Vacation rentals with a kayak in Fort Myers

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.

4.99 out of 5 average rating, 113 reviews

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

Step into the spacious and entertaining 3BR 2Bath nestled in a tranquil canal front area close to many restaurants, shops and attractions. Explore the city or lounge the day away under the fairy-tale tiki hut next to the swimming pool and the private dock. 🐕Pets Stay Free! ✔ 3 Comfy BRs ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Patio (Heated Pool & Spa, TV, Lounges) ✔ Yard (Tiki Hut, BBQ, Dining, Lawn) ✔ Private Dock and boats ✔ Smart TVs + PS4 + SONOS ✔ High-Speed Wi-Fi ✔ Free Parking

LocationOutdoor spacesDecor

4.97 out of 5 average rating, 232 reviews

The modern kitchen is equipped with white cabinetry and stainless-steel appliances. A circular table with seating for four is positioned near a large glass sliding door that allows natural light and offers views of the outdoor space. A ceiling fan adds comfort to the room.

Guesthouse in Iona

Waterfront Hideaway

This picturesque Airbnb is a hidden gem nestled along a canal, one minute boat ride to the Caloosahatchee River. The living room, bathed in natural light is perfect for taking in the scenic views. The spacious bedroom has a king-size bed, ensuring a night of blissful rest. The full kitchen is equipped with all modern appliances. Close to Sanibel & Fort Myers Beach. Bring your boat & dock it on the seawall, ready to set sail whenever your heart desires. Book now - your coastal paradise awaits!

ValueOutdoor spacesParking

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, 254 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!

ValueOutdoor spacesQuiet

4.89 out of 5 average rating, 9 reviews

Elite Living | Kayak | Joy Pool | Outdoor Kitchen!

🌴Welcome to your elite Fort Myers vacation rental 5 bedroom private pool home with outdoor kitchen, designed for peaceful stays, family vacations, & extended getaways. Located on a quiet cul-de-sac, this spacious home near Fort Myers beaches offers the perfect blend of privacy, convenience, and resort-style amenities. Conveniently located near shopping, grocery stores, restaurants, and just a short drive to beaches, marinas, and top local attractions—one of the most loved vacation homes in FL!

Outdoor spacesLocationNearby

4.98 out of 5 average rating, 205 reviews

A spacious outdoor seating area is featured, showcasing a glass-top table surrounded by six chairs. The patio is complemented by a gas grill on one side. Large sliding doors provide a view of the interior dining area and kitchen, blending indoor and outdoor settings.

Home in North Naples

Gulf Access Canal, Kayaks, Bikes, Dock, Wildlife

A renovated mid century modern house with natural peaceful views out of every window and slider. No detail spared, as it was going to be our forever home. Located on an ocean access canal, extremely safe, quaint and friendly neighborhood, just off 41. The backyard has a large shaded sitting area with a gas grill and fire pit. The dock hangs over the water with seating and swim ladder. 2 tandem kayaks, fishing rods & tackle, adult & children’s bicycles, beach chairs, and so much more.

Outdoor spacesLocationView

4.99 out of 5 average rating, 112 reviews

A sunlit pool area is framed by palm trees, with views of the canal and neighboring homes in the background. Comfortable loungers are positioned along the poolside, inviting relaxation amidst the tranquil waterfront setting.

Home in Fort Myers Beach

Paradise on canal minutes to Ft Myers Beach/Gulf

Beautiful 3 Bedroom, 3 bath home on a canal with a dock! Bring your boat or jet skis! Enjoy a relaxing stay watching the dolphins and manatee right off the dock. This exquisitely updated home has everything you need for a fantastic vacation. Especially location! 5 minutes to Ft Meyers Beach. Enjoy the resort right in your own backyard. New pool with hot tub and sun shelf. Enjoy beautiful sunsets off the huge patio. Trolly to beach at neighborhood entrance or walk to in minutes.

LocationOutdoor spacesGetting around

4.9 out of 5 average rating, 125 reviews

Cape Serenity- Luxury Waterfront Residence

This recently renovated, fully equipped home offers serenity and relaxation as you unwind in this gorgeous 3 bed, 3 bath residence. Located off the Caloosahatchee River, it is one of just a few select homes in the area that offers both privacy and luxury, along with direct accessibility to the gulf. Recent upgrades include a newly refinished pool deck, Ev charger, renovated kitchen and bathrooms and modern touches throughout to enhance your experience. Updated photos coming soon!

LocationOutdoor spacesDecor

4.9 out of 5 average rating, 138 reviews

Modern Canal Oasis | Heated Pool | Kayaks & Office

Modern 3-bed canal-front oasis featuring a private heated pool and stunning sunset views. Explore the waterways with provided kayaks or stay productive in the quiet, dedicated office. Ideally located just 10 minutes from downtown Cape Coral and a short drive to Sanibel and Fort Myers beaches. Enjoy a bright, open interior and a screened lanai built for ultimate relaxation. Perfect for families or remote workers. Trust our 12+ years of hosting for a seamless Florida getaway!

