Apartment holiday rentals in Little Gasparilla Island

#2) Bikes, Kayaks Sups, unmatched amenities & More

Welcome to Stump Pass Place! A perfect mix of comfort, nature and unmatched amenities. Just a 3 minute walk to our beautiful neighborhood beach or a just 4 minute walk to Stump Pass State Park at the end of our street. Here you can go to the beach, launch the water toys, and make some lifelong memories. Stump Pass State Park has one of the most beautiful pristine beaches in all of Florida! FREE Kayaks, Sups, beach cruiser bikes, beach chairs, umbrellas, boogie boards, coolers and so much more!

Upscale Beachfront 1+BR,Kayaks,SUPs,Pets OK

Cozy/Private 1+ Bedroom Private Waterfront Suite (King and Sleep Sofa) with Kitchen and Full Bath with the Beach literally 20 Steps from your Front Door. 2nd BR/Bath option available for a small fee.This rental is in a quiet residential area, far away from restaurants/bars. This property is one of the few remaining "Old Florida" regions of the Gulf Coast of Florida, with subtropical rainforest surrounding, a hammock waiting for you on the beach, and a dock for fishing or boating 100 yds away.

Dolphincove 5035B Sea Haven- Super host

Breathtaking sunsets with a short walk to the beach. We were totally rebuilt in 2024. New roof, brand new central a/c upstairs, reverse heating installed in December 2025. New wall A/c units in the studio apartments downstair, with the nest system. All new Key West beach decor and furniture- upscale and tasteful.. Luxury beds and pillows. pull out queen couch and day bed. totally furnished kitchen with stainless steel appliances. free use of 2 sets of washers and dryers in 2 garages.

Old Florida Charm near Beaches

Take it easy at this unique and tranquil getaway. Florida charm at its finest. Tropical garden setting in an historic home in your own private space. Walking distance to three restaurants including an original landmark restaurant, the Bean Depot. Fishing pier and boat ramp on the Myakka River to the gulf are also nearby. The house was originally owned by the Adams Family, makers of chewing gum ( chicklets and tea berry gum). Beautifully restored older home with lush tropical landscaping.

Vacation in Paradise

This vacation in Paradise is tucked along a freshwater canal that is full of wildlife. On the dock you can enjoy beautiful sunrises and sunsets. With a heated salt water pool. This is a duplex home that shares its outdoor space with the owner that lives on the other side of the duplex. The inside has a cozy beach theme. It has a work at home station with business Wi-Fi, also has cable television to each of the bedrooms and living room. It is stocked with every amenities you might need.

Bungalow across from the Beach!

Welcome to your private island retreat! This charming bungalow is tucked among swaying palms and the natural serenity of the island, offering the perfect blend of comfort and laid-back coastal living. Middle Beach Road is NOW OPEN, restoring full access to the entire island, all beaches, shopping, restaurants, and tiki bars. Enjoy a short walk to private beach access, nearby public beaches, dining, groceries, and island attractions—then relax outdoors to the soothing sound of the waves.

Marina front, pool, beach condo!

Enjoy water side living at our stylish condo. Amenities galore offer activities and relaxation for all. Your vacation place comes with the onsite pool/hot tub and ferry pick up to take you to Palm Island. Enjoy lunch or dinner at the island restaurant and stay for the most amazing sunsets. Or view the sunset from the comfort of your condo! You’re just minutes away from boating, fishing, kayaking or shark tooth hunting at any of the nearby beaches.

Family-Ready 2BR · King + Twins · Boca Grande

A second-floor 2BR flat in Boca Grande village, set up for families: king in the primary, two twins in the second, children's dinnerware stocked, babysitter recommendations on file, and a full kitchen for cooking breakfast before the beach. Beach: 120 steps. The Temp Restaurant is directly across the street. Book through us for 10% off golf carts and bikes from Gasparilla Adventures — how families actually explore the island.

Private cozy beach guest-suite w/parking next door

Discover your slice of paradise in Venice, Florida! Our charming Airbnb apartment offers a cozy and comfortable retreat in this coastal gem. With a great location, this apartment is your gateway to pristine beaches, local culture, and vibrant dining options. Perfect for a relaxing getaway, this apartment invites you to explore all that Venice has to offer. Book your stay today and experience the magic of Venice, Florida.

The Palms – 3BR Gulffront, Sand & Sunsets

Experience the beauty of Manasota Key from this spacious and newly updated 3-bedroom, 2.5-bath beachfront condo at The Palms. This corner unit sits on the first floor (just above covered parking), offering sweeping Gulf views, natural light throughout, and direct access to the beach, pool, and everything the island center has to offer — all within walking distance.

BeachBay SeaHouse - 1521

Best location/value on Manasota Key in Englewood, FL... 300 yards to pristine gulf beaches, 300 yards to boat ramp and dock on Lemon Bay if you have a boat or want to see dolphin or fish off the dock. 4/10s of a mile to several great restaurants and 1 mile to Stump Pass State Park and a few more miles to walk via the park to Stump Pass.

Super cute fun studio steps from everything beachy

This light and bright space makes you feel like you are outside, but can transform into a cool hideaway when you draw the curtains. The view of the pool creates a calm and happy space and encourages you to relax. A smaller space leaves more room for enjoying the true luxuries - the beach, the sunsets, and time together.