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Top Holiday Rentals in Chokoloskee

Our top choices for Chokoloskee holiday rentals

Deep Water Access with a Panoramic View of Chokoloskee Bay

10.0 out of 10, Exceptional, (54)
"Property was in great location Property owner was friendly "
Deep Water Access with a Panoramic View of Chokoloskee Bay

The Ultimate Fishing Retreat- Comfortable and Convenient!

2.0 star property
9.8 out of 10, Exceptional, (11)
"Great place"
The price is £345
includes taxes & fees
24 Aug - 25 Aug
The Ultimate Fishing Retreat- Comfortable and Convenient!

Waterfront 2 bedroom 1 bath with boat slip

10.0 out of 10, Exceptional, (46)
"We enjoyed our stay."
Waterfront 2 bedroom 1 bath with boat slip

Everglades Chokoloskee 3 bdrm Home w/ dock, marina, National Park,10,000 Islands

9.6 out of 10, Exceptional, (131)
"Well represented "
Everglades Chokoloskee 3 bdrm Home w/ dock, marina, National Park,10,000 Islands

Waterfront RV with Boat Slip in Chokoloske...Surrounded by Everglades Nat'l Park

10.0 out of 10, Exceptional, (4)
"Will book again"
Waterfront RV with Boat Slip in Chokoloske...Surrounded by Everglades Nat'l Park

Chokoloskee-incredible fishing while enjoying Florida with friends and family.

10.0 out of 10, Exceptional, (3)
"The three of us fly fished for 3 days with local guides. This house is 3 minutes from the boat ramp. Plenty of room."
Chokoloskee-incredible fishing while enjoying Florida with friends and family.

The Reel'em Inn, Chokoloskee Island Fisherman's Paradise

10.0 out of 10, Exceptional, (9)
"Fantastic house, quiet ,extremely clean and well stock, we loved it and would love to come back in the near future .Thank you Maureen and Brock for this dream place Maria and Richard G"
The Reel'em Inn, Chokoloskee Island Fisherman's Paradise

@cypresscottage

10.0 out of 10, Exceptional, (47)
"We had a great stat and would absolutely stay here again"
@cypresscottage

Cottage retreat with walking distance to the Dock 🐠

9.4 out of 10, Exceptional, (44)
"The owners were very nice and full of information. Great place to stay in the middle of the town minutes from everything!"
Cottage retreat with walking distance to the Dock 🐠

Naples Marina Getaway Studio now freshly REMODELED!

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!! "
The price is £164
includes taxes & fees
28 Aug - 29 Aug
Naples Marina Getaway Studio now freshly REMODELED!

Getaway in the Everglades

10.0 out of 10, Exceptional, (38)
"This was an amazing place with old Florida charm."
Getaway in the Everglades

River Wilderness Waterfront Cabins

2.5 star property
8.6 out of 10, Excellent, (268)
"I would recommend this place for pure rest and relaxation "
The price is £177
includes taxes & fees
24 Aug - 25 Aug
River Wilderness Waterfront Cabins

Cozy Cottage Goodland Fl.

10.0 out of 10, Exceptional, (50)
"Positive"
Cozy Cottage Goodland Fl.

Sunrise Waterfront Cottage

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."
The price is £272
includes taxes & fees
24 Aug - 25 Aug
Sunrise Waterfront Cottage

The Everglades House

10.0 out of 10, Exceptional, (6)
"We relaxed and enjoyed the wonderful wildlife "
The Everglades House

Everglades City Motel - Queen Room, 2 Beds, Kitchenette and Back Door

9.4 out of 10, Exceptional, (19)
"Great hosts "
The price is £96
includes taxes & fees
1 Sept - 2 Sept
Everglades City Motel - Queen Room, 2 Beds, Kitchenette and Back Door

Waterfront retreat with bay views, dog-friendly, & snowbird-ready

10.0 out of 10, Exceptional, (4)
"We had a very good stay at this house. It was clean, had everything we needed and was in a convenient location. We would definitely recommend. "
Waterfront retreat with bay views, dog-friendly, & snowbird-ready

Naples Studio Retreat w/ Resort Pool!

10.0 out of 10, Exceptional, (1)
"Excellent stay, nice location friendly staff, good accessibility for seniors. Only minor inconvenience was a small kitchen size. Would have been nice to have a toaster and blender, but breakfast was also offered."
Naples Studio Retreat w/ Resort Pool!

Quaint, Lakeside Queen Hotel Room

10.0 out of 10, Exceptional, (1)
"Comfortable beds nice location"
The price is £74
includes taxes & fees
24 Aug - 25 Aug
Quaint, Lakeside Queen Hotel Room

Cozy Naples Retreat w/ Community Pool & Water View

7.8 out of 10, Good, (6)
"Love this area to stay, my second time. Will be back again! "
Cozy Naples Retreat w/ Community Pool & Water View
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

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 Chokoloskee Bay.

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.