Title: Chokoloskee Island Vacation Rentals from CA $369: Short-Term Rentals for 2026 | Expedia.ca

[Chokoloskee Island Travel Guide](https://expedia.ca/Chokoloskee-Island.dx553248635976468286)[Hotels in Chokoloskee Island](https://expedia.ca/Chokoloskee-Island-Hotels.d553248635976468286.Travel-Guide-Hotels)[Flights to Chokoloskee Island](https://expedia.ca/Cheap-Flights-To-Chokoloskee-Island.d553248635976468286.Travel-Guide-Flights)[Chokoloskee Island Car Rentals](https://expedia.ca/Car-Rentals-In-Chokoloskee-Island.d553248635976468286.Car-Rental-Guide)[Chokoloskee Island Vacation Packages](https://expedia.ca/Chokoloskee-Island.d553248635976468286.Destination-Travel-Guides)

![The amazingly dark skies of Chokoloskee Island, FL provide great views of the night sky. While there, check out some of the boat tours and fishing charters. #beachtips #florida #chokoloskee #island #milkyway #astronomy #beach #ocean #BVSblue](https://images.trvl-media.com/place/3000430940/6a686070-6a7c-41a9-b800-f0b3cf385f24.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Noel Benadom

# Chokoloskee Island Vacation Rentals

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## Check prices for these dates

In two weeks

[Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=553248635976468286&startDate=2026-01-16&endDate=2026-01-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=553248635976468286&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=553248635976468286&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976468286&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Chokoloskee Island vacation rentals

![Outdoor pool](https://images.trvl-media.com/lodging/5000000/4820000/4816100/4816075/05f388f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/5000000/4820000/4816100/4816075/2b620275.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Twin Bed Cabin | Living area](https://images.trvl-media.com/lodging/5000000/4820000/4816100/4816075/f7ce4054.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Full-size fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/5000000/4820000/4816100/4816075/06b66d1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Everglades City

[](https://www.expedia.ca/Naples-Hotels-River-Wilderness-Waterfront-Cabins.h4816075.Hotel-Information)

8.6/10

Excellent

(271)

"I would recommend this place for pure rest and relaxation "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Shodo

CA $380

CA $433 total

includes taxes & fees

Jan 4 - Jan 5

[](https://www.expedia.ca/Naples-Hotels-River-Wilderness-Waterfront-Cabins.h4816075.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/113000000/112870000/112867300/112867210/c99fa7c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Towels, soap, shampoo, toilet paper](https://images.trvl-media.com/lodging/113000000/112870000/112867300/112867210/64bb4b1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112870000/112867300/112867210/c4b665b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112870000/112867300/112867210/42241b8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Ochopee

[](https://www.expedia.ca/Ochopee-Hotels-Charming-1-Bedroom-Cottage-With-AC-And-WiFi-On-A-Creek-With-Private-Deck-Dock.h112867210.Hotel-Information)

9.6/10

Exceptional

(9)

"Spotless room, nice kitchen and private location. Great deck with fire pit overlooking a tidal creek. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Paul

CA $274

CA $476 total

includes taxes & fees

Jan 7 - Jan 8

[](https://www.expedia.ca/Ochopee-Hotels-Charming-1-Bedroom-Cottage-With-AC-And-WiFi-On-A-Creek-With-Private-Deck-Dock.h112867210.Hotel-Information)

![Marina](https://images.trvl-media.com/lodging/96000000/95170000/95166000/95165998/db4560ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/96000000/95170000/95166000/95165998/5d94ab5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/96000000/95170000/95166000/95165998/7552d3a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/96000000/95170000/95166000/95165998/f32c4bec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Naples

[](https://www.expedia.ca/Naples-Hotels-Port-Of-The-Islands-Naples-Marina-Getaway.h95165998.Hotel-Information)

9.6/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Rodney

CA $158

CA $369 total

includes taxes & fees

Jan 8 - Jan 9

[](https://www.expedia.ca/Naples-Hotels-Port-Of-The-Islands-Naples-Marina-Getaway.h95165998.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/101000000/100410000/100401300/100401228/444a5cc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/101000000/100410000/100401300/100401228/c12b1cc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/101000000/100410000/100401300/100401228/9d08b425.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/101000000/100410000/100401300/100401228/b7d5390c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Naples

[](https://www.expedia.ca/Naples-Hotels-Marina-Fish-Boat-And-Relax-In-This-Paradise-In-Naples.h100401228.Hotel-Information)

9.8/10

Exceptional

(9)

"Perfect location. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jennifer E.

