Vacation rentals in Chokoloskee Island

4.99 out of 5 average rating, 123 reviews

A decorative lantern features a black metal top and a wooden frame with a weathered finish. Inside, a large cream-colored candle rests among sand dollar shells, providing a subtle coastal accent. The glass panels allow light to shine through, creating a warm ambiance.

Condo in Marco Island

Waterfront View, Boat Dock, Pool Wildlife &Fishing

Unique Waterfront Condo & Gorgeous Intercoastal Views, Wildlife, Fishing, Boat Dock. One block from Snook Inn! Adjacent Pool Steps Away from Back Patio. NEWLY REMODELED! Pool & Patio Overlook Beautiful Waterfront, Dolphins, Manatees, Exotic Birds. Main Floor with 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

Cottage in Everglades City

A spacious living area is complemented by a wooden ceiling and large windows providing views of the water and surrounding greenery. Modern kitchen amenities are visible, along with a dining area furnished with stylish seating, creating a seamless indoor-outdoor experience.

4.98 out of 5 average rating, 158 reviews

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.

5 out of 5 average rating, 37 reviews

A wooden sign reading 'Fakahatchee Strand Preserve State Park' is prominently displayed, indicating the entrance to the boardwalk. The background features a wide, open vista of wetland grasses under a blue sky with wispy clouds, emphasizing the natural beauty of the area.

Home in Ochopee

The Everglades House

We welcome you to your next adventure! This 3-bedroom home is located in a unique, historic "Old-Florida" style town known as Everglades City (a.k.a. Ochopee). Home includes beautiful & serene waterfront views where you can lie back, relax, read a book or have a drink, while your kids can fish from the dock! You can enjoy activities like airboat tours, eco/wildlife-tours, fishing guides, bicycling, kayaking, walk the nature trails local bars and restaurants. We look forward to hosting you!

Superhost

A peaceful wetland area is depicted, featuring still waters surrounded by lush greenery. Tall trees and shrubs create a natural border, while varied water plants are visible beneath the surface. The reflection of trees can be seen in the calm water, adding to the serene setting.

Condo in Everglades City

4.8 out of 5 average rating, 186 reviews

Everglade Isle Palms Condotel w/ Pool & Boat Ramp

It’s island time! Welcome to your home base for exploring the Florida Everglades. With all the comforts of home, our Condotel will be your ideal vacation spot. Explore Everglades National Park, the 10,000 islands, airboat tours, and more! Bring your boat or rent one for saltwater, brackish, & freshwater fishing- all from this unique & pristine area. Located in the heart of town, you’ll be in walking distance of several restaurants, ice cream parlors, and the grocery store.

4.94 out of 5 average rating, 31 reviews

Home in Everglades

Lostman's Lodge -Everglades City, Sunset View,Pool

Escape to the serene beauty of Everglades City at Lostman's Lodge, a spacious and beautiful waterfront property. This retreat offers accommodation for up to 10 guests, making it perfect for families, groups of friends, or couples seeking a tranquil getaway. With a main house and a charming pool house, a screened-in pool and hot tub, a dock, and amazing views of the water, this home is a true slice of paradise. It is not just a vacation rental; it's an experience!

4.89 out of 5 average rating, 209 reviews

Condo in Marco Island

By the Ocean

This building is located right in front the Marco Island Beach Access Point! This condo is very close to the JW Marriot, providing a convenient alternative. The condo has a pool - available all year -, tennis court, BBQ and laundry on each floor. All the common areas are fully available for your use and in excellent condition. And of course, you have a reserved parking space for your vehicle. This is an exceptional place to rest and enjoy with your family.

4.95 out of 5 average rating, 155 reviews

A modern bathroom features a glass-enclosed shower with marble-style tiles. A small window provides natural light while toiletries are neatly arranged on a shelf. A white toilet and a decorative plant add a touch of style, complemented by a textured rug on the floor.

Condo in Naples

Sea Shell Villa 1

Your will be close to everything when you stay at this centrally-located villa. Our villa is fully upgraded. Has a full kitchen, 1 bedroom with a queen bed and laundry room with a full size washer and dryer. There is a great variety of restaurants and shopping just minutes away. In just 15 minutes you can be at the famous Naples pier for a fun day at the beach. We also have Marco Island, which is one of the top beaches in the world, just 20 minutes away.

A wooden pathway bordered by lush greenery leads towards the beach, with swaying palm trees framing the view. Soft sand can be seen in the distance, meeting the inviting blue ocean under a clear sky.

4.96 out of 5 average rating, 107 reviews

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. The moment you pull into the driveway, you'll instantly feel those vacation vibes.

5 out of 5 average rating, 79 reviews

A spacious covered porch features a wooden dining table surrounded by chairs, with a decorative rug underneath. Ceiling fans circulate air while soft lighting from string lights enhances the inviting ambiance. The porch offers a view of the lush greenery beyond.

Home in Chokoloskee

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.

5 out of 5 average rating, 48 reviews

A shaded outdoor area is created with a concrete floor and exposed beams. A set of comfortable seating is arranged alongside a dining table. Two swings hang from the ceiling, and greenery is visible through the open space, enhancing the relaxed atmosphere.

Home in Chokoloskee

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.

Apartment in Everglades City

The bathroom features a clean white vanity with a sink and mirror above. A toilet and shelf are positioned nearby, displaying decorative plants and a framed picture. A soft pink towel hangs from a ring, adding a touch of color to the space.

