Pet-friendly holiday rentals in Bokeelia

McGregor’s Gem• Heated Pool 3BR/2BA River District

🌴 Welcome to McGregor’s Gem—your ideal Southwest Florida retreat! Dive into relaxation in your private heated pool, spread out across three bedrooms and two baths, and enjoy the perfect blend of peaceful tree-lined neighborhood living just minutes from the charming Downtown Fort Myers River District, world-class beaches, and top local attractions.☀️ Whether you’re traveling with family, friends, or on business, this home offers all the modern comforts you need for a relaxing, stress-free stay

Boater’s Paradise in Bokeelia!

Welcome to Bokeelia! Forget your worries in this spacious and serene space. Beautiful Newly Remodeled Home located right On the Water with Boat Lifts & Dockage, and plenty of parking for All Come and enjoy a Relaxing and Comfy Home. Boaters! We are across the street from the Public Boat Ramp, Minutes to Captiva & Sanibel Islands, Cayó Costa, Cabbage Key, and Boca Grande which is known for its sugar sand Beaches. Best of all, Amazing Fishing in Florida aka “Tarpon Fishing Capital of the World!”

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

Steps to Beach Captiva Includes CLUB & Golfcart

BOOKING SUMMER HOST PAYS AIRBNB FEE WINTER SPECIALS Golf Cart and Club amenities Included North Captiva Island Cottage! Just steps away from the Gulf's pristine shores, this cozy retreat offers a private hot tub, perfect for families and beach enthusiasts. Enjoy modern amenities, a well-stocked pantry, and a complimentary golf cart to explore the island. Pet-friendly(small fee) accessible by ferry, boat, or plane. With beach gear, access to the club pool, and unbeatable proximity to the beach

Blue Laguna - Vacation in paradise!

This bright, fully equipped welcoming three‑story home features a private heated pool and a rooftop observation deck with stunning 360‑degree water views. It offers three comfortable bedrooms and three full bathrooms for up to six guests, plus two screened lanais where you can relax in the island breeze and listen to the birds. A four‑seater golf cart is included, so you can easily explore the beaches and sandy paths of beautiful North Captiva Island. Also full access to Island Club amenities!

Key West Style Home w/ Hot Tub & Boat Lift

KEY WEST style stilted waterfront home in the heart of Matlacha! Visit all there is offer - walking distance to Blue Dog and Perfect Cup. Take a boat ride to Cabbage Key, Cayo Costa or Boca Grande! Upstairs and downstairs are screened in. The second floor is peaceful and tranquil overlooking the water and treetops. Home is a 2 bedroom, 2 bathroom, with additional bonus space with trundle bed. Home is perfect for boaters with double driveway, complimentary boat lift and cleaning station.

The Bokeelia Cottage

This tiny home is perfect for those seeking a peaceful retreat from every day life! Located in the quiet little fishing town of Bokeelia. Minutes from several boat ramps, restaurants, and the Bokeelia fishing pier. Take the local ferry out to the outside islands like Cayo Costa, Captiva, or Cabage Key or enjoy your time on the beautiful front porch overlooking your own private pond. Catch and release is always welcomed and don't be surprised if you see wild peacocks passing through!

Waterfront Oasis with Boat Lift & Hot Tub

Bask in endless sun at our Jugg Creek canal-front home, a stone's throw from Charlotte Harbor and iconic islands like Captiva and Boca Grande. Dive into 'Old Florida' with unspoiled beaches and cute eateries. Watch dolphins from your doorstep and savor rainbow sunsets. Our beautiful cottage boasts a outdoor hot tub and shower, screened in porch, grill, and kayaks with a kayak launch right on the dock. Docking is on us, with a new dock & 10k pound boat lift available April-December.

Peaceful Lakeview Retreat / Screened Porch & Bikes

Escape to a peaceful lakeview retreat on Pine Island. Relax on the breezy screened porch, unwind in the cozy living room, and enjoy two serene bedrooms with smart TVs and comfortable bedding. The home features modern bathrooms, a fully stocked kitchen, fast Wi-Fi, and in-unit laundry for convenience. Pet-friendly and close to trails, marinas, and seafood spots — perfect for birdwatching, biking, fishing, or simply soaking up the island’s quiet charm and natural beauty.

3/3 Loft Style Home in the Heart of Bokeelia!

Discover this stunning brand-new build located in beautiful Bokeelia! This property offers: 3 spacious bedrooms, each featuring king-sized beds and private bathrooms for comfort and privacy. An open loft overlooking the living room and kitchen, providing a modern and airy feel. A balcony with picturesque canal views, with plenty of room for boat trailer parking and the public boat ramp conveniently located just across the street! *Pet Friendly, $150 fee*

Gulf getaway! Boat dock, heated saltwater pool

Welcome to @TheGulfGetaway an incredible canal-side home built to make memories. You'll enjoy the comfort of a fully equipped home and many outdoor activities. House is within walking distance from bars & restaurants and has quick access to the Gulf of Mexico & nearby islands of Sanibel, Captiva & Cayo Costa by boat. Centered in a quiet familial neighborhood, the location of the home makes it easy to get around. 1 hr from Ft Myers Airport

Matlacha Waterfront Home | Gulf Access & Pool

Experience Matlacha from this stunning waterfront home with direct Gulf access, a heated private pool, a spacious dock, and a boat lift. Bright, refined, and deeply relaxing, it’s the perfect coastal escape for families and friends. Wake up to still waters, enjoy warm swims under the sun, and end each day with the kind of peaceful, unforgettable evenings that make you never want to leave.