Holiday rentals with a kayak in Sanibel

4.97 out of 5 average rating, 237 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!

LocationOutdoor spacesParking

4.99 out of 5 average rating, 261 reviews

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.

Home in Pelican

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!

Outdoor spacesValueAccuracy

4.91 out of 5 average rating, 140 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!

LocationValueQuiet

5.0 out of 5 average rating, 23 reviews

Home in Sanibel

Island Paradise-The Sandy Banana-across from beach

Relax and enjoy a little taste of paradise in this beautiful home with 3 master suites and a large loft area that has twin beds that double as a sofa, its own coffee bar and mini fridge. Tucked in and surrounded by beautiful sea grapes and palm trees you'll feel like its your own private oasis. Located on the quiet west end of Sanibel Island only a two minute stroll to one of the quietest beaches on the island. You're sure to enjoy nightly sunsets over the Gulf of Mexico during your stay!

LocationOutdoor spacesCondition

5.0 out of 5 average rating, 8 reviews

A screened balcony features two loungers positioned for views of the beach and ocean. Tall palm trees can be seen swaying in the breeze, while the beach is in the distance, separated by lush greenery and gentle waves lapping at the shore.

Condo in Sanibel

Serene condo steps from beach - Sandalfoot 1B2

Escape to the serene beauty of Sanibel Island at Unit 1B2, located on the second floor of the Sandalfoot Beachfront Condominium. Professionally managed by Gulf Coast Vacation Rentals, this delightful 1-bedroom, 1-bath beachfront condo offers an intimate, peaceful setting just steps from the beach. Completely renovated, Unit 1B2 features updated amenities that ensure a relaxing and convenient stay, while maintaining the charm that makes Sanibel so special. Sanibel Island is renowned for its

LocationValueGetting around

5.0 out of 5 average rating, 12 reviews

Home in Captiva

NEW! Beachfront!3BR Suites Sustainable Home+Dock

NEW LISTING!! 💰No nickel & diming—AirBnb & cleaning fees included! 🚤 Boat-access-only retreat with private dock 🏖️ Steps to pristine beach 🌊 Panoramic water views from every room 🛏️ 3 private queen ensuites 🍽️ Premium kitchen + grill ☀️ Tesla solar + 🚀 Starlink WiFi 🛁 Breathtaking sunset views 🛶 Kayak, SUP & e-bikes included 🌿 Surrounded by protected preserve; only one nearby home 🐬 Incredible wildlife viewing ✨ Perfect for nature lovers, anglers & tranquility seekers

LocationOutdoor spacesBiking

4.99 out of 5 average rating, 186 reviews

A spacious stilt home features large windows that provide ample natural light. An outdoor deck with seating overlooks the canal, surrounded by palm trees. A boat dock is visible alongside smooth stone pathways leading to the house, creating a tranquil waterside setting.

Home in North Naples

Waterfront ocean access canal, Kayaks, Bikes Beach

We renovated a key west style home into a modern beachy oasis. You can kayak, bike and boat to the beach right from the house! This safe waterfront neighborhood has tons of friendly people out walking, running, biking, dog walking, etc. The house is 1/4 mile to the beach as the crow flys. Beach entrances are 2 miles away. We have 2 nice adult bicycles, kayaks and fishing rods for you to use. Located just off Wiggins Pass Road between 41 and the ocean. Stilt home. Don’t even need a car.

Outdoor spacesLocationLaundry

4.91 out of 5 average rating, 11 reviews

Home in Sanibel

Sanibel Island House Beach Community/Pool Access

A Private natural getaway Located on the beautiful island of Sanibel Florida Two story freshly remodeled with garage 1920 total sq. ft of living area 2 Community pools in walking distance All new flooring , appliances , furniture, Outdoor Grill, Nautilus work out equipment Walk or ride with the provided beach bikes to the beach path High Speed Wi-fi, Dish Tv, Apple TV Smart tv's in every room World class shelling ,boating, fishing Nature trails, Shopping, Museums Blind Pass fishing

LocationOutdoor spacesGetting around

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.

4.99 out of 5 average rating, 114 reviews

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.

ValueLocationWi-Fi

4.97 out of 5 average rating, 29 reviews

A studio living space is displayed, featuring a kitchenette with modern appliances, including a full-sized refrigerator. A small dining table with blue placemats complements the area. Twin bunk beds are positioned against the wall, with cozy bedding visible. Natural light filters in through the windows.