LocationValueHeating

Superhost

Villa in Fort Myers

5 out of 5 average rating, 4 reviews

Mediterranean Waterfront Estate on Caloosahatchee

Experience Nascosto Estate, a Mediterranean waterfront sanctuary on the Caloosahatchee River. This extraordinary estate offers resort-style amenities, including a heated infinity pool with a cascading waterfall, sanded lounge, fire pit, private pier, and boat lift. Just minutes from Downtown Fort Myers, it provides absolute privacy, breathtaking river views, and magical sunsets—a one-of-a-kind escape where every moment feels unforgettable and memories last a lifetime!

LocationValueGrill

5 out of 5 average rating, 55 reviews

Caloosahatchee Hideaway II-Waterfront Retreat

Relax with the whole family at the Waterfront Caloosahatchee Hideaway II ! This CHARMING Farmhouse HOME away from HOME is a 2 Bedroom, 2 Full bathroom, duplex that sleeps 6! Close to Babcock Ranch, Grace River Island Resort, Spring Training Facilities. This home is fully stocked from the kitchen to the linens. The evening sunsets don’t disappoint! We provide fishing poles, paddleboards and kayaks for the adventurous folks. Plenty of blankets, pillows and bedding.

Outdoor spacesLocationAccuracy

4.93 out of 5 average rating, 118 reviews

A welcoming kitchen and dining area features a round wooden table surrounded by stylish white chairs. Brightly colored flowers are displayed in a vase on the table. The kitchen, equipped with modern appliances, is visible in the background, complemented by light-toned walls and flooring.

Home in Cypress Lake

SWFL: Lake McGregor House - Entire Home! 3B/2B

Our home is in a quiet, safe neighborhood perfect for remote work, family getaways, or long-term stays in a kid-friendly environment. Spacious & Fully Equipped: 3 bedrooms • 2 bathrooms • Full kitchen • Washer/dryer • 2-car parking • WiFi • Smart TV • Beach gear available (Cable/streaming not included). Prime Location: 10 miles from Fort Myers Beach, 7 mi from Downtown, and a 7-min walk to Publix, Walmart, and restaurants. RSW Airport is a 20-min drive.

ValueOutdoor spacesIndoor spaces

The outdoor area features well-maintained grass bordered by gravel and illuminated palm trees, enhancing the tranquil canal view. A dining table is set up for outdoor meals, while string lights provide soft lighting. The calm water reflects the colorful lights, creating a serene atmosphere.

5 out of 5 average rating, 52 reviews

Waterfront Family Retreat/Heated Pool/kayaks&Games

The price you see is the price you pay—no additional Airbnb guest service fees❤️ Experience the ultimate waterfront getaway at this stunning canal-front retreat, perfect for families and friends. Located in a peaceful southeast neighborhood close to everything, this home offers the perfect mix of relaxation and fun. Enjoy your private outdoor oasis with a heated pool, beautiful canal views, and space to relax, play, and unwind.! ☀️🏝️🌴🌊

Outdoor spacesLocationSleep quality

Popular amenities for Fort Myers kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

A tranquil pool area is highlighted by a clear blue swimming pool, with steps leading in. Lounge chairs are positioned nearby, and a shaded palapa provides a seating area, all overlooking a serene lake view framed by tropical plants and palm trees.

5 out of 5 average rating, 33 reviews

Tropical Villa Rosas on the water

LocationOutdoor spacesNearby

5 out of 5 average rating, 12 reviews

Gulf Access/Heated Pool & Jacuzzi/Up to 8

LocationOutdoor spacesAccuracy

4.98 out of 5 average rating, 54 reviews

The exterior of the property features a paver driveway leading to a two-car garage, framed by lush palm trees and manicured green lawn. The home's stucco facade is complemented by a terracotta tile roof and outdoor seating area, all set against a clear blue sky.

Home in North Fort Myers

Last-Min Deal: Hot Tub, Kayaks, Fishing & Pets

LocationValueIndoor spaces

An expansive swimming pool invites relaxation, with clear blue water reflecting the sky. Lush palm trees frame the edge, while docks extend over the calm river, offering space for kayaks and boats. Sunlit clouds add a serene backdrop to the inviting outdoor space.

4.95 out of 5 average rating, 41 reviews

Bay of Grace A Boater's Paradise Riverfront Gem

ValueLocationBeach

5 out of 5 average rating, 26 reviews

Cape Escape | Hot Tub | Heated Pool | Game Room

Outdoor spacesLocationView

4.98 out of 5 average rating, 48 reviews

Home in Bonita Bay

Waterfront Luxury | Saltwater Pool, Spa Near Beach

LocationOutdoor spacesQuiet

5 out of 5 average rating, 49 reviews

Paradise House w/ Dock/Jacuzzi/Kayak/Gameroom/BBQ

ValueOutdoor spacesGetting around

5 out of 5 average rating, 11 reviews

Home in Iona

Heated Pool Home Near Fort Myers Beach

LocationOutdoor spacesBackyard

Cottage rentals with a kayak

Cottage in Bonita Springs

A serene view of the Enchanted Cottage is showcased amidst lush tropical landscaping. Pathways with stone pavers lead towards the quaint entrance, bordered by various palms and flowering plants that enhance the peaceful garden setting.

