Captiva Homes with Pool

Captiva Homes with Pool

Welcome to Captiva, a charming island paradise located in Lee County, Florida. Known for its pristine beaches, crystal-clear waters, and breathtaking sunsets, Captiva is a sought-after destination for those seeking a luxurious and tranquil retreat.

Captiva offers a unique blend of natural beauty and upscale amenities, making it the perfect place to call home. With an abundance of outdoor activities such as boating, fishing, and water sports, residents can enjoy a vibrant coastal lifestyle year-round.

Homes in Captiva with pools are a popular choice among buyers looking to enjoy the ultimate in relaxation and entertainment. Whether you're hosting a poolside gathering with friends and family or simply unwinding after a long day, a pool adds a touch of luxury to your everyday life.

Imagine waking up to the sound of waves crashing and stepping outside to take a refreshing dip in your private pool before starting your day. With homes featuring pools in Captiva, you can experience resort-style living in the comfort of your own home.

If you're ready to experience the best of island living in Captiva, explore our listings of homes with pools and find your own piece of paradise in this idyllic coastal community. Live the life you've always dreamed of in Captiva, where every day feels like a vacation.

Newest Captiva Homes with Pool

$3,279,000
6 Beds ⋅ 7 Baths ⋅ TB8522459 MLS
Virtually Staged. Virtually Staged. Welcome to one of Captiva Island's most remarkable residences: a stunning Mediterranean-inspired estate nestled on the legendary Andy Rosse Lane, just steps from the Gulf of Mexico. Move-in ready and finished with fine stylings throughout, this multi-level home delivers the perfect blend of luxury island living, flexible accommodations, and exceptional investment potential as a short-term rental. Arrive via a classic paver brick driveway framed by lush tropical landscaping, climbing vines, and colorful blooms. The stucco façade, clay tile roofline, arched garage doors, and elegant balustrade balcony set a tone of timeless sophistication from the moment you pull in. A grand staircase sweeps up to the main entry, while a private elevator services every floor of the main house for effortless access. The ground level features a spacious two-car garage with ample storage, a large recreation room perfect for a game room, media lounge, or fitness space, and a full en suite bathroom, ideal for guests or extended stays without ever needing the upper floors. The heart of the home unfolds across a sweeping, light-filled main level featuring large-format travertine tile, soaring coffered ceilings, and graceful arched doorways. Dual chandeliers anchor a dramatic tray ceiling above the open-concept living and dining room, a space bathed in natural light through picture windows and French doors that open to the outdoors. The gourmet kitchen is a chef's dream, offering custom white cabinetry, a generous island with breakfast bar seating, a walk-in pantry, and a bold statement range hood that adds a touch of artful color. Two well-appointed guest bedrooms, each with a private en suite bathroom, provide comfort and privacy for family and visitors alike. The main level is rounded out by a convenient laundry room and a powder half bath for guests. The entire top floor exemplifies refined luxury. The primary suite is a true sanctuary, featuring two expansive walk-in closets and a spa-caliber bathroom that will take your breath away. A dramatic black clawfoot soaking tub with polished chrome fixtures rests beneath a crystal chandelier, flanked by a dual-sink vanity with backlit mirrors, a rich marble tile surround, and a separate oversized walk-in shower. Glimpses of the tropical landscape through the primary bath's windows complete this private retreat. A fourth bedroom with its own en suite bath completes the top floor, perfect for a home office, nursery, or additional guest quarters. A covered balcony walkway connects the main house to a fully independent in-law suite, a rare and coveted feature on Captiva Island. This self-contained retreat includes a private bedroom, full bathroom, and kitchenette, making it perfect for extended family, a live-in property manager, or a dedicated short-term rental unit. Directly below the in-law suite, a pool bath and bonus room offer additional flexibility for outdoor entertaining, equipment storage, or a cabana-style hangout. Situated on Andy Rosse Lane, Captiva's beloved main street, this home places you at the center of island life. Stroll to the Gulf beach in seconds, or walk to iconic local favorites like the Mucky Duck and the Bubble Room. Whether you're seeking a full-time residence, a personal island getaway, or a high-performing vacation rental, 11523 Andy Rosse Lane checks every box. Properties of this caliber, in this location, rarely come to market. Schedule your private showing today.

