Holiday houses in Pine Island Sound

LAST Minute! NEW Villa-Heated Saltwater Pool & Spa

Experience Cape Coral like never before all from this gorgeous 3bedroom, 3bath villa. This elegant villa boasts a vibrant interior decorated with Italian furniture and fully equipped kitchen. Begin your day with a few laps in the private pool before heading to the Yacht Club Public Beach, Sun Splash Family Waterpark or Pine Island to soak up some sun! After adventurous days, continue making memories back home with a family barbecue and a soak in the hot tub or have a movie night with loved ones!

Just Listed! Coastal Oasis with Private Pool

**Coastal Charm in Bokeelia – Pool, Kayaks, Bikes & More!** Welcome to your slice of paradise in beautiful Bokeelia, Florida—where coastal charm meets outdoor adventure! Nestled along a peaceful fishing pond just minutes from the Gulf, this 3 BR, 2 BA retreat offers everything you need for relaxation and fun. Home features a private pool, kayaks, bikes, and ping pong— Enjoy world-class fishing, sunsets on the lanai, or kayaking through Gulf waters. Come live Florida’s laid-back island life! -

1 house to shore-Golf Cart Pickleball, Dock Access

💰No nickel & diming — AirBnb & cleaning fees in nightly rate! 🌊 Amazing beach views & stunning sunsets 🛥️Shared boat dock - ask about availability 🏖️New beach chairs, umbrellas, kayaks, bikes, and outdoor games. 🎾Club Membership with pools, tennis and pickleball courts! 🚙 Golf cart included! 🐶 Pet-friendly! 💻 High speed internet 🛌🏽Westin Heavenly Beds for ultimate comfort and sleep ✅ Gourmet chef's kitchen 🏠 Professionally designed & extremely comfortable 😊24/7 local host support!

Garden Cottage - Tiny House

PLEASE NOTE: The cottage is separate from our house and living quarters. The bathroom is in the back of the main house, just a few steps from the cottage, private and not shared with anyone. We take special precautions to thoroughly clean and disinfect the bedroom and bathroom after each guest. You’ll love our place because of the location, the ambiance, the outdoor space, and the neighborhood. We have a dog and a cat. Our place is good for couples, solo adventurers, and business travelers.

AquaLux Smart Home

Unwind in style in this spacious and modern home. Here's what awaits you: Smart Home Technology: Control lights, temperature, and even the front door with voice commands or your smartphone for a seamless experience. Heated Saltwater Pool: Take a refreshing dip in the sparkling pool, perfect for year-round enjoyment. Dedicated Workout Area: Maintain your fitness routine with a private space equipped for exercise. Freshwater Canal Views: Wake up to calming water views and the sounds of nature.

Island Paradise Awaits You

Discover Emerald Palms, a one-of-a-kind tropical retreat on historic Pine Island. Surrounded by lush gardens, seashell walking paths, and a sparkling private pool, this hidden gem feels like your very own island within the island. This custom cedar stilt home is thoughtfully decorated to evoke the timeless spirit of Ernest Hemingway’s island hideaways, offering a cozy, nostalgic ambiance with all the conveniences you need for a relaxing stay. More than a vacation home — it’s an experience.

Waterside Cottage

Enjoy our peaceful little island paradise nestled beneath sprawling oaks and scattered palms just minutes from St James City’s restaurants and bars. Nearly 1/2 acre is yours to enjoy. Watch the manatees and dolphins swimming in the canal while you grill your catch of the day, or your fresh pick of the day from St James Fish House just down the street! Inside enjoy a fresh new contemporary and stylish cottage with everything you will need to make your stay comfortable, enjoyable and fun!

Private Cottage, Lucky Falcor Stables/Horse Farm

Relax and unwind at this private and unique cottage on a beautiful horse farm. Close to dining, shopping, a variety of boating, fishing, and other water activities. Visit the Matlacha Bridge to cast a line with other fishing enthusiasts, or take a leisurely bike ride to tour the island (bikes/helmets provided). Grab a water taxi and visit surrounding sister islands with beautiful, secluded beaches. Please see the host guidebook for places to eat, things to do, and best ways to get there.

Pet-friendly Villa w/ Heated Pool

Welcome to your CapeSideVilla! This modern 3-bed + Den, and 2-bath villa features a private, heated pool with additional cost. Located in a quiet, pet-friendly neighborhood, you're minutes from beaches, parks, nightlife, and top attractions. Lani mini fridge and board games included! Perfect for families, couples, friends, or remote workers, with high-speed internet, a full kitchen, and 1800 sq ft of living space. Make lasting memories in comfort, poolside, and beyond!!

Pine Island Pelican Suite: privacy, pool, gardens

Welcome to the Pelican Suite! Secure, private entrance, king bed, living area with kitchen and patio. This suite is separate from the upstairs main house. Adults only. King bed, ensuite private bathroom with shower; AC. WiFi, cable, TV. Exclusive use of screened guest lanai - kitchen, fridge, BBQ, gardens, secluded heated pool. Free parking. The Pelican Suite is ideal for a relaxing no-stress break in the sun!

Luxury Canalfront Pool Retreat w/ Upscale Finishes

Beautiful, modern NEW construction home with heated pool, on saltwater canal. Damage-free after hurricane Milton. FUN for families and tranquil for adults; fully stocked with electronic games table, pool toys and floats, outdoor games, arcade games, board games — much to enjoy! Enjoy indoor/outdoor living on expansive resort-style lanai and retreat to stylish finishes & luxe amenities throughout!

Paradise Found! - 3/2 Pool Home

Escape to our Tropical Oasis in Bokeelia, Pine Island, Florida! This 3-bed pool home offers comfort and style. Enjoy a private pool, lush surroundings, and amenities galore. Minutes from SWFL's best beaches, Cape Coral, Fort Myers, Matlacha, and Pine Island's restaurants and shops. Book now for a perfect blend of relaxation and adventure!