Title: Chokoloskee Vacation Rentals from CA $429: Short-Term Rentals for 2026 | Expedia.ca

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![Chokoloskee Bay in the Ten Thousand Islands of southwest Florida USA](https://images.trvl-media.com/place/3000430940/45c1f71e-4080-4de3-a99a-47252e083e3f.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/3000430940/45c1f71e-4080-4de3-a99a-47252e083e3f.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=3000430940&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 two months

[Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=3000430940&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=3000430940&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=3000430940&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Chokoloskee vacation rentals

![Interior](https://images.trvl-media.com/lodging/96000000/95170000/95166000/95165998/75af697d.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)

![Marina](https://images.trvl-media.com/lodging/96000000/95170000/95166000/95165998/7552d3a2.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

9.8/10

Exceptional

(17 reviews)

"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 $205

CA $429 total

includes taxes & fees

Feb 22 - Feb 23

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

![Exterior detail](https://images.trvl-media.com/lodging/122000000/121360000/121356400/121356333/b6aad401.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/122000000/121360000/121356400/121356333/10db9240.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/122000000/121360000/121356400/121356333/7d74cbaa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room](https://images.trvl-media.com/lodging/122000000/121360000/121356400/121356333/c2d6a8dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Resort-Style Studio 15 Mi to Everglades NP

[](https://www.expedia.ca/Naples-Hotels-Resort-Style-Studio-15-Mi-To-Everglades-NP.h121356333.Hotel-Information)

Naples

CA $127

CA $282 total

includes taxes & fees

Mar 1 - Mar 2

[](https://www.expedia.ca/Naples-Hotels-Resort-Style-Studio-15-Mi-To-Everglades-NP.h121356333.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/113000000/112870000/112867300/112867210/a7719f47.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)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112870000/112867300/112867210/1ce92cc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112870000/112867300/112867210/8b7b905f.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

(10 reviews)

"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 $445 total

includes taxes & fees

Feb 25 - Feb 26

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

![Terrace/patio](https://images.trvl-media.com/lodging/5000000/4820000/4816100/4816075/b0c661b9.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)

![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)

### River Wilderness Waterfront Cabins

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

Everglades City

8.6/10

Excellent

(273 reviews)

"The cabin was spacious with full kitchen and a screened in deck. The cabin was elevated the car park was directly under the cabin. The room was clean and the bed comfortable. Both main rooms had effective A/C. The staff was also helpful and connected us to local 2 hr boat tour that was really special. It was a unique experience."

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

Michael

CA $378

CA $431 total

includes taxes & fees

Feb 10 - Feb 11

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

![Interior](https://images.trvl-media.com/lodging/101000000/100410000/100401300/100401228/89cf0350.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)

![Lobby](https://images.trvl-media.com/lodging/101000000/100410000/100401300/100401228/b3dd9c4d.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)

### 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

9.6/10

Exceptional

(10 reviews)

"Perfect location. "

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

Jennifer E.

CA $205

CA $429 total

includes taxes & fees

Feb 19 - Feb 20

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

![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)

![Property grounds](https://images.trvl-media.com/lodging/43000000/42040000/42035500/42035406/f3b55701.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)

![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)

### Sunrise Waterfront Cottage 

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

Marco Island

10/10

Exceptional

(44 reviews)

"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 $400

CA $716 total

includes taxes & fees

Feb 10 - Feb 11

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

![Interior](https://images.trvl-media.com/lodging/122000000/121360000/121356400/121356328/b8f1d8b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/122000000/121360000/121356400/121356328/8c86bd3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/122000000/121360000/121356400/121356328/487eef7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, internet, bed sheets](https://images.trvl-media.com/lodging/122000000/121360000/121356400/121356328/d62e9e2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Exclusive 10,000 Islands Access: Naples Studio

[](https://www.expedia.ca/Naples-Hotels-Exclusive-10.h121356328.Hotel-Information)

Naples

CA $127

CA $282 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Naples-Hotels-Exclusive-10.h121356328.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=2026-02-23&endDate=2026-02-24&regionId=3000430940&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Chokoloskee%2C+Florida%2C+United+States+of+America&regionId=3000430940&latLong=25.81288%2C-81.362022&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=VACATION_HOME)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Chokoloskee%2C+Florida%2C+United+States+of+America&regionId=3000430940&latLong=25.81288%2C-81.362022&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=APARTMENT)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Chokoloskee%2C+Florida%2C+United+States+of+America&regionId=3000430940&latLong=25.81288%2C-81.362022&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=COTTAGE)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Chokoloskee%2C+Florida%2C+United+States+of+America&regionId=3000430940&latLong=25.81288%2C-81.362022&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=VILLA)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Chokoloskee%2C+Florida%2C+United+States+of+America&regionId=3000430940&latLong=25.81288%2C-81.362022&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=CONDO)

