Holiday rentals with a kayak in Don Pedro Island

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Top-rated Accommodation with a Kayak in Don Pedro Island

Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.

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Top Guest favourite

A canalfront area features a serene gazebo surrounded by lush green grass and white pebbles. The vibrant sunset sky adds warmth to the scene, and the private boat dock is visible in the background, enhancing the tranquil outdoor setting.

Home in Port Charlotte

5.0 out of 5 average rating, 106 reviews

Xanadu|Fishing/ Pool/Dock|Kayaks|Bar/Gazebo/ Kids

Welcome to XANADU Luxury Villa 🌊 your canalfront paradise with a private BOAT DOCK ☀TOP LOCATION📍, close to: beautiful beaches 🏖️ Gasparilla Island, Siesta Key, Englewood! ☀Dock Ideal to FISH 🎣| Deck🎴 ☀BAR🍷 ROOM Dancing Light 🪩 ☀DEDICATED WORKSPACE 💻 ☀GAME🎮 Room /Roblox/Arcades🕹️ ☀Smart TVs in every room📺 ☀HEATED Pool 🏊‍♀️ ☀Fast WIFI📶 ☀Ping Pong Area in Sand 🏓 ☀Fully equipped kitchen🍽️ ☀Pool Table and Games🎱♟️ ☀ Outside dining table😋/Fireplace ☀BBQ🍖Ice Maker🧊 ☀Self check in 🔐 Smart Lock

ValueLocationNearby

Top Guest favourite

Two individuals ride bicycles along a sandy beach at sunset, with vibrant hues of orange and purple in the sky. Gentle waves lap at the shore, and distant figures can be seen walking along the coastline, creating a serene beach atmosphere.

Cottage in Englewood

4.9 out of 5 average rating, 211 reviews

Unit #2 Free bikes/kayaks/walk to beach/2bed/2bath

Unit # 2 Beautiful 2 bedrooms 2 bath cottage, great space to relax with family and friends. With full kitchen/ garage/laundry/outdoor shower. WiFi/Free bikes, kayaks, beach toys. Great Lanai to spend wonderful afternoons. You will love to walk to the beach and enjoy the most breathtaking sunset pictures. cottage is fully furnished beach style for a wonderful vacation feeling. You have not only the beach and the bay to explore, but great restaurants/bars and more just walking distance. Enjoy!

Outdoor spacesValueCheckout

Top Guest favourite

Home in Don Pedro Island

4.94 out of 5 average rating, 17 reviews

Modern Island Oasis: steps2beach

🏝️Island fun + luxury🥂living = the perfect getaway! 👣 Just steps to the beach & the bay/dock 🦋 High-end fixtures & fittings: -Custom LED lighting modes -Stunning kitchen -Stylish tile floor -Gorgeous granite counter tops -Micromesh screened balcony: 100% bug free 🏠 The most luxurious home on LGI 🏓 Packed with toys+games 🛝THIS is your Paradise Playground 🥇 Guest Favorite: Rated Top 5% 🙋 For those who want to max out on fun, in luxury, style & comfort… 🎯 Look no further: this is the #1

Outdoor spacesLocationWalkability

Guest favourite

An aerial view of Manasota Key showcases the expansive beach lined with soft sand and crushed shell. The vacation home is highlighted, surrounded by lush greenery and close proximity to the warm Gulf waters, with clear blue skies enhancing the tranquil environment.

Bungalow in Englewood

4.83 out of 5 average rating, 122 reviews

LG Beach Bungalow on Gulf w/Bay Access & deck too!

Welcome to Golden Girl. Our 3 bedroom 2 bath home is totally renovated with all new furniture. A 2nd level observation deck, private hot tub, bunkroom sleeps 6, two bdrms with kings, queen sleeper sofa in LR, laundry, high speed WIFI, all new appliances, smart TV's, so much more! Lanai opens up to semi private beach and a quiet neighborhood of single family homes. There is Bay access too. Kayaks available for rent. There is a separate apartment above not included. The location cannot be beat!

Outdoor spacesLocationComfort

Top Guest favourite

An aerial view captures the Tropical Island Getaway, showcasing structures with teal roofs nestled among lush greenery. A pool is visible on the left, while the coastline stretches in the background, revealing sandy shores and the serene blue Gulf waters.

Condo in Don Pedro Island

4.97 out of 5 average rating, 66 reviews

Island Getaway Pool-Ferry-Grocery Delivery Incl.

10-minute passenger ferry ride to this boat-access-only, car-free island Locally Owned & Operated Updated LGI Condo with Magnificent Views 2 private SW facing decks offer a.m Sun, Gulf, Palm & Pool Views. Beautifully furnished with everything to enjoy your Island time Uncrowded shelled beach with Birds, Dolphin and Manatee -Venture out for Prime Fishing & Kayaking SWFlorida has to Offer There are no grocery stores or restaurants on the island, plan to bring everything you’ll need with you

Outdoor spacesLocationAir conditioning

Guest favourite

A wooden dock leads from the water to the main house, surrounded by native vegetation. The two-story structure features a rooftop deck, large wraparound porch, and palm trees framing the entrance under a clear blue sky.

Home in Don Pedro Island

5.0 out of 5 average rating, 21 reviews

Island Estate. Beach, Bay, Nature. Lux! Extras!

