Holiday rentals in Chokoloskee Island

Apartment in Marco Island

4.99 out of 5 average rating, 123 reviews

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

4.94 out of 5 average rating, 123 reviews

LUXE Oasis | 10 min Beach+5th Ave | HTD Pool• Crib

Welcome to Your Naples Getaway! Why our home is perfect for your vacation: 🏖️ Beaches Nearby – Just a quick 10–15 minute drive to Via Miramar and Lowdermilk Beach. 📍Prime Location – Nestled on a peaceful street only 7 minutes from the iconic 5th Avenue. 🏡 Resort-Style Comfort – Relax in our fully screened lanai featuring: • Heated private pool • Luxury chaise loungers • Outdoor TV • Gas grill for BBQ nights Unwind with a cocktail, take a sunset dip, or simply kick back under the stars!

Cottage in Everglades City

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.

4.97 out of 5 average rating, 111 reviews

Home in Marco Island

Boater’s Paradise at the Coastal Cottage!

Perfect ENTIRE HOME for a seaside retreat! Direct access 3/2 with boat lift and dock. Charmingly furnished and designed to delight. Enjoy amazing access to Florida's best boating, fishing and beaches- just 4 minutes from the dock to end of no wake zone and a 12 minute car drive to stunning local beaches. Enjoy upstairs screened lanai overlooking tranquil waters and feel your troubles melt away as you relax in the tranquil island vibe of Old Florida! Boat rental available at near by marina.

Home in Goodland, Marco Island

4.9 out of 5 average rating, 386 reviews

SWFl waterfront home with direct Gulf access

Private waterfront home in the quaint fishing village of Goodland. We are on a deep water canal with 40 foot of dock space to park your fishing boat, with direct access to the Gulf of Mexico and the 10000 Islands National Park. We have 3 marinas ,walking distance , to launch your boat and get gas. Our home has a 300 square foot screened in porch and a 450 square foot dock with southern exposure to watch the sunrise and sunsets . The Marco Island shopping and beaches are 5 miles away.

Superhost

Apartment 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.

4.97 out of 5 average rating, 112 reviews

Cottage in Goodland

Waterfront View Cottage

Come and stay at the only location on the island with the one of a kind exceptional view of the Everglades. Step right out to the waters edge of the Goodland Bay, where you will be able watch the dolphins right from your porch and private patio. The cottage has great sliding glass doors that hold the magnificent view of the water, right from the living room. A freshly remodeled fully furnished, up to date, 1 bedroom cottage. Dockage, kayaks, and bikes available.

4.95 out of 5 average rating, 155 reviews

Apartment 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.

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

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

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.

4.94 out of 5 average rating, 346 reviews

Flat in Everglades City

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.

Holiday rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Chokoloskee Island holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Chokoloskee Island

5 out of 5 average rating, 7 reviews

Apartment in Naples

Naples Tyme Retreat

TiffaniRating, 5 stars3 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!

4.76 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

Home in Ochopee

Paradise on Chokoloskee Island

JodieRating, 5 stars1 month 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!

5 out of 5 average rating, 6 reviews

Home in Bonita Springs

Luxurious 4-Bed Pool Home with Dock & Gulf Views,

AnnemieRating, 5 stars1 month ago

We had an absolutely great 4 day stay. The house is beautiful and the views are stunning. The description in the listing is completely accurate. We would for sure choose this place again for future stays.

4.98 out of 5 average rating, 47 reviews

Entire house: Pool : Kids play area

AmandaRating, 5 stars6 days ago

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

5 out of 5 average rating, 37 reviews

Welcome to Little Paradise

LucaRating, 5 stars2 weeks ago

We stayed for 2 nights with family and friends, and the experience was absolutely amazing! 🌟 The place is super clean, exactly like the pictures, and has such a peaceful atmosphere. The pool was spotless and perfectly warm, with jets that made it feel like a relaxing massage just what we needed to unwind! The house was very well equipped, with plenty of supplies and extra items available for guests to use. We appreciated the many towels and beach towels provided everything was thoughtfully prepared. 🏖️ Whether you’re coming with family, friends, or just looking for a romantic getaway, this place is a perfect choice. We absolutely recommend it to everyone and would love to come back! 💛

5 out of 5 average rating, 45 reviews

Home in Marco Island

Marco Island Private Getaway

SvetoslavRating, 5 stars1 month ago

Our family had an amazing stay at Robert’s place! The house offers everything you need and more! Quiet, private and peaceful location, spacious interior and a wonderful pool. We fehlt right at home and could really relax. The south beach with white powder sand and clear waters is just 10 minute drive from the house. If you want to have a proper vacation at a great house in a stunning location, look no further.