11523 Andy Rosse Lane, Captiva
$3,999,999
4 Beds ⋅ 4 Baths ⋅ A4695987 MLS
Not everyone can get here… and that’s exactly the point. Indiana Jones Adventure Meets Luxury Island Living | Rare Fly-In / Boat-In Captiva Estate. Set along the waters 300 feet of private white sandy beach & Gulf of America, this extraordinary Upper Captiva property offers one of the most unique lifestyles in Southwest Florida. Located on approximately 1.16 acres, this private island retreat is accessible by boat or private aircraft via Salty Approach Airstrip (FL90), Upper Captiva’s private 1,800-foot grass runway. The property also includes a hangar below the home, making it ideal for aviation enthusiasts. FL90 is best suited for experienced pilots flying light aircraft designed for short-field and turf operations, including planes in the style of Cessna 150, 152, 172, 182, 206, Piper Cub, Super Cub, Aviat Husky, Maule, Kitfox, and similar STOL-capable aircraft. For seaplane owners, welcome home. The residence features 5 bedrooms, 5 bathrooms, and over 3,900 square feet designed to capture panoramic water views and sunsets. A private elevator services all four levels. Inside, the home offers spacious living and entertaining areas with marble, tile, and wood flooring throughout. The chef’s kitchen includes premium appliances, wine and beverage refrigeration, ice maker, and an open layout ideal for hosting. Outdoor living is exceptional, with expansive terraces and gathering spaces overlooking the water. A new Trex waterfront deck leads to a private composite dock with boat lift, ideal for a 40-foot Viking for serious fishing adventures, plus a fast boat such as a Nortech or Midnight Express for island-hopping and cruising. The dock may also accommodate a seaplane. Additional features include whole-house generator, hurricane impact windows and doors with shutters, outdoor kitchen, poolside cabana, exercise room, multiple entertaining spaces, and well water, septic, and propane gas service. A rare combination of privacy, adventure, and luxury waterfront living in one of Southwest Florida’s most exclusive island communities. Created for those who crave privacy, adventure, and a true sense of escape, this estate offers a lifestyle few properties can match. Spend your mornings heading out by Viking for serious fishing, your afternoons cruising by fast boat to nearby islands, and your evenings enjoying panoramic sunsets over Pine Island Sound. With a hangar below the home, private dockage, expansive terraces, and resort-style outdoor living, every detail supports an effortless fly-in, boat-in island lifestyle. This is more than a residence. It is a gateway to one of the most extraordinary waterfront experiences in Southwest Florida. With exceptional access to Boca Grande’s renowned deep-water fishing right from your back door, this remarkable estate is designed for the buyer who expects the extraordinary. Complete with a private sauna and every luxury appointment. The 29'5" x 36'7" hangar-style garage offers substantial space for aircraft.

211 Kingfisher Drive, Captiva
$850,000
C7523822 MLS
Located atop one of the tallest ridges in Lee County—possibly all of Southwest Florida—this building lot will offer impressive sunset views and sweeping water vistas stretching west and northwest toward Boca Grande Pass and beyond. The lot fronts the famous Pink Path extending from the north to south end of the primary island body and is proximate to historic archeological explorations and findings on Useppa Island. The Collier Inn restaurant, pool, tennis, bocce and croquet facilities are just a short stroll down the path, while your boat can be moored at the Useppa Marina, just 5 minutes on foot or one minute by golf cart. All public utilities are available and ready. Zoning allows either a single-family or two-family (duplex) structure and island covenants will require an Old Florida design. The site is in the X flood zone, above any potential storm surge. Homeowners on bridgeless Useppa Island are required to have membership in the Useppa Island Club and Marina. The 110-acre Sanctuary Island is a private community and members-only club. With no need for gates or walls, it is surrounded by water, in the pristine Pine Island Sound and Charlotte Harbor Aquatic Preserves of Southwest Florida. Geographically it is Located in the same chain of barrier islands as Sanibel-Captiva, North Captiva, Cayo Costa and Gasparilla Islands, one island east of the Gulf of America. Accessible only by boat (or aircraft), the commute to the mainland is in a special class of its own. Just a 15-minute boat ride will deliver you to Boca Grande or Pine Island, and thence to all “civilized” conveniences of the mainland. The commute is special in a way that you will never tire of it. Just think-you are not stuck in traffic, or waiting for a light to change, fretting over the packed roads ahead. You are just watching the dolphins play and the birds dive, waving to passing boats with smiling passengers, and all of them wave with more than one finger-joyfully! Yes, not like the mainland! You might be sitting next to one of your Useppa neighbors, the one that has not been in a grocery store for months, because all their goods are delivered to the Shore Port, where the staff will transport them to the island, and her home. Who said it is inconvenient when you don’t have roads?

326 Useppa Island, Captiva
$750,000
C7523821 MLS
This oversized lot 440 in the Collier Preserve section of Useppa Island boasts 150 feet of water frontage on Pine Island Sound. Sharing a 2-slip dock with the adjacent owner, soo the boating life is conveniently at your doorstep. Useppa Island Club and Marina is a private community and members-only club. With no need for gates or walls, it is surrounded by water, in the pristine Pine Island Sound and Charlotte Harbor aquatic preserves. Geographically it is in the same chain of barrier islands as Sanibel-Captiva, visible to the south, although one island east of the Gulf. Accessible only by boat (or aircraft), the commute to the mainland is in a special class of its own. Just a 15-minute joyful boat ride will deliver you to Boca Grande or Pine Island, and thence to all “civilized” conveniences of the mainland. The commute is special in a way that you will never tire of it. Just think-you are not stuck in traffic, or waiting for a light to change, fretting over the packed roads ahead. You are just watching the dolphins play and the birds dive, waving to passing boats with smiling passengers. Yes, not like the mainland! You might be sitting next to one of your Useppa neighbors, who has all their goods delivered to the Shore Port, where the staff will transport them to the island, and her home. Who said it is inconvenient when you don’t have roads? And this beautiful lot will let you build the house of your dreams and join the ranks of the smart and lucky who have already landed on Useppa as a lifestyle choice.

440 Useppa Island, Captiva
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