Pet-friendly holiday rentals in Bokeelia

4.95 out of 5 average rating, 115 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

4.88 out of 5 average rating, 123 reviews

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.

Villa in Cape Coral

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!

The exterior of the home features a modern design with light blue siding and large windows. Lush palm trees surround the property, adding a tropical touch. A gravel driveway leads to the entrance, which includes a set of stairs leading to the main level.

5 out of 5 average rating, 19 reviews

Antigua Cay Retreat

Stylish and classy, with plenty of space to relax and enjoy one of Floridas most unique and special hidden treasures. Bokeelia on Pine Island! Beautifully remodeled home has 3 full bedrooms, as well as a bonus room with double futon downstairs at pool lanai. Lots of outdoor space around the pool, on the new boat dock as well as an upper level outdoor breakfast area that can be fully opened up to both main bedrooms via the oversized sliding glass doors to each bedroom. Also includes an elevator!

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, 58 reviews

Island Paradise - Hot tub, Bikes & Ocean fishing

Welcome to The Clubhouse – Your Private Island Escape Experience laid-back luxury on the serene Florida island 🏝️ just two blocks from the marina. This beautifully appointed retreat features an outdoor kitchen, fire pit, hot tub, and elegant indoor-outdoor living. Cruise the island on provided bikes, kids get to stay the new designer bunk space. Perfect for boating, fishing, or simply soaking in the sun. Refined comfort meets coastal charm — reserve your stay today, your island retreat awaits!

4.95 out of 5 average rating, 137 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

HOST PAYS AIRBNB FEE WINTER SPECIALS Golf Cart and Club amenities Included North Captiva Island Cottage! Just steps away from the Gulf's pristine shores, this cozy retreat offers a private hot tub, perfect for families and beach enthusiasts. Enjoy modern amenities, a well-stocked pantry, and a complimentary golf cart to explore the island. Pet-friendly(small fee) accessible by ferry, boat, or plane. With beach gear, access to the club pool, and unbeatable proximity to the beach STAY WITH US

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

Bask in endless sun at our Jugg Creek canal-front home, a stone's throw from Charlotte Harbor and iconic islands like Captiva and Boca Grande. Dive into 'Old Florida' with unspoiled beaches and cute eateries. Watch dolphins from your doorstep and savor rainbow sunsets. Our beautiful cottage boasts a outdoor hot tub and shower, screened in porch, grill, and kayaks with a kayak launch right on the dock. Docking is on us, with a new dock & 10k pound boat lift available April-December.

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

Savor Nature, Sip Cocktails and Embrace Sunsets. Beautifully designed 2 Bedroom home located right on the water. Take a kayak or Paddleboard down the canal and you are instantly in the most pristine waters of the Gulf of Mexico. Located one block away from the Jug Creek Marina where you will find Live entertainment, fresh seafood and any boating needs. Sit on the extensive screened in porch and watch the Manatees. We have everything you need to enjoy a wonderful getaway.

An aerial view captures the waterfront property, highlighting the silver-roofed house surrounded by lush greenery and palm trees. A long wooden pier extends into the calm waters of Charlotte Harbor, inviting activities like fishing and kayaking.

4.93 out of 5 average rating, 28 reviews

The Harbor House

Welcome to your private waterfront getaway in Bokeelia, Florida! Enjoy amazing views of Charlotte Harbor, fish from the 300-ft private pier, kayak , or relax by the pool. Watch dolphins, manatees, ospreys, pelicans, and bald eagles right from the property. Spend your days boating, fishing, exploring the island, or biking along the trails, then unwind as you take in a stunning sunset over the water. Whether you seek adventure or relaxation, this spot has something for everyone.

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, 30 reviews

Peaceful Lakeview Retreat / Screened Porch & Bikes

Escape to a peaceful lakeview retreat on Pine Island. Relax on the breezy screened porch, unwind in the cozy living room, and enjoy two serene bedrooms with smart TVs and comfortable bedding. The home features modern bathrooms, a fully stocked kitchen, fast Wi-Fi, and in-unit laundry for convenience. Pet-friendly and close to trails, marinas, and seafood spots — perfect for birdwatching, biking, fishing, or simply soaking up the island’s quiet charm and natural beauty.

4.94 out of 5 average rating, 362 reviews

Home in Fort Myers

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 screened lanai features a rectangular pool surrounded by tropical greenery. Outdoor dining furniture is visible near a glass table, offering a place to enjoy meals. Colorful pool floats and lounge chairs add to the inviting space, with the waterfront just beyond the pool area.

4.84 out of 5 average rating, 112 reviews

Peaceful Oasis

Enjoy the best of the Cape Coral Yacht Club neighborhood. We offer beautifully restored Terrazzo floors along with all new cabinetry, appliances and furniture. The interior of the house has been greatly improved since Hurricane Ian. The lanai, pool and waterfront offer you serene splendor and beauty that you will not want to leave. We provide the most convenient location in Cape Coral, just one mile from the downtown restaurant district.

