Holiday rentals in Gasparilla Island

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 🥇 Rated Guest Favorite 🙋 For those who want to max out on fun, in luxury, style & comfort… 🎯 Look no further: this is the one!

Beachfront North Captiva | Rooftop Deck | Hot Tub

No bridges. No cars. No crowds. Stella Maris sits directly on the Gulf on North Captiva — a private barrier island reachable only by boat. Step off your deck onto white sand. Watch dolphins from your 360° rooftop deck at sunset. 3 bedrooms, each with private en-suite bath. Cathedral ceilings, gourmet kitchen, formal dining with Gulf views, stone fireplace, hot tub, and included golf cart. Dual club access — Safety Harbor Club included; optional Island Club for pools, kayaks, bikes, and pool bar.

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!

Happily Ever After

We are off the main path and it is a quiet place to reconnect with what matters. We encourage our guests to unwind on our spacious comfy screen porch with chairs, table, and a futon chair for naps. Also use our large private maze outdoor shower. Be prepared for loads of sun and fun. Unlike most rentals ours includes all paper products, spices, plastic ware, toiletries, coffee, tea, all linens, beach chairs, noodle, sun screen, bug spray and GOLF CART available for RENT during your stay.

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...

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.

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!

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!

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 Retreats at Boca Grande - Boca Bay Watch

Watch the yachts cruise by en route to and from Miller's Dockside, while rocking on your private and serene breeze-filled balcony. Boca Bay Watch sleeps 8 and has 3 bedrooms and 3 bathrooms. This charming villa is a quick walk or golf cart ride downtown Boca Grande for shopping and dining. It is a most idyllic and exclusive community. Very walkable area allows for viewing of local palms and birds and exotic wildlife in addition to local attractions.

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