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GASPARILLA ESTATES - D6147273 - 9750 LITTLE GASPARILLA IS, BOCA GRANDE, FL 33921 92 Days on yellowkey
$10,000 Reduced | Single Family Home | 3 beds | 1.5 baths
Welcome to Waters Edge, a true hidden gem on Little Gasparilla Island, where turquoise water, gentle breezes, and total relaxation replace traffic, noise, and stress. Accessible only by boat or ferry, this canal-front island retreat offers the rare combination of private dockage, bay views, and walkable Gulf beaches, all in one unforgettable setting. This beautifully designed home makes it the perfect place to unplug and embrace island life. With 60 feet of private dock space, boaters, anglers, and water lovers will feel right at home. Bring your own boat or paddleboards, or take advantage of the kayaks provided for guest use, and explore the surrounding waters at your own pace. Inside, the open-concept living space is filled with natural light and water views from the kitchen, dining, and living areas. Three French doors open to the screened upper deck, creating seamless indoor-outdoor living, perfect for morning coffee, evening cocktails, and entertaining with friends. Stay connected even out on the island with Starlink high-speed internet throughout the home. Step outside and discover multiple outdoor spaces designed for relaxation and fun. The bayfront porch offers breathtaking sunrise views, while the lower-level deck is ideal for fishing, cleaning your catch, or simply unwinding by the water. A commercial ice machine keeps you stocked for the cooler and the cocktails all week long. After a beach day, rinse off in the large outdoor shower before settling in for a peaceful island evening. Just a short walk from the home, you'll find some of the most spectacular sunsets on the Gulf Coast, a nightly show that never gets old. Accessible only by boat or ferry, the island offers a peaceful setting far removed from the crowds. Little Gasparilla is a bridgeless barrier island, so you will need your own boat or arrange water taxi/ferry service to come and go. Days here are spent wandering along miles of unspoiled shoreline collecting seashells, enjoying the gentle Gulf breeze, or casting a line in some of Southwest Florida's best fishing waters. Details: All rates subject to 12% Florida Lodging Tax, cleaning fee, and reservation fee. A 3% credit card processing fee applies, avoid by paying via check. No smoking permitted.
Listing is courtesy of: TARPON REAL ESTATE, INC.
HIDEAWAY BAY BEACH CLUB PH 06 - D6147132 - 9400 LITTLE GASPARILLA IS #G9, BOCA GRANDE, FL 33921 94 Days on yellowkey
$6,900 | Condo | 2 beds | 2.0 baths
Welcome to your slice of paradise on Little Gasparilla Island, where swaying palms, turquoise waters, and soft sandy beaches set the tone for a truly relaxing coastal escape. Tucked away in Building G, Unit G9, this charming island retreat invites you to slow down, breathe in the salt air, and experience Old Florida at its finest. Accessible only by boat or ferry, the island offers a peaceful setting far removed from the crowds. Days here are spent wandering along miles of unspoiled shoreline collecting seashells, enjoying the gentle Gulf breeze, or casting a line in some of Southwest Florida's best fishing waters. As the sun begins to set, the sky transforms into a stunning display of color, creating the perfect ending to another day in paradise. Inside, the unit offers a comfortable and welcoming space with a light, coastal feel that reflects the beauty of its surroundings. The spacious open living area flows seamlessly into a fully equipped kitchen, making it easy to prepare a simple meal or gather after a day at the beach. Step outside onto the updated screened lanai and take in peaceful water views — the perfect spot to unwind and soak in the island atmosphere. Guests will enjoy easy beach access via a deeded beach access walkway, along with access to the community pool, grill, and picnic areas. The community dock is available on a first-come, first-served basis. Mainland parking and ferry service make island access convenient and stress-free. Little Gasparilla Island is known for its laid-back charm and natural beauty, making it an ideal destination for those looking to truly disconnect and unwind. Whether you're here for a romantic getaway, a peaceful retreat, or a memorable beach vacation, this island escape offers an experience that keeps guests coming back year after year. Book your stay and discover the kind of Florida that feels untouched and effortless. Applicable charges include tax, cleaning, and reservation fees, along with a credit card processing fee (waived for check payments). Skip the extra fees and enjoy more beach days-book direct with Tarpon Real Estate. No smoking permitted.
