Waterfront vacation rentals in Bokeelia

4.9 out of 5 average rating, 178 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 Matlacha

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.

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.

4.91 out of 5 average rating, 47 reviews

Boater’s Paradise in Bokeelia!

Welcome to Bokeelia! Forget your worries in this spacious and serene space. Beautiful Newly Remodeled Home located right On the Water with Boat Lifts & Dockage, and plenty of parking for All Come and enjoy a Relaxing and Comfy Home. Boaters! We are across the street from the Public Boat Ramp, Minutes to Captiva & Sanibel Islands, Cayó Costa, Cabbage Key, and Boca Grande which is known for its sugar sand Beaches. Best of all, Amazing Fishing in Florida aka “Tarpon Fishing Capital of the World!”

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.

5.0 out of 5 average rating, 31 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.

4.97 out of 5 average rating, 72 reviews

Island Paradise- Big 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!

4.91 out of 5 average rating, 143 reviews

A two-story beach house features a bright blue exterior and large windows, surrounded by palm trees and lush greenery. A wooden staircase leads to the entrance, with a deck visible on the upper level. The sandy area offers a welcoming beach environment.

Home in Captiva

Blue Laguna - Vacation in paradise!

This bright, fully equipped welcoming three‑story home features a private heated pool and a rooftop observation deck with stunning 360‑degree water views. It offers three comfortable bedrooms and three full bathrooms for up to six guests, plus two screened lanais where you can relax in the island breeze and listen to the birds. A four‑seater golf cart is included, so you can easily explore the beaches and sandy paths of beautiful North Captiva Island. Also full access to Island Club amenities!

4.99 out of 5 average rating, 145 reviews

A modern living area is highlighted by a spacious white sectional sofa, accented with a mustard yellow pillow. A glass coffee table sits atop a striped rug, while a charming yellow front door adds a pop of color. Decorative oars are mounted on the wall.

Cottage in Bokeelia

Romantic Getaway “Waterside” Dockage~Canal front

Also available: airbnb.com/h/aframeausable Minutes to open water and Jug Creek Marina! Wait till you see this freshly updated cottage! Bring your boat, or rent one nearby. There is a dock available here. Tarpon capital of the world, and Charlotte Harbor moments away! Boca Grande, Cayo Costa, Useppa, North Captiva, Sanibel and Cabbage Key, etc. a short boat ride away! The golf carts/kayaks/boats/bikes are available to rent at local resources! Jug Creek Marina is steps away with food & music!

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.

5.0 out of 5 average rating, 51 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.

Guest suite in Burnt Store

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.

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 restaurants. Visit the Matlacha Art Galleries. Fish off the dock. WELCOME!

4.85 out of 5 average rating, 393 reviews

A tranquil heated pool is surrounded by sleek tiled decking, reflecting sunlight in clear blue hues. A shaded area provides relief from the sun, while a boat dock can be seen in the background, accommodating vessels for easy access to water activities.

5.0 out of 5 average rating, 40 reviews

Waterfront Fisherman’s Retreat Quick Harbor Access

Welcome to your perfect Pine Island getaway! This charming 2-bedroom, 1-bath canal-front home is an ideal escape for fishing lovers, boaters, and anyone looking to relax in a peaceful island setting. Located on a quiet canal, the property offers direct access to Charlotte Harbor within minutes, making it easy to reach open water for fishing, boating, and exploring. Our private boathouse and lift are currently occupied, but guests who rent a boat are welcome to tie up at the dock.

The exterior of the waterfront property displays a spacious yard with a sandy area leading to the canal. Two boat docks are positioned for easy access, and several kayaks are neatly arranged alongside sun loungers. A large tiki hut provides a shaded gathering spot.

4.85 out of 5 average rating, 82 reviews

Blue Heron * fish, boat, wine, dine, relax, repeat

Welcome to the Blue Heron. This beautiful home will win your heart - a place to create amazing memories. Located in Bokeelia, this home offers tranquility and is the perfect spot to boat from, fish, enjoy family time, and simply relax. There are 2 boat docks and a boat ramp close by, we have kayaks and paddle boards to explore the waterways, bikes to explore the island, or stay home and make the most of the heated pool, fish from the dock, or hang at the private tiki bar!

4.94 out of 5 average rating, 156 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

Beach Getaway + Golf Cart & Club Access

HOST PAYS AIRBNB FEE 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 proximity/ steps to the beach

A spacious living area is furnished with a large sofa and complementary chairs, creating an inviting space. Two wall-mounted TVs display beach-themed visuals. Natural light floods in through large windows, enhancing the neutral decor, while textured flooring offers a warm, cohesive look.

