Apartment holiday rentals in Little Gasparilla Island

A scenic rooftop deck is highlighted, featuring several bright orange high chairs positioned along a railing. The expansive view showcases the turquoise waters of the Gulf, with a clear blue sky above and a glimpse of the sandy beach below.

4.96 out of 5 average rating, 23 reviews

#6) 30 Seconds To Beach Path/Tiki Bar/Bikes/Kayaks

Welcome to Stump Pass Place! A perfect mix of comfort, nature and unmatched amenities. Just a 30 second 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!

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4.94 out of 5 average rating, 17 reviews

Beachfront Gulf Condo | Englewood Beach| Pool

Relax at this Gulf-side Sunburst condo on Manasota Key, steps from the Gulf’s white-sand beach. Enjoy easy beach access, a step-out balcony w/views toward the Gulf, stunning sunsets, heated pool, and a bayside dock for fishing or boating. Walk to nearby restaurants and shops or unwind in the bright coastal living space. The condo includes: • King bedroom • Enclosed lanai sleeping area • Full kitchen • Comfortably sleeps 4 guests Perfect for couples, small families or a relaxing beach getaway.

LocationFamilyWalkability

5.0 out of 5 average rating, 5 reviews

2 BR/2 BA Beach Front Suite-Kayaks-SUPs-Bikes-Pets

Waterfront 2 Bed/2Bath (sleeps 7-8) so close to the water that you can hear the waves all day and night with the windows open. One bedroom is extra large with separate sitting and work area, and a king bed and queen sleep sofa and work area. The second bedroom has a queen bed and full size sleep sofa. Both have televisions. The kitchen seats 6. The front door is a double french door that opens out to a small sitting area where the BBQ grill is located, adjacent to the outdoor hot water shower.

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Apartment in Port Charlotte

A charming yellow house is embraced by tall palm trees and lush greenery. A welcoming entrance features a black wrought iron gate framed by vibrant tropical plants. Light cascades from the windows, reflecting the historic character of the home.

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.

LocationFamilySolo travel

4.95 out of 5 average rating, 138 reviews

Superhost

5.0 out of 5 average rating, 4 reviews

Charlottes Web- Your Seaside Sanctuary

Steps from the Gulf, Charlotte Web is a cozy beach retreat on Manasota Key. Enjoy ocean breezes, sunset strolls, and all the comforts of home — Wi-Fi, beach gear, and free parking included. Perfect for couples, families, or solo escapes. Relax, explore, and unwind in laid-back coastal charm. Explore nearby beaches, hunt for shark teeth, kayak through mangroves, or simply unwind. Whether it's a romantic escape, family trip, or solo getaway, Charlotte Web is your perfect island hideaway.

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5.0 out of 5 average rating, 23 reviews

Stylish 2BR Beach House |Gulf & Bay Access |Unit A

Welcome to Salt & Sand Suites –Unit A Newly renovated 2BR/1BA upstairs unit just two houses from Lemon Bay. Bright and brand new coastal space with private balcony, sliding glass doors, and an open kitchen-living layout with bar top-seating. Sleeps 6 with 2 king beds + a sofa sleeper. Includes a beach wagon, beach chairs, towels and an umbrella. Shared laundry on-site. Relax and unwind in a bright coastal space after a day in the sun on Manasota Key.

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Superhost

A serene sunset view is captured from a screened lanai, framed by palm trees. The colorful sky reflects over the waterway where boats are docked, creating a peaceful ambiance. Decorative sea life motifs are displayed on the walls, enhancing the coastal theme.

Apartment in Cape Haze

Condo w/ Marina and ICW views

This is a little slice of paradise, with amazing marina and water views of the Intercoastal waterways. This location is in the slower more peaceful part of Florida, there is a free water taxi ride that provides you access to a pristine private beach. Englewood beach is not far away either. Activities abound in this area, including kayaking, biking, walking trails, fishing, charters, boat rentals, golfing and many bars and restaurants.

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4.71 out of 5 average rating, 14 reviews

4.9 out of 5 average rating, 250 reviews

The exterior of a two-story building features a welcoming courtyard with tropical plants. Brightly colored adirondack chairs are positioned in front of green-shuttered windows. The entrance doors are painted a bold green, and stairs lead up to the second floor.

Apartment in Boca Grande

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.

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Apartment in South Venice

A comfortable bedroom features a spacious bed with crisp white linens, accented by decorative pillows. Two framed beach-themed images hang on the blue wall, and natural light filters through a nearby window, complemented by light, airy curtains.

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.

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4.92 out of 5 average rating, 235 reviews

Apartment in Port Charlotte

A screened-in balcony features a round table and two chairs, overlooking expansive water views. Decorative glass ornaments hang from the ceiling, adding a colorful touch to the serene setting. Lush green grass is visible just beyond the railing.

Condo on the water

1 week min. Beautiful turn-key, fully furnished 1BR/1BA condo with sofa sleeper—wake up to stunning water views. Well-behaved pets are okay. Perfect for relaxation or adventure, sleeps 4. All utilities & amenities included, plus washer/dryer & dishwasher. Resort-style features: Olympic-sized heated pool, gym, pickleball, boat launch, picnic spots, gas grill, pier & gazebo. Low season Apr–Dec, High season Jan–Mar

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4.93 out of 5 average rating, 14 reviews

A cozy corner of the living area is depicted, featuring a wicker chair adorned with patterned cushions. A rustic side table holds decorative items, while a warm wooden countertop is visible in the background, enhancing the inviting atmosphere of the space.

4.99 out of 5 average rating, 305 reviews

The Oz Courtyard 2.9 mi beach

The Oz House is old and funky... The Courtyard is a magical place with its own private garden, outside shower and gas grill . The pergola has a two person swing and night blooming Jasmin. Your own hammock and chimera all privately set away from the rest of the Oz House. The pool and hot tub are in the main gardens shared by all who visit Oz It’s a wonderful getaway for anyone wanting to just BEE...

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