Search Holiday Rentals in Chokoloskee

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
16 Jan - 18 Jan
In two months
27 Feb - 1 Mar
In three months
27 Mar - 29 Mar
In four months
24 Apr - 26 Apr

Our top choices for Chokoloskee holiday rentals

Outdoor pool
River Wilderness Waterfront Cabins

Villa in Everglades City

River Wilderness Waterfront Cabins
2.5 star property
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 ฿8,587
฿9,789 total
includes taxes & fees
10 Jan - 11 Jan 2026
River Wilderness Waterfront Cabins
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chokoloskee Hotel Reviews

Captain's Table Hotel

Captain's Table Hotel

10/10 Excellent
"Lovely balcony! Mini fridge, microwave, and sizable bathroom. "
Jessica 1-night trip
Posted 7 days ago
Captain's Table Hotel

Find out more about Chokoloskee

Search for holiday rentals in Chokoloskee on Expedia! You can easily find your home rentals, villas, holiday apartments in Chokoloskee using one of the methods below:

  • View our selection of featured holiday rentals in Chokoloskee
  • Use the map to find apartments and other holiday homes in the Chokoloskee neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chokoloskee while they last

Look no further and take a look at our great range of rental properties in Chokoloskee!

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.

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.