Holiday rentals with a kayak in Sanibel Island

4.98 out of 5 average rating, 241 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!

4.99 out of 5 average rating, 263 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!

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.

4.91 out of 5 average rating, 141 reviews

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!

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!

4.85 out of 5 average rating, 13 reviews

A spacious living area presents a comfortable sectional sofa adorned with colorful throw pillows. Natural light filters through wide sliding glass doors, leading to a view of the landscape. A sleek entertainment unit is positioned against the wall with a large flat-screen TV above.

Condo in Sanibel

Beachfront condo on Sanibel - Sandalfoot 2B1

Step into the perfect island getaway at Unit 2B1 at Sandalfoot Beachfront Condominium, located on East Beach near the Sanibel Lighthouse. Professionally managed by Gulf Coast Vacation Rentals, this inviting 1-bedroom,1-bath condo on the ground floor offers gulf views and is just steps from Sanibel Island's pristine, sugar-white beaches, offering you easy access to everything this tropical paradise has to offer. Recently renovated, the unit has been thoughtfully updated to provide you with the

Superhost

Home in Sanibel

4.91 out of 5 average rating, 11 reviews

Sanibel Island House Beach Community/Pool Access

A private natural getaway Located on the beautiful island of Sanibel, Florida Two-story, freshly remodeled with a garage 1920 total sq. ft of living area 2 community pools in walking distance All new flooring, appliances, furniture, outdoor grill, Nautilus workout equipment Walk or ride with the provided beach bikes to the beach path. High-speed Wi-Fi, Dish TV, and Apple TV Smart TVs in every room World-class shelling, boating, fishing Nature trails, shopping, museums Blind Pass fishing

5.0 out of 5 average rating, 13 reviews

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

4.99 out of 5 average rating, 116 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.

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.

4.9 out of 5 average rating, 128 reviews

Home in Cape Coral

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!

4.94 out of 5 average rating, 156 reviews

Last Minute Offers Beach + Golf Cart + Club

BOOKING FALL 2026 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

The Compass Rose is a multi-level home surrounded by lush greenery, showcasing a light blue exterior. A spacious rooftop deck with seating is visible, complemented by multiple balconies offering shaded areas. Palm trees and coastal vegetation frame the property in a relaxing coastal setting.