BOCA GRANDE NORTH PH C - D6143945 - 6010 BOCA GRANDE CSWY #C26, BOCA GRANDE, FL 33921 295 Days on yellowkey
$3,200 | Condo | 2 beds | 2.0 baths
Weekly rate shown, please see description for detailed pricing. Welcome to Boca Grande North #26 – Sunny Shores, a beautifully appointed 2-bedroom, 2-bath waterfront condo that captures the essence of island living on the serene North End of Boca Grande. With sweeping views of Charlotte Harbor, this retreat offers the perfect combination of comfort, elegance, and coastal charm. The spacious layout accommodates up to six guests in style. The primary suite features a plush king bed, private en-suite bath, and calming views that set the tone for restful nights. The guest suite is equally inviting, with a full-size bed and a queen bed, making it ideal for couples, or friends traveling together. Each space is thoughtfully designed with soothing coastal décor, soft linens, and ample storage. The open living area is bathed in natural light from large sliding doors that lead to your private balcony—an ideal spot to sip morning coffee as the sun rises over the bay or toast the evening with a glass of wine as dolphins play in the distance. The fully equipped kitchen boasts modern appliances, sleek countertops, and generous seating at both the dining table and bar, perfect for gathering over shared meals and conversation. Outdoors, you’ll find a sparkling community pool, tennis courts, and grilling areas designed for leisurely afternoons. For those drawn to the water, boat slips are available for rent, making it easy to explore the Gulf and surrounding islands by boat. Beach essentials—chairs, umbrellas, and towels—are provided so you can relax on Boca Grande’s world-famous beaches. This idyllic location places you just minutes from the island’s historic village, where charming boutiques, art galleries, and world-class restaurants await. Rent a bike or golf cart to explore shaded streets lined with 100-year-old banyan trees, visit the historic lighthouse, or cast a line in the renowned Boca Grande Pass, known as the tarpon fishing capital of the world. With air conditioning, high-speed Wi-Fi, Smart TV, self check-in, and thoughtful safety features, every detail is in place to ensure peace of mind and modern convenience. Boca Grande North #26 – offers more than a place to stay, it’s an experience of timeless beauty, coastal elegance, and the relaxed island lifestyle that makes Boca Grande so unforgettable. Off-season: $2,700 weekly/$11,580 monthly. Mid-season: $3,200 weekly/$13,710 monthly. In-season: $4,200 weekly/$18,000 monthly.
Listing is courtesy of: PARSLEY BALDWIN REAL ESTATE
GOLDEN BEACH RESIDENCE #6 - D6143778 - 480 GULF BLVD #6, BOCA GRANDE, FL 33921 295 Days on yellowkey
$4,800 | Condo | 3 beds | 2.0 baths
Weekly rate shown, please see description for detailed pricing. Welcome to the Turquoise Turtle – A Beachfront Escape in Boca Grande Discover coastal elegance at the Turquoise Turtle, a beautifully appointed 3-bedroom, 3-bath townhome perfectly situated in the serene Turtleback Colony community. With direct access to the Gulf of Mexico and a heated community pool, this retreat embodies the relaxed sophistication of Boca Grande. The primary suite offers a king-sized bed and private balcony access, where the soothing rhythm of the waves and pastel hues of sunrise create a tranquil start to the day. Two additional bedrooms, each with a queen-sized bed and en-suite bath, provide private sanctuaries designed for rest and comfort. The open living spaces are filled with natural light and coastal charm, leading to a spacious balcony where al fresco dining and breathtaking Gulf views await. A fully equipped kitchen with bar seating makes meal preparation effortless, whether enjoying a casual breakfast or gathering for sunset cocktails. Beyond your doorstep, stroll along Boca Grande’s pristine beaches, explore boutique shops, art galleries, and fine dining in the historic village, or visit the iconic Boca Grande Lighthouse and Maritime Museum. Golf cart rentals make it easy to discover the island’s hidden treasures, from banyan-lined streets to world-class fishing waters. Whether basking by the pool, collecting seashells on the shore, or savoring sunsets over the Gulf, the Turquoise Turtle offers the perfect blend of comfort, luxury, and timeless island charm. Off-season: $2,800 weekly/$16,290 monthly. Mid-season: $4,800 weekly/$20,580 monthly. In-season: $5,200 weekly/$22,900 monthly
BOCA GRANDE - D6143639 - 231 GILCHRIST AVE, BOCA GRANDE, FL 33921 297 Days on yellowkey
$5,600 | Single Family Home | 6 beds | 4.0 baths
Weekly rate shown, please see description for detailed pricing. Just moments from the sandy Gulf shoreline and a short walk to the charming streets of Boca Grande’s Historic District, Gilchrist Manor has an unforgettable setting for your island escape. This grand 6-bedroom, 5-bath coastal estate blends timeless architecture with modern updates, comfortably accommodating up to 12 guests in refined style. The primary suite showcases a king bed and spa-like en suite bath, while three additional bedrooms—each with a queen bed—give serene retreats filled with natural light. Two additional bedrooms feature twin bunk beds, creating a playful and convenient setup for younger guests. Throughout the home, thoughtful updates balance historic charm with modern comfort, highlighted by the fully appointed kitchen with butcher block countertops, premium appliances, and space designed for effortless entertaining. A formal dining room invites memorable gatherings, while the enclosed sunroom, complete with air conditioning, offers a tranquil spot to unwind with a book, sip morning coffee, or enjoy views of the lush grounds. A front porch and expansive yard provide more places to relax, whether hosting sunset cocktails or savoring a barbecue beneath swaying palms. Boca Grande itself is the epitome of island elegance. From Gilchrist Manor, you are just steps from pristine beaches where turquoise waters meet seven miles of powder-soft sand. Stroll into town to discover boutique shops, fine dining, and art galleries, or explore the island by golf cart or bicycle. Fishing, boating, golf, and tennis are all within easy reach, while spectacular Gulf sunsets create the perfect close to each day. For larger gatherings, Gilchrist Manor is one of three residences on this historic estate, which also includes the Fish House and Coastal Chic. Each may be rented individually or together to accommodate extended groups. Additional amenities include Wi-Fi, smart TVs, air conditioning, a washer and dryer, and concierge services to ensure every detail of your stay is seamless. Gilchrist Manor is more than a vacation home—it’s a piece of Boca Grande history reimagined for modern luxury living, offering the perfect balance of elegance, comfort, and island charm. Off-season: $5000 weekly/$21450 monthly Mid-season: $5600 weekly/$24000 monthly In-season: $6200 weekly/$26500 monthly