Guest suite in Sanibel

Sanibel on the Canal

Studio living space in quiet residential neighborhood. Twin bunk over full size bed, kitchen with electric frying pan, electric cooking plate, (no stove) microwave, full size refrigerator, dining space, couch, propane BBQ grill, Wi-fi, and TV with cable. Spa. 3 season pool . Bikes, 3 kayaks (one fishing). all Beach toys. Located on a canal - underwater lights assure plenty of fish viewing at night. Dolphins and manatees are frequent guests, and fishing is allowed from the dock.

ValueLocationBeach

4.95 out of 5 average rating, 99 reviews

A collage of views showcases a sunset over the water, the interior of a cozy bedroom with a spacious bed, a pool area with lounge chairs, and a living space featuring large windows that reveal lush palm trees and a serene landscape.

Home in Captiva

Ocean View, Heated Pool, Pickleball +Walk to Beach

❤We have OVER EIGHTY 5★ Reviews...Book with Confidence❤ ★ 2 Story, 2,115 Sq Ft Home w/ 2 Patios ★ Views of the Ocean on 2 sides ★ 5 Min Walk to Nearly Private Beach ★ Sleeps 8 - (2 Kings, 2 Twins, Sofa Bed) - 3 Bathrooms ★Fast Wifi, Keurig, & Smart TVs ★ Access to Heated Pool, Hot Tub & Pickleball ★ Pack N Play + Board Games ★ Experienced Hosts - (easy check-in, clear communication, clean home) You deserve to see some legendary Captiva Sunrises & Sunsets at least once in your life!

LocationValueView

A heated pool with a clear blue surface is surrounded by a cozy patio area. Lounge chairs provide a space for relaxation, while lush palm trees and vibrant greenery frame the serene waterfront view. A shaded umbrella offers a spot to enjoy the outdoors.

4.99 out of 5 average rating, 160 reviews

Luxury Canal Villa•Heated Pool•Dock•Kayaks•Arcade

Welcome to Sprocket Boathouse, a dream waterfront escape. Beautiful views, a sparkling heated pool overlooking one of the widest canals in Cape Coral, and with western sun exposure, the home gets ☀️ all day. Don’t miss the incredible sunsets and sunrises! You won’t be disappointed. Spend hours swimming, kayaking or fish off your own private dock (kayaks & rods included.) Make sure to keep a look out for all the wildlife! You can spot iguanas, turtles & herons on the waterfront.

ValueOutdoor spacesCheckout

Popular amenities for Sanibel kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a Kayak

4.9 out of 5 average rating, 144 reviews

Modern Canal Oasis | Heated Pool | Kayaks & Office

Outdoor spacesValueAmenities

Aerial view of a spacious waterfront property featuring a pool area enclosed by a screen. Lush palm trees surround the structure, with a boat lift visible along the water's edge. The ocean and distant buildings can be seen in the background.

5.0 out of 5 average rating, 19 reviews

Bayfront Bliss

Outdoor spacesLocationCondition

5.0 out of 5 average rating, 11 reviews

Seaside Villa Aqua

LocationAccessPool

4.96 out of 5 average rating, 46 reviews

Home in Pelican

Sunset Views | Waterfront Pool & Hot Tub Home

Outdoor spacesLocationCleanliness

4.95 out of 5 average rating, 21 reviews

Home in Fort Myers

Renovated 4/4 with Fishing, Pool, Boating, Beach

Outdoor spacesLocationRiver

5.0 out of 5 average rating, 21 reviews

An outdoor area features a sparkling pool alongside a relaxing jacuzzi, both enclosed within a screened lanai. Comfortable seating is arranged in a lounge area, and a set of wooden chairs is positioned near a small table, surrounded by lush greenery and natural light.

Home in St. James City

Salt Life Serenity

Outdoor spacesLocationAmenities

4.99 out of 5 average rating, 70 reviews

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.

