Chokoloskee Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Chokoloskee vacation rentals

A modern kitchen with white cabinets, stainless steel appliances, and a glass dining table.

1. Waterfront Everglades basecamp with dock, trailer parking, and direct bay access

Waterfront Everglades basecamp with dock, trailer parking, and direct bay access
Ochopee
9.8 out of 10, Exceptional, (21 reviews)
"Phenomenal place to stay. Enjoyed everyday we were there. "
United States
Devon G.
The price is CA $284
CA $669 total
includes taxes & fees
Dec 1 - Dec 2
Waterfront Everglades basecamp with dock, trailer parking, and direct bay access
A wooden deck with a glass door leading to a balcony overlooking a body of water.

2. River Wilderness Waterfront Cabins

River Wilderness Waterfront Cabins
2.5 star property
Everglades City
8.6 out of 10, Excellent, (301 reviews)
"Staff was accommodating. Perfect setting and location. We are a repeat customer."
United States
Tangela
The price is CA $274
CA $312 total
includes taxes & fees
Nov 18 - Nov 19
River Wilderness Waterfront Cabins
A lakeside property with a house, dock, and boat.

3. Amazing little fishing cabin on the water with a boat ramp in Everglades City

Amazing little fishing cabin on the water with a boat ramp in Everglades City
Everglades City
10.0 out of 10, Exceptional, (5 reviews)
"We had a fabulous stay."
United States
Christie
The price is CA $245
CA $459 total
includes taxes & fees
Nov 18 - Nov 19
Amazing little fishing cabin on the water with a boat ramp in Everglades City
A wooden deck with outdoor seating and a grill, surrounded by trees and a body of water.

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

Charming 1-bedroom cottage with AC and WiFi on a creek with private deck.
Ochopee
9.8 out of 10, Exceptional, (22 reviews)
"Cool place, beautiful inside"
United States
Sarah J
The price is CA $281
CA $469 total
includes taxes & fees
Nov 12 - Nov 13
Charming 1-bedroom cottage with AC and WiFi on a creek with private deck.
A spacious interior with a high ceiling, multiple levels, and a central staircase.

5. POI Resort Studio Near Everglades NP: Swim + Sail

POI Resort Studio Near Everglades NP: Swim + Sail
3.0 star property
Naples
The price is CA $128
CA $238 total
includes taxes & fees
Nov 16 - Nov 17
POI Resort Studio Near Everglades NP: Swim + Sail
A spacious living area with wicker furniture, a fireplace, and a staircase.

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

Marina Fish- Boat and Relax in this Paradise newly remodeled in Naples, Florida!
Naples
9.8 out of 10, Exceptional, (11 reviews)
"The host did a great jobThe resort was as advertised"
United States
Skip S.
The price is CA $120
CA $313 total
includes taxes & fees
Nov 13 - Nov 14
Marina Fish- Boat and Relax in this Paradise newly remodeled in Naples, Florida!
A spacious lobby with a central Christmas tree, multiple seating areas, and a staircase connecting floors.

7. Everglades Studio w/ Resort Amenities & Porch!

Everglades Studio w/ Resort Amenities & Porch!
Naples
6.6 out of 10, (4 reviews)
"Nice place to spend for a short stay. Unit not really set up for a long stay."
United States
James L.
The price is CA $62
CA $203 total
includes taxes & fees
Nov 16 - Nov 17
Everglades Studio w/ Resort Amenities & Porch!
A spacious living area with wicker furniture, a fireplace, and a staircase.

8. Naples Marina Getaway Studio DIRECT WATER VIEWS!

Naples Marina Getaway Studio DIRECT WATER VIEWS!
Naples
9.6 out of 10, Exceptional, (25 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
Rodney
The price is CA $134
CA $330 total
includes taxes & fees
Nov 13 - Nov 14
Naples Marina Getaway Studio DIRECT WATER VIEWS!
A modern living room with a sofa, armchair, and ottoman, a kitchen area with bar stools, and a ceiling fan.

