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.

Family · Location · Cleanliness

Lake Marlin Villa 2

WELCOME to this affordable, charming and unique villa, all spotless and immaculate, cleaned with passion, love and hospitality, to honor you; The GUEST of HONOR. This 2-bed, 2-bath, 2-car garage and plenty of outdoors, offers you the comfort of feeling home, yet the adventure of your getaway vacation. Overlooking the blue waters of Lake Marlin, away from traffic and noise pollution, yet close to stores, golf clubs and main roads taking you within minutes to Manasota Key and Boca Grande Beaches.

Location · Value · Getting around

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

Location · Family · Nearby

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!

Location · Value · Cleanliness

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!

Family · Location · Hiking

Vacation Paradise in Rotonda

This brand-new home with 3 bedrooms and 3 bathrooms is truly designed for comfort and relaxation. The spacious living room, huge kitchen, and big dining room are an open-layout living area. Our outdoor covered grilling area has outdoor furniture a hot tub, and a heated pool. Walking distance to Long Marsh Golf Club, a short drive to 3 more Gulf Clubs. A Playground for the kids and exercise paths are all here. Amazing 7 beaches to choose to visit with very good restaurants close to the area.

Family · Location · View

Last Minute Offers Beach + Golf Cart + Club

BOOKING FALL 2026 HOST PAYS AIRBNB FEE Golf Cart and Club amenities Included North Captiva Island Cottage! Just steps away from the Gulf's pristine shores, this cozy retreat offers a private hot tub, perfect for families and beach enthusiasts. Enjoy modern amenities, a well-stocked pantry, and a complimentary golf cart to explore the island. Pet-friendly(small fee) accessible by ferry, boat, or plane. With beach gear, access to the club pool, and proximity/ steps to the beach

Location · Family · Laundry

Island Getaway•Beach House•Water View•Dock•Pets

Embark on your next adventure at this unique and serene retreat that can only be reached by boat. LGI is a barrier island off the West Coast of Florida in the Gulf of Mexico between Sarasota and Ft Myers. Arrive at the island using your private boat or by boarding the water taxi, and be at our dock in just 10 minutes. There are no cars, shops, or restaurants on the island, the 7-mile beach is private and uncrowded. You can explore LGI by renting a golf cart or by walking

Family · Location · Decor

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..

Location · Family · View

Modern City Loft in Downtown River District

Welcome to Gun-Loft, a custom-designed modern sanctuary in the Downtown River District. This expansive 3500 square foot city loft is tailored for those seeking to embrace the cosmopolitan lifestyle, with the perfect blend of urban luxury and cultural richness. Whether it's a leisurely stroll to the Edison Ford Home, an exciting night out, or a culinary adventure in the restaurants nearby, Gun-Loft offers an unparalleled experience in the city's most coveted location.

Location · Value · Checkout

little Gasparilla Island Beach house-Dog friendly

Escape to Beach Hair Don’t Care on Little Gasparilla Island! This cozy 2BR, 2BA retreat sleeps 5 and is just steps from the bay and 100 yards from a private beach. Enjoy uncrowded beaches, fishing, wildlife, and water sports. Pet-friendly with a fully stocked kitchen, beach gear, boat slip, and golf cart access. Experience the serenity of this car-free island paradise, perfect for relaxing, unwinding, and making memories. Book your escape today!

Family · Location · Walkability

Paradise on the Bay

Waterfront pool home just a short drive to Boca Grande with all the amenities that you would expect. Enjoy spectacular sunsets over Lemon Bay. With more than 250 ft of seawall for deepwater dockage, this home can accomodate even the largest boats. Fantastic fishing from your front yard! Three bedrooms and two baths make this the perfect vacation destination for family and friends. 3 Kayaks and a canoe are available for your enjoyment.

Value · Family · View