Chokoloskee Vacation Rentals

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Vacation Rentals in Chokoloskee

Vacation Home in Ochopee

2.0 star property
9.8 out of 10, Exceptional, (13)
"Great place"
United States
Matt
$417 nightly
The price is $458
Dec 2 - Dec 3
Total with taxes and fees
The Ultimate Fishing Retreat- Comfortable and Convenient!

Apartment in Naples

9.6 out of 10, Exceptional, (14)
"Best stay I've had in a very long time. The place is awesome, great restaurant, nice and quiet, and close to everything. Will visit again!! "
United States
Rodney
$215 nightly
The price is $236
Dec 31 - Jan 1, 2026
Total with taxes and fees
Naples Marina Getaway Studio DIRECT WATER VIEWS!

Apartment in Naples

9.8 out of 10, Exceptional, (8)
"Perfect location. "
United States
Jennifer E.
$228 nightly
The price is $250
Dec 2 - Dec 3
Total with taxes and fees
Marina Fish- Boat and Relax in this Paradise newly remodeled in Naples, Florida!

Cottage in Ochopee

9.6 out of 10, Exceptional, (7)
"Very private and clean with everything you need for the weekend."
United States
Joseph C.
$316 nightly
The price is $347
Dec 5 - Dec 6
Total with taxes and fees
Charming 1-bedroom cottage with AC and WiFi on a creek with private deck & dock.

Villa in Everglades City

2.5 star property
8.6 out of 10, Excellent, (269)
"Rooms are dated but clean and the kitchens are well outfiited with dishes and cooking supplies. Parking under the unit is awesome. Would recommend for motorcycle riders. Check in and out was really smooth and hasle free."
United States
Randy
$285 nightly
The price is $315
Dec 2 - Dec 3
Total with taxes and fees
River Wilderness Waterfront Cabins

Apartment in Marco Island

10.0 out of 10, Exceptional, (44)
"The host always responded to my emails quickly and was very accommodating during my stay, she and her husband was great."
United States
Dean L.
$360 nightly
The price is $395
Dec 2 - Dec 3
Total with taxes and fees
Sunrise Waterfront Cottage
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Top Chokoloskee Hotel Reviews

Find out more about Chokoloskee

Everything you need to know about Chokoloskee vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chokoloskee vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chokoloskee vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chokoloskee vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chokoloskee. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chokoloskee in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $236 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chokoloskee rentals

At Expedia, we put the best Chokoloskee vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chokoloskee rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chokoloskee vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chokoloskee. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find vacation rentals in Chokoloskee?

Yes, there are vacation rentals close to the most popular attractions in Chokoloskee, or you can choose a more secluded option if you're looking for relaxation. Chokoloskee is known for its waterfront and seafood restaurants.

What are some of the best vacation rentals that Chokoloskee has to offer?

Deep Water Access with a Panoramic View of Chokoloskee Bay: Visitors give good reviews to this Chokoloskee vacation home rental, which is located on the beach and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games in this rental home to help you unwind. Another good choice for your trip to Chokoloskee is The Ultimate Fishing Retreat- Comfortable and Convenient!.

How many vacation rentals are there in Chokoloskee?

With 7 Expedia vacation rentals, you're sure to find just the right place for your Chokoloskee stay.

What can I see and do in Chokoloskee?

While exploring the area, visit family-friendly sights like Rookery Bay Reserve Lands, or get outside and enjoy nature at Everglades National Park. In the larger area, you’ll find Smallwood Store and Chokoloskee Bay.

What are vacation rentals like in Chokoloskee?

Vacation rentals are private accommodations you can reserve for a short or long stay in Chokoloskee. Vacation rentals offer extras like laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can offer a sense of safety away from shared hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for a family trip or a small group gathering.