Photo by Noel Benadom

Chokoloskee Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Vacation Rentals in Chokoloskee

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 CA $240
CA $629 total
includes taxes & fees
Sep 1 - Sep 2
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 CA $131
CA $318 total
includes taxes & fees
Sep 11 - Sep 12
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 CA $289
CA $329 total
includes taxes & fees
Aug 31 - Sep 1
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 CA $227
CA $495 total
includes taxes & fees
Sep 1 - Sep 2
Sunrise Waterfront Cottage

The Everglades House

10.0 out of 10, Exceptional, (7)
"We relaxed and enjoyed the wonderful wildlife "
The Everglades House

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!

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

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

9.8 out of 10, Exceptional, (8)
"It was a friendly neighborhood!"
Marina Fish- Boat and Relax in this Paradise newly remodeled in Naples, Florida!

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

4-bedroom house with pool steps from the dock!

10.0 out of 10, Exceptional, (40)
"Great clean comfortable lodging. Had a great fishing trip w the guys!"
4-bedroom house with pool steps from the dock!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chokoloskee Hotel Reviews

Find out more about Chokoloskee

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, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chokoloskee vacation rentals we have selected for you start as low as CA $131 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 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.