Vacation rentals with a kayak in Little Gasparilla Island

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Top-rated kayak rentals in Little Gasparilla Island

Guests agree: these kayak rentals are highly rated for location, cleanliness, and more.

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Guest favorite
Townhouse in Rotonda West
4.98 out of 5 average rating, 54 reviews

Water View 3bdr,2ba, Close to Beaches Golf/Fishing

If you are looking for a perfect location to rent a place in Florida, this is it. This is 2022 construction villa close to 5 beaches, golfing or fishing. Boca Grande Island is within minutes, enjoy the Island relaxed beaches. We provide everything you need, beach chairs beach umbrella and bikes. Enjoy BBQ on the patio and relax in enclosed lanai with beautiful lake view, sit down to a great movie or board game in the living room. Ann&Chuck Pool 5min Sasy tarts coffee pls &multiple places to eat

Guest favorite
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
4.89 out of 5 average rating, 187 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!

Guest favorite
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
4.8 out of 5 average rating, 105 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!

Guest favorite
A lighthouse is observed standing tall against a backdrop of serene blue waters and a sandy shore. The lightkeeper's balcony offers panoramic views of the ocean, reflecting shimmering sunlight, while the surrounding beach features gentle dunes and patches of vegetation.
Villa in Port Charlotte
4.95 out of 5 average rating, 20 reviews

"Everglade Kiss" 3b 2b BBQ, hot tub

"Everglade Kiss"3 bed 2 bath 1 car garage villa, quartz kitchen corner tops ,65 inch TV in living room, lanai has 16 jets hot tub , BBQ Back yard is shareable.South West Florida's prime boating and beaching communities with the Charlotte Harbor and The Gulf of Mexico minutes away.Community offers public sidewalks, parks, with boat ramp, picnic area, playground. The waterways provide place for kayaking, paddle boarding, and fishing. Enjoy a memorable visit when you stay in this unique place.

Top guest favorite
A contemporary two-story home is depicted overlooking a serene pond. A fountain creates gentle ripples on the water's surface, while palm trees and lush greenery frame the scene, contributing to an inviting outdoor setting.
Home in Placida
5 out of 5 average rating, 19 reviews

Sea La Vie

Escape to 3 acres of tropical bliss on exclusive Palm Island, where luxury meets seclusion. This beautifully updated 5-bedroom, 4-bathroom retreat offers breathtaking views of a serene pond and the Gulf of America. Heated pool & jacuzzi, 50-ft private boat dock, Home theater & game room, Kayaks, bikes, pool table, ping pong, and more, Fire pit, basketball court, volleyball, Steps from a private beach. Accessible only by private ferry, this is more than a getaway; it’s your slice of paradise.

Guest favorite
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 Placida
5 out of 5 average rating, 20 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 Aquatic Preserve, 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. 2 ensuite bedrooms. Bunk bedroom & loft.

Guest favorite
A well-lit bedroom features a spacious wooden bed with plush white bedding. Natural light enters through the window, which is adorned with horizontal blinds. Simple wall art complements the soothing color scheme, and a ceiling fan provides ventilation.
Farm stay in Punta Gorda
4.96 out of 5 average rating, 112 reviews

Peaceful Waterfront Orchard 1

bring the whole family including your pets to this peaceful orchard and garden oasis. the action packed backyard of this duplex proudly boasts over 40 fruit trees of various varieties including banana, orange, lemon, fig, mango, papaya... and many more! choose to fish from the dock in the backyard canal, go exploring with the kayaks or paddleboards, play in the sandbox, try out the slackline, or even say hi to the chickens in the coop (maybe even grab a few fresh eggs for breakfast).

Top guest favorite
A spacious home is set on a well-maintained lawn, featuring a white exterior complemented by lush tropical landscaping. Palm trees and shrubs enhance the entrance, while a smooth driveway leads to a two-car garage. The sky is clear and blue, adding to the inviting appearance.
Home in Port Charlotte
5 out of 5 average rating, 100 reviews

Elegant heated pool canal home in very quiet area.

Great location! Bring your dog, bring your boat and enjoy the Florida sun in your heated saltwater swimming pool. Fish off your private dock while watching for dolphins or manatee. You can meet the rest of the opacarophiles who walk to the beach to view the sunset. Relax in the jacuzzi with your favorite beverage. NOTE: Beach is sandy but the water is BRACKISH, not clear. This is mostly a retirement neighborhood. This is NOT a party house and not suitable for unattended children.

Top guest favorite
Cottage in Placida
4.98 out of 5 average rating, 63 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.

Top guest favorite
Home in Port Charlotte
4.94 out of 5 average rating, 16 reviews

Canal Home w/ Escape Room, Pool & Dock, Pets OK

"Start your stay with something totally unexpected: our QR Clue mystery adventure, included with every booking. As you settle into the home, you’ll discover hidden clues containing interactive puzzles woven through the living spaces. Make it to the end to solve a long-standing mystery and win a take-home prize as a keepsake. It's an escape room-style challenge designed for all ages to create fun, memorable moments without ever leaving the comfort of the house.

Guest favorite
A sandy beach stretches along the calm waters, showcasing gentle waves under a partly cloudy sky. Lush greenery lines the shoreline, and a wooden staircase leads to the beach, providing access to the serene outdoor environment.
Cottage in Englewood
5 out of 5 average rating, 33 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.

Guest favorite
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 Placida
4.96 out of 5 average rating, 57 reviews

Island Getaway Pool-Ferry-Grocery Delivery Incl.

*FREE Island Grocery delivery/staging Enjoy our Locally Owned and Operated, Newly 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 Gated Mainland Parking & Ferry to the Island incl. Walk the Uncrowded shelled beach with Birds, Dolphin and Manatee or Venture out for Prime Fishing & Kayaking SWFlorida has to Offer

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