Holiday rentals in Pine Island Sound

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! -

Island Paradise - Hot tub, Bikes & Ocean fishing

Welcome to The Clubhouse – Your Private Island Escape Experience laid-back luxury on the serene Florida island 🏝️ just two blocks from the marina. This beautifully appointed retreat features an outdoor kitchen, fire pit, hot tub, and elegant indoor-outdoor living. Cruise the island on provided bikes, kids get to stay the new designer bunk space. Perfect for boating, fishing, or simply soaking in the sun. Refined comfort meets coastal charm — reserve your stay today, your island retreat awaits!

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.

Coastal Cowgirl - Heated Pool

Have fun with the whole family in Southwest Florida. This bungalow is full of coastal cowgirl vibes and sits right on a gulf access canal. Everything from top to bottom is stocked and brand new. Bring the outdoor oasis in via large panoramic sliders, a covered lanai with a heated saltwater pool and hot tub, outdoor kitchen, and entertainment system. Watch wildlife float by or rent a boat and cruise through the canals to the gulf for amazing beach access. Coastal living at its finest.

Fishing and Nature Paradise

Savor Nature, Sip Cocktails and Embrace Sunsets. Beautifully designed 2 Bedroom home located right on the water. Take a kayak or Paddleboard down the canal and you are instantly in the most pristine waters of the Gulf of Mexico. Located one block away from the Jug Creek Marina where you will find Live entertainment, fresh seafood and any boating needs. Sit on the extensive screened in porch and watch the Manatees. We have everything you need to enjoy a wonderful getaway.

The FlipFlopper Beach House - North Captiva Island

FlipFlopper Beach House - well appointed family focused beach home only a 3 minutes walk from the White Sand Beaches on the Gulf of Mexico and 3 min walk to Island Club Amenities on North Captiva Island. Rate includes Luggage Deliver, use of Golf Cart and Members Access to The Island Club. Hard limit on 6 guests - rare exceptions but please ask - infants are not counted in the above 6 person limit! Private Hot Tub on the rear deck amongst the Sable Palms.

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!

Private Hot Tub | King Bed Loft | Hammock Swings

🛜500mbps+ WiFi 🏠Fully private + Private entrance 🌴Hammock Swings ☀️ Outdoor Patio 🦩Private Hot Tub 🥑Kitchenette w/ electric hot plate 😴King Size Bed Loft 📚Work Desk 📺 55 inch Smart TV + Roku ❄️ Cold A/C 🚘 1 parking space NOTE: Accessing the bed requires climbing a ladder. While sturdy and secure, it may not be suitable for guests with mobility limitations, so please consider this before booking.

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!