Holiday rentals in Gasparilla

Beach Chalet Gulf View

Experience the ultimate beach vacation in our stunning beachfront condo, located on the Gulf of Mexico. It offers breathtaking ocean views and direct access to pristine sandy beaches. The condo sleeps four and offers one bedroom with a king size bed with a private attached bathroom. It also has a queen size murphy bed and an additional full bathroom. The modern kitchen is fully equipped with all the essentials. Plus, the resort offers an onsite pool, fitness center, tennis courts & restaurant.

Coastal 2-Bedroom Home Close to Beaches

This quaint 2 bedroom home features 2 living spaces, game room, laundry room, fully stocked kitchen and is pet friendly. Each bedroom features a queen bed, and the living room has an additional queen sleeper sofa sleeping 6. This coastal home is perfect to gather & entertain friends & family. Grill out & enjoy the large, fenced in backyard. Located 2 miles to Englewood beach & a 15 minute drive to Boca Grande. The home is equipped with 4 beach chairs, corn hole, fire pit, game room and more!

Cozy & Beautiful Pool Villa in Sarasota County, FL

Welcome to our home! It’s our pleasure to host you! Your family & friends will be close to everything when you stay at this centrally-located place: shopping, dining, beaches, entertainment, Warm Mineral Springs, Aquatic Center, etc. This charming house located in a beautiful & quiet neighborhood, tastefully furnished & decorated, fenced for your privacy & perfect for making memories with family & friends. Plenty of amenities to make your stay as comfortable as possible. Great location.

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.

Tropical-Waterfront|Htd Pool-Spa-Dock-Kayaks-Bikes

Welcome to Villa Tropical — your private Punta Gorda retreat surrounded by water on three sides. With a saltwater pool and spa, private dock, steam shower, and plenty of space to unwind, this home blends peaceful luxury with all the tools for adventure. It’s a short 25-minute walk (or 10-minute bike ride) to Fishermen’s Village, with restaurants, shops, and harborfront views along the way. Bikes, kayaks, beach gear, and fishing gear all available to you for no additional cost.

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.

Stunning Villa in Golfer's Paradise/Canal Views

Welcome to your new home in Rotonda West! This 3-bedroom, 2-bathroom gem on Marker Rd is all about comfort, style, and tranquility. As soon as you step inside, you'll be greeted by a spacious and open floor plan that will make you feel right at home. We're excited to share that each room in the house is equipped with a TV for your entertainment pleasure. And guess what? Two of them even have Roku TV, so you can stream all your favorite shows and movies with ease.

Historic Boca Grande: 2 Bedroom Flat:#6 Special Rt

We made it through Milton and Helene and are ready to host you! A great, second floor, 2 bedroom, one bath flat in the heart of historic Boca Grande on the gorgeous Gasparilla Island. Across the street from The Temp Restaurant, and down the block from Hudson's Market. Going to the beach, no worries, it is just down the road. Just a 3 minute walk to the Gasparilla Inn. Guests receive a 10% discount on golf cart and bike rentals through Gasparilla Adventures.

Architect's waterfront home is a fisherman's dream

Who needs a pool when you have 10-minute access to the Gulf? Enjoy this unique, contemporary waterfront home designed and built by coastal architect FV Rossa. Imagine waking up to the sound of manatees in the private deep-water boat basin, then loading up your skiff for a day of fishing or beach hopping. This 3-story property is a fisherman's dream, located just off the intracoastal waterway from some of the most vibrant waters in Southwest Florida.

BRAND NEW Luxury Villa w/Heated and Chilled Pool

Brand new high-end 3 bedroom 3 bath designer home, elegantly decorated with incredible views and direct no-bridge Gulf access. Come and make your lifetime memories in this elegantly appointed executive villa. Located near Matlacha, Sanibel, Fort Myers, and Naples. Extra wide canal with only trees opposite, a salt water lagoon, and just off the spreader canal means incredible solitude and privacy in your elegant oasis retreat.

Private Heated Pool + Swim-Up Bar • Mins to Beach

Unwind in this thoughtfully designed 3-bedroom Florida retreat just 5 miles from Englewood Beach. Enjoy a private, heated pool with swim-up bar, screened lanai, and lush tropical privacy. Inside, you’ll find an open-concept living space, fully equipped kitchen, spa-style primary suite, and comfortable guest rooms. Ideal for families, couples, or friends seeking comfort, privacy, and easy access to beaches, golf, and dining.

Secluded Paradise,Heated Pool,Beaches and Golf n.

Our stunning retreat is designed for comfort and relaxation - with a spacious living room, fully equipped kitchen, and inviting bedrooms that can accommodate up to six guests. Enjoy the serenity and privacy of a pool area without neighbors, perfect for unwinding in peace. Savor delicious outdoor dining and stay connected with high-speed internet via STARLINK. Don't miss out on this amazing opportunity to escape to paradise.