Holiday rentals with a kayak in Little Gasparilla Island

5.0 out of 5 average rating, 97 reviews

A private heated pool area features clear water surrounded by comfortable seating and vibrant blue umbrellas. A large pink flamingo float is visible in the water, alongside other colorful poolside furnishings. Lush greenery is present in the background, enhancing the outdoor atmosphere.

Home in Port Charlotte

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

4.93 out of 5 average rating, 15 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

5.0 out of 5 average rating, 6 reviews

Island home w/POOL, Private DOCK & BEACH access!

Forget the crowds, if you're dreaming of a private beach escape, this spot has you covered! Located on the private Palm Island-ONLY accessible by 5 minute car ferry or private boat. Relax in this 3BR/3BA private retreat with a PRIVATE POOL & PRIVATE DOCK w/power&water in the backyard. Private BEACH access across the street, ultra comfortable premium mattresses, beach chairs/toys, kayaks, plus a fully equipped kitchen, outdoor dining space with grills easy for coastal living. No bridges to gulf!

4.82 out of 5 average rating, 118 reviews

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

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!

Townhouse in Don Pedro Island

A spacious open-concept living area features large windows allowing natural light and ocean views. A dining table with white chairs is positioned near the kitchen, with light wood flooring throughout. The sunset casts a warm glow, enhancing the inviting ambiance of the space.

4.98 out of 5 average rating, 55 reviews

Sunset Beach Cottage North

Spectacular panoramic views and access to what feels like your own private 7 mile sugar sand beach. 2 master BRs with balconies overlooking the beach and ocean. Elevator, hot tub, pool, kayaks, Blackstone grill, bikes, etc. Access to Palm Island is by 3 minute car ferry - which ensures a relaxing and tropical getaway. Incredible sunsets, shelling, fishing & wildlife. There is a restaurant on the island along with gift & ice cream shop. Beautiful place to relax, unwind & embrace island life.

4.89 out of 5 average rating, 183 reviews

An aerial view captures the coastline of Manasota Key, showcasing the blue-green waters and sandy beach. The surrounding area features a mix of residential buildings and green spaces, with multiple boats visible in the water and a bridge connecting to nearby islands.

Cottage in Englewood

Unit #1 Free kayak/bikes/walk to beach/fullcottage

Unit #1 Beach cottage very private and quiet, has a full kitchen, King bed in the master and queen sofa bed in the tv room, very comfortable, fast WiFi, AC & heat. All you need to relax and just have fun. Outdoor shower and laundry area, Private parking, Enjoy amazing sunsets/fishing/and restaurants and bars, all walking distance to the beach and bay. Kayaks/snorkel gear/beach toys are included. So start enjoying the beautiful sandy beach on Manasota Key, Lots of sea life and turtles.

4.95 out of 5 average rating, 41 reviews

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

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.

Cottage in Don Pedro Island

4.99 out of 5 average rating, 74 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.

5.0 out of 5 average rating, 59 reviews

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

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!

The beachfront cottage is surrounded by lush foliage, showcasing a two-story structure with a metal roof and large windows. Soft light spills from the interior, highlighting a welcoming atmosphere. A wooden walkway leads to the entrance, inviting guests to explore the natural surroundings.

4.9 out of 5 average rating, 29 reviews

Island Beachfront Cottage. Secluded! Lux! Extras!

Welcome to the most secluded spot on Little Gasparilla Island! Our Beach Cottage property is on the beach with all-natural surroundings: a state park, a mangrove lagoon, and the Gulf of Mexico. It boasts front views of the water and gorgeous island sunsets year-round. You'll have boat space on our private dock and amenities including kayaks, paddle boards, an outdoor bayside dining area, coffee bar with complimentary coffee, private grilling area, fire pit, and much more!

4.99 out of 5 average rating, 134 reviews

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

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)