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Chokoloskee Vacation Rentals

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Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Chokoloskee vacation rentals

Outdoor pool
River Wilderness Waterfront Cabins

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 ￥43,323
￥49,387 total
includes taxes & fees
Dec 31 - Jan 1, 2026
River Wilderness Waterfront Cabins
Terrace/patio
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.

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 ￥31,314
￥54,298 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Charming 1-bedroom cottage with AC and WiFi on a creek with private deck & dock.
Fridge, microwave, oven, coffee/tea maker
Sunrise Waterfront Cottage

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 ￥45,249
￥79,779 total
includes taxes & fees
Dec 30 - Dec 31
Sunrise Waterfront Cottage
Marina
Naples Marina Getaway Studio DIRECT WATER VIEWS!

Naples Marina Getaway Studio DIRECT WATER VIEWS!

Naples Marina Getaway Studio DIRECT WATER VIEWS!
Naples
9.6 out of 10, Exceptional, (15)
"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 ￥14,874
￥37,021 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Naples Marina Getaway Studio DIRECT WATER VIEWS!
Outdoor pool
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!

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 ￥18,788
￥42,618 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Marina Fish- Boat and Relax in this Paradise newly remodeled in Naples, Florida!
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

Captain's Table Hotel

Captain's Table Hotel

10/10 Excellent
"Lovely balcony! Mini fridge, microwave, and sizable bathroom. "
Jessica 1-night trip
Posted 4 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 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 Gulf Coast Visitor Center.

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.