Pet-friendly 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, 111 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

The modern exterior of the home is highlighted by a manicured lawn and tropical landscaping, featuring palm trees and colorful shrubs. A paved driveway leads to a two-car garage, while a covered entrance invites guests into the villa.

4.88 out of 5 average rating, 122 reviews

Heated Pool | Canal | Modern | New | Southern Exp.

Welcome to the brand new, absolutely stunning, Villa Southbreeze! This 3 bedroom, 2 bathroom vacation rental is fully furnished &equipped. Stunning high ceilings, huge 72" fireplace, office, laundry room all Samsung stainless-steel appliances, and much more. Out by the huge screened-in pool area you'll find a private electric heated pool, BBQ propane grill, several loungers, large table + chairs. The heated pool features two fountains and a shallow "beach area". Welcome to the villa Southbreeze!

4.9 out of 5 average rating, 163 reviews

The view from the dock features calm waters reflecting sunlight, with a backdrop of palm trees and charming homes lining the canal. Wooden posts mark the dock, while boats are visible along the shore, enhancing the peaceful coastal atmosphere.

Cottage in Hamlet

Mojito Island Cottage

Update: In September 2022 we were affected by Hurricane Ian. We had just over 5 feet of flooding in our treasured cottage. We have worked tirelessly to put everything back together. All new tile, walls, electric, lighting, furniture, and we even improved the bathroom! Spacious tropical home with water view from our back yard lanai. Boat Dock with Cleaning Fish Station, BBQ beautiful sunsets with fish jumping in our canal. New large kitchen and one block from art galleries, restaurants and bars.

A spacious living area features a leather sofa with a wooden coffee table at its center. Large windows invite natural light, complemented by a ceiling fan above. To the rear, the open layout leads to a dining area and kitchen, enhancing the bright and airy atmosphere.

4.98 out of 5 average rating, 109 reviews

Black Friday Sale! HotTub+Beach Gear+5 min to Town

-5 min to Downtown Cape/10 min to Yacht Club Beach, 20 min to Causeway Beach, 25 min to Ft Myers & Sanibel Beach -Tropical fenced backyard w/ pool, hot tub, gas firepit, swing chair, hammock & Blackstone grill -Beach essentials, boogie boards, umbrellas, beach wagon, cooler & chairs -Board games, ping-pong, corn-hole, darts, 2 kayaks+life jackets -2 Beach Cruiser bikes + helmets -Relaxing enclosed covered patio + string lights, neon sign & grass wall -Canal access for kayak launch 5 min away

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.

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!

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 screened-in pool area features a spacious swimming pool with clear blue water, surrounded by a concrete deck. Lush greenery and palm trees are visible through the screens, creating an atmosphere of tranquility and connection to the outdoors.

4.64 out of 5 average rating, 78 reviews

3/2 Heated Pool, Waterfront w/ Boat Lift!

Fresh and airy pool home on the water in St. James City! This property offers 3 bedrooms, 2 baths and a Florida room that offers ice cold a/c (heat available in the cooler months too) with a queen size swinging bed for extra sleeping! The pool is heated with amazing views overlooking the canal. Bring your boat! Room on the left side of the house for boat trailer parking. This property also includes a boat lift with an extended dock. *Pet friendly, $150 pet fee, 2 pets max.

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!

4.94 out of 5 average rating, 359 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.

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 St. James City pet-friendly home rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.99 out of 5 average rating, 137 reviews

Waterfront Retreat• Sunsets • Pool• Dock•Kayaks

A spacious living area is filled with natural light, featuring a large sectional sofa and a media console with a flat-screen TV. The open layout connects to a dining area with a round table and modern chairs, leading into a well-equipped kitchen with warm wooden cabinets.

4.98 out of 5 average rating, 113 reviews

Hot Tub/ King Bed - Cozy Home in Cape Coral!

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.

4.92 out of 5 average rating, 13 reviews

The Little Yellow Retreat with boat parking

The exterior of the home is illuminated at dusk, highlighting a welcoming entrance with decorative stone pathways. Lush greenery surrounds the property, and two palm trees add a tropical element. A soft glow from the porch light enhances the inviting atmosphere.

4.97 out of 5 average rating, 30 reviews

Fishing and Nature Paradise

An outdoor patio is presented with a colorful array of furniture, including a blue table and yellow benches. A shaded area features a seating arrangement with cushions, while vibrant greenery can be seen in the background. Natural light enhances the welcoming space.