CA $165

CA $369 total

includes taxes & fees

Jan 4 - Jan 5

[](https://www.expedia.ca/Naples-Hotels-Marina-Fish-Boat-And-Relax-In-This-Paradise-In-Naples.h100401228.Hotel-Information)

![Fridge, microwave, oven, coffee/tea maker](https://images.trvl-media.com/lodging/43000000/42040000/42035500/42035406/d48de0de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/43000000/42040000/42035500/42035406/w1242h931x0y1-a57d0d2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/43000000/42040000/42035500/42035406/234827f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/43000000/42040000/42035500/42035406/f3b55701.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Marco Island

[](https://www.expedia.ca/Goodland-Hotels-Quiet.h42035406.Hotel-Information)

10/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Dean L.

CA $357

CA $644 total

includes taxes & fees

Jan 4 - Jan 5

[](https://www.expedia.ca/Goodland-Hotels-Quiet.h42035406.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-01-17&endDate=2026-01-18&regionId=553248635976468286&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Chokoloskee+Island%2C+Florida%2C+United+States+of+America&regionId=553248635976468286&latLong=25.812324%2C-81.359523&adults=2&startDate=2026-04-03&d1=2026-04-03&endDate=2026-04-06&d2=2026-04-06&lodging=APARTMENT)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Chokoloskee+Island%2C+Florida%2C+United+States+of+America&regionId=553248635976468286&latLong=25.812324%2C-81.359523&adults=2&startDate=2026-04-03&d1=2026-04-03&endDate=2026-04-06&d2=2026-04-06&lodging=VILLA)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Chokoloskee+Island%2C+Florida%2C+United+States+of+America&regionId=553248635976468286&latLong=25.812324%2C-81.359523&adults=2&startDate=2026-04-03&d1=2026-04-03&endDate=2026-04-06&d2=2026-04-06&lodging=COTTAGE)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Chokoloskee+Island%2C+Florida%2C+United+States+of+America&regionId=553248635976468286&latLong=25.812324%2C-81.359523&adults=2&startDate=2026-04-03&d1=2026-04-03&endDate=2026-04-06&d2=2026-04-06&lodging=CONDO)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Chokoloskee+Island%2C+Florida%2C+United+States+of+America&regionId=553248635976468286&latLong=25.812324%2C-81.359523&adults=2&startDate=2026-04-03&d1=2026-04-03&endDate=2026-04-06&d2=2026-04-06&lodging=VACATION_HOME)

Houseboats

[](https://www.expedia.ca/Hotel-Search?destination=Chokoloskee+Island%2C+Florida%2C+United+States+of+America&regionId=553248635976468286&latLong=25.812324%2C-81.359523&adults=2&startDate=2026-04-03&d1=2026-04-03&endDate=2026-04-06&d2=2026-04-06&lodging=HOUSE_BOAT)

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## Top Chokoloskee Island Hotel Reviews

![Everglades Adventures Hotel Suites by Ivey House](https://images.trvl-media.com/lodging/58000000/57920000/57918300/57918264/aecfbdd5_y.jpg)

### Everglades Adventures Hotel Suites by Ivey House

10/10 Excellent

"Stay was excellent "

[](https://expedia.ca/Naples-Hotels-Everglades-Adventures-Hotel-Suites.h57918264.Hotel-Information)

![Port of the Islands Everglades Adventure Resort](https://images.trvl-media.com/lodging/2000000/1150000/1144200/1144178/b0f8ae7a_y.jpg)

### Port of the Islands Everglades Adventure Resort

10/10 Excellent

"A beautiful place in a very nice area! The Hotel has a lot of charm, the management is fantastic, the entire team very nice, kind and professional! Very recommendable for going into or out of the Everglades. Great Kajak and boat tours into the thousand island area. We had a wonderful time! Thanks!"