4.94 out of 5 average rating, 346 reviews

Explore the Everglades! - Private 1 BR Apartment

This 1 bedroom/ 1 bath apartment located in Everglades City is clean, simple, and comfortable. It is perfectly located to explore Everglades National Park as well as other preserves and wildlife refuges in southwest Florida. Everglades City is a tiny little town literally at the end of the road on the West coast of Florida, approximately 45 minutes from Marco Island and Naples.

4.91 out of 5 average rating, 148 reviews

A large alligator rests on the bank of a shallow waterway, partially surrounded by tall grasses and reeds. The texture of its scaly skin is visible, blending with the natural surroundings. Sunlight reflects off the water, enhancing the lush greenery.

Cabin in Everglades City

Everglades City waterfront cabin

Bring your boat to this waterfront community in the heart of the Everglades and the 10,000 Islands. Across from Everglades National Park. Great fishing and boating community.. cozy cabin Sleeps up to 4 guests. Large outdoor living space. 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.

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Other great vacation rentals in Chokoloskee Island

A neatly arranged bathroom countertop features a tray with two folded white towels, a bottle of facial cleanser, a bottle of micellar water, and a scented candle. The light marble surface reflects the modern finishes of the space.

5 out of 5 average rating, 16 reviews

Cozy and Stylish, 2 King, Close to Beach & 5th Ave

CarolineRating, 5 stars3 weeks ago

This property was immaculate! Everything you need/expect and more. The owner has done an amazing job. Very impressed. I hope to return soon.

5 out of 5 average rating, 7 reviews

Condo in Naples

Naples Tyme Retreat

TiffaniRating, 5 stars2 weeks ago

The perfect getaway. Just what we needed. We spent 8 wonderful nights in Kelly's spacious and beautifully decorated cottage. She always responded promptly to any questions we had and is a great host. The resort amenities were amazing! We loved spending our days at the pool. Would definitely stay again!

4.9 out of 5 average rating, 20 reviews

A welcoming porch area features comfortable wicker seating arrangements, including a spacious sofa adorned with nautical-themed pillows. A glass coffee table sits at the center, surrounded by decorative plants. Natural light filters through large windows, casting gentle shadows on the patterned rug.

Villa in Naples

Palms Villa

JessieRating, 5 stars3 weeks ago

Kristijan is a fabulous host! He made everything extremely easy, from check-in to check-out. He was very proactive and quick to respond for anything we needed! We felt right at home the second we walked in. Great house, great host!

4.76 out of 5 average rating, 25 reviews

Home in Chokoloskee

Waterfront Home on Chokoloskee a Fishermans Dream

PatrickRating, 5 stars3 weeks ago

I have been coming to Chokoloskee for over 20 years lucky enough to find this place near the Smallwood store I know exactly where I’ll be staying next time! For exceeded our expectations thanks again, Lynn! That was my original message for those wanting to visit. A day after our departure she contacted me for additional charges for laundry, indicating that we had more than our two adults and two children we could not find additional linens for their broken pullout bed, which sits at an angle like a rooftop, had to use a tablecloth as a mattress cover, and a blanket found in the utility closet. She then became very angry and nasty in her messages, I would not give her the time of day of ever returning, although the place is beautiful but the management has a poor attitude funny I’ve been coming to this island for 30 years after talking with a couple friends that live on the island they said she was crazy and now I know why lol best of luck to those of you that decide to visit. .

4.93 out of 5 average rating, 28 reviews

A kitchen drawer reveals a marble-patterned interior featuring a teal colander and a white strainer. The items are positioned neatly, showcasing practical cookware that is easily accessible for meal preparation.

Home in Ochopee

Paradise on Chokoloskee Island

JodieRating, 5 stars4 weeks ago

We loved staying at Mike's place with our 3 adult children to celebrate our youngest's birthday. It was a perfect venue and close to kayaking and the Animal Sanctuary & Alligator Park that we wanted to do/visit. Mike was very responsive to questions I had, and I would highly recommend his place!

A sparkling pool is surrounded by well-maintained landscaping, featuring lush greenery and palm trees. Comfortable seating arrangements, including lounges and chairs, are positioned nearby on a spacious patio, offering a serene outdoor space for relaxation.

4.98 out of 5 average rating, 47 reviews

Entire house: Pool : Kids play area

AmandaRating, 5 stars3 days ago

It was very quiet and peaceful. Nice place to get away and relax.

A modern kitchen features white cabinetry and a large island with seating for four. Stainless steel appliances, including a refrigerator and microwave, enhance the space. Natural light floods the area through multiple windows, illuminating the open layout connecting the kitchen to a cozy living area.

5 out of 5 average rating, 21 reviews

Blue Banyan Boathouse w/heated POOL. Boat DOCK!

AlindaRating, 5 stars1 week ago

This home was beautiful, the open layout was great. The bedrooms were spacious, beds were very comfortable. We spent the entire time on the back deck watching tv and hanging by the pool. The weather was not in our favor so the covered porch made such a difference for us. Highly recommend staying here. The host is very responsive and very kind. Thank you so much for letting us stay here!

A welcoming sign displays the name 'Piccolo Paradiso' alongside 'Bella Casa Rentals LLC,' set amidst lush greenery and palm trees. The sign is positioned on the ground, emphasizing the natural surroundings of the property.