Title: Chokoloskee Island Vacation Rentals from CA $324: 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)

![Everglades National Park showing general coastal views and a sunset](https://images.trvl-media.com/place/54987/dc2e0482-5a98-4b27-a953-3906734c065d.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Chokoloskee Island Vacation Rentals

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## Check prices for these dates

In two weeks

[Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=553248635976468286&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=553248635976468286&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=553248635976468286&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976468286&startDate=2026-04-17&endDate=2026-04-19&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)

![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)

![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)

![Balcony](https://images.trvl-media.com/lodging/5000000/4820000/4816100/4816075/ac13ec89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### River Wilderness Waterfront Cabins

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

Everglades City

8.6/10

Excellent

(271)

"Rooms are dated but clean and the kitchens are well outfiited with dishes and cooking supplies. Parking under the unit is awesome. Would recommend for motorcycle riders. Check in and out was really smooth and hasle free."

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

Randy

CA $378

CA $431 total

includes taxes & fees

Dec 31 - Jan 1, 2026

[](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)

![Interior](https://images.trvl-media.com/lodging/113000000/112870000/112867300/112867210/074e072e.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)

![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)

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

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

Ochopee

9.6/10

Exceptional

(7)

"The property was perfect if you’re looking for good amenities while still feeling removed from an urban or suburban environment. Loved being isolated, great view of the stars, cool ambiance on back deck, and interior was very comfortable. Perfect for access to both parks in the area!"

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

Ross P.

CA $274

CA $478 total

includes taxes & fees

Dec 27 - Dec 28

[](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)

![Outdoor pool](https://images.trvl-media.com/lodging/96000000/95170000/95166000/95165998/3195c2fb.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)

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

### Naples Marina Getaway Studio DIRECT WATER VIEWS!

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

Naples

9.6/10

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!! "

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

Rodney

CA $130

CA $324 total

includes taxes & fees

Dec 31 - Jan 1, 2026

[](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)

![Interior](https://images.trvl-media.com/lodging/101000000/100410000/100401300/100401228/89cf0350.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Naples

9.8/10

Exceptional

(9)

"Perfect location. "

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

Jennifer E.

CA $164

CA $361 total

includes taxes & fees

Jan 3 - Jan 4, 2026

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

![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34330000/34323400/34323344/343cf447.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, books](https://images.trvl-media.com/lodging/35000000/34330000/34323400/34323344/ac1ca614.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/35000000/34330000/34323400/34323344/24a334f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34330000/34323400/34323344/2dab6272.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Getaway in the Everglades 

[](https://www.expedia.ca/Everglades-City-Hotels-Getaway-In-The-Everglades.h34323344.Hotel-Information)

Everglades City

10/10

Exceptional

(41)

"Great property. Love the artwork and puzzles! "

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

Lisa S.

[](https://www.expedia.ca/Everglades-City-Hotels-Getaway-In-The-Everglades.h34323344.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)

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

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/43000000/42040000/42035500/42035406/36b55c0a.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)

### Sunrise Waterfront Cottage 

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

Marco Island

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 $395

CA $697 total

includes taxes & fees

Jan 1 - Jan 2, 2026

[](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.

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## Top Chokoloskee Island Hotel Reviews

![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)

![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

"Large comfortable room with everything we needed. "

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

![The Ultimate Fishing Retreat- Comfortable and Convenient!](https://images.trvl-media.com/lodging/107000000/106820000/106814600/106814514/f1e11f2e_y.jpg)

### The Ultimate Fishing Retreat- Comfortable and Convenient!

10/10 Excellent

"Highly recommend! From the location, the cleanliness, and the hospitality of the hosts (Chet and Tricia), everything was top notch. Would definitely look to stay here again in the future."

[](https://expedia.ca/Chokoloskee-Hotels-Our-Little-Slice-Of-Paradise.h106814514.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

" I like this hotel, will stay again. "

[](https://expedia.ca/Everglades-City-Hotels-Captains-Table-Hotel.h73778356.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 Fish- Boat and Relax in this Paradise newly remodeled in Naples, Florida!](https://images.trvl-media.com/lodging/101000000/100410000/100401300/100401228/444a5cc1_y.jpg)

### Marina Fish- Boat and Relax in this Paradise newly remodeled 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)

![Ivey House Everglades Adventures Hotel](https://images.trvl-media.com/lodging/2000000/1800000/1796600/1796579/4f3ed09f_y.jpg)

### Ivey House Everglades Adventures Hotel

10/10 Excellent

"Extremely clean! Staff are very helpful…I asked one staff person who gave his time to show me how to work the TV. Fantastic!"

[](https://expedia.ca/Naples-Hotels-Ivey-House-Everglades-Adventures-Hotel.h1796579.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 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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