[](https://expedia.ca/Naples-Hotels-Port-Of-The-Islands-Everglades-Adventure-Resort.h1144178.Hotel-Information)

![Naples Marina Getaway Studio DIRECT WATER VIEWS!](https://images.trvl-media.com/lodging/96000000/95170000/95166000/95165998/db4560ae_y.jpg)

### Naples Marina Getaway Studio DIRECT WATER VIEWS!

10/10 Excellent

"Very nice room and property - and affordable! Clean and comfortable."

[](https://expedia.ca/Naples-Hotels-Port-Of-The-Islands-Naples-Marina-Getaway.h95165998.Hotel-Information)

![Captain's Table Hotel](https://images.trvl-media.com/lodging/74000000/73780000/73778400/73778356/18e0c390_y.jpg)

### Captain's Table Hotel

10/10 Excellent

"Lovely balcony! Mini fridge, microwave, and sizable bathroom. "

[](https://expedia.ca/Everglades-City-Hotels-Captains-Table-Hotel.h73778356.Hotel-Information)

![Everglades City Motel](https://images.trvl-media.com/lodging/17000000/16210000/16202000/16201972/6fb45e63_y.jpg)

### Everglades City Motel

10/10 Excellent

"Room was very nicely remodeled. Set up well and clean."

[](https://expedia.ca/Naples-Hotels-Everglades-City-Motel-Everglades-Adventures-Inn.h16201972.Hotel-Information)

![River Wilderness Waterfront Cabins](https://images.trvl-media.com/lodging/5000000/4820000/4816100/4816075/05f388f0_y.jpg)

### River Wilderness Waterfront Cabins

10/10 Excellent

"The owner is very accommodating and friendly. "

[](https://expedia.ca/Naples-Hotels-River-Wilderness-Waterfront-Cabins.h4816075.Hotel-Information)

![Deep Water Access with a Panoramic View of Chokoloskee Bay](https://images.trvl-media.com/lodging/30000000/29630000/29623500/29623408/a4bd5fde_y.jpg)

### Deep Water Access with a Panoramic View of Chokoloskee Bay

10/10 Excellent

"We used this as a jump off point to kayak the waterway, wonderful position and stay"

[](https://expedia.ca/Chokoloskee-Hotels-Deep-Water-Access-With-A-Panoramic-View-Of-Chokoloskee-Bay.h29623408.Hotel-Information)

![Marina Paradise in Naples, Florida!](https://images.trvl-media.com/lodging/101000000/100410000/100401300/100401228/444a5cc1_y.jpg)

### Marina Paradise in Naples, Florida!

10/10 Excellent

"Cozy and confortable. Parking was sometimes sketchy but we got out sreps in!"

[](https://expedia.ca/Naples-Hotels-Marina-Fish-Boat-And-Relax-In-This-Paradise-In-Naples.h100401228.Hotel-Information)

![@cypresscottage](https://images.trvl-media.com/lodging/69000000/68030000/68024300/68024286/2e872dbc_y.jpg)

### @cypresscottage

10/10 Excellent

"Great property in the perfect location for us. The host was very responsive and the property is exactly as described / listed. Loved the design choices of the home and we felt very comfortable for our trip. We absolutely look forward to booking again in the future."

[](https://expedia.ca/Naples-Hotels-Cypresscottage.h68024286.Hotel-Information)

## Find out more about Chokoloskee Island

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Chokoloskee Island. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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Hotels