9. If you prefer wildlife over nightlife this is the place for you, Fakahatchee!

If you prefer wildlife over nightlife this is the place for you, Fakahatchee!
Copeland
10.0 out of 10, Exceptional, (6 reviews)
"This is the place to be if you want to be surrounded by nature in South Florida. The property had wildlife on it (and Patrick was nice enough to let us know when critters were near) and minutes away from beautiful hikes and mangroves. The house itself was nice and updated, and provided lots of privacy."
United States
Danielle
The price is CA $353
CA $629 total
includes taxes & fees
Nov 15 - Nov 16
If you prefer wildlife over nightlife this is the place for you, Fakahatchee!
A spacious lobby with a central Christmas tree, multiple seating areas, and a staircase connecting floors.

10. Resort-Style Studio 15 Mi to Everglades NP

Resort-Style Studio 15 Mi to Everglades NP
Naples
7.0 out of 10, Good, (2 reviews)
"The room was not very clean. The price was good but you get what you pay for. I would not stay here again! "
United States
Jodie M.
The price is CA $109
CA $257 total
includes taxes & fees
Nov 15 - Nov 16
Resort-Style Studio 15 Mi to Everglades NP
A spacious lobby with a central Christmas tree, multiple seating areas, and a staircase connecting floors.

11. Naples Resort Retreat w/ Pool Access!

Naples Resort Retreat w/ Pool Access!
Naples
6.6 out of 10, (4 reviews)
"Great potential needs work no bar restaurants as advertised "
United States
Mike S.
The price is CA $62
CA $203 total
includes taxes & fees
Nov 15 - Nov 16
Naples Resort Retreat w/ Pool Access!
A spacious lobby with a central Christmas tree, multiple seating areas, and a staircase connecting floors.

12. Pool Access: Everglades Resort Retreat!

Pool Access: Everglades Resort Retreat!
Naples
The price is CA $88
CA $232 total
includes taxes & fees
Nov 16 - Nov 17
Pool Access: Everglades Resort Retreat!
A spacious lobby with a central Christmas tree, multiple seating areas, and a staircase connecting floors.

13. Everglades Getaway 15 Mi to NP: Sail + Swim!

Everglades Getaway 15 Mi to NP: Sail + Swim!
Naples
The price is CA $88
CA $232 total
includes taxes & fees
Nov 16 - Nov 17
Everglades Getaway 15 Mi to NP: Sail + Swim!
A spacious lobby with a central Christmas tree, multiple seating areas, and a staircase connecting floors.

14. Dock, Pool & Tennis Courts: Naples Resort Retreat!

Dock, Pool & Tennis Courts: Naples Resort Retreat!
Naples
6.0 out of 10, (2 reviews)
"Super cute and updated. Pool was great. Short walk to beach. "
United States
Christy R.
The price is CA $110
CA $258 total
includes taxes & fees
Nov 16 - Nov 17
Dock, Pool & Tennis Courts: Naples Resort Retreat!
A spacious lobby with a central Christmas tree, multiple seating areas, and a staircase connecting floors.

15. Everglades Getaway 15 Mi to NP: Sail + Swim!

Everglades Getaway 15 Mi to NP: Sail + Swim!
3.0 star property
Naples
The price is CA $128
CA $238 total
includes taxes & fees
Nov 15 - Nov 16
Everglades Getaway 15 Mi to NP: Sail + Swim!
A spacious lobby with a central Christmas tree, multiple seating areas, and a staircase connecting floors.

16. Everglades Escape w/ Outdoor Pool & Marina Access!

Everglades Escape w/ Outdoor Pool & Marina Access!
Naples
8.0 out of 10, Very good, (3 reviews)
"Great Stay!!!"
United States
Ryan S.
The price is CA $88
CA $232 total
includes taxes & fees
Nov 16 - Nov 17
Everglades Escape w/ Outdoor Pool & Marina Access!
A spacious interior with a high ceiling, multiple levels, and a central staircase.

