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Chokoloskee Holiday Rentals

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Our top choices for Chokoloskee holiday rentals

River Wilderness Waterfront Cabins

River Wilderness Waterfront Cabins
2.5 star property
Everglades City
8.6 out of 10, Excellent, (271)
"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
The price is NZ$540
includes taxes & fees
2 Jan - 3 Jan 2026
River Wilderness Waterfront Cabins

Marina Fish- Boat and Relax in this Paradise newly remodeled in Naples, Florida!

Marina Fish- Boat and Relax in this Paradise newly remodeled in Naples, Florida!
Naples
9.8 out of 10, Exceptional, (9)
"Perfect location. "
United States
Jennifer E.
The price is NZ$459
includes taxes & fees
5 Jan - 6 Jan 2026
Marina Fish- Boat and Relax in this Paradise newly remodeled in Naples, Florida!

Naples Marina Getaway Studio DIRECT WATER VIEWS!

Naples Marina Getaway Studio DIRECT WATER VIEWS!
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
The price is NZ$408
includes taxes & fees
31 Dec - 1 Jan 2026
Naples Marina Getaway Studio DIRECT WATER VIEWS!

Charming 1-bedroom cottage with AC and WiFi on a creek with private deck & dock.

Charming 1-bedroom cottage with AC and WiFi on a creek with private deck & dock.
Ochopee
9.6 out of 10, Exceptional, (7)
"The property was perfect if you’re looking for good amenities while still feeling removed from an urban or suburban environment. Loved being isolated, great view of the stars, cool ambiance on back deck, and interior was very comfortable. Perfect for access to both parks in the area!"
United States
Ross P.
The price is NZ$580
includes taxes & fees
2 Jan - 3 Jan 2026
Charming 1-bedroom cottage with AC and WiFi on a creek with private deck & dock.

Getaway in the Everglades

Getaway in the Everglades
Everglades City
10.0 out of 10, Exceptional, (41)
"Great property. Love the artwork and puzzles! "
United States
Lisa S.
Getaway in the Everglades

Sunrise Waterfront Cottage

Sunrise Waterfront Cottage
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.
The price is NZ$872
includes taxes & fees
30 Dec - 31 Dec
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chokoloskee holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chokoloskee holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chokoloskee holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chokoloskee holiday rentals we have selected for you start as low as NZ$408 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chokoloskee rentals

At Expedia, we put the best Chokoloskee holiday 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 holiday.

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 holiday rentals in Chokoloskee?

Yes, there are holiday rentals close to the most popular sights in Chokoloskee, or you can select a more secluded option if you're looking for a relaxing stay. Chokoloskee is known for its waterfront and seafood restaurants.

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

Deep Water Access with a Panoramic View of Chokoloskee Bay: This highly rated holiday home rental in Chokoloskee is located on the beach, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most 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 holiday rentals are there in Chokoloskee?

With 7 Expedia holiday rentals, you're guaranteed 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 wider area, you’ll find Smallwood Store and Gulf Coast Visitor Center.

What are holiday rentals like in Chokoloskee?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chokoloskee. Holiday rentals provide amenities like laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a clean environment, holiday rentals can provide a sense of safety away from shared hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for family gatherings.