- [Hotels in Emerald Coast](https://expedia.ca/Emerald-Coast-Hotels.d553248635975748129.Travel-Guide-Hotels)
- [All Inclusive Resorts and Hotels in Fort Walton Beach - Destin](https://expedia.ca/Fort-Walton-Beach-Destin-Hotels-All-Inclusive-Hotel.0-0-d6023392-tAllInclusiveHotel.Travel-Guide-Filter-Hotels)
- [Hotels near Walt Disney World® Resort](https://expedia.ca/Walt-Disney-World-Resort-Hotels.0-l6034120-0.Travel-Guide-Filter-Hotels)
- [Hotels in South Florida](https://expedia.ca/South-Florida-Hotels.d6233792.Travel-Guide-Hotels)
- [All Inclusive Resorts and Hotels in South Florida](https://expedia.ca/South-Florida-Hotels-All-Inclusive-Hotel.0-0-d6233792-tAllInclusiveHotel.Travel-Guide-Filter-Hotels)
- [South Beach hotels](https://expedia.ca/South-Beach-Miami-Hotels.0-n6138745-0.Travel-Guide-Filter-Hotels)
- [Hotels in Anna Maria Island](https://expedia.ca/Anna-Maria-Island-Hotels.d553248622847118534.Travel-Guide-Hotels)

Flights

- [Cheap Flights to Anna Maria Island](https://expedia.ca/Cheap-Flights-To-Anna-Maria-Island.d553248622847118534.Travel-Guide-Flights)
- [Cheap Flights to Highway 30A](https://expedia.ca/Cheap-Flights-To-Highway-30A.d553248635976474465.Travel-Guide-Flights)
- [Cheap Flights to Fort Walton Beach - Destin](https://expedia.ca/Cheap-Flights-To-Fort-Walton-Beach-Destin.d6023392.Travel-Guide-Flights)

Cars

- [Car rental Tampa Airport (TPA)](https://expedia.ca/Car-Rentals-In-Tampa-Intl.d4280404.Car-Rental-Guide)
- [Car rental Orlando Airport (MCO)](https://expedia.ca/Car-Rentals-In-Orlando-Intl.d5194573.Car-Rental-Guide)
- [Car rental Fort Lauderdale Airport (FLL)](https://expedia.ca/Car-Rentals-In-Fort-Lauderdale-Hollywood-Intl.d5000262.Car-Rental-Guide)

Activities

- [Things to do in Southeast Florida](https://expedia.ca/Things-To-Do-In-Southeast-Florida.d6047949.Travel-Guide-Activities)
- [Things to do in South Florida](https://expedia.ca/Things-To-Do-In-South-Florida.d6233792.Travel-Guide-Activities)
- [Things to do in Emerald Coast](https://expedia.ca/Things-To-Do-In-Emerald-Coast.d553248635975748129.Travel-Guide-Activities)
- [Things to do in Florida Gulf Coast](https://expedia.ca/Things-To-Do-In-Florida-Gulf-Coast.d553248635974622901.Travel-Guide-Activities)

Packages

- [Central West Coast Florida Vacations](https://expedia.ca/Central-West-Coast-Florida.d6048187.Destination-Travel-Guides)
- [Anna Maria Island Vacations](https://expedia.ca/Anna-Maria-Island.d553248622847118534.Destination-Travel-Guides)
- [Walt Disney World® Resort](https://expedia.ca/Walt-Disney-World-Resort-Orlando.d6034120.Vacation-Attraction)
- [Highway 30A Vacations](https://expedia.ca/Highway-30A.d553248635976474465.Destination-Travel-Guides)
- [South Florida Vacations](https://expedia.ca/South-Florida.d6233792.Destination-Travel-Guides)

Vacation Rentals

- [Florida Panhandle Vacation Rentals](https://expedia.ca/Florida-Panhandle-Vacation-Rentals.d6048212.Travel-Guide-VacationRentals)
- [South Florida Vacation Rentals](https://expedia.ca/South-Florida-Vacation-Rentals.d6233792.Travel-Guide-VacationRentals)
- [Anna Maria Island Vacation Rentals](https://expedia.ca/Anna-Maria-Island-Vacation-Rentals.d553248622847118534.Travel-Guide-VacationRentals)

General

- [Visit Southeast Florida](https://expedia.ca/Southeast-Florida.dx6047949)
- [Visit Northern Florida](https://expedia.ca/Northern-Florida.dx6233767)
- [Visit Florida Panhandle](https://expedia.ca/Florida-Panhandle.dx6048212)
- [Visit Southwest Florida](https://expedia.ca/Southwest-Florida.dx6233839)
- [Visit Sanibel Captiva Island](https://expedia.ca/Sanibel-Captiva-Island.dx6326115)

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