A screened-in pool area showcases a clear blue pool surrounded by lush greenery. Comfortable lounge chairs are positioned along the edge, inviting relaxation under the palm trees. Soft sunlight filters through the screened structure, enhancing the tranquil atmosphere.

4.89 out of 5 average rating, 9 reviews

Bokeelia Oasis! Heated Pool, Sleeps 12!

Escape to this stunning tropical retreat in Bokeelia, where relaxation meets luxury! This beautiful home features two master suites, one with two king-size beds and the other with two queen-size beds, ensuring plenty of space for family and friends. Enjoy the comfort of two separate living areas, each with a sleeper sofa featuring two full beds, perfect for additional guests. Step outside to your private heated pool, soak up the Florida sun!

Popular amenities for Bokeelia pet-friendly home rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

5 out of 5 average rating, 53 reviews

Home in Captiva

Heated Pool•Golf Cart•Pool•Trusted Local Hosts

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.

4.93 out of 5 average rating, 67 reviews

AquaLux Smart Home

5 out of 5 average rating, 18 reviews

Island Paradise Awaits You

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.

4.87 out of 5 average rating, 31 reviews

Fisherman's island paradise - Southwest Florida

5 out of 5 average rating, 91 reviews

The welcoming entrance of the cottage features a light blue door and decorative white trim. Lush green plants and colorful flowers surround the doorway, enhancing the inviting atmosphere. A small hanging planter adds a touch of nature to the facade, with trees in the background completing the exterior view.

Home in Sunset Park

Inn Season Cottage-Cozy Florida Living

A modern living area features a sleek sofa and stylish armchairs, arranged around a contemporary coffee table. A large screen displays a celebratory message, while a well-equipped kitchen with bar seating is visible in the background. Natural light brightens the space through sliding glass doors.

4.83 out of 5 average rating, 66 reviews

Central Cape Casita

5 out of 5 average rating, 23 reviews

Island Dreams - Fun in the sun. A kayakers Dream

4.89 out of 5 average rating, 62 reviews

Home in Hamlet

Sunset POOL Waterfront Kayak bikes fish from dock

Pet-friendly home rentals with a pool

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

An infinity-edge heated pool is presented within a screened enclosure, surrounded by lush palm trees. Water views are visible beyond the pool area, reflecting the tranquil sunset sky. The pool deck features patterned tiles, creating a welcoming outdoor space for relaxation.

5 out of 5 average rating, 16 reviews

Indulgence - luxury waterfront Heated pool home

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.

4.9 out of 5 average rating, 86 reviews

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

5 out of 5 average rating, 137 reviews

A spacious outdoor area features a heated pool surrounded by a paved deck. Comfortable lounge chairs and an umbrella are positioned nearby, offering a relaxing space. The backyard is framed by greenery and a fenced perimeter, ensuring privacy and a serene ambiance.

Villa in Cape Coral

Casa Capri | Heated Pool | No Service Fee

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, 44 reviews

Pet-Friendly Tropical Oasis

4.92 out of 5 average rating, 52 reviews

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.

Villa in Cape Coral

Pet-friendly Villa w/ Heated Pool

4.83 out of 5 average rating, 186 reviews

Home in Fort Myers

Blue Beach Bungalow

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

Private, pet-friendly home rentals

4.92 out of 5 average rating, 13 reviews

Home in Fort Myers Beach

Ft. Myers Beach Retreat

5 out of 5 average rating, 9 reviews

Charming home away from home!

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

5 out of 5 average rating, 14 reviews

A private saltwater hot tub is surrounded by sheer curtains, allowing for a serene atmosphere. Soft blue lights illuminate the water, while the outdoor setting includes greenery visible through the curtains, creating a tranquil space for relaxation.

Cottage in Fort Myers

Salt Water Spa! Walk Everywhere!

Superhost

A cozy bedroom is shown featuring a spacious bed covered in a blue quilt. Two wooden chairs are positioned by large windows allowing natural light. Soft lighting is provided by two lamps on either side of the bed, and a striped rug adds texture to the wooden floor.

Apartment in Hamlet

4.74 out of 5 average rating, 27 reviews

Studio#1-Back Bay Sunsets in Matlacha

Shipping container in Fort Myers

4.82 out of 5 average rating, 11 reviews

Container Tiny Home, Yard, FGCU & Pet Friendly

5 out of 5 average rating, 21 reviews

The exterior of a newly remodeled home is shown, featuring a welcoming entrance with a railing and stairs leading up to the door. Lush palm trees and vibrant flower planters are positioned by the entrance, set against a clear blue sky.

Home in Fort Myers Beach

Beach Cottage

A single-story home with a light green exterior and a white metal roof is showcased in this image. A paved driveway leads to a garage, and a golf cart is parked in front. Lush palm trees frame the property, enhancing the welcoming ambiance.