Houseboats

[](https://www.expedia.ca/Hotel-Search?destination=Chokoloskee%2C+Florida%2C+United+States+of+America&regionId=3000430940&latLong=25.81288%2C-81.362022&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=HOUSE_BOAT)

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## Top Chokoloskee Hotel Reviews

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

### River Wilderness Waterfront Cabins

10/10 Excellent

"Cabin was clean and in good order. But the best part was the view from the back deck. How nice to look out over the water in the morning and watch the sun rise plus have so many different birds fly by. Complimentary canoes and bicycles also were such a nice addition. If you like quiet you'll love this place. Plus the lady in the office gave us such good advice as to what boat tours to take and we were especially satifsfied with that. We would definately stay here again."

[](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

"The room was very clean, spacious, great location. Restaurants and shops within walking distance and the staff was very polite, friendly and courteous. Thank you so much. I love your beautiful little town. "

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

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

### Everglades City Motel

10/10 Excellent

"Would stay here again"

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

![The Reel'em Inn, Chokoloskee Island Fisherman's Paradise](https://images.trvl-media.com/lodging/80000000/79450000/79443400/79443326/28038b63_y.jpg)

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

10/10 Excellent

"Very nice home in laid back area of Florida Brock and Maureen were so nice and easy to work with highly recommend"

[](https://expedia.ca/Chokoloskee-Hotels-The-Reelem-Inn.h79443326.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

"Clean and quiet. "

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

"Our room was very clean and comfortable. The floor in the bathroom shower area was very slippery and might need some hand rails to prevent falls. "

[](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

"Everything was at our finger tips and the host was quick to respond. Outstanding location for outdoor activities like biking & paddling, pool, pickleball courts (paddles & balls made available by host), kitchen well equipped, waterside to allow watching Marina activities, and great bathroom shower. We plan to return!"

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

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

### @cypresscottage

10/10 Excellent

"This home is exceptionally clean, well-maintained, and thoughtfully designed. As a retired builder and former architectural drafter, my husband was particularly impressed by the layout. The vaulted ceilings and abundance of natural light make excellent use of the lot’s orientation. The native landscaping is also a beautiful, intentional touch.Location & Logistics:• Boating: We brought a high-end flats boat (6–8” draft) but chose not to use the on-site dock due to low-tide mud concerns. However, the marina is only two blocks away, making it a non-issue.• Noise/Privacy: Being across from a Circle K can result in some night noise. A simple blind on the glass front door and sound machines in the bedrooms would easily solve this and add extra privacy.Final Verdict: The previous reviews are highly accurate and reliable. We had a great stay and would highly recommend this property!"

[](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

"The room was very suitable for an overnight stay. Very clean all the amenities you could use and the staff was very friendly and helpful"

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

## Find out more about Chokoloskee

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. 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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- [Apartments in Chokoloskee ](https://expedia.ca/Chokoloskee-Apartments.d3000430940-aaApartments.Travel-Guide-Accommodation)
- [Vacation Homes in Chokoloskee ](https://expedia.ca/Chokoloskee-Private-Vacation-Homes.d3000430940-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Condo Rentals in Chokoloskee ](https://expedia.ca/Chokoloskee-Condos.d3000430940-aaCondos.Travel-Guide-Accommodation)
- [Cottages in Chokoloskee ](https://expedia.ca/Chokoloskee-Cottages.d3000430940-aaCottages.Travel-Guide-Accommodation)
- [Villas in Chokoloskee ](https://expedia.ca/Chokoloskee-Villas.d3000430940-aaVillas.Travel-Guide-Accommodation)
- [Houseboats in Chokoloskee ](https://expedia.ca/Chokoloskee-Houseboats.d3000430940-aaHouseboats.Travel-Guide-Accommodation)
- [Motels in Chokoloskee ](https://expedia.ca/Chokoloskee-Motels.d3000430940-aaMotels.Travel-Guide-Accommodation)
- [RV Parks in Chokoloskee ](https://expedia.ca/Chokoloskee-RV-Parks.d3000430940-aaRVParks.Travel-Guide-Accommodation)
- [Resorts in Chokoloskee ](https://expedia.ca/Chokoloskee-Resort-Hotels.d3000430940-aaResortHotels.Travel-Guide-Accommodation)
- [Cabin Rentals in Chokoloskee ](https://expedia.ca/Chokoloskee-Cabins.d3000430940-aaCabins.Travel-Guide-Accommodation)

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