4.99 out of 5 average rating, 75 reviews

The Enchanted Cottage on the Imperial River

ValueOutdoor spacesFamily

Superhost

The exterior of the villa features a light-colored façade with a sloped roof and a well-maintained lawn adorned with tropical plants. A driveway leads up to a garage on one side, while a double entrance door provides access to the home.

Cottage in Cape Coral

4.67 out of 5 average rating, 54 reviews

Villa The Island Hideaway 2

Outdoor spacesLocationWalkability

4.9 out of 5 average rating, 281 reviews

A private heated saltwater pool is surrounded by vibrant palm trees, creating a lush outdoor oasis. White lounge chairs are positioned along the poolside, inviting relaxation under a clear blue sky. A well-maintained grassy area adds to the serene atmosphere.

Cottage in Naples Park

Cottage Close to Vanderbilt Beach Heated Pool

Outdoor spacesLocationAir conditioning

A tranquil waterway is visible, reflecting the surrounding structures and sky. A private boat dock extends into the canal, offering access to boats moored nearby. The scene features well-maintained properties lining the banks, framed by palm trees and grassy areas.

Cottage in Saint James City

5 out of 5 average rating, 8 reviews

Flamingo Bay Cottage

ValueOutdoor spacesHospitality

A bright and inviting living area features pastel yellow walls complemented by an array of furnishings in varied hues. The space includes a dining table with chairs, a cozy seating area with a striped sofa, and decorative artwork adorning the walls.

Cottage in Matlacha

4.88 out of 5 average rating, 42 reviews

The Coqui Palace

Outdoor spacesLocationTV

Cottage in Bonita Springs

An outdoor seating area features a round black table surrounded by six metal chairs, set against a backdrop of white siding. A potted plant sits in the center of the table. Sunlight filters through the nearby window, enhancing the inviting atmosphere.

5 out of 5 average rating, 19 reviews

Quiet Riverside Cottage in Downtown Bonita Springs

LocationOutdoor spacesAccuracy

A charming island cottage is surrounded by lush palm trees and tropical foliage. Two blue chairs are positioned on the gravel driveway, inviting relaxation. The entrance is framed by vibrant greenery, and a metal roof reflects the sunny skies.

Cottage in Bokeelia

4.7 out of 5 average rating, 216 reviews

Captains Cottage

LocationOutdoor spacesBathroom

The entrance of the bungalow is framed by lush tropical plants, with a welcoming pathway leading to double glass doors. The exterior walls are a soft pink hue, complemented by white window shutters. A decorative mat is positioned at the front door, enhancing the inviting appearance.

Cottage in Cape Coral

4.93 out of 5 average rating, 54 reviews

Boat Paradise Gulf Access 2,000 sf home 62 ft dock

LocationOutdoor spacesNearby

Other vacation rentals with a kayak

The outdoor area features a heated pool with illuminated waters, a spa, and a Tiki Hut. Soft lighting highlights the architecture of the home, including arched columns. Lounge chairs provide seating near the pool, with direct access to the indoor entertainment area visible in the background.

4.96 out of 5 average rating, 28 reviews

Luxury Oasis w/ Heated Pool, Theater Room & Dock!

LocationOutdoor spacesPool

5 out of 5 average rating, 18 reviews

Havana Luxos Waterfront | Heated Pool & Hot Tub

LocationOutdoor spacesLaundry

An open-plan living area features a spacious gray sectional sofa and a wooden coffee table, complemented by natural light from large sliding doors. The modern kitchen, equipped with stainless steel appliances, is visible in the background, along with a stylish wine wall displaying Italian wines.

4.81 out of 5 average rating, 37 reviews

Villa Amalfi! Luxury retreat. Heated pool.

LocationOutdoor spacesHospitality

5 out of 5 average rating, 8 reviews

Villa in Cape Coral

Waterfront Paradise Villa With Spa, Pool, Game Roo

LocationAmenitiesNearby

4.97 out of 5 average rating, 37 reviews

A waterfront beach house is showcased, featuring a wide driveway and lush green lawn. Palm trees and colorful landscaping surround the entrance, where a welcoming façade is visible under a clear blue sky, creating a relaxing atmosphere for guests.

Home in Fort Myers Beach

The Great Escape Beach House/ Pool/ Dock

LocationOutdoor spacesLayout

5 out of 5 average rating, 30 reviews

Tiki, Kayaks, Heated Pool, Canals, Fishing, Fenced

Outdoor spacesLocationLayout

Superhost

Home in Burnt Store

4.78 out of 5 average rating, 23 reviews

Waterfront Villa Capri | Dock + Gulf Access

ValueLocationCondition

An expansive outdoor area features a massive infinity pool reflecting the colors of the sunset. Lounge chairs are positioned around the pool, while the villa’s modern architecture and wide glass doors provide a seamless connection to the inviting interior space.