Little Gasparilla Island. Main house of 5-acre, beach-to-bay "old FL" estate. Bay in front, pristine beach in back. Very private, natural setting on the bay Florida Blueway KayakTrail and bordering Don Pedro nature preserve parkland. Kayaks & SUPs for exploring the bay, beach gear and games. Abundant birds, fish, shells, & wildlife. Manatee and dolphin are common. Accessible only by boat/water taxi. No stores, few people. 3 ensuite bedrooms plus a bunk bedroom with three singles

ValueOutdoor spacesKitchen

Guest favourite

Home in Englewood

5.0 out of 5 average rating, 9 reviews

Cape Haze Cottage

2023 Cape Haze Cottage , 3 bedroom 2.5 bath elevated canal front pool home. Quiet waterfront neighborhood with easy access to everything this amazing area has to offer. Screened lanai provides sunset views, private pool, outside shower, steps away from canal front for Kayaking and fishing or just watching the endless variety of nature. Situated just six minutes from stump pass by boat, access to the gulf , beaches and fishing both inshore and offshore. This is a piece of heaven.

Outdoor spacesLocationComfort

Top Guest favourite

A private pool area features a heated pool and spa, surrounded by a screened enclosure. The serene outdoor space includes textured stone decking and seating, while lush greenery frames the view. Panoramic sliding doors lead into an inviting interior living space.

Home in Placida

4.95 out of 5 average rating, 43 reviews

AMAZING Cape Haze Location -community kayak launch

Ready for warm sunshine, tropical breezes and lush landscaping? Spaniard's Retreat is the ideal location for your get away. This home is set in the charming Old Florida neighborhood of Cape Haze. Old banyan and pin-oak trees line the picturesque streets where homes are spaciously placed. Upon entering you will be greeted by the panoramic sliding doors overlooking the heated pool and spa. This truly feels like a private oasis. 3 bedrooms and 2.5 baths offer generous accommodations.

ValueOutdoor spacesSleep quality

Top Guest favourite

Cottage in Don Pedro Island

4.99 out of 5 average rating, 78 reviews

Island Getaway, Beach House, Dock, Pet Friendly

Take it easy at this unique and tranquil getaway only accessible by boat. Little Gasparilla Island is a bridge-less barrier island off Florida’s West Coast in the Gulf of Mexico. Access is for residents and renters only, you will arrive by your private boat or jump aboard the water taxi for a 10 minute ride to our dock. No cars, shops, or restaurants on the island. The 7 mile beach is private and uncrowded. Get around LGI by renting a golf cart or explore by foot-you decide.

ValueOutdoor spacesWalkability

Top Guest favourite

An aerial view captures a two-story home nestled along a quiet waterway with lush greenery surrounding it. Nearby, other residences and a private dock are visible. The scenic backdrop showcases calm waters merging with a blue sky, highlighting the tranquil atmosphere of the location.

Home in Englewood

5.0 out of 5 average rating, 65 reviews

Lux Home on Gulf w/Private POOL & 50ft Dock

Rest your feet & your soul as you getaway from it all! This luxurious little piece of paradise is tucked away on a quiet Gulf Coast waterway. 10min from Englewood Beach and 5 min from stores. Tie your boat up in the back yard to the private 50 ft dock. Spend your days fishing, catching sunsets or in the pool every evening! Easy access to Don Pedro Island, local sandbars, inlet and several restaurants, all at your fingertips! Pack your bags, kick back- paradise is waiting!

LocationOutdoor spacesBathroom

Guest favourite

An enclosed lanai features multiple large windows with views of Lemon Bay, allowing natural light to fill the space. A palm tree is visible outside, framed by the window panes. A decorative area rug is positioned on the wooden floor, enhancing the coastal ambiance.

Villa in Englewood

4.99 out of 5 average rating, 142 reviews

Stunning Bay Waterfront! Jaw dropping Water Views!

Spectacular Lemon Bay views! Upstairs at Blue Island Inn, waterfront “Bella Vista” with Bay & Pool views! 2 bedrooms; kitchenette & family room. Enjoy “Lemon Bay-front beach” in backyard. Low-key quiet vacationers. 1 car parking spot. No visitor parking. Free 2 kayaks. Login to your favorite streaming services with Smart TVs. Beautiful Blind Pass Beach, Englewood Beach, 5 restaurants & Tiki Bars are just 1.5 mile away or hop on Stumpy's Free Shuttle (tip based)

ValueOutdoor spacesCleanliness

Guest favourite

Cottage in Englewood

5.0 out of 5 average rating, 38 reviews

Private Beach-Luxury 4BR+SUPs&Kayaks-Pets-BBQ

Charming 4 Bed Cottage (sleeps 9), Private Beach to Gulf Across Street, with Large Screened Porch, Super Shark Tooth Hunting, Free use of 2 Kayaks and SUPs, Restaurants, Live Music, Golf, and Tennis . Uber Eats & Grocery delivery, 50 Minutes from Sarasota Airport (75 minutes from Fort Myers airport). Lush tropical rainforest in the "Old Florida" region on the Gulf surrounds this cute cottage. *Please note small extra $50 pp nightly fee for guests 7-9.

LocationOutdoor spacesWalkability