater pool and hot tub bordered by lounge chairs. A lanai with a screen enclosure provides views of the canal, while vibrant pink umbrellas and bar seating add a touch of color to the serene setting.

5 out of 5 average rating, 72 reviews

90Degree SaltWater Pool NEW Luxury Spa Gulf Access

A screened-in lanai features comfortable seating with a round table in the center. The vibrant rug adds color, while views of the landscaped yard and nearby water create a serene backdrop. Natural light filters through, enhancing the peaceful ambiance.

4.97 out of 5 average rating, 72 reviews

Exclusive Waterfront Retreat Pet Friendly & Dock

5 out of 5 average rating, 9 reviews

Cape Escape | Hot Tub | Heated Pool | Game Room

Home in Matlacha Isles-Matlacha Shores

The heated pool is enclosed by a white screened lanai, offering protection and visibility. Sunlight reflects off the water, creating a serene ambiance. The area features tile flooring and is surrounded by grass, providing space for relaxation and play.

4.95 out of 5 average rating, 43 reviews

Pet-Friendly Tropical Oasis

A spacious living area showcases a light-colored sofa arrangement with blue accent pillows. A contemporary coffee table sits in the center, complemented by a neutral area rug. The open layout reveals a modern kitchen and dining area, with natural light illuminating the space through large windows.