Home in St. James City

Enjoy the Salt Life w/Gulf Access Dock＋Kayak＋Bike

LocationOutdoor spacesAir conditioning

5.0 out of 5 average rating, 33 reviews

Riverview@EndPoint -Sunrises+Sunsets - Heat Pool

LocationValuePool

Cottages with a kayak

4.91 out of 5 average rating, 288 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

LocationOutdoor spacesBeach

4.94 out of 5 average rating, 83 reviews

An aerial view captures a serene coastal neighborhood surrounded by lush greenery, with the beach visible in the distance. The beach house is nestled among palm trees, indicating its close proximity to the shoreline and other scenic homes in the area.

Cottage in Captiva

The FlipFlopper Beach House - North Captiva Island

LocationOutdoor spacesPool

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, 55 reviews

Villa The Island Hideaway 2

Outdoor spacesLocationPool

5.0 out of 5 average rating, 36 reviews

A heated saltwater pool reflects the evening sky, showcasing vibrant hues of orange and purple. Lounge chairs are positioned around the pool area, and a tranquil lakeside view is visible, accentuating a peaceful outdoor space.

Cottage in Cape Coral

Sunset Cottage: Lake Front

Outdoor spacesLocationNearby

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, 76 reviews

The Enchanted Cottage on the Imperial River

ValueOutdoor spacesRiver

4.94 out of 5 average rating, 54 reviews

An outdoor patio area is furnished with four black metal chairs, an orange-adirondack chair, and a small table. A barbecue grill is positioned nearby on a paved surface. The backdrop features calm water and a colorful sky at sunset.

Cottage in Matlacha

Waterfront Matlacha Cottage - Sunsets & Fishing!

Outdoor spacesValueCleanliness

Cottage in St. James City

A screened-in deck features a circular dining table surrounded by two swivel chairs. Textured bamboo walls and wooden flooring enhance the space, while ceiling fans provide airflow. Large windows allow natural light and views of the surrounding area.

4.91 out of 5 average rating, 111 reviews

Waterfront/Kayaks/True Salt Life Bliss!

LocationValueFamily

Surrounded by tall palm trees, the cottage features a modern facade with large windows. A vibrant exterior showcases a blend of greenery and pebbled landscaping, creating a welcoming entrance. Colorful outdoor seating is positioned in the foreground for relaxation.

Cottage in Bokeelia

4.67 out of 5 average rating, 219 reviews

Captains Cottage

Outdoor spacesLocationDecor

Other holiday rentals with a kayak

Superhost

A serene waterfront view is captured, showcasing lush greenery in the foreground. A tall palm tree stands prominently, with the calm canal waters reflecting the surrounding landscape and sky. The scene features homes along the canal, framed by trees and foliage.

Condo in Sanibel

4.71 out of 5 average rating, 213 reviews

ON-SANIBEL 4 Kayaks 4 Bikes Wi-Fi - WATERFRONT

Outdoor spacesLocationShared spaces

Superhost

Villa in Fort Myers

5.0 out of 5 average rating, 5 reviews

Mediterranean Waterfront Estate on Caloosahatchee

ValueOutdoor spacesBeach

4.92 out of 5 average rating, 13 reviews

Villa in Iona

Bonaire Grand Luxury Villa

Outdoor spacesLocationPool

4.93 out of 5 average rating, 30 reviews

The exterior of a modern waterfront home is showcased, featuring a sleek metal roof and landscaped front yard. Palm trees are positioned in front of the elegant facade, while serene lake views can be seen in the background, reflecting the clear blue sky.

Villa in Pelican

NEW - Heated Pool & Spa - Gulf Access Lake - BBQ

LocationOutdoor spacesIndoor spaces

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.

4.98 out of 5 average rating, 42 reviews

The Great Escape Beach House/ Pool/ Dock

LocationOutdoor spacesHospitality

4.73 out of 5 average rating, 15 reviews

A screened pool area features a sparkling blue pool with built-in loungers for relaxation. Comfortable outdoor seating is available, with a hot tub in the corner. Bright blue skies filled with clouds enhance the vibrant atmosphere, while greenery stands tall in the background.

Home in Bonita Springs

Cozy 2 bedroom on the canal with pool and hot tub!

LocationValueHot tub

5.0 out of 5 average rating, 16 reviews

Water Front | Modern Open Concept | Beach Vibes

Outdoor spacesLocationAir conditioning

A covered outdoor space features a cozy seating area with a dark wicker couch and light blue cushions. A patterned rug lies beneath, with lounge chairs arranged nearby. A swimming pool is visible through the screened enclosure, alongside landscaped greenery and a clear sky.