17. POI Resort Studio Near Everglades NP: Swim + Sail

POI Resort Studio Near Everglades NP: Swim + Sail
Naples
4.8 out of 10, (3 reviews)
"Room shown was still in use when we arrived then substituted for a non upgraded, dirty room. Heavy chemical cleaner smell, floors, kitchen, and bathroom not clean or anywhere near what was shown in listing pictures. Felt like a bait and switch. Emailed Evolve Travel upon checkout, a formal claim initiated by them. 5 days later still no resolution. "
United States
Liane H.
The price is CA $88
CA $232 total
includes taxes & fees
Nov 16 - Nov 17
POI Resort Studio Near Everglades NP: Swim + Sail
A spacious lobby with a central Christmas tree, multiple seating areas, and a staircase connecting floors.

18. Resort-Style Naples Studio w/ Marina Access!

Resort-Style Naples Studio w/ Marina Access!
Naples
The price is CA $110
CA $258 total
includes taxes & fees
Nov 16 - Nov 17
Resort-Style Naples Studio w/ Marina Access!
A spacious lobby with a central Christmas tree, multiple seating areas, and a staircase connecting floors.

19. Exclusive 10,000 Islands Access: Naples Studio

Exclusive 10,000 Islands Access: Naples Studio
Naples
The price is CA $88
CA $232 total
includes taxes & fees
Nov 16 - Nov 17
Exclusive 10,000 Islands Access: Naples Studio
A spacious lobby with a central Christmas tree, multiple seating areas, and a staircase connecting floors.

20. Near the Everglades: Studio at Port of the Islands

Near the Everglades: Studio at Port of the Islands
Naples
6.0 out of 10, (2 reviews)
"Very quiet, adjacent to marina with a nice pool. Staff was very friendly and responsive."
United States
Sally G.
The price is CA $109
CA $257 total
includes taxes & fees
Nov 16 - Nov 17
Near the Everglades: Studio at Port of the Islands
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 Hotel Reviews

A building with a porch, stairs, and palm trees.
Ivey House Everglades Adventures Hotel

Ivey House Everglades Adventures Hotel

Ivey House Everglades Adventures Hotel
Everglades City

10/10 Excellent

The staff are super nice and helpful. Enjoyed our stay
Canada
Koreena
Reviewed October 16, 2026
Ivey House Everglades Adventures Hotel

Find out more about Chokoloskee

Everything you need to know about Chokoloskee 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 vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chokoloskee vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chokoloskee. 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chokoloskee vacation rentals we have selected for you start as low as CA $62 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chokoloskee rentals

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

Frequently Asked Questions

Can I find vacation rentals in Chokoloskee?

Yes, there are vacation rentals close to the most popular attractions in Chokoloskee, or you can choose a more secluded option if you're looking for relaxation. Chokoloskee is known for its waterfront and seafood restaurants.

What are some of the best vacation rentals that Chokoloskee has to offer?

The Reel'em Inn, Chokoloskee Island Fisherman's Paradise with Pool: This Chokoloskee vacation home rental offers an outdoor pool, a balcony, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of books.

How many vacation rentals are there in Chokoloskee?

With 6 Expedia vacation rentals, you're sure to find just the right place for your Chokoloskee stay.

What can I see and do in Chokoloskee?

Big Cypress National Preserve and Everglades National Park are a couple of lovely local spots to get outside and enjoy nature. Chokoloskee Bay and Smallwood Store are other places to visit while you're in town.

What are vacation rentals like in Chokoloskee?

Vacation rentals are private accommodations you can reserve for a short or long stay in Chokoloskee. Vacation rentals offer extras like laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can offer a sense of safety away from shared hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for a family trip or a small group gathering.