4.98 out of 5 average rating, 56 reviews

Island Paradise - Hot tub, Bikes & Ocean fishing

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

4.94 out of 5 average rating, 64 reviews

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.

Home in Hamlet

Key West Style Home w/ Hot Tub & Boat Lift

An aerial view captures the lush tropical landscape, featuring a private pier extending over tranquil waters. Surrounding palms frame a spacious deck area, with shaded spots underneath fabric canopies. Nearby, the vibrant blue pool contrasts against the natural greenery, providing a serene oasis.

4.79 out of 5 average rating, 42 reviews

Tropical Island Oasis Full Home

Pet-friendly home rentals with a pool

4.97 out of 5 average rating, 31 reviews

Dog Friendly | Pool, Kayaks, Dock, & Gulf Access

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.

4.93 out of 5 average rating, 15 reviews

Pine Island paradise, priced right.

An aerial view showcases a modern villa surrounded by lush green landscaping, with a stone driveway leading to the entrance. The property is positioned along a scenic canal, offering waterfront access, while neighboring houses and boats line the peaceful waterway.

4.93 out of 5 average rating, 30 reviews

Aqua Vista - Luxury Vacation Rental Cape

A shaded patio area features two turquoise lounge chairs positioned near a sparkling pool. A small table holds a bottle of champagne and a bowl of oranges. In the background, spacious arched windows and a bright, inviting interior are visible.

5 out of 5 average rating, 7 reviews

Villa Serena

5 out of 5 average rating, 9 reviews

Intervillas Florida - Villa Xanadu

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 covered outdoor area showcases a private salt-water pool, with comfortable seating arranged around it. Lounge chairs are positioned near the pool, and soft lighting hangs overhead, enhancing the inviting space. The backdrop features large windows that connect to the interior living area.

4.92 out of 5 average rating, 49 reviews

Pet-friendly Villa w/ Heated Pool

A spacious waterfront home is surrounded by lush greenery and palm trees. The Mediterranean-inspired architecture features a red-tiled roof and large front entrance, along with a neatly paved driveway leading to a two-car garage. Bright blue skies provide a clear backdrop.

4.97 out of 5 average rating, 116 reviews

Gone Coastal!! Spa+Heated Pool Amenities Galore!

Private, pet-friendly home rentals

The outdoor area features a screened lanai with a spacious heated pool surrounded by a stone patio. Comfortable seating arrangements and a dining set provide options for relaxation and meals. The scene is complemented by views of the lush greenery beyond the pool area.

4.87 out of 5 average rating, 31 reviews

Waterfront sanctuary / Paid heated Pool Cape Coral

The living area features a comfortable sofa arrangement under a ceiling fan, with large windows allowing natural light. The spacious bedroom showcases a four-poster bed, sleek furniture, and warm lighting. An enclosed patio displays a dining setup with colorful tableware, adjacent to a heated pool visible through expansive screen panels.

5 out of 5 average rating, 90 reviews

WF Oasis~Htd Pool~Spa~Pets4Free~BBQ~Big Lanai~Dock

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, 29 reviews

Peaceful Lakeview Retreat / Screened Porch & Bikes

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

A cozy living area contains a comfortable beige sofa and a black reclining chair. A white coffee table is situated in front of the sofa. Natural light filters through the window curtains, illuminating the space. A ceiling fan and wall-mounted TV enhance the inviting atmosphere.

5 out of 5 average rating, 18 reviews

Impulse 25 Beach Cottage

4.88 out of 5 average rating, 33 reviews

The exterior of the beach house is showcased, featuring a covered porch with wooden railings and an American flag. Tropical palm trees surround the property, and stairs lead to the elevated entrance, highlighting the inviting design and island charm.

Home in Captiva

2/2 SandDollars, CLUB, Boat Slip

The exterior of The Crab Shack showcases a charming blue facade with a welcoming sign. The landscape features a pebble area with a palm and decorative pathway. A cozy porch is visible, providing an inviting entry. The overall setting reflects a relaxed coastal atmosphere.

5 out of 5 average rating, 6 reviews

The Crab Shack-Cozy Cottage in Flamingo Bay-2B/1B

A spacious outdoor deck is furnished with two comfortable wicker chairs featuring blue cushions. A small table is seen nearby, alongside a patterned rug and decorative elements like fish-themed wall art. Sunlight filters through the open structure, creating a bright and relaxing atmosphere.