Holiday rentals with outdoor seating in Gasparilla Island

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.

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

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!

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!

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.

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 North Unit-Great Price & Location

Boca Grande Beach House - North Unit, is half of a 1-story duplex. It has 2 bedrooms, living/dining rm, a fully stocked kitchen & 1 bathroom with step-in shower. There is a large screened porch across the back and a generous side yard with table & 4 chairs, 2 lounge chairs. We are directly across the street from the beach & tennis courts are down the street. It is a short walk to the Community Center with a playground for kids and to the charming town of Boca Grande..

Happily Ever After

Welcome to our treehouse!! Surrounding our home are wonderful sea grapes and palms. If you like privacy look no further. We are off the main path. We encourage our guests to unwind on our spacious screen porch with chairs, and tables. Be prepared for loads of sun and fun. Our rental 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.

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.

Beach Loft · King Bed · Adults Only · Boca Grande

A timber-framed loft in the heart of Boca Grande village — king bed up the spiral staircase, village views from above, and everything within walking distance. Adults only: this is the couples retreat in the portfolio. Beach: 120 steps. The Temp: across the street. Hudson's Market: half a block. Golf carts from Gasparilla Adventures — 10% off with your reservation.

"Salt of the Sea" - beachfront and pet friendly!

Experience the ultimate escape at "Salt of the Sea," a charming 1 bedroom/ 1 bathroom beachfront cottage located on the serene Little Gasparilla Island, a unique bridge-less barrier island. Here, you'll find no stores, no restaurants, no bars, and no cars – just pure relaxation and a chance to unplug from the hustle and bustle of everyday life.