Photo by Noel Benadom

Chokoloskee Island Holiday Rentals

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

Holiday Rentals in Chokoloskee Island

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

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

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 Ultimate Fishing Retreat- Comfortable and Convenient!

2.0 star property
9.8 out of 10, Exceptional, (12)
"Great place"
The price is NZ$787
includes taxes & fees
25 Sept - 26 Sept
The Ultimate Fishing Retreat- Comfortable and Convenient!

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

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

10.0 out of 10, Exceptional, (10)
"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

Cottage retreat with walking distance to the Dock 🐠

9.4 out of 10, Exceptional, (48)
"Good location to visit surrounding areas."
Cottage retreat with walking distance to the Dock 🐠

@cypresscottage

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

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 NZ$408
includes taxes & fees
29 Sept - 30 Sept
River Wilderness Waterfront Cabins

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 NZ$412
includes taxes & fees
30 Sept - 1 Oct
Naples Marina Getaway Studio now freshly REMODELED!

Historic Home in the Heart of Everglades City

Historic Home in the Heart of Everglades City

The Everglades House

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

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!"
The price is NZ$379
includes taxes & fees
25 Sept - 26 Sept
Marina Fish- Boat and Relax in this Paradise newly remodeled in Naples, Florida!

4-bedroom house with pool steps from the dock!

10.0 out of 10, Exceptional, (41)
"Great clean comfortable lodging. Had a great fishing trip w the guys!"
4-bedroom house with pool steps from the dock!

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

9.4 out of 10, Exceptional, (6)
"Very private and clean with everything you need for the weekend."
The price is NZ$597
includes taxes & fees
25 Sept - 26 Sept
Charming 1-bedroom cottage with AC and WiFi on a creek with private deck & dock.

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 NZ$640
includes taxes & fees
25 Sept - 26 Sept
Sunrise Waterfront Cottage

Lostman's Lodge -Everglades City, Sunset View,Pool

10.0 out of 10, Exceptional, (11)
"Great accommodations and beautiful scenery "
Lostman's Lodge -Everglades City, Sunset View,Pool

Cozy Cottage Goodland Fl.

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

Paradise on the Bay

10.0 out of 10, Exceptional, (14)
"We very much enjoyed our stay! Nice cottage and waterfront property’"
Paradise on the Bay
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 Island Hotel Reviews

Find out more about Chokoloskee Island

Find out more about Chokoloskee Island

Everything you need to know about Chokoloskee Island 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 Island 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 Island holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chokoloskee Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chokoloskee Island. 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 Island 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 Island holiday rentals we have selected for you start as low as NZ$379 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chokoloskee Island rentals

At Expedia, we put the best Chokoloskee Island 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 Island 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 Island 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 Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.