Holiday rentals with a fireplace in Little Gasparilla Island

A private swimming pool is surrounded by lush tropical foliage and colorful flowering plants. A decorative fish sculpture adds a whimsical touch, while comfortable seating is visible in the background beneath palm fronds.

5 out of 5 average rating, 18 reviews

Paradise Cottage Island Oasis

An enchanting, GROUND LEVEL tropical Palm Island paradise that delivers the epitome of off the grid, private island living. 7 minute walk to sugar sand beaches offering buckets of seashells, shark’s teeth & award winning sunsets! Return home to your private, swimming pool surrounded by mature, tropical foliage that has the look and feel of a Caribbean resort. Follow the winding path that leads to the harbor with dock: toss a line, boat to no bridges out to GOM, launch kayaks, take in nature!

4.89 out of 5 average rating, 19 reviews

Sunset Beach House

This beautiful beachfront house is located on Little Gasparilla Island with three-bedroom/two-baths. It is tucked away, just off the main drag of this quiet, “off the beaten path” island. Escape your busy life on the mainland and enjoy outdoor living space with amazing 180-degree views of the Gulf of Mexico. Enjoy your private beach path and shared dock, which is perfect for fishing! You can catch your dinner and come back to the house and grill it on deck while watching a breath-taking sunset.

4.97 out of 5 average rating, 105 reviews

Home in Bokeelia

The Snook & Rod Club (Waterfront)

Welcome to the Snook & Rod Club. If you want a place to relax, bring your family, or friends this is the place to be! We are on a canal with a 50' captains walk you can tie your vessel to while you stay. Our island getaway property is located on the northern end of Pine Island (off of FT Myers/ Cape Coral) in the quiet community of Bokeelia FL. We are perfectly located in a neighborhood of canals right down from Jug Creek Marina and are set up for retired couples, families, or fishing buddies

4.97 out of 5 average rating, 29 reviews

A sunlit outdoor area is marked by white gravel and features palm trees swaying in the breeze. The private dock is visible in the background, extending over the water, with a clear blue sky complementing the serene waterfront setting.

Home in Englewood

Bayfront home in Englewood, FL

Beautiful BayFront home welcomes you to a vacation like no other. This 4 bedroom/2 bathroom home with a boat dock allows you to truly experience the beauty of Englewood, FL in the best way possible. Bring your family and friends and enjoy looking out the windows and seeing dolphins and/or manatees multiple times throughout the day. Fish off the dock and catch Snook and many more kinds of amazing sea life. You're also just a short walk across the street to the beach to watch gorgeous sunsets.

A wooden dock leads from the water to the main house, surrounded by native vegetation. The two-story structure features a rooftop deck, large wraparound porch, and palm trees framing the entrance under a clear blue sky.

5 out of 5 average rating, 21 reviews

Island Estate. Beach, Bay, Nature. Lux! Extras!

Little Gasparilla Island. Main house of 5-acre, beach-to-bay "old FL" estate. Bay in front, pristine beach in back. Very private, natural setting on the bay Florida Blueway KayakTrail and bordering Don Pedro nature preserve parkland. Kayaks & SUPs for exploring the bay, beach gear and games. Abundant birds, fish, shells, & wildlife. Manatee and dolphin are common. Accessible only by boat/water taxi. No stores, few people. 3 ensuite bedrooms plus a bunk bedroom with three singles

5 out of 5 average rating, 20 reviews

A contemporary dining area features a round table set for four, surrounded by sleek chairs. Large glass walls provide abundant natural light, revealing views of the outdoor space. A modern chandelier hangs above, adding an elegant touch to the inviting atmosphere.

Home in Rotonda West

Turtle Bay - minutes to Boca Grande!

Welcome to Turtle Bay Haven – Your Dream Escape on the Gulf Coast! Stay in your own private natural oasis, surrounded by lush greenery and the vibrant tropics of Florida wildlife. - Grocery Stores: just 5-10 min away - Dining Options: A variety of local restaurants are just min away. - Boca Grande: 11 mi (20 min) away, known for stunning beaches. - Manasota Key Beaches : 10 mi (20 min) - Activities: Kayaking, paddleboarding, fishing, hiking, biking, and over 20 golf courses await!

4.95 out of 5 average rating, 21 reviews

Home in Arcadia

Manoir Folie à Deux – Tuscan Countryside

Tuscan-inspired countryside estate on 12.33 private acres in Arcadia, FL. This timeless, one-of-a-kind home features 4 bedrooms, 4.5 baths, a grand chef’s kitchen with 48” professional stove and refrigerator, plus a second full kitchen in the private MIL suite. Enjoy a resort pool, serene pond, gazebo, concert piano, billiards, Monopoly table with upstairs dry bar, and a private home theater. Gated and surrounded by peaceful country life. Minutes from Arcadia and Punta Gorda.

5 out of 5 average rating, 57 reviews

An aerial view captures a two-story home nestled along a quiet waterway with lush greenery surrounding it. Nearby, other residences and a private dock are visible. The scenic backdrop showcases calm waters merging with a blue sky, highlighting the tranquil atmosphere of the location.

Home in Englewood

Lux Home on Gulf w/Private POOL & 50ft Dock

Rest your feet & your soul as you getaway from it all! This luxurious little piece of paradise is tucked away on a quiet Gulf Coast waterway. 10min from Englewood Beach and 5 min from stores. Tie your boat up in the back yard to the private 50 ft dock. Spend your days fishing, catching sunsets or in the pool every evening! Easy access to Don Pedro Island, local sandbars, inlet and several restaurants, all at your fingertips! Pack your bags, kick back- paradise is waiting!

4.92 out of 5 average rating, 13 reviews

Home in Englewood

The Salty Sister Retreat

Updated and fully furnished with coastal flair, this cozy beach bungalow puts you minutes from adventure—kayak Lemon Bay, explore Manasota Key, island-hop to Boca Grande, or chase sunsets on Venice Beach. Just 5 miles to turquoise waters and less than 1 mile to Stump Pass and Cape Haze Marinas. “Dance with the waves... let the rhythm of the water set your soul free.” – Christy Ann Martine BOOK NOW and launch your Gulf Coast adventure at The Salty Sister Retreat!

A weathered driftwood log is positioned on a sandy beach, with calm waves gently lapping at its base. The sky above is filled with soft hues of orange and pink, suggesting a sunset. A person sits on the log, gazing at the horizon.

4.98 out of 5 average rating, 50 reviews

Salty Mermaid on Little Gasparilla Island/LGI

Charming beach house on Little Gasparilla Island (LGI) The Salty Mermaid offers a unique tropical paradise with 7 miles of undisturbed white sandy beaches. Embrace the old Florida Island vibe. Enchanted island steeped in pirate lore, legend has it, the spanish pirate Jose Gaspar, nicknamed Gasparilla, made this beautiful island his secret base hideaway. Local legends whisper of buried treasures hidden beneath the islands sandy shores. Come get Salty!

5 out of 5 average rating, 263 reviews

Apartment in Englewood

The Oz Parlor 2.9 mi beach

The Oz Parlor apartment was originally the main house of this whimsical property. It has loads of charm It is a great place to relax and Just Bee... Please note I don’t have cable TV my TVs are wireless I have Netflix, Amazon I will also add additional streaming channels opion request. Located in the Historic District of Englewood a lovely walk to fine restaurants, Indian Mound Park on Lemon Bay and 2.9 miles to Englewood Beach.