5.0 out of 5 average rating, 12 reviews

Serenity by the Sea

Come enjoy the island life. Bring your boat and enjoy fishing in the Gulf of Mexico. FREE use of boat dock. Large driveway that will fit boat trailer and cars. 3 bedrooms with queen beds. 2 bathrooms. Full kitchen. Dining room with table for 6. Plenty of seating inside and outside of home to spread out and relax. Close to Pine Island Center and Matlacha. **We currently have our home listed for sale so are only accepting reservations 90 days in advance.**

Popular amenities for Bokeelia waterfront rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

4.62 out of 5 average rating, 149 reviews

Grouper Room in Matlacha * Fishermens Paradise

A serene waterway lined with palm trees accompanies buildings on either side. A glimpse of the local community's charm is visible, featuring docked boats and lush greenery. The clear blue sky enhances the relaxed atmosphere of this coastal setting.

4.8 out of 5 average rating, 124 reviews

Pet-Friendly Waterfront Motel Botel

Apartment in St. James City

Two vibrant blue Adirondack chairs are positioned on a covered porch, inviting relaxation. A welcome sign is displayed nearby, and a potted plant adds a touch of greenery. A decorative rug with a palm leaf design creates a cozy atmosphere on the outdoor space.

Island Castaway--Free Kayaks

4.93 out of 5 average rating, 105 reviews

4.87 out of 5 average rating, 170 reviews

A tranquil waterway is depicted, surrounded by lush green trees and residential homes. The clear blue sky reflects over the shimmering water, creating a calm and peaceful scene. Two docks are visible, providing access for boats along the serene canal.

Apartment in Cape Coral

The Cape (1) /Gulf access.

4.99 out of 5 average rating, 157 reviews

Apartment in Cape Coral

Vacation in Paradise

4.75 out of 5 average rating, 12 reviews

Waterfront in Sunny Matlacha w/Kayaks-Pets ok!

5.0 out of 5 average rating, 15 reviews

Waterfront in Matlacha!

5.0 out of 5 average rating, 26 reviews

Apartment in Sanibel

Sundial E304: Gulf Front 3BR w/Stunning Ocean View

Waterfront house rentals

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.

4.96 out of 5 average rating, 92 reviews

Key West Style Home w/ Hot Tub & Boat Lift

5.0 out of 5 average rating, 51 reviews

Renovated in 2025 Heated pool and 10klb Boat Lift

4.91 out of 5 average rating, 46 reviews

Paradise Pool Waterfront Kayak bike fish from dock

5.0 out of 5 average rating, 9 reviews

Home in St. James City

Charming 2-BR Home w/ AC, Dock & Peaceful.

4.71 out of 5 average rating, 17 reviews

Relaxing waterfront retreat with pool

4.96 out of 5 average rating, 28 reviews

Waterfront | Speakeasy | Boat Dock | Free Kayak

4.99 out of 5 average rating, 76 reviews

Gulf Access | Waterfront Dock | Walk to Town

4.93 out of 5 average rating, 43 reviews

A two-story island home features a light-colored exterior with a wide staircase leading to an upper patio, adorned with tropical plants. The front yard showcases a circular driveway with palm trees and vibrant flowers, complemented by two garage doors.

Home in St. James City

The Sandy Pelican

Waterfront condo rentals

4.94 out of 5 average rating, 120 reviews

Captiva Beach Villa On The Gulf Beach !

4.95 out of 5 average rating, 121 reviews

A panoramic view of a sandy beach stretches out towards the horizon under a clear blue sky, dotted with white clouds. Beach chairs are set up along the shore, with lush green vegetation in the foreground, leading to the water's edge.

Condo in Sanibel

100+ 5 Star Reviews and Right on The Beach!

Condo in Fort Myers Beach

The eight-story building stands prominently along the vibrant green waters of Lovers Key State Park. Lush landscaping surrounds the property, with residential docks and a restaurant visible along the water's edge, enhancing the serene coastal environment.

Lovers Key Resort/Ft Myers Beach/Condo/Pool/View

4.94 out of 5 average rating, 192 reviews

4.97 out of 5 average rating, 145 reviews

A living area features a black leather sofa, accent chairs, and a flat-screen TV on a light-colored media console. Two framed botanical prints are displayed on a yellow wall, while large sliding glass doors provide sweeping views of the bay and natural light.

Condo in Punta Rassa

2nd Floor Beachfront Condo Sanibel Harbour

4.95 out of 5 average rating, 58 reviews

A private pool is positioned beside a canal, framed by a white railing. Comfortable lounge chairs are arranged on the patio, overlooking calm waters reflecting a soft sunrise. Lush greenery and neighboring homes create a peaceful backdrop.

Condo in St. James City

Island Time Private Poolside Retreat !

4.85 out of 5 average rating, 33 reviews

Captiva Hide-A-Way 1A

4.9 out of 5 average rating, 72 reviews

Beach front, Beach Villa 2001

The living area features a light-colored sofa and two dark armchairs, accented by a colorful artwork on the wall. A ceiling fan provides airflow, while large windows offer views of the marina and invite natural light into the space.