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!

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.

5.0 out of 5 average rating, 12 reviews

Coastal 2BR Beach Getaway | Gulf + Bay | Unit B

Salt & Sand Suites – Unit B Newly renovated 2BR/1BA upstairs unit just steps from Lemon Bay and a short walk to the Gulf. This bright, coastal space features an open kitchen -living area with bar-top seating and a private balcony. Perfect for relaxing after a day in the sun. Sleeps up to 6 with 2 king beds and a sofa sleeper. Fully equipped kitchen for effortless dining. Beach-ready amenities include chairs, towels, umbrella, and a wagon. Outdoor shower and shared laundry available on-site.

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.

4.93 out of 5 average rating, 215 reviews

A bright living area includes a cozy sectional sofa and a round dining table adorned with a simple green centerpiece. A wall-mounted television displays scenic imagery. Natural light fills the space through multiple windows with shades, creating a welcoming environment.

Apartment in Boca Grande

2BR + Private Patio

Beautifully renovated ground-floor flat in the heart of historic Boca Grande — your serene island retreat. Mornings on your private patio, then 120 steps to one of Florida's most pristine gulf beaches. The Temp Restaurant is directly across the street; Hudson's Market and Sister's Pizza are steps away. Sleeps 4—king bedroom, twin bedroom, full kitchen. Perfect for couples, families, or friends exploring Gasparilla Island. Guests receive 10% off golf cart & bike rentals at Gasparilla Adventur

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.

4.95 out of 5 average rating, 138 reviews

Superhost

4.87 out of 5 average rating, 118 reviews

Starfish 1B | Walk to beach access | Dog Friendly!

Check into Starfish Stays and enjoy a 2-bedroom apartment a short walk from Manasota Key Beach. Bright, clean, and beachy, this unit offers the perfect mix of comfort and coastal charm. ✨ Fully renovated 2-bedroom apartment with pull-out sofa sleeps up to 6 🏖 Steps from the beach with private beach access 🐾 Dog-friendly — your furry friend is welcome! 🏖 Includes beach chairs, towels, and skim boards 🍳 Fully stocked kitchen with pots, pans, dishes, utensils. 🧺 On-site laundry building

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.

4.96 out of 5 average rating, 327 reviews

The Oz Tree House 2.9 m beach

The Tree house apartment has its own entrance and off street parking. Two blocks from Dearborn St. and 2.9 miles to the beach. Light and airy in a private setting with gardens, hammock, fire pit a quiet and peaceful, walking distance to everything the historic district of Old Englewood has to offer. Public tennis courts, great restaurants with live music and once a week a fantastic Farmers Market comes to town! Lemon Bay and Indian Mound are a nice walk to enjoy the sunsets

Apartment in Port Charlotte

Riverfront Condo w Water Views-Heated Pool

Experience the vibrant setting of this 2BR 2Bath condo, ideally situated on the shores of the Myakka River. Take in the area's scenic beauty, stunning views, and diverse selection of water activities, attractions, and landmarks. After a day of exploring, return to our home for a rejuvenating stay. ✔ 2 Bedrooms ✔ Open Design Living ✔ Full Kitchen ✔ Balcony ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Community Amenities ( Heated Olympic size Pool, Gym, Clubhouse, Dock)

5.0 out of 5 average rating, 12 reviews

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.

4.92 out of 5 average rating, 235 reviews