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

Boaters Bayshore Bungalow w/HOT TUB view of water.

BRING YOUR BOAT! This ranch home is located on a canal with direct access to the Gulf/Naples Bay(no bridges). Amazing water sports access. In the cool/hip Bayshore Arts district! Great restaurants, Naples Botanical Gardens, boating, 3 miles to DT Naples and 4 to the best beaches. This is a perfect family/friends vacation spot. We have all the gear to enjoy this location. Quiet neighborhood/newly renovated/great views. Coffee on the deck with sunrise in front of you or drinks at sunset. Serenity

Dolphin Pardise Waterview, Wildlife, Pool &Fishing

Unique Waterfront Condo & Gorgeous Intercoastal Views, Wildlife, Fishing, Boat Dock. 1 block from Snook Inn! Adjacent Pool Steps Away from Patio. NEWLY REMODELED! Pool & 2 Private Patios overlook Beautiful Waterfront, Dolphins, Manatees, Exotic Birds. Main Floor -no steps. If you love water and WILDLIFE, this place is for you! Fishing on the dock-Fishing Poles and Tack Supplied, pull your boat right to the back door. TONS of wildlife. Dock is lit at night, watch the sea life! NON SMOKING UNIT

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!

Waterfront ocean access canal, Kayaks, Bikes Beach

We renovated a key west style home into a modern beachy oasis. You can kayak, bike and boat to the beach right from the house! This safe waterfront neighborhood has tons of friendly people out walking, running, biking, dog walking, etc. The house is 1/4 mile to the beach as the crow flys. Beach entrances are 2 miles away. We have 2 nice adult bicycles, kayaks and fishing rods for you to use. Located just off Wiggins Pass Road between 41 and the ocean. Stilt home. Don’t even need a car.

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! Delightful rustic home- perfect for a seaside retreat!. Designed for dockside enjoyment: hammocks, swing chairs, outdoor dining. Enjoy a taste of old Florida! - 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

Everglades City waterfront cabin

Bring your boat to this waterfront community in the heart of the Everglades and the 10,000 Islands. Across from the Marjory Stoneman Douglas Visitor Center, Everglades Gulf Coast Center. Great fishing and boating community. The cabin is cozy and rustic. Sleeps up to 4 guests. There is a screened outdoor living space overlooking the water. Community heated pool. 20$ boat launch fee to be paid next door at Glades store. Loft space and utility room are off limits to guests.

Tropical paradise 5 minutes from the beach

Come on in and unwind in this peaceful and one-of-a-kind oasis just a short 5-minute drive from Wiggins Pass beach! Feeling adventurous? Hop on a bike and you'll be there in a little over 15 minutes. Located in North Naples, this charming house is fully stocked with everything you need to cook, discover, unwind, and rejuvenate, this space even boasts its own private backyard facing the preserve. The moment you pull into the driveway, you'll instantly feel those vacation vibes.

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.

⭐ Rare Waterfront Western Exposure Vacation Home

This dream getaway home is located in the heart of Marco Island with everything you need for an unforgettable trip! Enjoy the convenience of being only minutes away from South Marco Beach, with its white sand and clear blue skies, and the best restaurants such as Da Vinci's, Marco Prime, The Snook Inn, The Oyster Bar and shopping on the Island! Wind down your day watching breathtaking Western exposure sunsets from your own waterfront patio and dock...