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Chokoloskee Island Vacation Rentals

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Vacation Rentals in Chokoloskee Island

The Ultimate Fishing Retreat- Comfortable and Convenient!

2.0 star property
9.8 out of 10, Exceptional, (11)
"Great place"
$417 nightly
The price is $458
Sep 1 - Sep 2
Total with taxes and fees
The Ultimate Fishing Retreat- Comfortable and Convenient!

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

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!! "
$211 nightly
The price is $231
Sep 11 - Sep 12
Total with taxes and fees
Naples Marina Getaway Studio now freshly REMODELED!

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 "
$216 nightly
The price is $239
Sep 1 - Sep 2
Total with taxes and fees
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."
$328 nightly
The price is $360
Sep 1 - Sep 2
Total with taxes and fees
Sunrise Waterfront Cottage

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!

Everglades Condo 15 Mi to Nat'l Park: Boat & Swim!

3.0 star property
Everglades Condo 15 Mi to Nat'l Park: Boat & Swim!

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."
$316 nightly
The price is $347
Sep 1 - Sep 2
Total with taxes and fees
Charming 1-bedroom cottage with AC and WiFi on a creek with private deck & 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.
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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 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 Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chokoloskee Island vacation 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 low season months. For more hustle and bustle, you may prefer to visit Chokoloskee Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $231 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chokoloskee Island rentals

At Expedia, we put the best Chokoloskee Island 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 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 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 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.