House holiday rentals in Gasparilla Island

Bayfront “Boat House” w/dock and island beach Lux!

Waterfront guest house of a secluded 5-acre, bay-to-beach compound on private Little Gasparilla Island. Water all around! Dock in front, beach out back. Nature abounds. Great boating, fishing, sunning, shelling, birding, etc. Outdoor kitchen, fire pit, beach gear (chairs, games, shades) and paddling gear (kayaks, SUPs). Fun for kids and adults! . TRULY UNIQUE! See pictures & reviews. 2Bedroom (1K, 1Q), 2Bath. Experience Old Florida in modern comfort. Boat access only, WATER TAXI available.

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

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!

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!

Beachfront Oasis w/ Golf Cart and Paddle Boards!

💰No nickel & diming : AirBnb & cleaning fees included! 🤝 local concierge support for a stress-free stay! 🏖️ Beachfront paradise, bordered by untouched nature on both sides— serene, and truly private 🚲 2 bikes + 🛶 2 paddleboards included for island adventures on land and sea 🛺 Golf cart provided for carefree island cruising 🛏️ Oversized primary suite: king bed, lounge areas, desk & full ensuite bath 🏡 Detached casita with private king suite—ideal for guests, couples, or quiet retreats!

Luxury Retreats at Boca Grande - Grande Canal

Three bedrooms, two bath retreat located a few blocks from town and the white sandy beaches of Boca Grande. Full kitchen with island and family room. A separate workspace lets you work remotely. Enjoy the deck, porch, pool, and dock. Fish and crab off the dock. Bring your boat or charter one. Stroll the barrier islands and marvel at the tropical palms, flowers, and birds. Recharge and restore yourself in nature, in town. Very walkable, only a few blocks downtown to restaurants and shopping.

Perfect Beach House Excellent Location

Perfect Beach House, Excellent Location - Quiet Street & Very Short Walk to Beach. This Pilot Street beach house is the perfect getaway for your vacation. Three bedrooms, two full bath with a large great room and extended outdoor living space. Kitchen fully renovated (granite counters, new stainless appliances, bar stool seating). All new mattresses. The premier location in Boca Grande near the beach, walk to town, shop, dine at one of the 14 restaurants with fresh local catch...

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!

BG Beach House South Unit - Great Price & Location

Boca Grande Beach House - South Unit - is half of a 1-story duplex. The South Unit has 2 bedrooms, a combination living room/dining rm, well stocked kitchen & bathroom with a step-in shower. There is a large screened porch across the back and a generous side yard. We are directly across the street from the beach and tennis courts are down the street. It is a short walk to the Community Center where there is a playground for kids and to the charming town of Boca Grande.

Salty Mermaid on Little Gasparilla Island/LGI

Charming beach house on Little Gasparilla Island (LGI) The Salty Mermaid offers a unique tropical paradise with 7 miles of undisturbed white sandy beaches. Embrace the old Florida Island vibe. Enchanted island steeped in pirate lore, legend has it, the spanish pirate Jose Gaspar, nicknamed Gasparilla, made this beautiful island his secret base hideaway. Local legends whisper of buried treasures hidden beneath the islands sandy shores. Come get Salty!

Luxury Beachfront Property

RARE BEACHFRONT PROPERTY: This is private island living at its finest. This house boasts a beautiful open floor plan with each room having a view of the beach and Gulf of Mexico. The property is gated and has a secure backyard. Walk just steps onto the powdered beach sand and Gulf of Mexico. Property is a 30-day minimum. Minimum night rent is 7 nights. If rented for less than 30 days, we will block off the rest of the calendar days in that 30-day period.

Luxury Beach/Gulf Front 1 BR, hot tub & deck

Welcome to Paradise Palms. This 2nd level 1 BR is totally renovated with all new furniture, large private deck & hot tub, bedroom with king, queen sleeper sofa in LR, laundry, high speed WIFI, all new appliances, plenty of closets, smart TV's, & music wing. Walk out your door to a semi private beach, and a quite, neighborhood of single family homes. There is Bay access too, Kayaks available for rent. his is a 2nd story unit with another unit below.