Vacation rentals in Chokoloskee Island

Goodland Water view Cottage

Experience the breathtaking beauty of a sunrise from our charming coastal cottage in Goodland FL. With a stunning direct view of the water right from the living room, you can immerse yourself in the tranquility of island life. Our cottage is thoughtfully equipped to meet all your basic needs, ensuring a comfortable stay for up to three guests. Enjoy the convenience of boat dockage and trailer parking, making it easy to explore the surrounding waters and embrace the natural beauty that awaits you

Park Shore Resort Modern Top Floor 2 Bed 2 Bath

You have found THE BEST condominium in Naples! This wonderful and tranquil get-away is set in a tropical paradise in the heart of Park Shore. A modern 2 bedroom, 2 bath with one king bed, two twin beds and one sofa bed, sleeps 6 people. This top floor unit with elevator gives you a breath-taking view over a beautiful resort which offers heated pool, tennis, pickleball, and poolside restaurant Hogfish Harry. The beach is only a mile away! Let us welcome you to your own personal piece of paradise!

Magical Gateway in Naples FL

You'll fall in love with this tinny but magical place in the heart of Naples, modern open concept,high end finishes, a lot light, 2 BR queens beds, fine blinens, full bathroom with marble, enclosed pool, spacious back yard and a wood burning fire pit, 2 parking spaces just few steps from your front door. This place is near to all Naples has to offer, beautiful beaches, dining & nightlife, it is only 3km from the beach, 3 km from 5th ave in Old Naples and less than a mile from shopping centers.

The Cypress Cottage!

Welcome to the Cypress Cottage! A home designed with sportsmen & nature enthusiast in mind. Whether you are exploring inland in Big Cypress or Navigating through the Everglades & Ten-Thousand Islands you'll have a comfortable place to re-charge with panoramic views of mangrove jungle. Cypress Cottage offers parking for (4) vehicles with room left over for your boat or kayak trailer. Our dock offers the perfect place to keep your boat so you can make the most of your Everglades Adventure.

Paradise House on Chokoloskee Island

Relax with the whole family in this newly remodeled, quiet and peaceful place to stay on Chokoloskee Island. Great location to Big Cypress NPres, Everglades NP, Boating, hiking, kayaking, trails, lots of outdoor activities, museums, in a quiet, peaceful, safe neighbor. You are in walking distance to a fabulous Cuban Restaurant, marina and boat ramp. There is plenty of parking, bring your boat. Because some of our clients have allergies we DO NOT allow pets. ASK US ABOUT OUR KAYAK RENTALS!

3BR w/HUGE 2k sq ft Lanai & Seasonally Heated Pool

Welcome to your peaceful Bonita Springs retreat, perfectly located near Naples, Ft. Myers, shopping & beaches! This isn’t just a rental, it’s our 2nd home and we treat it as such. You'll experience "exceptional" the minute you enter this stunning, open concept interior. Further, it boasts a striking 2000 sq ft screened-in lanai w a seasonally heated pool. This outdoor oasis doubles your living space and offers a flying pest barrier and significant UV protection. Breathe/Smile/Unwind

The Reel'em Inn, Chokoloskee Island Paradise

Take in the tropical feel of Chokoloskee Island in an impeccably maintained 3 bedroom/2 bath single family stilt home nestled in the canopy of Royal Poinciana trees and palms. This fisherman's paradise is a unique find in a small fishing village in the heart of the Everglades National Park. Captain Brock Wagner is available for full day private fishing charters. After a day of fishing or kayaking simply relax in a rocking chair on the 600 sqft screen porch.

Coastal Paradise! Kayaks+Bikes+Fishing+Boat Dock

Direct back bay access+ boat dock & lift+ kayaks + bikes. 1 mile to Everglades National Park! Minutes to shops & dining! Adorable spacious home- perfect for a seaside retreat!. Designed for dockside enjoyment: hammocks, swing chairs, outdoor dining - 5 minute boat ride to beach -12 minute car ride to beach -Walk to waterfront dining & live music -Kayak in the Everglades -Fish off the dock -Cool, rustic Old Florida vibe -Bring your boat or rent one

"Waterfront & OceanAccess Oasis with Private Pool"

Discover your perfect getaway at our stunning 3-bedroom, 2-bathroom home on Marco Island, accommodating up to 6 guests. Relax in your private pool or bring your boat and use our boat lift, easy Gulf access. Enjoy beautiful beaches, world-class dining, and shopping nearby in Naples. Our home is equipped for ultimate comfort, offering peaceful, family-friendly vibes. (No pets allowed, $$$ fine for violations), no loud music, trailers, or parties.

Chokoloskee/Everglades City

Enjoy this cozy stilted home on Chokoloskee Island, located in the Everglades. The double lot makes it easy to travel with your boat, trailer or RV. 2 boat ramps are located less than 5 minutes away. There is plenty to do such as exploring Everglades National Park, kayaking or fishing the Ten Thousand Islands, and enjoying the freshest seafood. 6 bikes are available to use. The entire property is fenced in making it great for pets.

675 FantaSea | New Heated Resort Pool & Fire Pit

Spend the day outside morning, noon & night and live out your FantaSea vacation! Lounge on the deck or in the heated pool on the sun shelf. On a cool night sit by the fire and relax in the Adirondack chairs. Desirable designer interior with coastal decor has the comfort of home with the feel of the sea. We are just a few minutes away from white sandy beaches with beautiful sunsets, amazing restaurants and upscale shopping centers.

Backwater Paradise

Clean, updated, and perfectly centered in middle of the island. Rental is a first floor 2 bedroom/2 bathroom unit with separate entrance. Living room opens up to the backyard with tranquil views of the water and docks. Take a complimentary backpack beach chair and take a short ride to the beach which is only a straight 1 mile ride down Winterberry Drive.